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Holiday rentals in Assateague Island

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Top-rated holiday rentals in Assateague Island

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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

4.97 out of 5 average rating, 34 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, 33 reviews

Central Location & Parking! Walk to Restaurants!

Ask me about seasonal weekly & monthly discounts! Enjoy a relaxing experience at your vacation home just steps away from Maddox Blvd. Providing easy access to shopping, dining, and the beach road. This beautifully renovated home features luxury vinyl plank flooring, bright kitchen, white cabinets, granite counter tops and a 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.

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 Chincoteague Island

4.97 out of 5 average rating, 207 reviews

Jay’s Retreat: EV Charger-Fire Pit-Kayaks-Bikes

Welcome to Jay's Retreat, your perfect escape just minutes from Assateague National Seashore and the iconic Chincoteague Ponies! This fully equipped 1,000 sq. ft. home features 3 cozy bedrooms, a fire pit for starry nights, kayaks, bikes, and a private dock for your water adventures. Enjoy swimming, fishing, hiking, and bird watching right at nature’s doorstep. With linens and towels included, plus an EV charger for your convenience, you’ll have everything you need for a memorable getaway.

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, 110 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 Chincoteague

4.98 out of 5 average rating, 42 reviews

cozy sunset cottage

Feel at home as soon as you walk in. Indulge in a coastal retreat that embraces you with a beach-inspired ambiance from the moment you arrive. Experience the carefree comfort of this centrally-located home, thoughtfully designed to exude a beach-like charm. And don't miss the special touch—an inviting screened-in outdoor lounge area where you can relax, unwind, and soak up the coastal vibes, creating cherished moments reminiscent of blissful days by the shore.

Home in Rehoboth Beach

4.84 out of 5 average rating, 62 reviews

As Seen In Dwell-Stunning Modern Coastal Getaway

Newly renovated beach getaway! Modern design with coastal charm redefines vacation rentals! screened in porch with swing bed, deck with outdoor shower. Gourmet kitchen, an open living/dining area, sectional, fireplace, TV. 3 bedrooms each have their own personality. Enjoy a queen sized bunk bed, a bohemian guest room, and master suite with king bed, private bathroom. The neighborhood has views of Rehoboth Bay, is 2 miles from the beach.

Guest favourite

Apartment in Tangier

5 out of 5 average rating, 16 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!

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.

Guest favourite

Townhouse in Berlin

4.9 out of 5 average rating, 83 reviews

Bayside Townhouse w/ amazing amenities

Vacation memories are made in the 3BR townhome situated in quiet private community. The property features an indoor and outdoor pool, clubhouse, basketball and tennis courts, kayak dock, crabbing fishing dock and much more! We are 10 minutes drive to OC and about 12 minutes to assateague island. Sleeps 8 Now includes an EV (J1772) charger!

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Popular amenities for Assateague Island holiday rentals

Free parking on premises

Air conditioning

Other great holiday rentals in Assateague Island

Guest favourite

Flat in Ocean City

4.93 out of 5 average rating, 15 reviews

Fabulous Ocean Block Condo!

Guest favourite

Home in Bethany Beach

5 out of 5 average rating, 30 reviews

Relax in Bethany! Great Location- 1 Block to Beach

Guest favourite

Apartment in Ocean City

4.96 out of 5 average rating, 23 reviews

Lux Bayfront Unit with Stunning views!

Guest favourite

Home in Ocean View

4.81 out of 5 average rating, 21 reviews

5 Bedroom-Award Winning Bear Trap Golf Community

Townhouse in Ocean City

4.86 out of 5 average rating, 22 reviews

Bahama 32 Big Groups ok

Tiny home in Salisbury

4.83 out of 5 average rating, 120 reviews

Cattail's Branch

Guest favourite

Home in Selbyville

5 out of 5 average rating, 35 reviews

Stunning Sunrise & Water View 1 mile from Beach

Guest favourite

Barn in Frankford

5 out of 5 average rating, 8 reviews

Amazing Beach Barn Suite

Destinations to explore