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House holiday rentals in Assateague Island

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Top-rated house rentals in Assateague Island

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Home in Rehoboth Beach

4.79 out of 5 average rating, 621 reviews

Contemporary 1 Bedroom 2 level home

The unit has keyless entry system, A/C, brand new full size W/D, large patio w/grill, remote controlled open&close sky lights w/built in shades, new carpet, YoutubeTV/Netflix/Hulu/Amazon Prime Video & walk to the beach and attractions w/out crossing **pet friendly** **LOCATION** Intersection of Washington st & Jefferson St. supplied for guest: sheets blankets bath towels Shampoo/conditioner soap toilet paper paper towels trash bags Back pack type beach chairs (3) Beach umbrella Bikes (2)

3–10 Feb

$169 SGD per night

Guest favourite

Home in Berlin

4.78 out of 5 average rating, 174 reviews

OC, Md great amenities in community, near beaches

MERMAID DREAMS where you can just have FUN or just RELAX. We are 5 miles out from OC and Assateague beaches. Our community, Assateague Pointe, is a beautiful gated community, with 2 great pools, baby pool, big splash pool, a rec center, a fishing/crabbing pier, pond with paddle boats, 2 playgrounds+ more. For kiddos of all ages, we are located right next door to Frontier Town, which has awesome water slides , western shows, mini golf, a rope course, ice cream shop.. short term stays ONLY

2–9 Oct

$284 SGD per night

Guest favourite

Home in Chincoteague Island

4.9 out of 5 average rating, 166 reviews

Rest A'Shored charming Chincoteague getaway

Spacious open floor plan great for entertaining family and friends with all the modern amenities you need! Eat inside at the large dining room table or enjoy the cool evening breeze outside on the fully screened in porch. 3 bedrooms and 2 full baths can comfortably accommodate 2 families with children or 3 couples. Located on Willow street, you are just a short walk to the Chincoteague carnival grounds and Main Street. We are dog friendly as we know they are really part of the family!

4–11 Jan

$290 SGD per night

Guest favourite

Home in Ocean View

4.92 out of 5 average rating, 530 reviews

Tiny House at Good Earth, near Bethany Beach

A custom-built "Tiny House" located right between our new dinner theater and our garden dining area. True to the show "Tiny House Nation"; cool interior with custom woodwork, stairs to a lofted bed. Fully functioning kitchen. Spacious bathroom & shower. We provide TVs and internet in the units but the quality of service is not guaranteed. We are in a rural area and sometimes it's slow or not working at all. If TV and internet are super important for your stay we may not be the right fit.

27 Dec – 3 Jan

$168 SGD per night

Guest favourite

Home in Accomac

4.98 out of 5 average rating, 219 reviews

Heartsong Farmhouse , a nature lover's retreat.

Heartsong Farmhouse was completely renovated in 2019. Beautiful hardwood floors, brand new furniture, in a modern farmhouse style with a Boho vibe. The entire home is filled with beautiful natural light and the brick walls ensure a peaceful nights sleep. The yard is completely surrounded by a 15ft hedgerow of holly, magnolia and camellias, like walking into a secret garden. You will feel welcome from the moment you drive up. The Farmhouse is also beautifully decorated for the holidays.

22–29 Sep

$217 SGD per night

Guest favourite

Home in Chincoteague

4.96 out of 5 average rating, 126 reviews

Charming Island Home "Sandy Pines"

Come and enjoy a nice, relaxing vacation at this charming island home. "Sandy Pines" lies just a half a block from the water and a block and a half from the bridge to Assateague (where the beach is. The downstairs features a living room and dining room, 2 bedrooms (equipped with two twin beds each), a lovely kitchen, full bathroom and screened porch. On the second level you'll find the master bedroom with a private full bathroom, movie/game/yoga room, and a 2nd fully screened porch.

