Pet-friendly vacation rentals in Chesapeake Beach, MD

Days spent relaxing on the sandy shores, exploring the local shops and eateries along The Boardwalk, or visiting The Walters Art Museum await when you book this 3-bedroom, 2-bathroom North Beach vacation rental! Featuring a fully equipped kitchen, an inviting interior, and a furnished deck with Chesapeake Bay views, this home provides a comfortable place to unwind after a day’s adventures. Whether you’re seeking a peaceful escape or an exciting retreat, this abode has you covered! -- THE PROPERTY -- STR00866 | Pet Friendly w/ Fee | Chesapeake Bay Views | Near Restaurants & Beaches Bedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: 2 Twin Beds | Living Room: Full Sleeper Sofa OUTDOOR LIVING: Deck, outdoor seating & dining, yard INDOOR LIVING: Amazon Fire TVs w/ cable, dining table, breakfast bar, 2 walk-in showers, ceiling fans KITCHEN: Stainless steel appliances w/ dishwasher, cooking basics, dishware/flatware, pod coffee maker, microwave, toaster, ice maker, spices, knife set GENERAL: Free WiFi, central heating & air conditioning, complimentary toiletries, hair dryer, washer/dryer, laundry detergent, hangers, linens/towels, trash bags/paper towels FAQ: No fence before bay, 1 exterior security camera (facing out), pet fee (paid pre-trip) ACCESSIBILITY: Single-story home, 3 steps to enter PARKING: Driveway (3 vehicles) ADDT’L ACCOMMODATIONS: An additional property is available down the street with a separate nightly rate. If you would like to reserve both rentals, please inquire for more information prior to booking -- THE LOCATION -- ATTRACTIONS: The Boardwalk (3 miles), Jug Bay Wetlands Sanctuary (15 miles), Watkins Nature Center (23 miles), Watkins Regional Park (23 miles), National Building Museum (35 miles), The Walters Art Museum (54 miles) SUN & SAND: North Beach (1 mile), Chesapeake Beach (2 miles), Brownies Beach (3 miles), Bayfront Beach (4 miles), Randle Cliff Beach (4 miles), Masons Beach (11 miles), Deale Beach (13 miles) OUTDOOR ADVENTURES: North Beach Pier (1 mile), Never E-Nuff Charters LLC (2 miles), Chesapeake Beach Boat Rentals (2 miles), Chesapeake Beach Fishing (3 miles), Chesapeake Paddle Sports (11 miles), Queen Anne Canoe Launch (23 miles), Jacksons Landing at Patuxent River Park (25 miles) AIRPORTS: Ronald Reagan Washington National Airport (40 miles), 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 - Pet friendly w/ $150 fee (+ fees & taxes, 1 max) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: This single-story home requires 3 steps to enter - NOTE: This property may not be suitable for young children due to the unfenced bay area - NOTE: Your safety matters. This property features 1 exterior security camera located on the front of the home facing the driveway. The camera is outward facing and does not look into interior spaces. The camera records video and sound when activated by motion Licence number: STR00866

Highlighted by its coastal charm and scenic location, this well-appointed North Beach home is well-suited for small groups to enjoy a relaxing stay on Chesapeake Bay. This 2-bedroom, 2-bathroom vacation rental features Smart TVs, free WiFi, a screened porch with a convertible dining table and pool table, and a large fenced yard for your furry friend. After a sunny day spent relaxing at the beach or exploring town attractions, you can gather around the fire pit to unwind under the stars. -- THE PROPERTY -- Anne Arundel County STR Reg: STR-00460 | Pet Friendly w/ Fee | View of Chesapeake Bay | 2 Mi to North Beach Town Bedroom 1: Queen Bed | Bedroom 2: Queen Murphy Bed | Loft: King Bed INDOOR LIVING: Smart TVs, sunroom w/ sitting area, laptop-friendly work area, cable/satellite TV OUTDOOR LIVING: Screened porch w/ outdoor dining area & convertible pool table, solo stove fire pit, charcoal grill, 2 kayaks, fenced yard, patio, walk to Rose Haven Memorial Park KITCHEN: Cooking basics, dishware/flatware, dishwasher, stove/oven, microwave, coffee maker, coffee grinder, blender, toaster oven, spices GENERAL: Free WiFi, linens/towels, complimentary toiletries, washer/dryer, ceiling fans, window A/C units, hair dryer, laundry detergent, trash bags/paper towels FAQ: 3 steps required to access, 1 exterior security camera (outward facing), pet fee (paid pre-trip) PARKING: Driveway (4 vehicles) -- THE LOCATION -- BEACHES: North Beach Boardwalk/Beach (2.3 miles), Chesapeake Beach Veterans Memorial Park (2.9 miles), Brownie’s Beach (4.2 miles), Bayfront Beach (4.4 miles), Breezy Point Beach (9.2 miles) OUTDOOR RECREATION: Rose Have Memorial Park (190 ft), Herrington Harbor Yacht Club (0.3 miles), Tyler’s Tackle Shop & Crab House (2.9 miles), Reel Attitude Charters (3.3 miles), Katherine Charter Fishing (3.3 miles), Fishing Creek Chesapeake Beach Maryland (3.3 miles), Chesapeake Beach Fishing (3.4 miles), Chesapeake Adventures Sportfishing (21.5 miles) ATTRACTIONS: Chesapeake Beach Water Park (3.1 miles), Chesapeake Beach Railway Museum (3.4 miles), Jug Bay Wetlands Sanctuary (14.2 miles), Six Flags America (23.6 miles) NEARBY EATS: Traders Seafood Steak & Ale (3.0 miles), Abners Crab House (3.3 miles), Rod ‘N’ Reel Restaurant (3.4 miles), Boardwalk Cafe (3.4 miles) WASHINGTON D.C. (~36 miles): United States Capitol, The White House, Lincoln Memorial, National Mall, Smithsonian National Air and Space Museum, attractions, sightseeing, events, nightlife, restaurants AIRPORTS: Ronald Reagan Washington National Airport (36.4 miles), Baltimore/Washington International Thurgood Marshall Airport (45.0 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/ $75 fee (+ fees and 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 3 steps to access - NOTE: Your safety matters. This property features 1 exterior security camera. The camera is a Ring doorbell located on the front entry. The camera is outward facing and does not look into interior spaces. The camera records video and sound when activated by motion Licence number: STR00460

