Vacation rentals in Chestertown, MD with free parking

Fenced Backyard | Furnished Deck | Family Game Nights Step into a storybook at 'Sage Bungalow' in Chestertown, where historic streets and riverside breezes set the scene for adventure. Head downtown to explore local art galleries, enjoy a picnic in the leafy serenity of Wilmer Park, or glide along the Chester River on a boat cruise. After a fun day, retreat to the 2-bed, 2-bath home to cozy up by the fire or settle in for a night of board games. Your Eastern Shore escape awaits! -- THE PROPERTY -- SLEEPING ARRANGEMENTS - Bedroom 1: 1 king bed - Bedroom 2: 1 queen bed - Living Room: 1 queen sleeper sofa OUTDOOR LIVING - Deck w/ dining space & charcoal grill - Covered porch w/ 2 chairs - Fenced backyard INDOOR LIVING - Smart TV, fireplace - Dining table - Walk-in shower, shower/tub combo - Board games, books - Ceiling fans in bedrooms KITCHEN - Stove/oven, refrigerator, dishwasher - Cooking basics, dishware/flatware - Cuisinart dual coffee maker (drip & single-serve pod, coffee provided) - Microwave, toaster, blender, ice maker - Limited spices (salt, pepper, garlic salt, paprika, tajin, cinnamon & dill weed) GENERAL - Free WiFi - Central heating & A/C - Complimentary toiletries, hair dryer - Washer/dryer, laundry detergent, hangers - Linens/towels, trash bags/paper towels FAQ - Pet fee (paid pre-trip) ACCESSIBILITY - Single-story home, 8 steps to enter PARKING - Driveway (1 vehicle) - EV outlet (bring your own charging cable) -- THE LOCATION -- - 0.3 miles to Washington College - 0.5 miles to Historical Society of Kent County - 0.7 miles to Chestertown Historic District: Chestertown Farmers Market (every Saturday from 8:00 AM to 12:00 PM), Chestertown Tea Party Festival (Memorial Day weekend), parks, restaurants, art galleries, shops - 1 mile to Chester River - 18 miles to Eastern Neck National Wildlife Refuge - 67 miles to Baltimore/Washington International Airport -- REST EASY WITH US -- Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - Pet friendly w/ $50 fee (+ fees & taxes, dogs only, 2 max) - No events, parties, or large gatherings - Must be at least 18 years old to book - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - This single-story home requires 8 steps to enter

Secluded History - in the Land of Pleasant Living Located five miles from Chestertown, Thornton is a magnificent 6,000 square foot manor house built in 1815 and is currently owned and cared for by the twelfth-generation family. Having undergone two additions over the years, it was recently restored and renovated to include a modern cook’s kitchen. Thornton has a graceful combination of the finest finishes from both the past and the present. Thornton Farm comprises a 300+ acre traditional and organic crop farm with 2500’+ of shoreline on Morgan Creek. You will immediately get a sense of the grace and grandeur of Thornton as you drive down the long tree-lined lane leading to the high grounds of the farm. During the day you’ll enjoy the bucolic privacy while evenings will leave you awestruck by the twinkling stars overhead. It’s possible to believe that Thornton is where the earth stops and the night sky begins. Among other features of this exquisite, classic and charming house are manicured grounds, swimming pool, bass fishing pond, extensive walking paths, and a Merlot grape vineyard. The large library/family room has a gas burning fireplace and big screen television for everyone to enjoy. Although you may consider venturing into Chestertown to sample the local cuisine and flavors, Thornton promises to make the decision a difficult one, as would be expected when vacationing at a quintessential Eastern Shore Estate. PROPERTY FEATURES: Pool: Swimming pools are open from May 15 - October 15. Be sure to bring your own pool towels. Acreage: 300 +/- acres of complete privacy. Fireplaces: 1 gas. Firepit: Firewood is not provided. Grill: Propane grill. Propane is provided. Pet Friendly: This is a pet friendly rental. WiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds. BED SIZES: Single Bed - Twin Sized - 1 / King - 1 / Queen - 1 / Queen - 1 / Queen - 1 / Single Bed - Twin Sized - 1 / Single Bed - Twin Sized - 2 / THIS IS A LUXURY RENTAL: Guests that stay at one of our luxury rentals unlock private access to a world of privilege. Benefits include: An ESVR representative greeting you upon arrival. They will ensure the rental meets our white glove standard, provide a tour of the property and answer any questions. Upgraded essentials package to include: paper towels, trash bags, toilet paper per bathroom, dishwasher pods, laundry pods, and full size (soap, shampoo and conditioner) per bathroom for your entire stay. Access to our proprietary app (A Day With ESVR) for guests that provides guests access to curated maps featuring all of the best places and experiences Maryland’s Eastern Shore has to offer. Access to our dynamic and fully integrated mobile-first welcome book designed to delight and support guests with property information and direct messaging with a guest service representative throughout your stay. Access to our concierge services to help with booking nearby activities, tours and more.

Book a tranquil East Coast getaway at this 60-acre vacation rental in Millington, MD. This secluded waterfront property offers the ultimate escape for you and your crew. Take the 2 included kayaks out on the Chester River, have a backyard cookout, and soak in the rejuvenating private hot tub while you’re here. Made up of two 120-year-old houses with 7 bedrooms and 4 bathrooms on-site, this expansive vacation rental is one of a kind. Take some much-needed time off and stay at this serene retreat! -- THE PROPERTY -- Private Hot Tub | 60-Acre Property | Chester River Access On-Site Bedroom 1 (Main House): Queen Bed, Full Bed | Bedroom 2 (Main House): 2 Full Beds | Bedroom 3 ( Main House): Full Bed | Bedroom 4 (Main House): Twin Bed | Bedroom 5 (Guest House): Queen Bed | Bedroom 6 (Guest House): Queen Bed | Bedroom 7 (Guest House): Twin Bed OUTDOOR LIVING: Fire pit (wood provided), cornhole, paddle board, 3 kayaks, gas grill, porch w/ swing GUEST HOUSE: Fully equipped kitchen, electric fireplace, deck w/ seating INDOOR LIVING: TVs w/ cable/satellite, board games, fireplace (decorative only), books, exposed wood interior KITCHEN: Stove/oven, fridge, microwave, dishwasher, coffee maker, cooking basics, dishware & flatware, toaster, complimentary coffee, tea & snacks, spices GENERAL: Lockbox entry, complimentary toiletries, free WiFi, central A/C & heat, hair dryer, iron/board, trash bags & paper towels, linens & towels, washer/dryer, laundry detergent FAQ: Stairs required, 1 exterior security camera (facing entryway of Main House) PARKING: Driveway (6 vehicles) -- THE LOCATION -- SUN & SAND: Betterton Beach (17 miles), Woodland Beach (27 miles), Fraland Beach (28 miles), Augustine Beach Access Area (34 miles) WINE TASTING: Crow Vineyard & Winery (9 miles), Casa Carmen Wines (11 miles), Broken Spoke Winery (20 miles), Chateau Bu-De, LLC Bohemia Manor Farm (20 miles) NATURE ESCAPE: Unicorn Lake (3 miles), Sassafras NRMA (14 miles), Fork Branch Nature Preserve (24 miles), Ferry Park (25 miles), Brecknock County Park (29 miles), Sandy Point State Park (42 miles) SET SAIL: Georgetown Yacht Haven (12 miles), Duffy Creek Marina (13 miles), Chesapeake Boating Club (51 miles), Salem Boating Club Inc (55 miles), Baltimore Boating Center (82 miles) ANIMAL SANCTUARY: Woodland Beach State Wildlife Management Area (18 miles), Pelot Bird Sanctuary Trailhead - MD Ornithological Society (24 miles), Bombay Hook National Wildlife Refuge (26 miles), Augustine Wildlife Area (33 miles), ABA’s Heron Watch (35 miles), Supawna Wildlife Refuge Observation Point (53 miles) AIRPORTS: Philadelphia International Airport (66 miles), Baltimore/Washington International Thurgood Marshall Airport (72 miles) -- REST EASY WITH US -- Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: The property requires stairs to access - NOTE: The fireplace is not for guest use - NOTE: Your safety matters. This property features 1 exterior doorbell camera located next to the front door of the Main House facing the front entryway. It does not look into any interior spaces. The camera records video and sound when activated by motion. It will record when it first senses motion and 30 seconds after the last motion is detected