14–21 Sep

$383 SGD per night

Guest favourite

Home in Chincoteague

4.98 out of 5 average rating, 194 reviews

★ Pearl in the Pines: Kayaks-Fire Pit-Bikes-Beach-Pet Friendly

Fully equipped 1200 sf home-3 Bdrm residence-with fire pit, 2 kayaks, 4 bikes, towels & linens. Pearl in the Pines is literally at nature's front door within a few miles from Assateague National Seashore (the beach), home of the world famous Chincoteague Ponies. Enjoy: Swimming in the bay and ocean Bicycling Fishing, crabbing, clamming Kayaking, paddle boarding; boating Hiking Bird Watching Nature photography Hunting Nature Trails Great Restaurants & Brew Pub Boat Tours Ponies

6–13 Mar

$192 SGD per night

Guest favourite

Home in Rehoboth Beach

4.97 out of 5 average rating, 115 reviews

Charming 1.7 mi to beach,bdwk, restaurants! Quiet

No shared spaces in this Charming 4 room suite in single family home in nice neighborhood, close to Rehoboth Beach, bike/run/walk path to Lewes (4 mi). or Rehoboth, less than 2 miles. Great shopping, in town and TAX FREE! outlets 1/8th mi. large loft, King bedroom after climbing a SPIRAL STAIRCASE with large screen TV's upstairs and down. Bathroom downstairs. Living room with TV and couch and full kitchen. Parking in front. ** Host has her own private suite and entrance.

16–23 Jan

$133 SGD per night

Guest favourite

Home in Crisfield

4.95 out of 5 average rating, 254 reviews

Cozy Home near Waterfront in Crisfield, MD

Our home is close to great views, restaurants and shopping, the beach and family-friendly activities. You’ll love the sunsets over the water and viewing working boats in the harbor. Great for couples, solo adventurers, business travelers, and families (with kids). Beach is walking distance and the boat launch is 1/2 mile away. New library, playground, fishing, crabbing and gorgeous sunsets are all close by. Owners live only 15 minutes away for anything you may need.

26 Jan – 2 Feb

$221 SGD per night

Guest favourite

Home in Ocean City

4.97 out of 5 average rating, 120 reviews

Pet Friendly SFH w/ fenced yard, 2blocks to BEACH!

PET FRIENDLY with fenced in yard, 2 blocks to the beach! 2024 Summer rentals avail. Sunday - Sunday. An 8min walk to the beaches of N. Ocean City! Our home is located in a quiet neighborhood, between the beach & bay! You'll have access to a fenced backyard, full kitchen, smart TV, & WIFI. We expect guests to be courteous to neighbors. Parties & loud music are not permitted. **Not traveling with pets? Check out our ocean side condo near Northside Park!**

26 Nov – 3 Dec

$397 SGD per night

Guest favourite

Home in Cambridge

4.92 out of 5 average rating, 180 reviews

Guest House: Farm homestead

Quiet country guest house with 1 BR/ 1 BA, queen sleeper sofa and fully stocked kitchen. Coffee/creamer/sugar provided. Come relax & enjoy the row boat and paddle boat, fishing in the ponds (C&R, No Pond Access from August 24 thru January 30 annually), grill on the deck, watch the bikers roll by (Ironman course) or finish your day by the fire-pit with s'mores! All this and only 3 miles to town and on the Eagle Man and Iron Man race course.

28 Jun – 5 Jul

$172 SGD per night

Guest favourite

Home in Chincoteague Island

4.91 out of 5 average rating, 188 reviews

We’ve Thought of Everything So You Can Relax!

Completely renovated May 2018! Relax and enjoy nature in our home with a light and airy coastal feel in every room. Get away from the sights and sounds of traffic and city chaos in our private, secluded cul-de-sac location. Take a peek at the water through the trees from our private, second floor deck. Listen to the song birds, ducks, toads and frogs all flourishing in the undeveloped lots surrounding our property.

24–31 Jan

$437 SGD per night

Holiday rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for house rentals in Assateague Island

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home in Ocean Pines

4.96 out of 5 average rating, 113 reviews

Little house in Berlin, Md.