Step into this charming coastal cottage and let North Beach welcome you to a relaxing getaway! The 3-bedroom, 2-bathroom vacation rental has been newly renovated to ensure a seamless and stress-free stay. Venture into town and explore beachfront shops, fresh seafood dining, and beautiful architecture throughout. On perfectly sunny days, build sandcastles at nearby beaches or book a fishing charter for extra thrills! Return home and prepare a home-cooked meal before settling in for a movie night. -- THE PROPERTY -- Anne Arundel County STR Reg: STR00572 | Newly Renovated | Pet Friendly w/ Fee Bedroom 1: King Bed | Bedroom 2: Twin Bunk Bed | Bedroom 3: Queen Bed | Living Room: Full Futon COTTAGE LIVING: Smart TVs w/ Roku, dining table, furnished sunroom, en-suite bathroom, ceiling fans, furnished deck KITCHEN: Stainless steel appliances, stove/oven, microwave, dishwasher, refrigerator, dishware/flatware, Keurig coffee machine, toaster, knife block GENERAL: Free WiFi, washer/dryer, linens/towels, complimentary toiletries, central air conditioning, hair dryer FAQ: Stairs required, Ring doorbell (facing front entry), pet fee (paid pre-stay) PARKING: Driveway (4 vehicles), free street parking -- THE LOCATION -- SAND & SUN: North Beach Boardwalk/Beach (2.2 miles), Chesapeake Beach Veterans Memorial Park (2.9 miles), Brownie’s Beach (4.2 miles), Bayfront Beach (4.4 miles), Breezy Point Beach (9.2 miles) OUTDOOR FUN: Rose Haven Memorial Park (0.3 miles), Herrington Harbor Yacht Club (0.3 miles), Tyler’s Tackle Shop & Crab House (3.1 miles), Reel Attitude Charters (3.6 miles), Katherine Charter Fishing (3.6 miles), Fishing Creek Chesapeake Beach Maryland (3.6 miles), Chesapeake Beach Fishing (3.6 miles), Chesapeake Adventures Sportfishing (21.5 miles) LOCAL ATTRACTIONS: Chesapeake Beach Water Park (3.3 miles), Chesapeake Beach Railway Museum (3.6 miles), Jug Bay Wetlands Sanctuary (13.6 miles), Six Flags America (24.1 miles) WASHINGTON, D.C. (~35 miles): United States Capitol, The White House, Lincoln Memorial, National Mall, Smithsonian National Air and Space Museum, attractions, sightseeing, events, nightlife, restaurants AIRPORTS: Ronald Reagan Washington National Airport (37.2 miles), Baltimore/Washington International Thurgood Marshall Airport (43.0 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/ $150 fee (+ fees & taxes, max 1 pet) - 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 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 Licence number: STR00572

Experience the Difference: Professionally Managed by iTrip Annapolis Family Rental only! This brand new custom home was built with stunning views of the Chesapeake Bay and all the bells and whistles, including a large private pool (open late April-end of Oct), hot tub (available year round) and game room on a semi-private beach. The four-season screened-in porch naturally stays warm in the winter from the sun and cools from the bay breeze with the windows open. The home is a perfect retreat for one or more large families traveling together on a private resort-like getaway. Upon entering the home, you will be wowed by the fully-loaded great room, complete with a flatscreen TV, electric fireplace, designer furniture and views of the waterfront landscape. The gourmet kitchen has luxury appliances, a breakfast bar, a dining table for 8 and high-end stainless-steel appliances. Before heading upstairs, check out the private office, which doubles as another bedroom with a Queen sleeper sofa, located off the main entryway. The home has two ensuite bedrooms: one on the main floor, with its own sliding door to the rear deck, and the other on the 2nd floor, with its own private office and sitting room. There are two additional bedrooms on the 2nd floor which share a bathroom and a bunk room on the lower level. All the bedrooms have views of the backyard and the Bay. Also located on the lower level is a decked-out game room (Pop-a-shot basketball, shuffleboard, ping pong, foosball table, and a card table) and full bath. Head outside to the furnished patio, complete with a hot tub and custom pool. Then make your way down to the beach. There’s plenty of parking and a keyless front entry. Located in Tracy’s Landing, this home is wonderful for families and friends looking to hunker down in the luxurious resort-like atmosphere. You’ll leave this place feeling completely rejuvenated! Come see for yourself! *Inquire about multi-day discounts for 5+ days SLEEPING ARRANGEMENTS 5 BR / 4.5 BA / Sleeps: Main Floor Suite: -King Bed -Private Bathroom with Double Vanity, large soaking tub and shower -Flatscreen TV -Private waterfront patio Main Floor Office/Bedroom -Queen Sleeper Sofa -Half bath on main floor and shared full bath in the 2nd floor hall 2nd Floor Suite: -King Bed -Private En Suite Bathroom with tub/shower and double vanity -Private sitting room with lounge chair and desk -Flatscreen TV -Water views 2nd Floor King Bedroom: -King bed -Flatscreen TV -Water views -Shared full bath in the Hall 2nd Floor Twin Bedroom: -Two Twin beds -Water views -Shared full bath in the Hall Lower Level Bunk Room -2 sets of bunks (4 Twin beds) -Shared full bath in the Hall HIGHLIGHTS: -Private Heated Pool and hot tub (Pool Closed end of Oct-late April - hot tub available year round) -Furnished screened-in porch -Chaise pool-side lounge chairs -Firepit -Games: Pop-a-shot basketball, Foosball, Ping-pong, Shuffleboard, Card table -Kayaks (7) and life jackets (available May-Nov) -BBQ Gas grill (propane tank provided) -Spacious open kitchen Breakfast bar seating for 3 -Dining room table seats 6-8 -High Speed Internet and WiFi -Multiple flatscreen Internet-based TV’s throughout the home -Luxury linens, complimentary toiletries Starter Kit, and boutique-level service -Coffee pot + Keurig -Parking for multiple cars/SUVs in driveway -Washer & dryer located inside the home -Dogs allowed with $150 non-refundable fee per pet paid prior to checkin. -Keyless entry. Drive straight to your rental home and enter the front door with an electronic lock code. Property Distance to: -Annapolis – 23 miles -Washington, DC – 34 miles -Baltimore - 49 miles -Tysons, VA – 50 miles *Amenity & Supplies starter pack: coffee, sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid. * All beds are ready made for you with freshly-laundered sheets & towels. House Rules: No smoking or parties Must be 25+ to rent, with an adult present at all times For your security, we have one door camera facing the outside of the home and a noise decibel monitor that is compliant with the law. Check-in: 4:00 PM, Check-out: 11:00 AM License: STR00744

