Vacation rentals in Deale, MD with free parking

2,350 Sq Ft | Walk to Marinas & Dining A maritime paradise awaits at this bright and inviting Deale vacation rental! Start the morning by taking in the still waterway from the living room or deck before casting lines off the boat dock. Don't forget to soak up the sun at North Beach Boardwalk as well! As evening falls, grill your prized catch and enjoy a family cookout or stroll to a restaurant of your choice. Book this premier Chesapeake Bay getaway today! -- THE PROPERTY -- STR01041 OUTDOOR LIVING  - 2 decks, 2 dining areas, lounge seating - Gas grill - Boat dock INDOOR LIVING  - Smart TV - 2 dining tables - Breakfast bar KITCHEN  - Stove/oven, refrigerator, dishwasher - Microwave, toaster - Drip coffee maker (bring your own coffee) - Cooking basics, dishware/flatware ACCESSIBILITY - Multi-level home, step-free entry - Bedroom on 1st floor PARKING - Driveway (4 vehicles) -- THE LOCATION -- - Seamless access to Chesapeake Bay - Shipwright Harbor Marina & Rockhold Creek Marina down street - 0.7 miles to Herrington Harbour North & 9 miles to Herrington Harbour South - 11 miles to North Beach Boardwalk - 19 miles to historic Downtown Annapolis - 30 miles to Washington, D.C. - 43 miles to Baltimore -- 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 SECURITY CAMERA INFORMATION - 3 exterior devices - Location: front of home, right side of home, back of home - Coverage: driveway, entrance, pier Licence number: STR01041

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

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

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

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

With calm bayside waters, plenty of fishing opportunities, and a variety of family-friendly attractions, Chesapeake Beach truly offers something for everyone, and there's no better launch point to explore it all than this 2-bedroom, 1-bath cottage. Aside from the property's convenient location (just a half mile to beaches), you'll love the thoughtfully curated outdoor amenities, including a private hot tub, a fire pit, a bar, and more. The perfect couple's getaway or family vacation awaits! -- THE PROPERTY -- Walk to Beaches | Private Outdoor Oasis | Beach Gear Provided Say goodbye to the generic hotel rooms and hello to this sunny Chesapeake Beach vacation rental, equipped with all the amenities and at-home comforts for a stress-free getaway on the coast. Bedroom 1: Queen Bed | Bedroom 2: Queen Bed | Living Room: Sleeper Sofa COTTAGE DETAILS: Smart TV, dining table, books, board games, tropical beach house decor OUTDOOR ENTERTAINMENT: Furnished deck w/ forest view, dining set w/ umbrella, heating lamp, patio w/ cushioned lounge set & hot tub, tropical bar, hammock, sanded backyard w/ gas fire pit, gas grill KITCHEN: Stainless steel appliances, cooking basics, spices, dishware & flatware, Keurig coffee maker w/ K-cups GENERAL: Free WiFi, washer/dryer, towels/linens, complimentary toiletries, hair dryer, central heating & air conditioning FAQ: Access only by stairs, exterior security cameras (4, facing out) PARKING: Driveway (8 vehicles) -- THE LOCATION -- BEACH DAYS: Bayfront Beach (0.5 miles), Brownies Beach (1.1 miles), North Beach (3.0 miles), Breezy Point Beach (4.6 miles) OUTDOOR ADVENTURES: Chesapeake Beach Veterans Memorial Park (2.0 miles), Wetlands Overlook Park (3.4 miles), American Chestnut Land Trust (10.4 miles), Battle Creek Cypress Swamp (16.4 miles), Flag Ponds Nature Park (22.4 miles) FAMILY OUTINGS: Chesapeake Beach Railway Museum (1.8 miles), Chesapeake Beach Waterpark (1.9 miles), Bayside History Museum (3.0 miles), North Beach Boardwalk (3.0 miles), Six Flags America (25.6 miles) AIRPORTS: Ronald Reagan Washington National Airport (38.4 miles), Baltimore/Washington International Thurgood Marshall Airport (47.7 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 4 exterior security cameras. Camera 1 faces the front door, camera 2 faces the back door, camera 3 faces the side yard, and camera 4 faces the patio area. The cameras are outward facing and do not look into interior spaces. The cameras may actively record video and/or sound while guests are in residence