Experience comfort and tranquility at this 3-bedroom, 2.5-bath vacation rental in Rock Hall, MD! Perfect for families, this charming home features a furnished balcony for sipping your morning coffee, a fully equipped kitchen for preparing delicious homemade meals, and easy access to the Rock Hall Community Park next door. When you're ready to venture out, consider riding the provided bicycles around town or exploring the Eastern Neck National Wildlife Refuge. Your getaway awaits! -- THE PROPERTY -- Walk to Rock Hall Community Playground | Near Rock Hall Harbor | Quiet Location Bedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: 2 Twin Beds INDOOR LIVING: Smart TV, dining table, beverage refrigerator (2nd floor), board games, ceiling fans KITCHEN: Keurig & French press coffee makers (coffee & sugar provided), cooking utensils, dishware & flatware, dishwasher, ice maker, microwave, toaster, water filter OUTDOOR LIVING: Furnished balcony, deck, yard, playground views GENERAL: Free WiFi, keyless entry, central air conditioning & heating, hair dryer, hangers, in-unit laundry machines, linens/towels, trash bags/paper towels, clothes steamer, bicycles ACCESSIBILITY: 2-story home, exterior steps to enter, bedroom & bathroom on 1st floor FAQ: Quiet hours (10:00 PM-7:00 AM) PARKING: Driveway (1 vehicle), carport (1 vehicle) -- THE LOCATION -- OUTDOOR SPOTS: Rock Hall Community Park & Playground (0.4 miles), Rock Hall Landing Marina (1 mile), Eastern Neck National Wildlife Refuge (6 miles), Tolchester Beach & Marina (7 miles), Mitchell Bluff (8 miles) HOT SPOTS: The Mainstay (0.5 miles), Caulk's Field Monument (6 miles), Chestertown (14 miles), Wilmer Park (14 miles), Chester River Yacht & Country Club (14 miles) LOCAL EATS: Java Rock Coffee House & Cafe (0.5 miles), Waterman's Crab House (0.9 miles), Harbor Shack (1 mile) AIRPORT: Baltimore/Washington International Thurgood Marshall Airport (77 miles) -- REST EASY WITH US -- Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No outside fires allowed at the property - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: This 2-story home requires exterior steps to enter. While there is a bedroom on the 1st floor, an additional interior staircase is required to access the remaining bedrooms on the 2nd floor - NOTE: Please observe quiet hours from 10:00 PM to 7:00 AM

This short-term rental has an occupancy of 10 individuals with a max. of 8 guests being 18 years or older. Working Farm on Reeds Creek This lovely working farm is on a peninsula situated between Grove Creek and (surely not to your surprise) Reed Creek, which is just off of the Chester River. On this peninsula, historically called Wright’s Neck, sits the Reeds Creek house, built by Colonel Thomas Wright in 1775. The Creek Cottage, a second home on the property, is a modern addition to the 170-acre farm offering privacy in the presence of a historical setting and powered by solar energy. Enjoy the private surroundings of the farm from the cottage’s private pool or take a stroll or a leisurely bike ride to the sandy beach on Reed Creek. Get a sense of history by booking your stay at The Creek Cottage on Reed Creek Farm today. PROPERTY FEATURES: Acreage: 170 acre farm. Waterfront: Reed Creek Dock: 100ft dock with 3ft MLW, water and electricity. Water Toys: 2 single kayaks, 2 canoes and 2 paddle boards are available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency. Pool: Swimming pools are open from May 15 - October 15. Be sure to bring your own pool towels. Heat is available for an additional fee. Please contact us if you want to add this option. Fireplaces: Wood-burning. Firewood is not provided. Fire Pit: Propane is provided. Grill: Propane grill. Propane is provided. Pet Policy: This property is dog friendly for up to two medium size dogs 60lbs and under. WiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds.

Ideal felicity and perfection! This 3,600 square foot, 4-bedroom, 3.5-bathroom Wye River waterfront was designed with your comfort in mind, the open floor plan features a modern interior and incorporates a flow-through living, entertaining and dining area and a generous foodie inspired kitchen. Drift off to sleep each night in the opulent main suite that comes complete with an ensuite bathroom, direct access to an expansive deck, and water views. The wonderfully secluded property boasts a beautiful built-in swimming pool, private dock, and paved ramp to launch your boat. While this rental provides wonderful privacy, it’s also a five minute car ride from the Queenstown Outlets, and a ten minute car ride from several popular waterfront restaurants, farmers markets, and grocery stores. You will love this waterfront vacation home! Well placed in a sought-after Queen Anne’s County neighborhood. This unique home will book fast! PROPERTY FEATURES: Waterfront: Wye River Dock: Private dock with MLW 3’. Electricity is available for guest use. Guests are permitted to tie a boat to the dock. Boat Ramp: Private paved boat ramp onsite for boat launch. Water Toys: 2 adult kayaks and 1 adult paddle board are available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency. Pool: 20 x 40 private pool. Swimming pools are open from May 15 - October 15. Be sure to bring your own pool towels. Grill: Propane grill. Propane is provided. WiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds. BED SIZES: King - 1 / King - 1 / Queen - 2 / Bunk Bed - Pyramid | Single over Double - 1 /

Become enveloped by Maryland hospitality when you stay at ‘The Winchester,’ a gorgeous home right on the water. With stunning features both inside and out, this 3-bedroom, 2-bath vacation rental has everything you need for a relaxing trip to the East Coast. Relax in the bright interior and enjoy the fully equipped kitchen or the Smart TVs. You can enjoy the seasonal pool or head out onto the water for some outdoor fun. The surrounding towns also have lots to do from dining to shopping and more! -- THE PROPERTY -- Walk to Beach & Playground | 2,000 Sq Ft | Dock | Stainless Steel Appliances Bedroom 1: King Bed | Bedroom 2 (Murphy Room): Queen Murphy Bed | Bedroom 3 (Treehouse): Queen Bed, Twin Bunk Bed OUTDOOR LIVING: Private pool (Memorial Day - Labor Day, depth 4'), gas grill, furnished patio, outdoor dining area, fire pit (firewood provided), gazebo, life vests, private pier w/ boat dock, crab traps & live box INDOOR LIVING: Smart TVs, 2 dining tables, gas fireplace (available in colder months), walk-in closet KITCHEN: Breakfast bar w/ seating, dishwasher, refrigerator, stove/oven, microwave, drip coffee maker, Crockpot, blender, toaster, spices, cooking basics, dishware & flatware, high chair GENERAL: Free WiFi, central A/C, linens/towels, washer/dryer, ceiling fans, hair dryers, hangers, iron/board, trash bags & paper towels, 3 exterior security cameras FAQ: Stairs required for access, bedroom & bathroom on 1st floor PARKING: Driveway (4 vehicles), carport (1 vehicle) -- THE LOCATION -- OUTDOOR ADVENTURE: Winchester Creek (on-site), Long Point Park (1.1 miles), Jackson Creek Landing (1.2 miles), Grasonville Park (1.2 miles), Ewing Pond Park (2.0 miles), Kent Narrows Public Boat Ramp (3.3 miles), Ferry Point Park (3.4 miles), Queenstown Harbor Golf (4.9 miles), Old Love Point Park (7.0 miles), Terrapin Nature Park (7.6 miles), Washington Hunters Oak Country Club (7.9 miles), Mowbray Park (8.2 miles), Queen Anne's County Parks (8.8 miles), Matapeake Park (9.3 miles), Kentmorr Marina (12.2 miles), Sandy Point State Park (12.7 miles) AREA ATTRACTIONS: Watermen's Monument (2.4 miles), Chesapeake Bay Environmental Center (2.6 miles), Stevensville Historic District (6.4 miles), Old Wye Mill (9.5 miles), Chesapeake Bay Maritime Museum (31.9 miles), Six Flags America (38.0 miles) Washington D.C. (49.1 miles): Arlington National Cemetary, Ford’s Theater, National Gallery of Art, Smithsonian National Air and Space Museum, Smithsonian National Museum of Natural History, United States Holocaust Memorial Museum, National Museum of African American History and Culture, Washington Monument, United States Capitol, World War II Memorial, Lincoln Memorial, Vietnam Veterans Memorial, Korean War Veterans Memorial GOOD EATS: La Piazza Pizza & Italian Restaurant (1.3 miles), Hunter's Seafood and Market (1.4 miles), Fisherman's Inn Restaurant (2.5 miles), The Narrows Restaurant (2.5 miles), The Jetty (2.5 miles), Bridges Restaurant (2.5 miles), Fisherman's Crab Deck (2.6 miles), Harris Crab House (2.6 miles), Adams Grille & Tap House Kent Island (4.3 miles) AIRPORT: Baltimore/Washington International Thurgood Marshall Airport (36.8 miles) -- REST EASY WITH US -- Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: The property requires stairs to access - NOTE: Your safety matters. This property features 3 exterior security cameras: 1 camera is located on the front of the house facing the door and pool area, 1 camera is facing the driveway entrance, and 1 camera is facing the rear side of the carport and driveway. The cameras are outward facing and do not look into interior spaces. The cameras actively record both video and sound

