Holiday houses in Deal Island Historic District

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Top-rated holiday rentals in Deal Island Historic District

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Guest favourite

Home in Solomons

4.96 out of 5 average rating, 26 reviews

Solomons Yellow House - Waterfront

This is a beautiful completely renovated light filled historic waterfront 3 bedroom house in the Avondale section of Solomons, MD. Solomons is a historic fishing village on the Western Shore of the Chesapeake Bay and is bounded by the Patuxent River to the South. Baltimore and DC are less than an hour away. The property slopes gently down to a private & protected cove of the Chesapeake Bay. There is a crab shack and dock where sunsets can be viewed and cocktails appreciated.

Guest favourite

Guest suite in Cambridge

4.95 out of 5 average rating, 477 reviews

Sailwinds Waterview Loft at Cambridge Creek

Waterview second story loft apartment in downtown Cambridge, MD with private entrance and secure bike storage! Located just 4 blocks from Route 50 and only 2 blocks from the Choptank River! This amazing space is within walking distance to seafood restaurants, shops, public boat ramp, beach, and parks! Close to all local attractions including the Choptank River Lighthouse, Sailwinds Park, Harriett Tubman UnderGround Railroad, Blackwater Refuge, Eagleman/Iron Man, and so many more!

Superhost

Cottage in Heathsville

4.83 out of 5 average rating, 75 reviews

Riverfront Retreat with PRIVATE POOL and BEACH!!

Welcome to your riverfront retreat. Only a 2 hour drive from DC/RVA, this riverfront cottage has everything you need to get away. After spending time on your private beach, relax in your own pool, before spending the evening relaxing in the screened in porch or by the firepit. Sunny? Take out the kayaks, stand up paddle boards or cornhole. Rainy? The home is furnished with TVs, chromecasts, high speed internet, board games and puzzles. Follow us on IG @riverfront_retreat for more

Top Guest favourite

Home in Fruitland

4.97 out of 5 average rating, 129 reviews

Amazingly convenient yet secluded.

Our place has views; the yard has beautiful shade trees that set the mood for deep relaxation. One can walk to Walmart, Denny's, Hampton Inn Suites, Ruby Tuesdays and many other business's in minutes. Ocean City is about a 35minute drive. Salisbury University is a five minute drive. UMES is a 13 minute drive.This home is ideally located. A retired teacher on one side is your closest neighbor; on the other property is a caregiver. Needless to say this is a very safe place; enjoy.

Guest favourite

Home in Cambridge

5 out of 5 average rating, 14 reviews

"Riverside Retreat"

Welcome to your dream vacation in the historic city of Cambridge, Maryland! This charming well appointed Riverview rental is the perfect home base for exploring all that this fascinating city has to offer. With its rich history, vibrant culture, and stunning natural beauty, Cambridge is an ideal destination for relaxation and exploration. Within walking distance to great restaurants, shopping, marinas and a historic downtown area that will both entertain and delight you!

Guest favourite

Home in Cambridge

4.98 out of 5 average rating, 126 reviews

Waterfront Getaway w/ Pier - Sleeps 10, 4 bedrooms

Escape to our charming & serene waterfront retreat, perfectly situated on the picturesque Choptank River. This 4-bedroom home accommodates 10 guests w/ 7 comfortable beds & offers the ideal blend of relaxation & adventure. Our property comes fully equipped with bikes, kayaks, paddleboards & yard games for endless fun. Unwind and relax on the new pier. The river offers gorgeous sunrises and sunsets. Your perfect waterfront getaway awaits you!

Guest favourite

Cottage in Lottsburg

4.98 out of 5 average rating, 83 reviews

Enchanting Edge of the World Cottage

Escape to a serene retreat with stunning views of the Nation’s River. This unique cottage-style home was built to feel like being in the middle of the sea, offering breathtaking scenery from every angle. Relax with a book from the classic collection, enjoy coffee on the hammock, or grill on the patio. With your own Rip-Rap shoreline, fishing is just steps away. Don't miss your chance to experience this tranquil getaway. Book now!

Superhost

Tiny home in Salisbury

4.83 out of 5 average rating, 127 reviews

Cattail's Branch

Enjoy the lovely setting of this romantic spot in nature. Tiny house sits on Widow Hawkins Branch Creek and backs up to Johnson Wildlife Mtg Area. Great for bird watchers and nature lovers. Enjoy sitting by the fire pit or relaxing on spacious deck overlooking creek. Quiet and peaceful. Fully equipped kitchen, Queen bed, bathroom, pull out queen sofa bed with privacy wall to make 2rd bedroom. Close to beaches and town.

Guest favourite

Condo in Tangier

5 out of 5 average rating, 18 reviews

The Tarryn Elizabeth Unit A

What better way to enjoy a getaway or family vacation than on a peaceful quiet island where the beach is clean and spacious and some of best fishing and crabbing in the world! Rent a four wheeler and drive on the beach 24/7 or lounge on the porch and soak in the sun, and not to mention the unlimited hi speed Internet with smart TVs in all 3 rooms for all your relaxing needs if you should choose to stay in the home!

Guest favourite

Home in Lusby

4.89 out of 5 average rating, 63 reviews

Beachfront Oasis with Amazing Views

Perfect getaway home to relax and enjoy peaceful beach views. This beachfront home is perfect for a romantic weekend getaway or a family vacation. Enjoy long walks on the beach, conversations at the fire pit in the evening, kayaking or hunting for fossil sharks teeth. The perfect escape from DC, the home is just over an hour from the city and located in the quiet, private beach community.

Guest favourite

Cottage in Saint Leonard

4.96 out of 5 average rating, 136 reviews

Block to Beach, Screened deck, Hot Tub, No CF

Relax at this renovated cottage with views of the Chesapeake Bay! Features large screened deck, hot tub, around corner from private community beach where you can find fossils and shark teeth! (4 min drive to larger community beach.) (No cleaning fee and multi night discounts! Message us for monthly rates.)

Guest favourite

Guest suite in Piney Point

4.95 out of 5 average rating, 258 reviews

Spectacular beachfront walk-out in Piney Point MD

A beautiful 1000ft private beachfront walk-out to be enjoyed couples, families and even your pet. If you're interested in an incredible beach sanctuary, birds, turtles, kayaking or just reading a book listening to the waves - our sanctuary is your sanctuary. Please join us!