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 Enjoy stunning western-facing views across the river and a natural tidal pond from this sprawling historic home that sits on 1.5+ acres. The light-filled farmhouse is located on Persimmon Point, which is positioned between Harness Creek and the South River. It is a peninsula rich in local lore that includes Native American oysters mounds, pirate hideouts, tobacco farming and world champion cows. Some history: Once the home was part of the original Wimbledon Farm. From the 1930’s, Wimbledon Farm grew abundant produce and tobacco. The last magnificent tobacco barn in Annapolis is on the property next to the house. Wimbledon was also famous for their dairy. Their dairy cows and bulls attracted breeders from around the world and famously started the “Carnation” milk herd. The dairy barn was immense and the milk came into the small milk house, which is now the charming "Milkhouse Suite". Here the milk was chilled and sent out to be bottled and delivered. Today: The house offers a special, very private family retreat just minutes to downtown Annapolis. The home was renovated to its current beauty by opening the entire back of the house to the water with windows and connecting the main house to the "milk house". All of the living space, and 4 of the 5 bedrooms, are on the main floor. The lofted upstairs bedroom is perfect for the younger crowd with 3 twin beds and room to enjoy each other’s company. The open floor plan, deck and terrace provide multiple living spaces inside and out. There are 2 full baths and room for 10 guests to sleep comfortably. Enjoy the outdoors on stone patio with fountain and dining tables, a pair of Adirondack chairs on the back deck under the shady wisteria pergola, and a BBQ grill. Inside, the dining table seats 8 with room for 3 more at the breakfast bar. Across the lush lawn, there is also a small pier on the pond for kayak launching or fishing fun for small anglers. Guests can also get away from the day by lounging on the creek side on the front porch swing. Local activities: Great Frogs Winery (less than ½ mile away down the street), Quiet Waters Park (hiking trails, ice skating, SUP rentals) and kayaking or biking. SLEEPING ARRANGEMENTS 5 BR / 2 BA / Sleeps 10 adults (2 children): Milk House Suite: -Main Floor -Queen Bed -Living room with Full sofa sleeper -Private en-suite bathroom large tile shower -Private entrance and water views Main Floor King: -King bed -Private entrance to front porch Main Floor Queen: -Queen bed Main Floor Twin -Built-in Twin Bed Upstairs Loft -3 Twin beds -Full Hall Bath with stand-up Shower and clawfoot Tub HIGHLIGHTS: -Outdoor waterfront furnished terrace and deck - access to decks or porch from main entries -Small fishing and boat launch pier on the pond -Kayaks -Mulitple living spaces: family room, living room and loft -BBQ Gas grill (propane tank provided) -Dining room table with seating for 8 -Breakfast bar with seating for 3 -Vermont casting gas stove -High Speed Internet and WiFi -Flatscreen TV’s -Luxury Westin Heavenly mattress in milk house, fine linens, complimentary toiletries Starter Kit, and boutique-level service -Parking for multiple cars in driveway -Full-size washers/dryers located on the main floor Property Distance to: -Downtown Annapolis – 4 miles -U.S. Naval Academy – 4 miles -Washington, DC – 33 miles -Baltimore - 33 miles -Great Frogs Winery - .4 miles -Quiet Waters Park - 4.2 miles by land - closer by sea! *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 house at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking/no pets. Be respectful of the house and contents - it is someone’s home and the owners live in the home when not renting it. Please respect the neighbors and neighborhood. No parties, events or smoking of any kind. License: STR00542