The Perfect Escape! This exceptional 5-bedroom, 3-bathroom shore house sits on a 1+ acre waterfront lot and boasts endless nautical activities, including kayaking, a private pier, and a large pool overlooking the Chesapeake Bay. Offering a welcoming interior and providing large entertainment spaces, an expansive great room, first-floor master bedroom suite, and sunroom. Drift off to sleep each night in the oversized main suite that comes complete with an ensuite bathroom and picture-perfect water views. Enjoy the indoor/outdoor lifestyle in the beautifully maintained backyard which includes a brand-new stone patio, large in-ground heated pool (Heat is available for an additional fee), gas firepit, and large grassy areas for yard games with spectacular views. An ideal destination for any vacation. With an exceptional location in a desirable section of Queen Anne’s County. Please Note: This house is in a quiet residential neighborhood, so is not compatible with any loud parties, and it is imperative that if you bring a pet that the pet not be allowed off property without a leash. The westerly view over the water provides exceptional sunsets - enjoy a nightly sunset cocktail and experience the waterfront lifestyle you’ve been looking for. Book this one quickly or miss out. PROPERTY FEATURES: Waterfront: Chesapeake Bay Dock: 50ft private dock. No water or electricity is available. Guests are permitted to tie a boat to the dock. Water Toys: 1 kayak is available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency. Pool: 20 x 40 private pool. Swimming pools are open from May 15 - October 15. Be sure to bring your own pool towels. Heat is available for an additional fee. Please contact us if you want to add this option. Grill: Propane grill. Propane is provided. Pool Shed: Pool toys, loungers, tables, pool toys, a beverage fridge and yard games. Pet Friendly: Owner will consider pets, call reservations at 443.664.4039 to inquire. WiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds. BED SIZES: King - 1 / Sleep Sofa - Double - 1 / Sleep Sofa - Double - 1 / Queen - 1 / Queen - 1 / Bunk Bed - Single over Single - 2 / Single Bed - Twin Sized - 2 /

Welcome to our Chesapeake Oasis! Quiet Queenstown is a beautiful and historic part of Maryland’s Eastern Shore bordering the Chesapeake Bay. We welcome you to enjoy a home away from home at our 4-bedroom ranch-style house. Off the beaten path and perfect for multi-generation families, you’ll enjoy the privacy of being off the main road but within a short drive to all that the Eastern Shore has to offer. Relax, unwind, and enjoy! This is a 1-story, 4-bedroom, 2.5-bath property with a beautiful, communal kitchen overlooking the back yard and the cove. The fully-appointed kitchen includes a large island with a breakfast table for groups who like to socialize around good food. We also have a formal dining room and a wine bar with temperature-controlled cooler. The en suite primary bedroom features a king bed, window seats overlooking the cove, and a large internet-enabled smart TV. The three other bedrooms feature one king bed, one queen bed, and one bunk bed (twin XL on top and queen on the bottom bunk). All four bedrooms have internet-enabled smart TVs with wi-fi apps for you to log in to your favorite streaming services. An additional office space features a pull-out with full size mattress, and a 65” smart TV, perfect for movie nights! Bring your friends and family to enjoy your stay with the variety of bedroom options available. Guests have access to the entire home, including the wide-open front yard and fenced-in back yard, the dock, and the laundry. (The garage is currently reserved for storage.) Guest internet is included with your stay; fiberoptic service to the house provides terrific wi-fi speeds for your devices in the +500 Mbps up/down range. With Sadler’s Cove in our back yard, you’ll have easy access to the water if you choose to bring your own canoe or kayak. The bucolic views of the neighboring farm and the serenity of Sadler’s Cove lend themselves to a slower pace and peaceful moments on the back deck or around the firepit with your favorite beverage or glass of wine. The conserved forest on the opposite shore is home to blue herons, hawks, bald eagles, terrapins, and a multitude of other wildlife. We recommend a rental or personal car being used to navigate around Queenstown and to/from our home. There is ample parking provided at the house and no easy access to public transportation in the area. To help ensure a smooth, secure, and enjoyable stay for all guests, please review the following important information before booking: Check-In & Identity Verification Policy All reservations require the primary guest (the booker) to complete a secure online check-in process prior to arrival. This includes: -Uploading a valid, unexpired government-issued photo ID -Uploading a selfie to confirm identity -Reviewing and signing our rental agreement This process is similar to hotel check-in and is required because we do not typically have staff on site. Check-in instructions will only be provided once this process is complete. If you would like to review the rental agreement before booking, please feel free to contact us. In some cases, we may also request a security deposit and/or apply a damage waiver fee in accordance with booking channel policies. * It typically takes ~1 hour to screen a guest after they book this property and could take several hours if we are busy before we are able to provide them with check-in information. If you make a last minute reservation, we ask you to please be patient and please do not expect to gain access to the property immediately. Guest Count & Occupancy Policy Each listing includes a maximum number of guests based on unit type and local regulations. Additional guests are welcome for an added nightly fee: -4 & 5+ bedroom units: $50 per guest, per night after 8 or 10 guests, respectively Please ensure your guest count is entered accurately at booking. We will confirm the number of guests after reservation. If the guest count changes, pricing may be adjusted accordingly. For safety and compliance purposes, exterior security cameras are used to verify occupancy. Unreported additional guests may result in additional charges. Pet Policy This is a pet-friendly property. While our cleaning team is thorough, guests with severe pet allergies should be aware that dogs, cats, or other animals may have stayed in the space previously. Pet fees: $30 per night, per pet $150 per week, per pet $300 per month, per pet Pet fees are included in the accommodation rate as long as you choose the appropriate quantity of pets when completing a booking. We confirm this with all guests post booking confirmation. Local Reservation Policy Reservations under 7 nights from guests residing in the local area may be subject to cancellation at our discretion. We handle exceptions on a case-by-case basis. Early Check-In & Late Check-Out Policy Early arrivals and late departures are not guaranteed and must be approved in advance. If approved, the following fees apply: -Up to 1 hour: $150 -1–2 hours: $300 -2–3 hours: $450 -3+ hours: $600 or the cost of an additional night (whichever is greater) Please do not assume availability without confirmation. Smoking Policy Smoking is not permitted anywhere on the property, including indoor and outdoor areas. If evidence of smoking is found, an additional cleaning fee of $500 will be applied in accordance with the booking channel’s cleaning and damage policies. Special Request Policy Requests for items such as pack-n-plays, high chairs, or other non-standard amenities should be submitted at least 7 days before check-in to ensure availability. Requests made closer to arrival will be accommodated if possible but cannot be guaranteed. We understand that this is a detailed list, and we truly appreciate you taking the time to review it. These guidelines help us maintain a safe, well-cared-for property and ensure a great experience for every guest. Our goal is always for you to feel comfortable, welcome, and well taken care of during your stay.