Big Amenities: Pool Hot Tub Amazing Views! Clearview is the answer to your getaway needs. With a swimming pool, hot tub, and views that go on and on, you can stake your claim to this spot and relax throughout your stay! Those who want to venture out can mingle with the Tilghman Island locals, watch the fresh catch come in straight from the Bay, or enjoy a sunset cruise from nearby Dockside Express. Gourmet dinners at one of the local restaurants or a day trip into St. Michaels will have the foodie leaving more than satisfied. Learn about watermen and the health of the Chesapeake by visiting nearby Phillips Wharf Environmental Center. Talbot County STR License STRN- 26-26 PROPERTY FEATURES: Waterfront: Chesapeake Bay Dock: 60ft with 2.5ft MLW and electricity. Water Toys: 1 single and 1 tandem kayak 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. Hot Tub: Seasonal and available for guest use from May through November. Fireplaces: Wood-burning. Firewood is not provided. Grill: This property has a propane grill. Propane is provided Pet Policy: 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.

Talbot County STR License #STN-22-20 This 3-bedroom, 2-bathroom Tilghman Island water view retreat offers a character-filled interior and contains a first-floor bedroom and a flow-through living/dining area offering plenty of natural light. Cooking and entertaining have never been easier thanks to this spacious kitchen that has been beautifully maintained and is outfitted with an electric oven and butcher block countertops. Preparing breakfast has never been more beautiful as you watch the sunrise over the stunning water views. Adding to the home’s appeal are well-maintained hardwood floors throughout. The over 1.3 acre fully fenced professionally landscaped outdoors offers a large deck for outdoor dining and features a breathtaking crepe myrtle, several persimmon trees, and dozens of fig bushes. A true outdoor paradise by day and perfect for stargazing at night. Just the rural oasis you are looking for. Conveniently set in a historic Tilghman neighborhood It’s a short walk to the Tilghman Island Country Store, Dogwood Harbor, The Waterman Museum, Two if by Sea, Wylders, Characters, and Marker 5 or just a 15 minute car ride to Saint Michaels and 25 minutes to Downtown Easton. See for yourself what this vacation rental has to offer. Book your stay today before you miss out!

Talbot County STR License STN-22-32 This impressive 5BR, 4.5BA waterfront home was fully renovated in 2020 and provides the perfect place to host your family get-togethers. The magnificent, panoramic views of Harris Creek and Tilghman Island are framed eloquently by an expansive great room with 12’ x 8’ glass bifold doors that open fully onto a large outdoor deck facing the water - effectively inviting the outdoors in! The great room seamlessly connects to the nearby chef-inspired kitchen, overflowing with counter space and a large butcher block island perfect for communal cooking - get those kids busy cutting potatoes! Between the house and the waterfront, there’s ample space for unwinding on the hammock, playing a pickup game of soccer, searching for crabs or fossils on the 300-foot shoreline or lounging around the pool - all of which is visible from the kitchen and great room - perfect for keeping an eye on the kids while cooking or entertaining. Rainy days? Hole up in the library to read a book, play some board games...or curl up on the couch to stream a movie on the projector screen. Or head into St Michaels - it’s only an 11-minute drive from some of the cutest restaurants, local mom & pop shops, boutiques, cafes, bars, wineries and farmers markets. Such a charming example of Talbot County’s overall charm. Enjoy Chesapeake Bay living at its finest! This unique vacation home won’t last long. Book your getaway today.

Talbot County STR License STN-22-27 This 4-bedroom, 1.5-bathroom waterfront getaway features a character-filled interior and features a separate dining room. A foodie’s dream, this well-equipped recently updated kitchen is space efficient. Retreat to the comfortably sized main bedroom that comes complete with spacious closets. Out back, you’ll find the ultimate rural retreat, equipped with a large outdoor deck, private pool and hot tub. The perfect location for outdoor fun. Your search for the finest vacation living is over. Nestled in a sought-after Talbot County neighborhood. Don’t miss out on relaxing at this fabulous home. Book your getaway today.