8–15 Dec

$211 SGD per night

Home in Ocean Pines

4.88 out of 5 average rating, 115 reviews

Tortuga Cottage: Your All- Season Getaway

18–25 Oct

$319 SGD per night

Guest favourite

Home in Rehoboth Beach

4.99 out of 5 average rating, 119 reviews

Secluded beach beauty with private, heated pool

20–27 Sep

$978 SGD per night

Guest favourite

Home in Ocean City

4.94 out of 5 average rating, 219 reviews

Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB

14–21 Jul

$998 SGD per night

Guest favourite

Home in Ocean City

4.98 out of 5 average rating, 109 reviews

Stunning Bayview Home with Own Private Pool

6–13 Apr

$1,285 SGD per night

Guest favourite

Home in Frankford

4.93 out of 5 average rating, 165 reviews

A Bethany Beach Gem

18–25 Nov

$218 SGD per night

Guest favourite

Home in Ocean City

4.86 out of 5 average rating, 159 reviews

Beach Paradise IV-Downtown Luxury Condo Bay View

18–25 Dec

$205 SGD per night

Guest favourite

Home in Ocean City

4.93 out of 5 average rating, 151 reviews

Right behind Alley Oops & Crab Bag. Walk to beach

16–23 Sep

$562 SGD per night

Weekly house rentals

Home in Onancock

4.78 out of 5 average rating, 121 reviews

Charming Waterfront Cottage on Cedar Creek

4–11 Nov

$318 SGD per night

Guest favourite

Home in Ocean Pines

4.99 out of 5 average rating, 101 reviews

Charming Waterfront Cottage w/2 King Suites + Dock

28 May – 4 Jun

$508 SGD per night

Guest favourite

Home in Chincoteague

4.87 out of 5 average rating, 78 reviews

"3 Sisters" Ivy's Cottage-Lovely downtown cottage

7–14 Dec

$110 SGD per night

Home in Berlin

4.87 out of 5 average rating, 46 reviews

2BR home close to beach in "coolest" town

14–21 Oct

$138 SGD per night

Guest favourite

Home in Berlin

5.0 out of 5 average rating, 34 reviews

Amazing 2 Bedroom home close to the beach!

15–22 Dec

$117 SGD per night

Guest favourite

Home in Chincoteague

4.95 out of 5 average rating, 96 reviews

Adorable Beach Cottage Just Steps From Town & Bay

10–17 Nov

$211 SGD per night

Guest favourite

Home in Newark

5.0 out of 5 average rating, 16 reviews

Nature Retreat near Assateague, Berlin, Ocean City

9–16 Sep

$456 SGD per night

Home in Berlin

4.79 out of 5 average rating, 99 reviews

BAYFRONT is our backyard! HEAVENLY VIEWS!!

21–28 Dec

$246 SGD per night

Private house rentals

Guest favourite

Home in Pittsville

4.97 out of 5 average rating, 74 reviews

Wagon Wheel Cottage

4–11 Nov

$155 SGD per night

Guest favourite

Home in Berlin

5.0 out of 5 average rating, 26 reviews

Lovely springtime; enjoy Clifton Retreat.

$143 SGD per night

Guest favourite

Home in Oak Hall

4.95 out of 5 average rating, 40 reviews

Converted Railroad Bank - 15 MINS to Chincoteague

14–21 Sep

$212 SGD per night

Guest favourite

Home in Berlin

4.97 out of 5 average rating, 66 reviews

Luxury home, 1.5 miles to Assateague Island, Md.

21–28 Feb

$868 SGD per night

Guest favourite

Home in Selbyville

5.0 out of 5 average rating, 26 reviews

The Lighthouse Cottage 9 miles from the resorts

6–13 Feb

$161 SGD per night

Guest favourite

Home in Chincoteague

4.98 out of 5 average rating, 56 reviews

Waterfront-Views from all rooms-CI bay sunset

19–26 Feb

$402 SGD per night

Guest favourite

Home in Berlin

5.0 out of 5 average rating, 13 reviews

Salty Air Retreat, 3 BR, 2 Bath, 4 miles to OC, Md

7–14 Mar

$566 SGD per night

Guest favourite

Home in Chincoteague

5.0 out of 5 average rating, 29 reviews

Saltwater Cowgirls' Cottage

15–22 Feb

$439 SGD per night

Destinations to explore