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

Find gorgeous gathering spaces inside and out at this light-filled three-story waterfront home on a protected inlet of the Chesapeake Bay. Here in Bay Ridge, you’ll have a private dock, access to the bay beaches, and a stunning setting for family vacations and special holidays. You’ll be within five miles of historic downtown Annapolis, home to charming shops, great eateries, and the U.S. Naval Academy. Spend sparkling summer days outdoors, where several beautiful spaces await you. Sip your first cup of morning coffee in an Adirondack chair on the deck, taking in a serene view of the bay below. Launch your kayak from the dock, watch your kids play in the gently sloped backyard, and gather for evening barbecues on the shaded patio beneath the deck. One of the guest bedrooms boasts direct patio access. As you step inside the front door, you’ll be greeted by a grand spiral staircase and a wall of windows framing the lake. One of Annapolis’ leading interior designers recently renovated the entire home. At the heart of the house is a two-story great room with generous seating, a smart TV, and doors that lead outside to the deck. To one side of the great room sits a formal dining room and a wet bar for entertaining. To the other is an expansive kitchen overlooking the lake with stainless steel appliances, including an in-island gas stove, a light-filled breakfast nook, and a full laundry room. Step into the hot tub and simmer as you relax your body. Other notable features can be found at every turn, including a private home office for remote work, a huge den downstairs with another smart TV and kitchen, a quiet room for yoga, and a fantastic game room with air hockey, foosball, and a game table. THINGS TO KNOW Streaming services are available with guests’ own account credentials. Smoking is prohibited on the property. The gas fireplace is not operational.

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

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.

The Chesapeake Bay awaits you at this Annapolis vacation rental! 'Admiral's Post' is situated under 4 miles from the city’s historic downtown. This 4-bedroom, 3.5-bath home is the perfect launch point for your next adventure. Connect with family and friends around the fire pit, fire up the gas grill for a cookout on the deck, and prepare your favorite meals in the kitchen. When you’re not enjoying the comforts of your home away from home, scope out the US Naval Academy, or historic Annapolis! -- THE PROPERTY -- Annapolis STR License STR22-145145 | Indoor Fireplace | Stainless Steel Appliances | Workspace Bedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen Bed | Bedroom 4: Twin Sleeper Sofa INDOOR LIVING: 2 smart TVs, 2 window A/C units, 6-person dining table, walk-in closet KITCHEN: Stove/oven, microwave, refrigerator, blender, coffee grinder, coffee maker, toaster, cooking basics, dishware/flatware, dishwasher, garbage disposal, ice maker, water filter, spices GENERAL: Free WiFi, central air conditioning, washer/dryer, linens/towels, complimentary toiletries, hair dryer, iron/board, trash bags/paper towels ACCESSIBILITY: 3-story home, stairs required to access, 2 bedrooms on basement level FAQ: 2 exterior security cameras (facing out) PARKING: Garage (1 vehicle), driveway (1 vehicle), free street parking (first-come, first-served) -- THE LOCATION -- NEARBY (< 1.0 miles): Starbucks, Dunkin', CVS, 7-Eleven, Giant Food, PNC Bank, Rocco's Pizza, Jack's Fortune Chinese Restaurant US NAVAL ACADEMY: US Naval Academy Museum (3.8 miles), Alumni Hall (4.0 miles), Navy-Marine Corps Memorial Stadium (4.1 miles), Memorial Hall (4.5 miles) HISTORIC DOWNTOWN: Annapolis Maritime Museum & Park (3.1 miles), Annapolis City Dock (3.4 miles), Maryland State House (3.6 miles), William Paca House & Garden (3.7 miles) OPT OUTSIDE: Quiet Waters Park (2.1 miles), Annapolis City Marina (2.8 miles), Sandy Point State Park (12.6 miles), Herrington Harbour South (26.8 miles) SHOPPING: Annapolis Town Center (4.9 miles), Westfield Annapolis Mall (5.7 miles), Arundel Mills (23.4 miles) AIRPORT: Baltimore/Washington International Thurgood Marshall Airport (25.6 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: Three steps are required to access the front door, and eight steps are required to access the backyard from the back deck. There are two bedrooms on the top floor and two bedrooms on the basement level. All bedrooms require stairs to access - NOTE: Street parking is available across the street from the property. Cars cannot be parked in front of the home due to the community mailbox - NOTE: Your safety matters. This property features 2 exterior security cameras: 1 camera is located on the front entrance facing the driveway, and 1 camera is on the back of the house facing the garden. They are outward facing and do not look into interior spaces. The cameras record video and sound when activated by motion Licence number: STR22-145145;RENT-002919-2024