Pets Welcome w/ Fee | 5 Mi to St. Michaels | Go Kayaking Experience classic Eastern Shore living at this 4-bedroom, 2.5-bath Bozman home — ideal for families, friends, and anyone craving a peaceful escape. The vacation rental boasts a fishing dock, a hot tub to unwind in the evenings, and acres of lawn where kids and pets can roam. Enjoy the spacious custom kitchen, gathering spaces, and thoughtful touches like shelves stocked with games. Head to Tilghman Island for even more adventure! -- THE PROPERTY -- STN-24-6 SLEEPING ARRANGEMENTS - Bedroom 1: 1 queen bed - Bedroom 2: 1 king bed - Bedroom 3: 2 full beds - Bedroom 4: 1 twin daybed w/ 1 twin trundle - Additional Sleeping: 1 portable crib OUTDOOR LIVING - Hot tub, 20'x40' swimming pool (heated w/ fee) - Private yard (unfenced) - Creek access w/ fishing dock - Kayaks & paddleboard - Furnished deck w/ Solo Stove fire pit - Charcoal grill, bicycles - Covered front porch w/ seating INDOOR LIVING - Multiple Smart TVs w/ cable - Nintendo console - Wood-burning fireplace - 2 dining tables & breakfast bar - Board games, toys & books KITCHEN  - Stove/oven, refrigerator, dishwasher - Microwave, toaster, blender - Drip coffee maker & Nespresso Vertuo (bring your own coffee) - Ice maker, cooking basics, spices - Dishware/flatware - Trash bags & paper towels GENERAL  - Free WiFi - Washer & dryer (detergent provided) - Central A/C & heating, ceiling fans - Linens/towels, complimentary toiletries - Iron/board, hair dryer - Keyless entry FAQ - Pet fee (paid pre-trip) - Optional nightly pool heat fee (paid pre-trip, applied to entire stay) ACCESSIBILITY - 2-story home, 5 steps to enter - All bedrooms & full bathrooms on 2nd floor PARKING - Driveway (4 vehicles) - RV/trailer parking allowed on-site (240V outlet in garage; no hookups) - Tesla-compatible EV charger (24 Amp) -- THE LOCATION -- - 3-acre plot on Harris Creek: fishing, crabbing, canoeing, paddleboarding & kayaking - 5 miles to Chesapeake Bay Maritime Museum, waterfront dining & local shops - 14 miles to Dogwood Harbor - 15 miles to Phillips Wharf Environmental Center - 76 miles to Baltimore/Washington Int'l 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) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - This 2-story home requires 5 steps to enter; all bedrooms and full bathrooms are located on the 2nd floor - There is an optional pool heat fee of $50/night (+ fees & taxes, paid pre-trip, applied to entire stay) - Due to the clay-heavy soil and water retention in the area, mosquitoes can be more common after rain. You are encouraged to bring bug spray or citronella products for added comfort outdoors

Beautiful Private Retreat with Pool located on Covey Creek The Bird’s Nest on Covey Creek is a comfortable and well-appointed 5-bedroom, 3.5 bath high-end waterfront rental with lots of amenities. The expansive lawn offers broad water views of the Chesapeake Bay. Conveniently located within 15-minutes of all the conveniences of downtown Cambridge. If you care to venture out to shop or enjoy an occasional round of golf or a day at the spa, the Hyatt Regency is a short drive. The Bird’s Nest is a true family retreat. There are lots of water toys to enjoy poolside and several kayaks to venture out into the Creek. There are multiple living areas for family and friends to gather, a cozy billiards room with pool table, as well as quiet spaces to escape. You and your guests will enjoy hanging out on the waterfront or gathering around the pool. There is a large stone patio for outdoor dining and watching the sunset. The gourmet kitchen is well stocked and is the perfect place to prepare your daily creations. PROPERTY FEATURES: Waterfront: Covey Creek Dock: A private pier with 1-2ft MLW. 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: Swimming pools are open from May 15 - October 15. Be sure to bring your own pool towels. Fireplaces: 2 gas. 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: King - 1 / Single Bed - Twin Sized - 2 / King - 1 / Queen - 1 / Queen - 1 / Queen - 1 / Double Bed - 1 / Single Bed - Twin Sized - 2 /

Shorely, this is a true outdoor paradise! Originally a waterman’s cottage, Neavitt Cottage has been tastefully updated (super fast wifi!) while maintaining its original charm and character. Located along Balls Creek, which branches off the Choptank River, Neavitt Cottage’s location in the quaint village of Neavitt provides a peaceful and quiet country setting, yet is just minutes away from all that St. Michael’s has to offer. Enjoy crabbing, fishing, kayaking, boating, and sunset views off the new dock or have land based fun playing cornhole in the expansive backyard. The large screened in back porch is the perfect place to relax or enjoy your summer crab feast and has unobstructed views of the water. The sandy beach offers an easy kayak launch and kids will love to explore the shoreline. Bald eagles, herons, osprey, and all sorts of waterfowl make the creek their home and you can get up close and personal on a quiet kayak ride, 2 dual person kayaks are included for your use, so please bring your lifejackets! The house is also fully stocked with board games, puzzles, and books for those quiet summer days. This is the perfect spot to make lasting memories with your family and friends while enjoying the Eastern Shore lifestyle! Neavitt Cottage offers an open floor plan featuring 2 first floor bedrooms and open kitchen, dining, and living areas. Two additional bedrooms and a full bathroom are upstairs. Talbot County STR License ST-643-DER PROPERTY FEATURES: Waterfront: Balls Creek Dock: Private dock with 3.5’ MLW, fish cleaning table, multiple water and 120V electrical hookups. Guests may tie a boat to the dock. Water Toys: 2 dual kayaks are available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency. Outdoor Toys: Cornhole is available for guest use. Grill: Propane grill. Propane is provided. Fireplace: Wood fireplace is available for guest use. Wood is NOT provided. Pet Policy: Pets are not permitted. WiFi: Reliably fast (good for 6-8 people or up to 10 devices) BED SIZES: King - 1 / Queen - 1 / Queen - 1 / Single Bed - Twin Sized - 2 /

