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 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

After relaxing at the beach (just a 7 min walk away), unwind on our deck "watchin' the tide rollin' away!" Get the best of the bay & the beach with this dog-friendly hidden gem! Imagine evenings enjoying the bay breeze as you crack crabs on the deck! Relax inside our open-concept great room that allows everyone to be together. Fish on our private dock or use it for your own boat or jet-ski to dock there. Witness spectacular sunsets with our Kayaks. Enjoy a well lit, private work space to virtual work w/ high speed internet! A new wood CRIB now in master suite for restful sleep! The pools and tennis/pickleball courts are only a few blocks away for your enjoyment! Plus, a truly unique OUTDOOR MOVIE EXPERIENCE for all our guests to make for the best Vacay EVER!

Jan 15 – 22

G$21,821 GYD per night

Superhost

Home in Onancock

4.78 out of 5 average rating, 120 reviews

Charming Waterfront Cottage on Cedar Creek

Come unwind in this comfy cottage right on the water. Situated on a 2 acre wooded lot, this colonial home offers peaceful seclusion and unbelievable water views from every room. This 1930’s cottage has modern updates and plenty of room, with two large bedrooms downstairs and a delightful bedroom suite upstairs. Restaurants and shopping await in the historic town of Onancock, only a 5-minute drive or an even quicker boat ride away. Private dock for swimming and fishing, two kayaks for guest use.

Feb 27 – Mar 6

G$45,387 GYD per night

Superhost

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)

Feb 24 – Mar 3

G$25,852 GYD per night

Guest favorite

Home in Salisbury

4.99 out of 5 average rating, 149 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.

Dec 11 – 18

G$35,756 GYD 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

Aug 14 – 21

G$42,598 GYD 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 4 – 11

G$25,260 GYD 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 21 – 28

G$25,453 GYD per night

Guest favorite

Home in Accomac

4.98 out of 5 average rating, 218 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.

Jan 14 – 21

G$32,808 GYD 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.

May 11 – 18

G$57,896 GYD 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.

Nov 11 – 18

G$33,404 GYD per night

Guest favorite

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.

Aug 25 – Sep 1

G$26,057 GYD per night

Guest favorite

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.

Feb 7 – 14

G$66,142 GYD per night