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.

Featuring the most sought-after Chesapeake Bay view, this luxurious newly built waterfront Annapolis retreat is ready for you and your family and friends! The porch and balcony are where you will spend most of your time on the rocking chairs or comfy outdoor couch taking in the Chesapeake Bay. The back patio and gardens offer alfresco dining with a gas grill and a beautiful teak umbrella table with seating for six. The warm living area looks out to the Bay with a large comfy couch, swivel chairs, and a gas fireplace. Spend relaxing evenings on the amazing stone porch with Adirondack rockers - take in the famous Annapolis sailboat races from there and the second-floor balcony! The lower-level rec room has a big couch that converts to a queen sleeper, two comfy chairs with ottomans, a game table and four chairs, a large screen TV, and a wet bar. The large and bright kitchen is open to the rest of the main floor for continuous views of the Bay. All top-of-the-line, brand-new appliances, gorgeous cabinetry and surfaces, an eat-in kitchen bar with seating, a prep island with sink, and a wall-mounted kitchen TV. Enjoy your meals at the dining table for 10-12 or dine alfresco on the back deck on the large teak table with an umbrella for shade. THINGS TO KNOW This home is not appropriate for events due to parking and neighborhood restrictions.

Conveniently located near major hospitals, medical centers, shopping, restaurants, and major highways, this vacation rental in Upper Marlboro makes commuting easy throughout Prince George’s County and the Washington, D.C. metro area. Perfect For: - Traveling nurses - Physicians - Medical residents - Physical and occupational therapists - Healthcare professionals on temporary assignments - Corporate travelers - Military personnel -- THE PROPERTY -- HOU-0239-2026-STR-H MAIN FEATURES - Dining room - 2 living areas - TVs, fireplace - Primary bathroom w/ soaking tub & walk-in closet - Washer & dryer - Deck, large backyard KITCHEN - Refrigerator, stove/oven, microwave - Drip coffee maker, toaster - Cooking basics, dishware & flatware ACCESSIBILITY - Single-level home, steps to enter PARKING - Driveway parking (4 vehicles) -- THE LOCATION -- - 12 miles to University of Maryland Capital Region Medical Center - 14 miles to MedStar Southern Maryland Hospital Center - 20 miles to Doctors Community Medical Center - 20 miles to Anne Arundel Medical Center - 10 miles to Watkins Regional Park: walking trails, picnic areas, playgrounds, miniature train, and nature center - 15 miles to Prince George’s Sports and Learning Complex: indoor track, fitness center, aquatic center, and sports facilities - 11 miles to Largo Town Center: shopping, grocery stores, restaurants, and everyday services - 0.7 miles to Marlton Golf Club: public golf course for recreation - 4 miles to Show Place Arena: hosts equestrian events, concerts, and community events - 4 miles to Prince George’s Equestrian Center: equestrian competitions and special events -- 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 ADDITIONAL INFORMATION - Tenant in basement unit on-site SECURITY CAMERA INFORMATION - 2 exterior devices - Location: front & back - Coverage: driveway, street, backyard Licence number: HOU-0235-2026-SFR;HOU-0239-2026-STR-H