Looking for that “shore” lifestyle? This 3,800 square foot, 8-bedroom, 5-bathroom waterfront estate on Brooks Creek offers an unforgettable vacation experience. Imagine yourself watching beautiful sunsets with an abundance of wildlife while relaxing on the enormous front porch. Family gatherings have never been easier, with an oversized living room, huge dining room, spacious screened-in sunroom, a chef-inspired kitchen and detached guest house all situated on an expansive 16.5 acre yard. If you’re looking for that shore lifestyle, this is the place for you! Enjoy an oversized private dock perfect for fishing, crabbing, launching kayaks and paddleboards, sitting around the firepit and making memories that will last a lifetime. You will enjoy a prime location in a high-end section of Dorchester County. Just a 20-minute car ride to historic downtown Cambridge where you can experience local boutiques, restaurants, cafes, and bars. A rare vacation rental opportunity. Book your stay today! PROPERTY FEATURES: Waterfront: Brooks Creek Dock: Private dock. Water is available. Guests are permitted to tie a boat to the dock. Pool: Swimming pools are open from May 15 - October 15. Be sure to bring your own pool towels. Water Toys: 2 kayaks and 1 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. Games and Gear: Crabbing gear, video game table console with 400 “old School” video games and corn hole are available for guest use. Fireplace: Wood burning. Wood not provided. Firepit: Wood burning. Wood not provided. Grill: Propane grill. Propane is provided. Pet Friendly: This is a pet friendly rental. WiFi: This property is equipped with Starlink internet. BED SIZES: King - 1 / Queen - 1 / Queen - 1 / Double Bed - 1 / Double Bed - 1 / Queen - 1 / Queen - 1 / Queen - 1 /

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

Experience the Difference: Professionally Managed by iTrip Annapolis Relaxing Waterfront Retreat Near Annapolis – Pet Friendly & Packed with Perks! Escape to a tranquil waterfront retreat with stunning views of the Chesapeake Bay and Bridge! This spacious one-level home is nestled on a private street in a water-privileged community just outside Annapolis, perfect for families and couples seeking relaxation. Book your serene Chesapeake Bay escape today and make unforgettable memories! Highlights You’ll Love: Sunroom: Walls of windows for sunrise coffee & happy hour views Outdoor Living: Fenced yard, fire pit, wrap-around deck, charcoal grill Kayaks Included: Launch from a nearby small beach Community Perks: Crabbing pier, playground, basketball court, larger beach Sleeping Arrangements (Sleeps 8): Primary Suite: Queen bed, en suite bath, flat-screen TV King Room: Shared hall bath, flat-screen TV Twin Room: Twin daybed + trundle (2 twins), shared hall bath Living Room: Queen sleeper sofa Extras & Amenities: 2 adult kayaks + fillet Flat-screen TVs in living room & bedrooms High-speed internet & WiFi Dining table for 6–8 Full-size washer/dryer Small dogs (under 30 lbs) welcome ($150 pet fee per dog) Driveway parking for 2+ cars Pack-n-Play available (assemble at own risk) Accessibility ramp to deck Prime Location: Downtown Annapolis – 4 miles U.S. Naval Academy – 5 miles DC – 35 miles | Baltimore – 20 miles Starter pack: toiletries, coffee, paper goods, cleaning essentials Beds made with freshly-laundered linens & towels House Rules: At least one guest must be 25+ No smoking, parties, or events Quiet hours: 9pm–8am Check-in: 4:00 pm | Check-out: 11:00 am License: 144985

Experience the Difference: Professionally Managed by iTrip Annapolis Waterfront Oasis with Private Dock, Firepit & Kayaks Welcome to the Pearl of Oyster Harbor – a tranquil waterfront retreat on the Annapolis Neck Peninsula. This charming cottage offers the best of all worlds: stunning natural beauty, water activities, and modern comforts. Outdoor Features: Private dock for boating, kayaking (3 total kayaks: two adult and one youth), or paddleboarding (inflatable SUP included) Expansive lawn perfect for cornhole, yard games, or simply soaking up the view Firepit for cozy evenings with s’mores and stories Hammock for relaxing with a good book or simply enjoying nature Parking for 3-4 cars on the driveway Indoor Highlights: Bright, airy sunroom with harbor views for board games and family time Sleek, modern kitchen with large picture windows framing the waterfront Living room featuring a smart TV and gas fireplace for cozy evenings Small desk and WiFi printer for remote work convenience Neighborhood amenities: Swimming beach Exercise: Beach volley ball court, 1-mile exercise circuit course, 12’ climbing wall, 16’ rope climb, Fishing pier and boat ramp Playgrounds, nature preserve, picnic areas, beach gazebos Starter Amenity Pack: We’ve got you covered with essentials to make your stay stress-free, including: Coffee, sweeteners, dish soap, and paper towels Soap, shampoo, conditioner, and hand sanitizer Freshly-laundered sheets and towels for every guest Sleeping Arrangements (3 BR / 2 BA, Sleeps 8): Front Queen Bedroom: Queen bed, shared full bath in the hall Waterfront Bedroom: Full bed, shared full bath in the hall Bunk Bedroom: Twin bunk beds (two twins), shared hall bath Loft: Full bed above the living room House Rules: Family rentals only; one guest must be at least 25 years of age No smoking, parties, or events Quiet hours from 9:00 pm to 8:00 am Dogs allowed with $150 per pet non-refundable fee paid prior to checkin. Check-in: 4:00 pm | Check-out: 11:00 am Property Distance to: -Downtown Annapolis – 4 miles (10 mins) -U.S. Naval Academy – 4.5 miles (12 mins) -Washington, DC – 35 miles -Baltimore - 20 miles Create lasting memories at The Pearl (of Oyster Harbor), where waterfront tranquility meets thoughtful amenities and outdoor fun. Book your stay today for an unforgettable Chesapeake Bay escape! License: 000346

