Deal Island Historic District vacation rentals

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Top-rated vacation rentals in Deal Island Historic District

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Heathsville

4.96 out of 5 average rating, 24 reviews

Renovated waterfront cottage with private dock

Escape, relax and relish in the beauty of the Little Wicomico River and Bay! Swim, float, or fish off the private dock with a sandy bottom perfect for kids. Grab a set of kayaks and spend the day exploring. Or, bring your own boat/jetski to the deep-water dock. Enjoy sweeping views of the river and direct water access. Make Smores at the firepit. The Sunnybank Ferry is a quick walk or take your car across and explore Reedville. High speed WiFi/Netflix/streaming while you're not playing outside!

Top guest favorite

Home in Reedville

5 out of 5 average rating, 11 reviews

Main & Guest House on a Private 5-acre Waterfront

Coastal Winns is a secluded retreat located 3hrs south of DC in Reedville, known as "The Fisherman's Town". This 5 acre property includes 2 beautifully decorated homes with views of the Chesapeake Bay & a private beach. Perfect for fishing, quiet getaways, retreats & family gatherings. Includes BBQ grills/griddle, kayaks, crab cages, 3 decks, fire pit (firewood provided), corn hole, hammock, games, picnic area, swing & obstacle play set. Boat landing 3 min drive/0.4 miles away from property.

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 favorite

Home in Fruitland

4.97 out of 5 average rating, 128 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 favorite

Cottage in Delmar

4.93 out of 5 average rating, 82 reviews

The Good Vibe Cottage

NEW & EXCLUSIVE FULLY RENOVATED ENCHANTING COTTAGE Three bed, 3 Bath Cedar Cottage tucked away on a three-acre parcel with a large circle driveway lined with mature trees. A serene pond with a bridge, fountain, and three-person covered swing allows you to relax and savor the outdoors. House will comfortably sleep up to 8 people and has plenty of safe parking. Make sure you say hi to the friendly ducks and take in the gardens full of beautiful butterflies.

Top guest favorite

Home in Lexington Park

4.96 out of 5 average rating, 162 reviews

Private beach retreat in historic St. Mary's City

Nestled next to historic St Mary's City and a lovely state park, your Lucas Cove Beach home awaits you with your own private sandy beach and pier with vast views of the water, new salt water hot tub steps away from the beach, four beautifully furnished bedrooms with Casper mattresses, an upstairs deck with adirondack chairs to take in the water views and amazing sunrises while sipping a beverage or just relaxing, high speed Wi-Fi. Kayaks avail for rent.

Guest favorite

Cabin in Lusby

4.99 out of 5 average rating, 83 reviews

Your own private beach? Horizon views of the bay?

Modern beachfront Panabode log cabin with stunning views from the home, hot tub, fire pit, kayaks or larger decks. Sit on the swing and watch your family play in the sand on the beach or in the shallow water (usually about 3-4' feet for quite a way out.) Spot Eagles, pelicans, hummingbirds, dolphins, crab & oyster boats... Bring your own bed linen & towels (see below for sizes.) No pets allowed at any time. No additional guests or visitors.

Guest favorite

Home in Lusby

4.92 out of 5 average rating, 12 reviews

Chesapeake Bay Waterfront View

Indulge in your dream vacation at our one-of-a-kind bay house! This three-level home offers unmatched water views that will captivate you. Strategically located 15 min away from Solomons Island, for a city escape, with exclusive access to 2 private sand beaches and a lake. Our home is a delight, a blend of comfort, fun and tranquility. Highlights: Breathtaking Water Views Gourmet Kitchen Screened Deck Private beaches

Guest favorite

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 favorite

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.

Superhost

Home in Saxis

4.86 out of 5 average rating, 138 reviews

ISLAND BREEZE Near Chincoteague Island

Waterman’s fishing village Surrounded by water on three sides & Virginia Wildlife Refuge on fourth side. Walking distance to beach (located on Dennis Lane) Kayaking & Canoeing Wildlife Fishing Pier Boat Ramp Marina Public Pavilion Ice Cream Shop 1-Restaurant (Capt E’s Hurricane Grill & Tiki Bar) Museum Multiple Seafood Shanty’s (Steamed Crabs Available during season)

Top guest favorite

Home in Lusby

4.99 out of 5 average rating, 294 reviews

Cove Point Beach Cabin

My place is close to shopping, restaurants and dining in Lusby and Solomons Island, the Chesapeake Bay, and family-friendly activities. You’ll love my place because of the comfy beds, the coziness, and the views. My place is good for couples, solo adventurers, business travelers, and families (with kids). No pets allowed.

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What guests are saying

"Elderberries" Chesapeake Bayfront Cottage

4.7 out of 5 average rating, 20 reviews6 months ago

Had a great time at the Elderberries cottage! The views were spectacular, and you could take them in from the enclosed porch, the open deck, and even the living room. The entire setup was perfect for a vacation/remote work getaway, and the kitchen has everything you need. WiFi worked great, and the smart TV supported pretty much any streaming service you'd want. Rachel was friendly and super responsive; we hope to stay there again sometime.

Cabin in Reedville

What guests are saying

Spacious and private waterfront, sleeps 10

4.92 out of 5 average rating, 79 reviews3 weeks ago

The location for this house is beautiful! We loved the private dock and spacious backyard. We stayed in late March so it was a bit cold some days but we still had a great time using the provided Kayaks and sitting on the dock and watching the beautiful surroundings. The location was perfect to have some s'mores nights around the firepit. The hosts were VERY responsive. The few times I had questions they replied within minutes and were very accomodating with our requests. They were very proactive with instructions and generously mentioned a foldable crib for the infant in our group - although we had our own that we used. The kitchen had all of the dinnerware and cookware that we needed for the meals that we made. The living areas were open and inviting. It was perfect for our group. One thing to watch for is the very steep driveway. It took a few times to get used to. We would definitely stay there again when we visit our family in the area.

Home in Lusby

What guests are saying

Hope Haven Cottage

5 out of 5 average rating, 31 reviews6 months ago

Mildred and Spencer are the best hosts ever! From Spencer’s transportation between the boat and the cottage to the yummy smells of freshly baked cinnamon rolls upon arrival to an extra-special treat of a beautiful and tasty 50th anniversary cake for my parents arranged by Mildred through the town baker, this visit to Tangier was incredible! Mildred and Spencer are my new island besties! I love them and the welcoming people of Tangier so much. Hope Haven Cottage is a hidden gem I hope to visit again and again.

Home in Tangier

What guests are saying

Farmhouse by the bay! Beach and pier access.

4.94 out of 5 average rating, 31 reviews6 months ago

We had a lovely stay at Patrick’s place! It had everything we needed for a long weekend on the shore. A very comfortable home. Patrick was extremely responsive and helpful, with easy check in and check out. The kitchen was particularly lovely and well appointed! The house number is a little small so keep an eye out. And the mosquitos were fierce - don’t forget bug spray! Thanks, Patrick!

Home in Madison

What guests are saying

The Cove - 9 Rooms and Conference center

5 out of 5 average rating, 3 reviews21 months ago

Wide open space for our event with a sink, full sized fridge, and mini ice maker. Lots of tables and two bathrooms there as well. 9 hotel style rooms with Jacuzzis, bathrooms, AC, and more. Complimentary gifts and great recommendations along with prompt and helpful responses. My only suggestion is to better sell how good this property is. As of writing this review, the page says there are only 6 beds but there are nine. The pictures of the event area don't properly convey how large and nice it is. Very happy with everything and I'm already trying to find a reason to book this location again next year.

Hotel room in Crisfield