House vacation rentals in Assateague Island

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Top-rated house rentals in Assateague Island

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Guest favorite

Home in Salisbury

4.99 out of 5 average rating, 151 reviews

Salisbury Cottage

Relax in a quiet part of Salisbury in this cozy, newly renovated 3 bedroom, 2 full bath home. A farmhouse feel welcomes you home after a long day at work, a sports trip, or vacation. Enjoy all new furniture including luxury bedding and smart TVs. Centrally located and close to downtown for shopping and dining at one of the many local restaurants. Only 30 minutes from the beaches of Ocean City & Assateague Island. One mile from Tidal Health PRMC and a half block away from Salisbury University.

Oct 8 – 15

R3,453 ZAR per night

Guest favorite

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

Oct 10 – 17

R2,391 ZAR per night

Guest favorite

Home in Reedville

4.98 out of 5 average rating, 120 reviews

Sunkissed Cottage-private, natural waterfront home

Want a cozy, private getaway surrounded by nature, lush trees, beautiful sunsets on the Little Wicomico? Sunkissed Cottage is cheerful home full of wonderful amenities! Enjoy drinking coffee on the porch watching the deer and birds. Take a 2 minute walk down our path through the woods to our waterfront where you can enjoy the water. Our home has high speed internet, smart tvs in every bedroom, corn hole boards, firepit and gas grill. The kitchen is well stocked for all your culinary needs.

Aug 7 – 14

R3,344 ZAR per night

Guest favorite

Home in Chincoteague Island

4.97 out of 5 average rating, 179 reviews

★ Jay’s Waterfront Retreat: Private Dock- Kayaks-Fire Pit-Bikes-Beach-Pet Friendly ★

Fully equipped 1000 sf home-3 Bdrm residence-with fire pit, 2 kayaks, 4 bikes & Private Dock. Linens & towels included Jay's Retreat is 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

Feb 9 – 16

R2,662 ZAR per night

Guest favorite

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.

Dec 2 – 9

R2,309 ZAR per night

Guest favorite

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.

Sep 10 – 17

R2,973 ZAR per night

Guest favorite

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.

Sep 16 – 23

R5,246 ZAR per night

Guest favorite

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.

Oct 4 – 11

R3,022 ZAR per night

Guest favorite

Home in Cambridge

4.92 out of 5 average rating, 182 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.

Oct 17 – 24

R2,359 ZAR per night

Guest favorite

Home in Tangier

4.98 out of 5 average rating, 139 reviews

Watermans Hideaway, Tangier Island, Chesapeake Bay

The Waterman’s Hideaway is a two story, coastal inspired home located on main street at the center of town and a short walk from Tangier’s restaurants, gift shops and tour boat docks. Guests can enjoy the deck overlooking the spacious backyard or lounge under the shade tree at the front of the property where they can interact with the locals passing bye as they go about their daily routines.

Dec 15 – 22

R3,269 ZAR per night

Guest favorite

Home in Ocean View

4.87 out of 5 average rating, 447 reviews

Private place near Bethany Beach

Our place is close to Bethany Beach and conveniently located to Fenwick Island, Ocean City Maryland, Rehoboth Beach, Tax Free Outlet Shopping, Golf, Fishing, Surfing, or Hunting. You’ll love our place because of the quiet wooded location perfect for relaxing near all the beaches of the Delaware Eastern shore. This area is a wonderful place to visit all year round.

Nov 18 – 25

R2,152 ZAR per night

Guest favorite

Home in Reedville

4.96 out of 5 average rating, 205 reviews

Waterfront FamilyFriendly Home Improved for 2023

NEW IMPROVEMENTS for. 2023! Nautically furnished home on the water and a cul-de-sac which offers a relaxing and safe getaway space for guests. Large windows along the waterside provide for views from most rooms in the house. Watch the boats come and go from Smith Point Marina, or charter a boat for cruising or fishing.

Mar 21 – 28

R3,069 ZAR per night