Experience the Difference: Professionally Managed by iTrip Annapolis This adorable cottage sits on 3 picturesque acres overlooking the Magothy River. The charming, newly-furnished River Cottage is perfect for an escape for two! There is a full kitchen with complimentary coffee and a waterfront back patio - the perfect place to enjoy enjoy a glass of wine. Head further outside to the waterfront pier and fire pit overlooking the Magothy River. The Cottage shares the property with the main house, River Breeze, which is also available for rent. The River Cottage is wonderful for a couple coming in for that special Naval Academy or boat show event, or looking to take in the sights and sounds of Greater Annapolis. Enjoy the many restaurants, historical attractions, and shops just a short drive to downtown Annapolis, or stay put and enjoy the lush, expansive property and spoil yourself with the million dollar views from your very own private patio! SLEEPING ARRANGEMENTS 1 BR / 1 BA / Sleeps 2 adults: Bedroom -Queen bed -Flatscreen TV -Full hall bath with stand-up shower HIGHLIGHTS: -Private waterfront pier -Full kitchen -Water access from private pier on the Magothy River -Game room with pool table, bar stools and TV, shared with main house. -Charcoal Grill -Shared firepit with the main house with seating for 6 -Eat-in kitchen seats 4 -High Speed Internet and WiFi -Big Flatscreen TV’s -Luxury linens, complimentary toiletries Starter Kit, and boutique-level service -Parking in the driveway -Dogs allowed if $150 pet fee per pet is paid prior to check-in. Property Distance to: -Downtown Annapolis – 11 miles -U.S. Naval Academy – 11 miles -Washington, DC – 35 miles -Baltimore - 19 miles * Amenity & Supplies starter pack, coffee and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid to get you going. * All beds are made for you with freshly-laundered sheets & towels. House Rules Reservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking. Dogs allowed if $150 pet fee is paid prior to check-in. Be respectful of the house and contents - it is someone’s home and the owners do come back from time to time to stay in their property. Please respect the neighbors and neighborhood. License: STR00484

Experience the Difference: Professionally Managed by iTrip Annapolis *Ask us about renting the 1Bedroom/1Bath River Cottage on the same property. This stunning historic home, located on 3 picturesque acres overlooking the Magothy River, has been renovated and professionally-decorated from top to bottom. The open space has a massive eating, living and family room space, suitable for a multi-family visit. Separating the cozy conversation/gaming swivel-chair space from the oversized family room space is a custom bar height dining table with seating for up to 12, designed specifically to fit this special space. Head out to the waterfront screened-in patio and enjoy a glass of (complimentary!) wine. Head further outside to the new circle of artfully-crafted chairs around the firepit overlooking the private pier and beach. The home is ideal for families looking for all of the living and sleeping space on one floor. The house has 4 bedrooms and 3 full baths. The bedrooms are divided into 2 wings - a family wing and a guest wing. The Family wing has the spacious master suite features a private newly-renovated bath with combo bathtub/shower and private entrance to a cozy enclosed temperature-controlled sleeping porch off the Master suite with twin daybeds, perfect for sipping coffee or wine and enjoying the view, or alternatively can be utilized as twin beds! The 2nd guest room on the same wing has sleeping for 5 in the Queen bedroom, twin with trundle and pullout twin futon with private bath with shower in the hall. The Guest wing is a waterfront Queen bedroom with its own door out to the back patio and a shared full bath in the hall. The second guest room on the wing has a platform King bed with plenty of closet space. The beautifully-decorated spacious eat-in kitchen has been supplied with everything guests need for their stay. There is also a full laundry room/mudroom. Head out to visit your neighbors at the sweet 1-bedroom cottage next-door or inquire about renting that as an additional space (which may be rented by a 3rd party during your stay). The home has plenty of parking and space to explore with the pups and little family members. The home is wonderful for families and friends coming in for that special Naval Academy or boat show event, or looking to take in the sights and sounds of Greater Annapolis. SLEEPING ARRANGEMENTS 4 BR / 3 BA / Sleeps 8 adults and 4-8 kids/teens: Family Wing: Grand Master Suite: -King bed -Private temperature-controlled sleeping porch with 2 Twin beds -Private bathroom with combo bathtub/stand-up shower -Flatscreen TV Guest Bedroom across the hall from Master Suite: -Queen bed -Twin with Twin Trundle -Twin futon -Full Hall Bath with stand-up shower Guest Wing: Queen Waterfront Guest Bedroom: -Queen bed -Private entrance to waterfront porch -Full hall bath with stand-up shower King Bedroom: -King Bed -Full hall bath with stand-up shower HIGHLIGHTS: -Private waterfront pier -Massive waterfront covered screened-in patio with a dining table and plenty of seating -BBQ Gas grill (propane tank provided) -Extra large gathering space with living, dining and family room areas -Gourmet kitchen -Water access from private pier on the Magothy River -Paddle board (located in the boat house) -Covered temperature-controlled sleeping porch -Game room with pool table, bar stools and TV. -Firepit with seating for 6 -Dining room table seats 12 -Eat-in kitchen seats 6 -High Speed Internet and WiFi -Big Flatscreen TV’s -Luxury linens, complimentary toiletries Starter Kit, and boutique-level service -Parking for multiple cars in driveway -Full Laundry room with Washer & dryer located inside the home -No smoking -Dogs allowed if $150 pet fee is paid prior to check-in. Property Distance to: -Downtown Annapolis – 11 miles -U.S. Naval Academy – 11 miles -Washington, DC – 35 miles -Baltimore - 19 miles * Amenity & Supplies starter pack, coffee and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid to get you going. * All beds are made for you with freshly-laundered sheets & towels. House Rules Reservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking. Dogs allowed if $150 pet fee is paid prior to check-in. Be respectful of the house and contents - it is someone’s home and the owners do come back from time to time to stay in their property. Please respect the neighbors and neighborhood. License: STR00484

