Holiday rentals in Assateague Island

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Top-rated holiday rentals in Assateague Island

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Superhost

Apartment in Ocean City

4.88 out of 5 average rating, 89 reviews

Luxurious Oceanfront Retreat with Amazing Views!

This stunning recently renovated direct Oceanfront condo features a designer king-sized bedroom, a chef's kitchen, a sunny living area with a 65" 4K smart tv, and unobstructed beach and ocean views that can't be beaten! Every detail is designed to give guests a stylish and sophisticated place to relax while offering all of the upscale amenities you'd expect in a luxury vacation rental. Located on the Ocean City Beach with unobstructed Beach and Ocean Views! 13 Min Drive to Ocean City Boardwalk

Guest favourite

Apartment in Ocean City

4.89 out of 5 average rating, 38 reviews

OCMD family vacation rental 2BR, 2BA, Pool.

Top floor end unit with large (private) wrap around balcony giving views of the ocean and bay! (54th street Bayside, 1 block from the beach). This 2 bedroom/2 bath is nicely furnished and can accommodate 8 guests. The kitchen is fully equipped with full sized fridge, microwave, dishwasher, washer/dryer, whirlpool tub, central A/C, cable and wifi. Location is perfect for walking to restaurants, miniature golf, shops and nightlife. Rental includes: pool/Hot tub, fitness center,two parking spots.

Guest favourite

Home in Chincoteague

5 out of 5 average rating, 38 reviews

Central Location-Walk to Restaurants & Activities!

Ask me about seasonal weekly & monthly discounts! 🌟 Guest Favorite 🌟 Enjoy a relaxing experience at your vacation home just steps away from the Beach road🏖. Easy access to shopping, dining, and the beach. This beautifully renovated home features LVP flooring, bright kitchen, white cabinets, granite counter tops and tiled backsplash. 🏡 1st floor is open concept with 1/2 bath and laundry. The 2nd level has 2 bedrooms and 2 full bathrooms. The primary suite features a private bath & balcony. 😎

Superhost

Home in Ocean City

4.78 out of 5 average rating, 23 reviews

The Oliver House

This property boasts breathtaking views of the Ocean City skyline and is nestled in a quiet neighborhood in West Ocean City. Bring your boat, paddle boards, kayaks and firewood for the most incredible vacation. Crabs and clams are plentiful and the kids can enjoy playing in the small beach area while splashing or swimming in the bay. Although you may never want to leave, it's a short drive to Ocean City's beaches and boardwalk, Assateague Island and the quaint must-see town of Berlin, Maryland.

Superhost

Home in Georgetown

4.78 out of 5 average rating, 18 reviews

Salty Roots Ranch_Yard & Game Room_Mins to Milton

Country Vibes at the Delaware Beaches. Expertly designed for large group vacations. 5 bedrooms, 2 living spaces, immense backyard, games, activities, & more. Traveling for sports? Only 5 minutes to Sports at the Beach. De Turf and Sandhill fields also close proximity. Tourism at your fingertips with Historic Downtown Milton & World Famous Dogfish Head within 5 minutes travel. Broadkill, Lewes, Rehoboth beaches all under 20 minutes. Cape Henlopen State Park, Fort Miles Museum, & more to explore!

Guest favourite

Apartment in Ocean City

4.87 out of 5 average rating, 71 reviews

UNIQUE Bay Front Sanctuary Condo

Gorgeous upscale Bay Front Condo - This is your quiet, secure patrolled dream vacation. You will have a spacious one bedroom, one bath open-concept condo that can sleep 4. Watch the magnificent sunsets from your dining room or private balcony on the beautiful Bay. Fish right from your pier, bring your kayak or enjoy the views from the lovely picnic area. Walk across the street to the famous Ocean City Boardwalk and beach. Enjoy parasailing or jetski without even getting into your car!!

Guest favourite

Home in Selbyville

4.95 out of 5 average rating, 19 reviews

The Villa at Bayside Resort

Introducing a stunning, professionally decorated vacation rental property nestled in the heart of the prestigious Bayside Resort. Property Features: 4 beautifully-appointed bedrooms, 3.5 baths A spacious loft A sun-soaked living area Sun room, An elegant dining room, perfect for memorable family meals A scenic patio off of a wooded lot, offering a serene outdoor retreat. Bayside Amenities: Golf course 4 pools Fitness center Tennis courts Playground Kayaking Trails Concert Venue

Guest favourite

Home in Chincoteague

4.9 out of 5 average rating, 111 reviews

Chincoteague Island Creekside Cottage

Creekside Cottage delivers all the feels... July 2020 USA Today "Best Coastal small town". Private dock off large back yard for crabbing or catching the sunset, minutes away from the Chesapeake Bay and Historic downtown, 10 minutes to Chincoteague National Wildlife Refuge (Ponys) and the Beach (golf cart friendly). Everyone can hang on the huge sectional in the eve and play board games or catch up. Smart TV, Wifi, Large cooks kitchen (dbl oven), Table extends to 124". Make Memories!

Guest favourite

Home in Ocean City

5 out of 5 average rating, 6 reviews

Retreat at Sunset Landing

Escape to your ideal vacation retreat! This two-bedroom, two-bathroom rental is perfectly situated near top dining spots like Fager's Island, Tap House, and Bad Monkey. Just a short walk away, you'll find yourself on the sandy shores of the beach or the tranquil waters of the bay. Plus, for some added fun, there are putt-putt golf courses nearby. Experience the ultimate beach getaway with all the comforts you desire, right at your fingertips.

Guest favourite

Apartment in Rehoboth Beach

4.93 out of 5 average rating, 102 reviews

Cozy condo, 3 pools, and 4 beds in Rehoboth Beach

Get ready to relax immediately in this cozy and bright condo in a quiet community. The condo is a WALK-UP 3rd floor with vaulted ceilings, multiple balconies, and a relaxing screened porch with a view. We provide linens for the beds, bath towels, boogie boards, and beach chairs. Just over a mile from the beach and within walking distance are 3 community pools, a brewery, a grocery store, seafood restaurants, a water park, and more.

Guest favourite

Apartment in Tangier

5 out of 5 average rating, 17 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!

Superhost

Home in Ocean View

4.88 out of 5 average rating, 8 reviews

Modern Escape~4 Mi from Bethany Beach

Sand, sun, and endless family fun await your crew at this newly built Ocean View vacation rental! Nestled in the quiet community with access to top-notch amenities, and a prime location just 4 miles from the shores of Bethany Beach. After long days of swimming and shopping return home to prepare a feast in the fully equipped kitchen and unwind with a family favorite on the TV.