Cottage in Center of Historic St. Michaels This lovely in-town cottage is close to all the amenities and charms of historic St. Michaels. Enjoy outstanding restaurants and boutiques, ice cream parlors, coffee shops, art galleries and more, all within a few steps of this beautiful home! Try the local winery, distillery, and brewery for tastings of hand-crafted spirits (no driving required!). Head toward the Miles River waterfront for freshly caught and steamed crabs. If you want to venture farther, within just a couple of blocks you can easily rent bikes, kayaks, or paddleboards and let your adventurous side soar. Offering modern conveniences in a quintessential Eastern Shore village, Carpenter Alley Cottage is a fabulous place to stay! PROPERTY FEATURES: Pet Policy: This is a pet friendly rental. 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: Bunk Bed - Single over Single - 1 / Queen - 1 / Queen - 1 / Queen - 1 /

Adventures await at this 4-bedroom, 2-bathroom Lusby, MD, vacation rental! This waterfront home features a private dock, pool, and deck for a serene view of St. Leonard Creek. Take the paddleboards out on St. Leonard Creek or have fun at Calvert Cliffs State Park. While you’re there, relax on the sandy beach with the family. Come back to this home away from home and eat at the outdoor dining area. After dinner, gather around the Smart TV to watch your favorite movie. -- THE PROPERTY -- Washer/Dryer | Waterfront | Seasonal Pool (Unheated, Opens May 14th) | Deck Bedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: 3 Twin Beds | Bedroom 4: 2 Twin Bunk Beds INDOOR LIVING: 3 Smart TVs, sectional sofa OUTDOOR LIVING: Dining area, crab traps, stand-up paddle boards, kayak,-the outdoor pool is not heated KITCHEN: Dishwasher, fridge, stove/oven, microwave, coffee maker, dining table GENERAL: Free WiFi, central air conditioning, linens, towels, complimentary toiletries, hangers, ice maker, trash bags, paper towels FAQ: Seasonal outdoor pool (unheated), 2026 opening date: May 14, Stairs required, 1 exterior security camera (facing out), pet fee (paid pre-trip), linens/towels not provided for stays of 7 nights or more PARKING: Driveway (4 vehicles) The outdoor pool is not heated -- THE LOCATION -- THINGS TO SEE & DO: Annmarie Sculpture Garden & Arts Center (8 miles), Jefferson Patterson Park and Museum (14 miles) OUTDOOR FUN: St. Leonard Creek (on-site), Maryland Kayak Outfitters (2 miles), Woodland Branch (3 miles), Flag Ponds Nature Park (4 miles), Calvert Cliffs State Park (4 miles) NEARBY: St Leonard (6 miles), Port Republic (8 miles), Prince Frederick (13 miles), Washington (57 miles) AIRPORT: Ronald Reagan Washington National Airport (57 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/ $100 fee (+ fees & taxes, 2 dogs only) - 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 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 (including devices linked to the camera such as the alarm system’s motion detector) or when the video doorbell button is pressed - NOTE: While the bottom of the pool is discolored, the water is cleaned and serviced every week - NOTE: The outdoor pool is open seasonally and closes in the fall; for 2026, it is scheduled to open May 14, subject to maintenance personnel availability. - NOTE: Stays over 7 days do not include linens or towels. It is recommended you supply your own

Experience the Difference: Professionally Managed by iTrip Annapolis Watch the sunrise on the private beach at Oh Happy Bay. The quaint two-story, cottage has a private beach on historic Bembe Beach with direct access to safe, shallow water for swimming, paddle boarding, and boating (small boat mooring). Commissioning Week families will be spoiled by the direct line of sight for the Blue Angels air show. The home is ideal for a large extended family traveling together. Enter the home into the beautifully-renovated kitchen with all new appliances and an adjoining dining room with water views and seating for 6-8. The main floor has a guest room with a Queen bed and full bath with a stand-up shower in the hall. The family room is equipped with a Full-size sleeper sofa. Head outside to the private backyard, with a deck, screened-in gazebo, lounge chairs and a picnic table for outdoor dining, cocktails or morning coffee (sampler starter pack included in your stay). Head back inside and up the stairs to the large family suite with 2 bedrooms, a connecting full bath (with 2 entrances), a sitting room and access to the private 2nd floor balcony. The main bedroom has a King bed and sitting area large enough for a portable crib or air mattress. Across the hall is the guest room with the full bed. The shared bath has 2 vanities, a stand-up shower and soaking tub. Also in the hall is the full-size washer and dryer. The home has plenty of parking and space to explore with the pups and little family members. Located walking distance to Annapolis Sailing School and Capital SUP (Paddleboard lessons and rentals), the Eastport Water Taxi (with water access to downtown Annapolis). Annapolis Maritime Museum and Quiet Waters Park are just a short drive away. SLEEPING ARRANGEMENTS 3 BR / 2 BA / Sleeps 8 adults: Upstairs Waterfront Bedroom: -King bed -Sitting room -Waterfront balcony -Queen air mattress available in the closet -Shared bathroom with stand-up shower and soaking tub -Flatscreen TV Guest Bedroom across the hall from King Bedroom: -Full bed -Shared bathroom with stand-up shower and soaking tub Main Floor Bedroom: -Queen bed -Full hall bath in the hall with stand-up shower Family Room -Full Sleeper Sofa -Full hall bath with stand-up shower HIGHLIGHTS: -Private beach with access to Chesapeake Bay -Screened-in patio gazebo with dining table for 10 -Back deck with seating, picnic table and beachside seating -Charcoal BBQ grill -Gourmet kitchen -Dining room table seats 6-8 -High Speed Internet and WiFi -Big Flatscreen TV -Stand-Up paddle boards, life jackets, beach toys, small boat mooring (this is a mooring ball or permanent anchor system off the beach where small boats can be moored) - Available in the summer months only (May-October) -Luxury linens, complimentary toiletries Starter Kit, and boutique-level service -Outdoor shower -Parking for multiple cars in driveway and on street -Full Laundry room with washer & dryer located inside the home Property Distance to: -Downtown Annapolis – 4 miles -U.S. Naval Academy – 4.5 miles -Washington, DC – 34 miles -Baltimore - 35 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, the neighbors and neighborhood.