Experience the Difference: Professionally Managed by iTrip Annapolis Spread out for Commissioning Week on this historic 3-acre property on the Severn River! There is both a beautiful spacious 4 Bedroom home AND a separate cottage with a 1 bedroom and 1 bath. This stunning historic home, located on 3 picturesque acres overlooking the Magothy River, has just been renovated and professionally-decorated from top to bottom. The open space has a massive eating, living and family room space, suitable for a multi-family visit. Separating the cozy conversation/gaming swivel-chair space from the oversized family room space is a custom bar height dining table with seating for up to 12, designed specifically to fit this special space. Head out to the waterfront screened-in patio and enjoy a glass of (complimentary!) wine. Head further outside to the new circle of artfully-crafted chairs around the firepit overlooking the private pier and beach. The home is ideal for families looking for all of the living and sleeping space on one floor. The house has 4 bedrooms and 3 full baths in the main house. The bedrooms are divided into 2 wings - a family wing and a guest wing. The Family wing has the spacious master suite features a private newly-renovated bath with combo bathtub/shower and private entrance to a cozy enclosed temperature-controlled sleeping porch off the Master suite with twin daybeds, perfect for sipping coffee or wine and enjoying the view, or alternatively can be utilized as twin beds! The 2nd guest room on the same wing has sleeping for 5 in the Queen bedroom, twin with trundle and pullout twin futon with private bath with shower in the hall. The Guest wing is a waterfront Queen bedroom with its own door out to the back patio and a shared full bath in the hall. The second guest room on the wing has a platform King bed with plenty of closet space. The beautifully-decorated spacious eat-in kitchen has been supplied with everything guests need for their stay. There is also a full laundry room/mudroom. The sweet 1-bedroom cottage next-door is perfect for the additional family members needing some of their own space. The home has plenty of parking and space to explore with the pups and little family members. Enjoy the many restaurants, historical attractions, and shops just a short drive from downtown Annapolis, or spoil yourself with the million dollar views from the screened-in patio! **COVID - 19 Extra Special Precautions: Our guests’ and staff’s health is our top priority. Our cleaners are taking every precaution when cleaning this home and making sure they meet CDC standards. We are going above and beyond to ensure all surfaces and touch points are being cleaned thoroughly and disinfected (including all light switches, faucets, doorknobs, cabinet handles, remotes, etc.). Main House SLEEPING ARRANGEMENTS: 4 BR / 3 BA / Sleeps 8 adults and 4-8 kids/teens: Family Wing: Grand Master Suite: -King bed -Private temperature-controlled sleeping porch with 2 Twin beds -Private bathroom with combo bathtub/stand-up shower -Flatscreen TV Guest Bedroom across the hall from Master Suite: -Queen bed -Twin with Twin Trundle -Twin futon -Full Hall Bath with stand-up shower Guest Wing: Queen Waterfront Guest Bedroom: -Queen bed -Private entrance to waterfront porch -Full hall bath with stand-up shower King Bedroom: -King Bed -Full hall bath with stand-up shower Cottage - SLEEPING ARRANGEMENTS 1 BR / 1 BA / Sleeps 2 adults: Bedroom -Queen bed -Flatscreen TV -Full hall bath with stand-up shower -Full kitchen Eat-in kitchen seats 4 HIGHLIGHTS: -Private waterfront pier -Massive waterfront covered screened-in patio with a dining table and plenty of seating -BBQ Gas grill (propane tank provided) -Extra large gathering space with living, dining and family room areas -Gourmet kitchen -Water access from private pier on the Magothy River -Covered temperature-controlled sleeping porch -Game room with pool table, bar stools and TV. -Firepit with seating for 6 -Dining room table seats 12 -Eat-in kitchen seats 6 -High Speed Internet and WiFi -Big Flatscreen TV’s -Luxury linens, complimentary toiletries Starter Kit, and boutique-level service -Parking for multiple cars in driveway -Full Laundry room with Washer & dryer located inside the home -Non-Smoking -Dogs allowed if $150 pet fee per pet is paid prior to check-in. Property Distance to: -Downtown Annapolis – 11 miles -U.S. Naval Academy – 11 miles -Washington, DC – 35 miles -Baltimore - 19 miles *************** * Welcome Gift Basket * Amenity & Supplies pack, a starter set of soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid to get you going * All beds are made for you with freshly-laundered sheets & towels. House Rules Reservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking. Dogs allowed if $150 pet fee is paid prior to check-in. Be respectful of the house and contents - it is someone’s home and the owners do come back from time to time to stay in their property. Please respect the neighbors and neighborhood. License: STR00484

Discover the charms of Queenstown, Maryland, with a stay at this lovely 4-bedroom, 2.5-bath vacation rental! Packed with family-friendly amenities, this home has everything needed for a peaceful getaway with loved ones — including a spacious deck, a fully equipped kitchen, and a cozy living room with a fireplace. Spend your day strolling through Terrapin Nature Park, then return home for a cookout on the grill or a family game night around the dining table. -- THE PROPERTY -- 2,336 Sq Ft | Furnished Deck | Spacious Yard | Fire Pit Bedroom Suite: King Bed | Bedroom 2: King Bed | Bedroom 3: King Bed | Bedroom 4: Full Bed | Additional Sleeping: Pack 'n Play HOME HIGHLIGHTS: Smart TVs, electric fireplace, home gym, large dining table, board games, gas grill KITCHEN: Fridge, stove, dishwasher, Keurig/drip coffee maker, microwave, cooking basics, toaster, dishware/flatware, trash bags/paper towels, high chair GENERAL: Free WiFi, keyless entry, central heating & A/C, complimentary toiletries, linens/towels, washer/dryer, ceiling fans, hair dryer, iron/board FAQ: 2 external security cameras (facing out) ACCESSIBILITY: Multi-level home, 3 steps to enter, interior stairs required to access bedrooms PARKING: Garage (2 vehicles), driveway (8 vehicles), EV charger -- THE LOCATION -- OUTDOOR ADVENTURE: Queenstown Harbor Golf (6 miles), Ewing Pond Park (6 miles), Kent Narrows Public Boat Ramp (10 miles), Ferry Point Park (11 miles), Terrapin Nature Park (14 miles), Sandy Point State Park (20 miles) AREA ATTRACTIONS: Old Wye Mill (3 miles), Watermen's Monument (9 miles), Chesapeake Bay Environmental Center (9 miles), Stevensville Historic District (14 miles), Chesapeake Bay Maritime Museum (25 miles), Six Flags America (44 miles) WASHINGTON, D.C. (55 miles): Arlington National Cemetery, Ford’s Theater, National Gallery of Art, Smithsonian National Air and Space Museum, Smithsonian National Museum of Natural History, United States Holocaust Memorial Museum, National Museum of African American History and Culture, Washington Monument, United States Capitol, World War II Memorial, Lincoln Memorial, Vietnam Veterans Memorial, Korean War Veterans Memorial AIRPORT: Baltimore/Washington International Thurgood Marshall Airport (48 miles) -- REST EASY WITH US -- Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: This multi-level home requires 3 steps to enter and interior stairs are required to access all the bedrooms - NOTE: Your safety matters. This property features 2 external security cameras: 1 camera located on the front porch facing the front entry and 1 camera located on the garage facing the entrance. The cameras are outward facing and do not look into interior spaces. The cameras record video and sound when activated by motion

