Vacation rentals in Trappe

4.93 out of 5 average rating, 127 reviews

A bright living area features a yellow sofa and an oversized ottoman, set against a backdrop of large glass doors overlooking the river. Natural light floods the space, highlighting the modern design and comfortable furnishings. A dining table is also visible, along with a seating area by the window.

Home in Preston

River House on the Choptank

Welcome to the River House! Stay in our renovated home on the Choptank River of MD's Eastern Shore, with your own low-tide beach and magnificent sunsets. We offer a peaceful location and thoughtful detail, creating a memorable getaway for a relaxing weekend or remote work location. Enjoy a day on the river with our paddle board or 2 kayaks, and end the day around the firepit. In cool weather, cozy up next to the fireplace. Also, visit nearby towns--St. Michaels, Easton, Oxford, and Chestertown.

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4.98 out of 5 average rating, 41 reviews

A spacious living area features a large gray sectional sofa set on a soft rug. A ceiling fan is visible above, and the open kitchen area showcases light cabinetry and modern appliances. Sunlight filters through tall windows, illuminating the room.

Condo in Cambridge

The Drinking Gourd: Stunning Cambridge Penthouse

The Drinking Gourd is a beautiful 2 bedroom, 1 bath penthouse located in the heart of the historic district of downtown Cambridge, MD. It features 15 foot ceilings, exposed brick, and original mahogany millwork throughout. The fantastic downtown pubs, galleries, museums, and boutiques are literally right outside the door, and the stunning Cambridge Marina is a short 4 blocks away. Cambridge has a wonderful food culture as well as local breweries and wine bars all within walking distance.

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A spacious backyard features a circular fire pit surrounded by Adirondack chairs. A picnic table sits to one side, and a hot tub is partially shielded by evergreen trees and a wooden fence, providing a serene outdoor retreat.

4.94 out of 5 average rating, 187 reviews

Peaceful Historic House Near Water, with Hot Tub!

Peaceful 3 bedroom/1.5 bath Victorian house near the water. Located in Historic West End, this 1900 house has been recently renovated to accentuate its historic charm while delivering all the modern comforts. Just a short walk from Long Wharf Park, the Choptank River Lighthouse, and downtown Cambridge with great restaurants and shops. Amenities include air conditioning/heating, a hot tub, WIFI, a back deck and grill, front porch with rocking chairs, and a fire pit with Adirondack chairs.

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4.99 out of 5 average rating, 657 reviews

The exterior entrance of a converted corn crib features natural wood siding and a gabled roof. Large double doors framed by lantern-style lights open into a welcoming space, complemented by potted plants on either side. Lush green trees and a gravel path are visible in the surrounding landscape.

Guesthouse in Easton

Chill in The Crib! Easton, Maryland

Welcome to Maryland's Eastern Shore and your own private space in a converted corn crib, complete with the comforts of home. The space includes a vaulted ceiling, queen-sized Casper® mattress, quality linens, heat & AC, wireless Internet, a coffee counter, stocked bar fridge, full bath w/ shower (includes quality bath supplies), and a private entrance. Our space is permitted for ONLY TWO INDIVIDUALS (No children under 8 years of age.), and please limit your visit to one vehicle only.

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An aerial view captures a sprawling, waterfront property surrounded by lush greenery. The modern home sits prominently on a well-manicured lawn, leading to a serene bay. The driveway winds through tall trees, with clear blue water visible in the background.

4.97 out of 5 average rating, 115 reviews

Osprey's Retreat Waterfront w/ private beach/dock

Enjoy a weekend escape or extended vacation for up to 6 guests at this freshly renovated gem located on LeCompte Bay . Beautiful waterfront property with a private sandy beach, located just 5 minutes outside of town with plenty of outside activities including a dock and fire pit. Super clean & comfortable, modern home & furnishings featuring a first floor premier, well appointed kitchen. This home is provided with everything you need for a fun, relaxing get-a-way on the Bay.

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A covered deck area features a large black dining table surrounded by striped chairs. A ceiling fan is present above. Scenic views of the water and shoreline are framed by tall trees, creating a serene outdoor dining space.