Escape to this charming house in Edgewater, MD, where a beach and play area are just a short walk away. With a water view within 100 yards of the community beach, this spacious and open living design offers a tranquil retreat. Recently furnished with all new furniture and beds, including a king bed on the main floor with an en suite bathroom with a walk-in shower, and two queen beds with a dedicated office space boasting water views, streaming available with the Roku equipped TV’s, this home is perfect for a relaxing getaway. Enjoy the convenience of a full bath with a tub upstairs, a half bath, and laundry off the kitchen. Ideal for remote work, the quiet and walkable neighborhood provides a peaceful setting. Two adjustable bicycles are available for easy riding in the neighborhood, and the partially fenced backyard includes a fence enclosure for small dogs. The 12 x 20 shed space, known as the ’Coastal Clubhouse,’ is a great spot for rainy day activities or small family gatherings, featuring an L-shape lounger and a table with seating for six. This dog-friendly property is equipped with modern amenities such as a washer/dryer, central AC, internet, and a fully stocked kitchen with appliances like a fridge, stove, oven, dishwasher, microwave, coffee maker, and more. Additionally, enjoy beach access, a kayak, paddle board w/vests, blankets, and other essentials provided for a comfortable stay. Conveniently located near Navy-Marine Corps Memorial Stadium, historic restaurants, downtown Annapolis, and other attractions, this home is the perfect base for exploring the area. Whether you’re looking to relax indoors or explore the outdoors, this Edgewater retreat offers the best of both worlds. From water activities like sailing and stand-up paddle boarding to nearby attractions like water parks, winery tours, and museums, there’s something for everyone to enjoy. Book your stay now and experience the beauty and convenience of this lovely vacation rental.

This is a gorgeous home with in ground *heated* "6 month" pool & "9 month" hot tub - less than a mile walk from USNA gate 1! *We offer complimentary access to our hot tub! Just let us know 60+ min before you’d like to use it.* **We charge a fee of $100 per night for pool heating. This is an additional fee, and we will send you a request once your booking is confirmed.** **Please note that we can heat either the pool or the hot tub, but not both at the same time.** ***Please be informed that the pool and hot tub are closed daily at 10:00 PM, in accordance with the City of Annapolis quiet hours regulations. Consequently, the hot tub and pool heater are not operational after 10:00 PM.*** This is an immaculate property with 3 stories plus a finished basement. It has a wonderful wood front porch and a *HUGE* backyard - perfect for pets or for entertaining close family and friends. It is also a short walk to USNA (~1 mile). It has the following must-have amenities/features: -In ground 6 month (Apr-Oct) 18’x25’ salt water pool (3.5-5 ft depth) - we shut the pool down in late October and re-open it in early April -Elevated in ground 9 month (Mar-Nov) 8’x8’ hot tub (~3 ft depth) - we shut the hot tub down at the end of November and re-open it in early March -4x chaise lounges + expansive sun umbrellas -Multiple king-sized beds -TVs in 3 of the 5 bedrooms -Indoor gas-powered grill -Nearby parking garage (~1 block away) Floor by floor configuration: 1st floor - foyer, living room (couch is a sleeper sofa), dining room, kitchen, powder bathroom 2nd floor - master bedroom / bathroom suite (king bed + smart TV), non-master bedroom (king bed), full non-master bathroom 3rd floor - master bedroom (queen bed + twin bed sized sleeper sofa + spacious desk + smart TV), non-master bedroom (queen bed), full non-master bathroom (shared / not ensuite), nook with daybed which flips into king-sized sleeper sofa. Basement - bonus room perfect for kids with trundle (2x connected twin beds + smart TV), powder bathroom Outside - front porch with furniture, back porch / large fenced in yard with furniture and an in ground pool/hot tub. Total of 5 bathrooms (2x powder baths / 3x full baths). Please note there is street parking available in front of the house but it is for vehicles with parking permits only except for limited transient parking. There is a paid parking garage that is about a block away. Guests have access to the entire house and backyard except for locked storage closets. There is a free public bus that leaves from the Knighton Garage which is 1 block away from this property. We recommend parking here since you might get a ticket if you park on the street during the day. You can park on the street for up to 2 hours per day from 8 am to midnight. You can park for free on the street from midnight to 8am. This means that if you park on the street at 10pm you can move you car as late as 10am the next day and avoid getting a ticket. 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: $100 -1–2 hours: $200 -2–3 hours: $300 -3+ hours: $400 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. Permit number: 002213-2025 County permit number: STR-00031 You must be 25 years or older to rent this property. City/town permit number: STR-146270. License number: 146270

A Tranquil Contemporary St. Michaels Waterfront Cottage featuring a separate 1st floor newly renovated garage apartment with its own kitchen. This 6BR, 4.5 BA vacation paradise is conveniently located between the charming towns of St Michaels and Easton, Bayside The Point is just a stone’s throw away from numerous shops, boutiques, and dining experiences to please the entire family. The house is nestled among trees at the far end of a private road and provides a truly safe, peaceful and tranquil haven. With only birdsong and the gentle rustling of trees in the cool southerly breeze, you can be assured of a completely restful and private vacation. Set on a point, the aptly named Solitude Creek wraps around this lovely house, affording you water views from every room. The master suite benefits from a private deck where you can begin your day with freshly brewed coffee and a soul-warming sunrise. A large south-facing deck with ample outside dining area will enable you to make the most of outside living on your well-earned break. Take a dip in the pool, catch crabs and fish off the dock, relax by the firepit or just enjoy a delicious BBQ. This house is well-appointed, with a clean and modern feel. Glass doors line the whole back of the house, providing beautiful, uninterrupted views down Solitude Creek. The resident Ospreys are normally just a few feet offshore; these magnificent birds coupled with the shimmering waters will provide you with hours of viewing pleasure. Talbot County STR License STN-23-37 PROPERTY FEATURES: Waterfront: Solitude Creek Dock: 750 feet of shoreline with 80 ft of private dock with 4.5 ft MLW Guest House: 1st floor newly renovated garage apartment with its own kitchen. Water Toys: 2 kayaks, 1 canoe, 2 paddle boards and crabbing gear is available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency. Pool: 600 sq ft private swimming pool. Swimming pools are open from May 15 - October 15. Be sure to bring your own pool towels. Grill: Propane grill. Propane is provided. Hot Tub: 6 person hot tub is available for guest use. Firepit: Wood provided. Pet Policy: This is a pet friendly property. 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 / Queen - 1 / Queen - 1 / Double Bed - 1 / Single Bed - Twin Sized - 2 / Single Bed - Twin Sized - 1