Plan your trip to the Baltimore suburbs when you book this whimsical getaway in Pasadena! Situated 20 miles from the heart of downtown and providing easy access to the peaceful waterfront, this 3-bedroom, 2-bathroom house is the ideal spot no matter what your itinerary entails! Stay home to revel in the vacation rental's modern interior and don't forget to step outside to enjoy the screened porch, soak in the private hot tub, or sit beside the koi pond. Relaxation is sure to come easy here! -- THE PROPERTY -- Anne Arundel County STR Reg STR-00502 | Private Hot Tub | Pet Friendly w/ Fee | Koi Pond w/ Waterfall Bedroom 1: Queen Bed | Bedroom 2: European King Bed (63"x79") | Bedroom 3: Full Bed | Living Room: Full Sleeper Sofa | Additional Sleeping: Twin Rollaway Bed, Pack ‘n Play OUTDOOR LIVING: Screened-in porch w/ dining table & seating, fenced yard, fire pit, gas grill, water access INDOOR LIVING: Smart TVs, board games, foosball table, ceiling fans, laptop-friendly workplace KITCHEN: Dishwasher, coffee maker, Crockpot, microwave, toaster, cooking basics, spices GENERAL: Free WiFi (1 GB), central air conditioning/heating, washer & dryer, complimentary toiletries, linens & towels, hair dryer, Bumbo seat FAQ: Pet fee (paid pre-trip), stairs required for access, 1 Ring doorbell camera & 1 external security camera (facing out), quiet hours (10:00 PM-7:00 AM) PARKING: Driveway (6 vehicles), street parking (first-come, first-served) -- THE LOCATION -- BALTIMORE HOT SPOTS: Fort McHenry (14.2 miles), Fells Point (16.5 miles), Inner Harbor (19.1 miles), National Aquarium (19.5 miles), Baltimore Museum of Art (22.7 miles) OTHER DAY TRIPS: Annapolis (14.6 miles), Washington D.C. (41.1 miles) GET OUTSIDE: Fairview Marina (4.3 miles), Pleasure Cove Marina (4.8 miles), Fort Smallwood Park & Beach (5.0 miles), Downs Park Dog Beach (7.5 miles) EAT & DRINK: Fifer’s Seafood (1.0 miles), Hysteria Tap House (1.3 miles), The Rumor Reel (4.4 miles), Garry’s Grill (5.9 miles), Broken Oar Bar & Grill (6.5 miles) AIRPORT: Baltimore/Washington International Thurgood Marshall Airport (14.4 miles) -- REST EASY WITH US -- Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - Pet friendly w/ $50 fee (+ fees & taxes) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: The property requires stairs to access - NOTE: Please observe quiet hours from 10:00 PM to 7:00 AM - NOTE: This property sleeps 8 guests in 4 beds, with room for 9 total by using the twin rollaway bed - NOTE: Your safety matters. This property features 2 exterior security cameras. Camera 1 is a Ring doorbell device with an exterior security camera facing the front outdoor entry and camera 2 is on the left side of the house facing out. The cameras do not look into interior spaces. The cameras record video and sound when motion is detected by the device (including devices linked to the camera such as the alarm system’s motion detector) or when the video doorbell button is pressed Licence number: STR00502;STR00502

Lovely and serene-the perfect spot to nurture your soul! This 5,000 square foot, 5-bedroom, 5-bathroom waterfront was designed with your comfort in mind, the open floor plan features a modern interior and incorporates a separate dining room, flow-through living area and a generous bonus suite. The appliances enhance this gorgeous recently remodeled kitchen, equipped with quartz countertops and sprawling island. Drift off to sleep each night in the opulent main suite that comes complete with an ensuite bathroom, private balcony, and water views. The wonderfully secluded backyard boasts a patio dining space and a 18’x39’ built-in swimming pool with tanning ledge. You will love this waterfront vacation home! Well placed in a sought-after Talbot County neighborhood. This unique home will book fast! Talbot County STR License STRN-22-36 PROPERTY FEATURES: Waterfront: Leeds Creek Dock: Private dock with bench and beautiful views. Guests are not permitted to tie a boat to the dock. Water Toys: 2 kayaks are available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency. Pool: Brand new 18’x39’ built-in swimming pool with tanning ledge. Guests swim in pool at their own risk. Pickleball Court: Pickleball court for guest use. Grill: Propane grill. Propane is provided. Pet Friendly: This is a pet friendly rental. WiFi: Available for guest use. BED SIZES: King - 1 / King - 1 / Queen - 1 / Queen - 2 / Bunk Bed - Single over Single - 1 / Sleep Sofa - Queen - 1 /

Escape to 'The North Bay Cottage,' a charming 3-bed, 2-bath retreat in Charlestown's Waterfront Historical District! Just a 4-minute walk to coastal bliss, it offers easy access to Charlestown Public Beach & Ramp—perfect for sun-seekers and boaters. Explore Susquehanna State Park or the Chesapeake Bay Maritime Museum, then unwind at your home away from home, featuring a fully equipped kitchen, cozy living spaces, and a tranquil backyard. Make lasting memories at this coastal getaway! -- THE PROPERTY -- Newly Updated | Electric Fireplace | Free WiFi | 1,400 Sq Ft | Walk to Charlestown Beach Bedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: 2 Full Beds HOME FEATURES: Smart TVs, dining table, ceiling fans, covered front porch, outdoor seating KITCHEN: Refrigerator, stove/oven, drip & Keurig coffee maker, microwave, dishwasher, dishware & flatware, spices, Tupperware, baking sheets, cookware, blender GENERAL: Washer & dryer, towels, linens, complimentary toiletries, central heating & air conditioning, keyless entry FAQ: 1 exterior security camera (facing entryway) ACCESSIBILITY: 2-story home, exterior staircase to enter PARKING: Driveway (4 vehicles), trailer parking -- THE LOCATION -- ATTRACTIONS: Great Wolf Lodge Water Park (6 miles), Lock House Museum (8 miles), The Havre de Grace Maritime Museum (9 miles), Plumpton Park Zoo (12 miles), Turkey Point Lighthouse (15 miles) OUTDOOR RECREATION: Charlestown Public Boat Ramp (0.1 miles), North East River (0.7 miles), North East Community Park (4 miles), Kayak Ramp (8 miles), Perryville Boat Ramp (8 miles), Millard Tydings Memorial Park (9 miles), Marina Park (10 miles), Elk River Boat Launch (11 miles), Susquehanna State Park (14 miles), Iron Hill Park (14 miles), Bohemia River State Park (20 miles) LOCAL BITES: The Wellwood Restaurant (490 ft), Market Street Cafe (0.2 miles), Pier 1 Restaurant (3 miles), Bella Pizza (3 miles), Woody's Tacos & Tequila (3 miles), Nauti Goose Restaurant (4 miles), Steak & Main (4 miles) AIRPORTS: Philadelphia International Airport (52 miles), Baltimore/Washington International Thurgood Marshall Airport (54 miles), Ronald Reagan Washington National Airport (87 miles) -- REST EASY WITH US -- Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Early check-in and late check-out may be available upon request; please reach out to the Guest Contact to coordinate - Any check-in before 4:00 PM or late check-out after 11:00 AM is subject to an additional fee - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: This 2-story home requires an exterior staircase to enter. Interior stairs are required to access all the bedrooms on the 2nd floor - NOTE: Your safety matters. This property features a Ring doorbell device with an exterior security camera facing the front outdoor entry. The camera does not look into any interior spaces. The camera actively records video when motion is detected by the device

Experience the Difference: Professionally Managed by iTrip Annapolis Spacious custom home - Perfect for Naval Academy families and long visits to Annapolis Enjoy your stay in this expansive custom-built Severna Park home! Spacious enough to comfortably sleep 12, in the 6 bedrooms and 5 bathrooms, including a luxurious King Suite with a private deck, spacious spa bath and walk-in closet. The fully finished lower level is a retreat of its own, complete with a sports bar, entertainment space with games, multiple flat-screen TVs and bedroom and full bath. Outdoors, relax on the expansive deck and backyard or enjoy quiet mornings on the front porch by the gas fire table. Located on a peaceful cul-de-sac with plenty of parking for multiple cars. Sleeping Arrangements - sleeps 14: King Suite (2nd Floor): King bed, private bathroom, sun porch, walk-in closet (available only for guests who book 7 nights or more), with a Twin plus Twin trundle bed Junior Suite (2nd Floor): Queen bed, En Suite Bath Guest Bedroom 3 (3rd Floor): Queen bed, shared full bath Guest Bedroom 4 (2nd Floor): 2 Twin beds, shared full bath Main Floor Guest Room: Queen bed, Full bath in the hall Lower Level Guest Room: Queen bed, Full bath in the hall Entertainment & Dining Main Floor Family Room: Oversized sectional, big screen TV, gas fireplace Basement Entertainment Space: Wet bar with seating for 12-14, large TV, pool table, Arcade game, Dartboard, Table Shuffleboard, backyard access Dining: Kitchen bar seating for 5, dining table for 8 Highlights 2 Outdoor porches, BBQ gas grill, gas fire table, seating for 12 Spacious kitchen High-speed Wi-Fi, luxury linens, complimentary toiletries Parking for multiple cars on the driveway cars laundry room Convenient location to Annapolis, DC and Baltimore: -U.S. Naval Academy - 11 miles -Washington, DC- 39 miles -Baltimore - 23 miles House Rules Must be 25+ to reserve; adult must be present No smoking, no pets, no events/parties (strictly enforced) Check-in: 4:00 pm | Check-out: 11:00 am All ready with fresh linens, starter toiletries, and a welcome pack to make your stay comfortable from the start! License: 000988