4.99 out of 5 average rating, 225 reviews

Sunset Breezes - quiet waterfront retreat

Enjoy well equipped waterfront home styled after historic lighthouses. Relax in the hammock by the water under the pines; Enjoy smores by the fire pit. Wood included. Free use of 4 kayaks, 2 paddleboards, and a 3 person canoe. Yard games include corn hole, croquet, & bocce. Dine on the deck while enjoying beautiful sunsets. Bring your cameras for local wildlife. NEW Fun & Fitness Barn: sauna, golf simulator, free weights, game space and more. Ask about access code and hours.

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An aerial view captures the waterfront home surrounded by lush greenery and a circular driveway. The expansive water body in the background reflects the sky, while a dock is visible along the shoreline, enhancing the serene landscape.

5.0 out of 5 average rating, 52 reviews

Magical Waterfront Home Dock, Firepit, Family Fun!

Heron's Rest is a stunning home w/ arguably the best water views in Cambridge from nearly every room, expansive patio, fire pit and dock - a peaceful place to gather with family and friends. Incredible location to explore the stunning and historic Eastern Shore and charming historic Cambridge. Easy drive to the Atlantic beaches--you CAN have it all- kayak, fish, birdwatch, explore Blackwater Wildlife Refuge, Easton, St. Michael's. Rare location w sunset and sunrise views!

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Apartment in St. Michaels

A bright yellow building features large blue shutters and a welcoming entrance. A sign is placed outside, and vibrant flowers border the steps. In the background, another structure is visible, along with flags proudly displayed.

4.98 out of 5 average rating, 160 reviews

Blue Crab Lodge

Welcome to your charming and cozy short-term rental above the heart of St. Michaels' vibrant community! Nestled right above the delightful aroma of freshly brewed coffee, this unique and inviting space offers the perfect blend of comfort and convenience. Stepping outside, you'll find yourself in the heart of St. Michaels' quaint streets. The rental's prime location provides easy access to the town's boutique shops, waterfront promenades, and a diverse array of restaurants.

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4.93 out of 5 average rating, 194 reviews

A serene waterfront view is presented, featuring a wooden dock extending over still water. Lush green grass fills the foreground, while trees line the opposite bank, creating a natural backdrop under a partly cloudy blue sky.

Home in Woolford

Waterfront Getaway with Dock

Bicyclist's and outdoorsman's dream! Beautiful rancher on two waterfront acres just 4 miles from Blackwater Wildlife Refuge and Harriet Tubman National Park. 10 minute drive from downtown, the Hyatt, and the Ironman starting point as well. Ironman and Eagleman races actually pass right by! Bright, sunny, and newly renovated, it's a great place to hang your hat after a day of hunting, fishing, bicycling, or triatholon-ing! Or just take a weekend to relax on the water!

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4.99 out of 5 average rating, 98 reviews

A scenic view of a spacious green lawn bordering a tranquil waterway. A white house is positioned near the water's edge, surrounded by trees and a clear blue sky. The peaceful setting is enhanced by the gentle reflection of the landscape in the water.

Home in Oxford

Stunning Chesapeake waterfront home

Spectacular new waterfront home in beautiful historic Oxford, comfortably sleeps 10 with perfect set up for 2 families. Enjoy Town Creek and Tred Avon water views from every room and angle. Gorgeous sunsets from the wraparound porch, stargazing and fishing from the dock. Walk to Morris Street for a relaxed coffee, stroll through Town Park, or take the Ferry to St. Michaels. The Town of Oxford has issued short term rental license # STR25-06 for this property.

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A bright living area is highlighted by a comfortable sofa and a round coffee table. A flat-screen television is mounted above a decorative fireplace. Natural light enters through multiple windows, and a dining table can be seen in the background, surrounded by chairs.

4.9 out of 5 average rating, 78 reviews

The Oyster House

The Oyster House is a newly restored guest house in the upstairs of a circa 1796 house that is steeped in hospitality history. It's located on historic High St. in Cambridge and was one of the first hotels in this town founded along the Choptank River. A family of creatives has been lovingly restoring this home to contain two guest houses along with a future art gallery. We hope you come time and again and witness the unfolding of more beautiful history.

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