Experience the Difference: Professionally Managed by iTrip Annapolis Escape to this spectacular custom-built waterfront estate in Edgewater, MD—just 15 minutes from downtown Annapolis. Styled like a modern ski chalet and nestled on nearly 2 private acres with a private pier and beach access, this one-of-a-kind retreat offers sweeping views of the South River, expansive indoor and outdoor living spaces, and every amenity for your perfect stay. The Space Step inside to a stunning open floor plan with soaring ceilings and panoramic water views. Gather in the main living area with its 2-story windows, cozy gas fireplace, and two flatscreen TVs. The gourmet kitchen is a chef’s dream, featuring a double oven, two cooktops (including one in the oversized butler’s pantry), a warming drawer, double refrigerator, wine cooler, and ice maker. For more casual fun, head to the spacious lower level—perfect for kids and teens—with a giant sectional, game and ping-pong tables, flatscreen TV, work desk, and a full bath. Sleeping Arrangements:Sleeps 12 Adults + 4 Kids + 2 Babies | 6 Bedrooms | 6.5 Bathrooms Main Level Queen Suite (Sleeps 2): Queen bed, en-suite bath with double vanity & walk-in shower King Guest Room (Sleeps 2): King bed, full bath across private hall Full Bunk Room (Sleeps 2 adults or 4 kids): 2 full beds, full bath in hall Second Floor Family Suite (Sleeps 2 adults + 2 babies): King bed, nursery with crib & rocking chair, portable crib, luxurious en-suite bath with whirlpool tub, shower, double vanity King Suite (Sleeps 2): King bed, en-suite bath with soaking tub, shower, double vanity Double Full Bunk Room (Sleeps 2 adults or 4 kids): Two full beds, en-suite full bath Recreation Room (Lower Level) Massive couch Game and ping-pong tables Flatscreen TV Large work desk Full bath with tiled walk-in shower Additional Amenities High-speed WiFi Multiple flatscreen TVs Washer & dryer Luxury linens and complimentary starter kit of toiletries, soaps, paper products, and kitchen essentials Keyless entry – drive up and enter via private side door with electronic code Ample driveway parking Nearby Attractions Londontowne Public Gardens – 5 mins Downtown Annapolis – 15-20 mins U.S. Naval Academy – 18 mins Marine Corps Memorial Stadium – 15 mins Washington, DC / Baltimore – ~30 miles each Important Notes Owners may dock their boat and use the beach (not deck or house) during Summer/Fall No pets, parties, or smoking Renter must be 25+ and present during the stay Security features include an exterior-facing door camera and a legal decibel monitor Check-in: 4:00 PM | Check-out: 11:00 AM Experience a luxurious, family-friendly escape On The Waterfront—your private retreat just minutes from Maryland’s capital. License: STR00714

Furnished Sunroom | Family Friendly | Half-Mi to Marina Make your way to this lovely Tilghman Island vacation rental, ideal for a trip filled with sailing, fishing, and savoring the area’s fresh seafood! Spend your days out on the bay, whether it's enjoying a scenic boat tour, kayaking through peaceful inlets, or watching for wildlife along the shoreline. As the sun sets, gather on the beautiful patio of this 2-bedroom, 2-bath home, where you can unwind and create lasting memories together. -- THE PROPERTY -- STN-24-17 SLEEPING ARRANGEMENTS - Bedroom 1: 1 queen bed - Bedroom 2: 2 twin beds HOME HIGHLIGHTS - Smart TV w/ Netflix, large dining table - Patio w/ dining set, umbrellas & grill (propane provided) KITCHEN - Refrigerator, stove/oven, dishwasher - Keurig (starter coffee provided), toaster, microwave - Cooking basics, dishware & flatware GENERAL - Free WiFi - Central A/C & heating - Washer, dryer, laundry detergent, iron & board, linens & towels - Complimentary toiletries, hair dryer, hangers ACCESSIBILITY - Single-story home, 3 steps to enter - Bedrooms on 2nd floor PARKING - Driveway (2 vehicles) - No garage access -- THE LOCATION -- - 0.3 miles to Tilghman Watermen's Museum - Half-mile to Tilghman Island Marina: fishing, boat tours, kayaking - 13 miles to Chesapeake Bay Maritime Museum - 85 miles to Baltimore/Washington Int'l Thurgood Marshall 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 - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - This single-story home requires 3 steps to enter and stairs are required to access the 2nd-floor bedrooms Licence number: STN-24-17;05-182255