Love at First Sight Welcome to “Heron’s Roost,” an exceptional 3-bedroom, 2.5-bathroom haven nestled on 10 picturesque, wooded acres with 400 feet of waterfront on Grace Creek. This charming residence is designed for your comfort, featuring a thoughtfully laid-out floor plan that encompasses a charming living room, beautifully decorated bedrooms upstairs and down, and a seamless flow between the kitchen and dining areas. Step outside to discover a wonderfully secluded backyard oasis, complete with an outdoor dining area, gazebo, duck blind, grill, oversized outdoor chess/checkerboard, and a private 75 ft dock. Whether you’re enjoying a morning coffee amidst the calming water views or hosting a sunset get-together, this spacious estate offers the perfect backdrop for relaxation and exploration, surrounded by well-established trees that provide ample privacy and shade. Located in a quaint Talbot County neighborhood with shaded streets ideal for biking and walking, you’ll have kayaks and canoes ready for launch right from the sandy beach! Or bring your own small boat and use the boat ramp adjacent to the dock. Revel in the nearby charm of St. Michael’s, where you can explore mom-and-pop shops, specialty boutiques, farmers markets, wineries, local cafes, bars, and restaurants. Don’t miss your chance for ’love at first sight’—book your serene getaway today and experience the tranquility of waterfront living! Talbot County STR License STN 24-9 PROPERTY FEATURES: Waterfront: Grace Creek Dock: Private dock and 2’ MLW. Guests are permitted to tie a boat to the dock. Water Toys: 2 kayaks and 2 canoes are available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency. Crabbing Gear: Crabbing gear is available for guest use. Grill: Propane grill available for guest use. WiFi: High speed broadband internet is available through Breezeline internet. BED SIZES: Queen- 1 / Full - 1 / Full - 1 / Twin - 2

Located just a block away from the Chesapeake Bay and Bay Ridge community beaches and a few miles from Annapolis’ historic downtown area, this roomy home will be perfect for a memorable family vacation! There are warm and inviting social rooms for gathering, quiet nooks for some me-time, and sprawling outdoor spaces. The large deck overlooking the lawn into a wooded area offers a very private and serene setting. A sizeable outdoor table with seating and a gas grill is perfect for warm-weather barbecues and meals alfresco. The spacious living room is adjacent and open to the kitchen with big, comfy furnishings. The sitting area off of the kitchen has more comfortable furnishings and a big-screen TV. The inviting den has leather furnishings and a TV. The open and updated kitchen features a full Sub Zero refrigerator and a full Sub Zero freezer, a fantastic island for prepping, and all the amenities. A separate dining room has seating, the kitchen table provides additional seating, and the kitchen island has stools. There is a big game room on the lower level with a pool table, air hockey, and foosball table. Adjacent to that is a huge room with a beautiful big bar, stage, and an impressive home theater. Additional perks include free WiFi, Comcast Xfinity cable TV, and a Sonos music system throughout the home. THINGS TO KNOW

Experience the Difference: Professionally Managed by iTrip Annapolis Available for Commissioning Week 2025! Charming 1905 Eastport Duplex: Historic Character Meets Modern Comfort Step into a beautifully-preserved piece of history with this charming 1905 duplex in the heart of Eastport. Offering a seamless blend of old-world charm and modern amenities, this home is perfect for families, professionals, or anyone seeking a cozy, yet stylish getaway. Main Floor: The spacious open layout on the main floor includes a large living area, a dedicated office/desk space, and a convenient powder room. The inviting dining area opens to a gourmet kitchen, fully equipped with stainless steel appliances, perfect for cooking up a feast. The main floor also features a private, fenced backyard, ideal for relaxing or entertaining. Upstairs: Two generously-sized King bedrooms provide a restful retreat, complete with luxury linens and a shared full bath. One bedroom boasts a private balcony overlooking the serene backyard and the front King bedroom has its own flatscreen TV and desk space. A bonus loft space offers additional room for kids or younger families to relax and enjoy their own shows. Additional Features: Parking for up to 3 cars Private fenced backyard with a patio deck and and gas fire pit Covered front porch, perfect for enjoying the neighborhood Gas grill (propane included) High-speed WiFi and a big-screen TVs for entertainment Dedicated workspaces on each level for remote work or study Full washer & dryer for your convenience Dog-friendly Perfect Location: Situated just steps away from Eastport’s vibrant cafes, restaurants, and bars, this home offers easy access to everything the neighborhood has to offer. Water access for paddle boarding and kayaking (BYO) is just a short stroll away. Plus, you’re only: 1.5 miles from the U.S. Naval Academy 30 miles from Washington, D.C. 25 miles from Baltimore House Rules: No smoking, parties or events Dogs ok if $150/per pet fee paid prior to checkin Must be 25+ to book Check-in: 4:00 pm | Check-out: 11:00 am License: 001832