Master Shipwright offers you downtown convenience, history, and charm as well as, a true Annapolis waterfront experience on Spa Creek. Four painstakingly renovated floors bring this home into this century without losing the shipbuilding history that surrounds it. The photos truly do not describe this incredible home. Walk into the front door into the street-side formal living room on the main level - comfortable and cozy. Pass through the formal dining room to a magnificent loft-type sitting room that opens to the lower-level sitting room. Floor-to-ceiling, two stories of windows bringing the glimmering Spa Creek inside! Wander down the waterside staircase (there are two, one at the main entrance and this one) into yet another comfy lounge space. The lower level sitting room sits beneath the main level sitting room and shares the splendor of two-storied windows. Proceed into the family room and enjoy the big comfy seating looking out to the patio. There is also a beautiful big dining table here. The kitchen is a large space off of the family room with an island and casual dining table embraced by a fireplace. Unique tile work, lots of counter space, and quality appliances provide you with everything you need and beyond to create and enjoy a family dinner. It features a gas stovetop, oven, microwave, large double-door refrigerator with drawer freezer and drink station, Keurig coffee maker, dishwasher, toaster oven, and all of the pots, pans, and dishware you need for memorable family gatherings. There are three unique dining areas in this home! The cozy, warm kitchen dining area is perfect for casual dining and offers to seat everyone. The formal dining room on the main level offers beautiful views with pre or post-dinner cocktails on the adjoining balcony. The lower-level family room also boasts a long fabulous dining table for a casual meal and game night. Walk out your doors to the patio, lawn, and water’s edge which has a dock for your boat and water toys. From the top down, the main-level balcony features two cushioned chaises and a gorgeous fire table surrounded by more Adirondacks. The lower-level walkout opens to a stone patio with chairs, a lawn, and two deep water docks for your boat and water toys. Additionally, a propane grill is available for warm-weather barbecues. THINGS TO KNOW

On the quiet Lake Ogleton off of the Chesapeake, this waterfront home with a gorgeous new pool, hot tub, and private pier will be a place for you and yours to relax and make memories. This beautiful Frank Lloyd Wright-inspired contemporary home with plenty of waterfront amenities boasts renovated interior and exterior spaces. The kitchen space has been designed to gather friends and family with top-of-the-line amenities for preparing and enjoying a gourmet meal. Two dishwashers and double refrigerators are an entertainer’s dream. Use the dumbwaiter to easily send everything up to the third floor for dining with a view. The kitchen features a large island with seating and a dining table. Dine outside under the shade of large umbrellas. The third-floor rooftop has incredible views. The third-floor loft has an additional sitting area with a TV, a wine cooler, and a refrigerator. A warm, formal living room has a massive fireplace with reclining couches, water views, and a TV. An adjacent sitting room has a gas fireplace and seating with water views. The large covered front porch has big, comfy furnishings to snuggle into and take in the sunrises over the water. Each of the bedrooms has been uniquely outfitted with your comfort in mind. The primary bedroom features a gas fireplace and water views, while one guest bedroom boasts bay views and an en suite bathroom. Things to Know Check-in time: 4:00 p.m. Check-out time: 10:00 a.m. The pool is open from May 20 until Labor Day. All guests shall abide by the good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m. No smoking is permitted anywhere on the premises.

Experience the Difference: Professionally Managed by iTrip Annapolis Arrive by car or boat to this waterfront home, located in Crownsville, just outside of Annapolis. The private pier is open to guests and offers many water sporting opportunities during your stay! Nestled in the desirable quiet Arden on the Severn community. There are kids’ and adult kayaks, canoes, stand-up paddle boards, fishing poles and crab traps. There are plenty of life jackets in the meticulous boat house. Sit on the back deck with unobstructed water views of the Severn River through the new glass railing. The deck has plenty of seating, a dining table and a gas grill. Head inside the home to the living space on the main floor that stretches across the kitchen, family and dining rooms - all with MILLION DOLLAR WATER VIEWS. The Main Floor Master Bedroom has a King bed (split with individual controls), master bath with multiple shower heads, a bidet and a walk-in closet. There are two more guest rooms on the main floor with Queen beds that share a full bath in the hall. The lower level is perfect for families with a large guest room with Queen Bed, a full bath and bunks for 4 kids or teens. Additional outdoor living space includes a large back yard, downstairs covered patio and a built-in firepit. The home is wonderful for families and friends coming in for that special Naval Academy or boat show event, or looking to take in the sights and sounds of Greater Annapolis. SLEEPING ARRANGEMENTS 4 BR / 3 BA / Sleeps 8 adults and 4 kids/teens in bunks: Main Floor Suite: -King bed (Split with individual controls) -Private Bathroom with Shower, bidet and vanity -Large walk-in closet Bedroom 1 on Main Floor: -Queen bed -Full Hall Bath Bedroom 2 on Main Floor: -Queen bed -Full Hall Bath Bedroom on lower level: -Queen Bed -Full Hall Bath Bunk Room on lower level -2 Bunks (4 Twin beds) -Full Hall Bath HIGHLIGHTS: -Wrap-around deck with glass railing and water views a dining table and plenty of seating -Water access from private pier on the Severn River -BBQ Gas grill (propane tank provided) -Spacious kitchen with stainless steel appliances -Covered Patio on lower level -Firepit -Adult and kid kayaks (Life jackets provided) -Lower level recreation room with foosball and indoor/outdoor ping pong table and TV -Dining room table seats 10-12 -High Speed Internet and WiFi -Smart Flatscreen TV’s -Luxury linens, complimentary toiletries Starter Kit, and boutique-level service -Parking for multiple cars in driveway -Full Laundry room with washer & dryer located inside the home -Dogs allowed with $150 non-refundable fee paid prior to checkin Property Distance to: -Downtown Annapolis – 13 miles -U.S. Naval Academy – 13 miles -Washington, DC – 32 miles -Baltimore - 25 miles *Amenity & Supplies starter pack, coffees and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid. * All beds are made for you with freshly-laundered sheets & towels. House Rules Reservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking. Be respectful of the house and contents - it is someone’s home and the owners do come back from time to time to stay in their property. Please respect the neighbors and neighborhood. No parties, events or smoking of any kind. License: 000327

This short-term rental has an occupancy of 16 individuals with a max. of 12 guests being 18 years or older. Experience spectacular sweeping views of the Chesapeake Bay Bridge from this fully renovated, well-appointed 6-bedroom, 5.5-bath waterfront home, just minutes from downtown Annapolis! The main level is designed for entertaining, featuring a great room with an open kitchen concept, an oversized island with seating for six, and a cozy seating area. Enjoy meals with family and friends in the light-filled sunroom that comfortably accommodates twelve. Discover the secret Pirate’s Cave hiding next to the laundry room, a fun-filled game room with a big screen TV equipped with table tennis, darts, air hockey, and foosball—perfect for all-day entertainment with family and friends. The brand new 20x40 swimming pool offers a basketball hoop and a relaxing tanning ledge where you can watch the sun set behind the Bay Bridge. The pool area is adjacent to a covered gazebo deck, an ideal spot for enjoying a crab feast from one of the local restaurants or a glass of wine. The property also features a new private pier, providing an idyllic setting for crabbing, fishing, and bird watching. Spend tranquil mornings casting a line or catching crabs, and enjoying the serene beauty of local wildlife. The pier offers ample seating for relaxation and is the perfect vantage point for observing the stunning Chesapeake Bay sunsets over the bridge. Gather around with drinks on the rear deck outfitted with a gas fire pit and plenty of seating. Or seat around the fire pit in the backyard making smores and watching the night sky. Younger guests will be thrilled by the pirate-inspired treehouse and play area, featuring a climbing wall, pirate plank, swings, slide, hammock, and treehouse! PROPERTY FEATURES: Waterfront: Chesapeake Bay. Pool: 20 x 40 private pool with a basketball hoop. Swimming pools are open from May 22 - October 15. Be sure to bring your own pool towels. Dock: 150 ft x 6 ft private dock for fishing and crabbing. Game Room: Billiards, ping pong table, air hockey, foosball, and darts Outdoor activities: cornhole, basketball hoops and Tree house. Grill: Propane grill. Propane is provided. Fireplaces: Outdoor gas fireplace table. Pet Policy: Pets are not permitted. WiFi: 1000 mpbs, reliably fast (good for 8-10 people or up to 12 devices)