Community Sports Courts | Near Golf Courses | 7 Mi to Northwest Stadium Seeking a relaxed base for your next stop in the Washington, D.C., area? This Upper Marlboro vacation rental is perfect for a stress-free stay! Whether attending an equestrian event, in town for a game, or traveling for business at Joint Base Andrews, you’ll find an unbeatable balance of comfort and convenience at this sleek 3-bedroom, 2.5-bath townhome. Secure your dates and start planning your capital visit today! -- THE PROPERTY -- HOU-0219-2025-STR-H SLEEPING ARRANGEMENTS - Bedroom 1: 1 king bed - Bedroom 2: 1 queen bed - Bedroom 3: 1 queen bed COMMUNITY AMENITIES - Tennis courts - Basketball courts HOME FEATURES - Smart TVs - Reclining sofas & love seat - Dining table - Patio KITCHEN - Refrigerator, stove/oven, microwave, dishwasher - Drip coffee maker (starter coffee provided) - Dishware & flatware, cooking basics GENERAL - Keyless entry, self check-in, free WiFi - Towels/linens, complimentary toiletries, hair dryer - Iron/board, trash bags/paper towels - Central heating & A/C, ceiling fans FAQ - 3 exterior security cameras (facing out) ACCESSIBILITY - 2-story townhome, stairs required to access PARKING - Reserved spaces (2 vehicles) - Free street parking (1 vehicle) -- THE LOCATION -- - 5 miles to the Show Place Arena, Prince George's Equestrian Center - 11 miles to Joint Base Andrews - 17 miles to Capital One Arena, 18 miles to Nationals Park - 6 miles to the Dutch Village Farmers Market - 20 miles to the National Mall, Smithsonian Museums - 23 miles to Ronald Reagan Washington Nat’l Airport, 30 miles to Baltimore/Washington Int’l Thurgood Marshall 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 - No pets allowed - 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 townhome requires using stairs to access - Your safety matters. This property features 3 exterior security cameras. Camera 1 is by the front door, facing outward. Cameras 2 and 3 are on the rear of the house, facing the patio and back windows. These cameras do not look into any interior spaces. They record video and sound when activated by motion Licence number: HOU-0219-2025-STR-H

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.

Escape to this stunning five-level house nestled on a quiet and expansive 5-acre property in Annapolis, MD. With decks on every level offering breathtaking views, a pool, putting green, and a dock with four kayaks, this vacation rental is a true oasis for outdoor enthusiasts. Lifejackets are conveniently stored in the garden shed for your safety and peace of mind. Enjoy the modern amenities of this home, including a pool, lake views, central AC, and high-speed internet. The property features a firepit, multiple outdoor seating areas including a deck, patio, and balcony, as well as a gas grill for al fresco dining. Inside, you’ll find a fully equipped kitchen with all the essentials, a cozy living room with a fireplace, and comfortable sleeping arrangements with king and queen beds. For entertainment, take advantage of the three Ring doorbell cameras for added security, cable TV, DVD player, board games, and children’s games. Explore the surrounding area with winery tours, beachcombing, bird watching, and water activities like kayaking, swimming, and paddleboarding. After a day of adventure, unwind in the secluded and peaceful setting of this remarkable property. Conveniently located near restaurants, cinemas, museums, and shopping, this house offers the perfect blend of tranquility and accessibility to local attractions. Whether you’re seeking a relaxing retreat or an active getaway, this Annapolis vacation rental has everything you need for a memorable stay. Book now and experience the best of Maryland’s waterfront living!

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