Nestled in the charming village of Grasonville, Windward Cove offers an idyllic retreat for those seeking a blend of luxury and serenity. This stunning four-bedroom, three-bathroom waterfront home comfortably sleeps up to eight, making it perfect for families or groups of friends. The spacious layout includes an inviting living room with a gas fireplace, perfect for cozy evenings by the fire. The kitchen is a chef’s dream, fully equipped with modern appliances including a refrigerator with an icemaker, a dishwasher, and a Keurig coffee maker, ensuring you have everything needed for a comfortable stay. The bedrooms are generously sized and thoughtfully designed. The primary suite is located on the main floor, featuring a luxurious king bed and an en-suite bathroom with a luxurious bathtub. Two additional queen bedrooms share a hall bathroom, offering both privacy and convenience. An upper-level bedroom provides a quiet retreat with its own en-suite bathroom. Outdoors, Windward Cove truly shines. The waterfront location on Little Greenwood Creek offers the perfect setting for fishing or simply enjoying the peaceful sounds of nature. A private dock with 1 tandem and 2 single kayaks allows for easy access to the water, while the backyard deck is ideal for barbecues and outdoor dining. The screened porch provides a perfect spot to unwind with a book or a glass of wine, while the grill is available for your cooking needs. The home also features a well-equipped lower-level recreation room with a pool table, ping pong table, and a sectional sofa, making it an excellent space for games and relaxation. The sunroom offers additional seating and a tranquil space to enjoy the views. Additional amenities include a home gym, high-speed Wi-Fi, and cable TV, ensuring you have all the comforts of home. Located just a short drive from Annapolis, you can explore historic sites and enjoy the vibrant city life. Kent Island beaches are perfect for a day of sunbathing and swimming, while the Chesapeake Bay offers opportunities for boating and fishing. The Cross Island Trail is a must-visit for outdoor enthusiasts, providing miles of scenic routes to hike or bike. Windward Cove is not just a place to stay; it’s a place to create lasting memories. Whether you’re looking to relax by the water, explore the local attractions, or enjoy some friendly competition in the game room, this home offers the perfect setting for your getaway. Book your stay at Windward Cove today and experience the best of Maryland’s Eastern Shore. PROPERTY FEATURES: Waterfront: Little Greenwood Creek Dock: 40ft dock with 2ft MLW. Water and electricity are available for guest use. Water Toys: 1 tandem kayak and 2 single kayaks are available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency. Fireplace: Gas fireplace is available for guest use. Gym: Home gym is available for guest use. Game Room: Pool table and ping pong table are available for guest use. Grill: Propane grill. Propane is provided. Pet Friendly: This is a pet friendly rental. WiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds. BED SIZES: Queen - 1 / Queen - 1 / King - 1 / Double - 2 /

Nestled on the serene waterfront of Leeds Landing, this expansive single-story retreat is the perfect haven for families and friends. Boasting a prime location, this home sits on a tranquil 2+ acre lot on Leeds Creek, offering stunning views and direct access to the Miles River. The deep water dock (MLW 4’) makes it easy to enjoy fishing, crabbing, or boating adventures. Inside, the spacious living area is designed with comfort in mind, featuring five cozy bedrooms and three full bathrooms, comfortably accommodating up to ten guests. The master suite offers a luxurious king bed, while additional bedrooms include a queen bed, a crib, two bunk beds, and a twin bed, ensuring everyone has a restful place to sleep. The sunroom and screened porch provide breathtaking views of the backyard pool and waterside fire pit, perfect for relaxing or enjoying evening meals. The fully equipped kitchen has everything you need to prepare a meal, and the dining area seats all guests comfortably. The outdoor dining area, complete with a gas grill and outdoor seating, is ideal for barbecues and al fresco dining. For those who enjoy water activities, a canoe is provided, and a private pool is available for a refreshing dip. Just a short distance away, explore the charming town of Easton, MD, where you can visit the Easton Historic District, enjoy dining at local favorites like The Easton Crabhouse, or take a stroll along the scenic Miles River. Whether you’re seeking adventure or relaxation, this waterfront retreat promises an unforgettable getaway. Book your stay today and experience the perfect blend of comfort, convenience, and natural beauty. Talbot County License ST-969-LEE PROPERTY FEATURES: Waterfront: Leeds Creek Dock: 100ft with 4ft MLW, water and electricity. Water Toys: 1 canoe is available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency. Pool: Swimming pools are open from May 15 - October 15. Be sure to bring your own pool towels. Firepit: Firewood is not provided. Grill: Propane grill. Propane is provided. Pet Friendly: Owner will consider pets, call reservations at 443.664.4039 to inquire. WiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds. BED SIZES: King - 1 / Crib - 1 / Queen - 1 / Queen - 1 / Queen - 1 / Bunk Bed - Single over Single - 2 / Single Bed - Twin Sized - 1 /

Experience the Difference: Professionally Managed by iTrip Annapolis Kent Island Chesapeake Bay Cottage with Private Pool & Sunset Views Welcome to your dreamy poolside getaway! This charming summer cottage offers a private pool and breathtaking views of the Chesapeake Bay. The oversized wrap-around deck is perfect for sipping morning coffee or enjoying stunning Bay sunsets. (Pool is open April through October.) Sleeps up to 11 Guests 3 Bedrooms • 3 Bathrooms • Ideal for up to 8 adults + 2-3 children Main Floor (Upstairs): King Suite Bedroom: King bed + En Suite Full Bath Twin Suite Bedroom: 2 Twin beds + En Suite Bath Open Family Room: Queen Sleeper Sofa + Full-size Daybed Lower Level: Private Guest Room: Queen Bed + Full Hall Bath Sleeping/Family Room: Full Bed + Twin Daybed Highlights: Private Backyard Pool (open April 23–October) Wrap-Around Deck with Chesapeake Bay Views Multiple Dining Areas: Indoor Dining Table (seats 8) Deck Dining Table (seats 6) Poolside Table (seats 6) Front Yard Table (seats 6) Weber Propane Grill High-Speed Internet & WiFi 3 Flatscreen TVs 3 Bicycles for guest use NASA-developed AquaSpace Water Filter Luxury Linens + Complimentary Toiletries Starter Kit Full Washer & Dryer Circular Driveway Parking for 4–5 Vehicles Note: Home uses window A/C units (no central air) Keyless Entry through garage door keypad Location: Downtown Annapolis – 19 miles (~25 mins) U.S. Naval Academy – 19 miles Washington, DC – 48 miles Baltimore – 43 miles House Rules: Minimum Age: One guest must be at least 25 years old No Smoking, No Pets, No Parties or Events Respect the home as if it were your own – this is a cherished private residence. Please be courteous to neighbors and observe quiet hours. Check-in: 4:00 PM Check-out: 11:00 AM Experience the Difference: Professionally Managed by iTrip Annapolis