House vacation rentals in Assateague Island

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Popular amenities for Assateague Island house rentals

House rentals with a pool

Guest favorite
Home in Ocean Pines
5 out of 5 average rating, 5 reviews

Ocean Pines 2BR 1BA Cottage with Fire Pit

Chelsea and Elizabeth Rating, 5 stars3 weeks ago
Our family has a beach house in Ocean Pines, and we are looking to purchase our own in the coming years. We have stayed in all parts of ocean Pines and love it so much, we came across this house a couple months ago and I’m so glad we did! We spend most of the summer in Ocean Pines had different rentals and will definitely be coming back specifically to this one!! it’s perfect for our small family and pet friendly! The house was small but spacious, quiet and tranquil. 10/10 highly recommend!
Superhost
Home in Berlin
5 out of 5 average rating, 4 reviews

Mins to Golf & Beach! Private Pool & Luxe Firepit

CaroleRating, 5 stars2 weeks ago
Lindsay and Andrew’s Summer Breeze home in Berlin met all of our expectations. We particularly enjoyed the pool, grill and outdoor amenities - which made it perfect for our family holiday weekend getaway. The house is well kept, comfortable, neatly stocked with all essential amenities as described and, is staged and modeled exactly as pictured in the photos. We appreciated a quiet retreat, off the beaten path, yet we had an easy and quick drive to stores, restaurants and to the Ocean City boardwalk. As hosts, they were very responsive and efficiently communicated what we needed to know in advance, making our stay easy and smooth. From the booking process to assisting us with a couple of adjustments, they did not hesitate to help us. If there is an opportunity for us in the future, we’d love to stay again. Thank you Lindsey and Andrew!
Guest favorite
Home in Ocean City
4.95 out of 5 average rating, 255 reviews

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

ErikaRating, 5 stars2 weeks ago
Beautiful spot! Great location, close to all the happenings of Ocean City, but peaceful and quiet at the house…perfect set up. Great neighborhood. The house is beautiful, all the beds very comfortable. The back deck is gorgeous, thoroughly enjoyed that space and taking the kayaks out on the canal! It’s worth bringing your own linens and towels, we packed everything into a large tote and it worked out perfectly. Very responsive and friendly host! We had a great time here and plan to return. Highly recommend!
Top guest favorite
Home in Ocean City
5 out of 5 average rating, 30 reviews

Direct Ocean Front - Beach Retreat Condo!

AliceRating, 5 stars3 weeks ago
We had a wonderful stay at Chris and Loreees place! Super responsive when needed and clear instructions for check in and out. Private, quite, clean building and condo and we had everything we needed. The views were stunning & exactly as pictured. Walking distance to many stores, restaurants, and 7-11 next door for convenience. I would recommend staying here!
Guest favorite
Home in Rehoboth Beach
4.99 out of 5 average rating, 126 reviews

Secluded beach beauty with private, heated pool

BennyRating, 5 stars9 months ago
This is a great property! The house is gorgeous, the grounds are clean, kept and very private. The house was fully stocked with kitchenware, pool accessories, & decorated tastefully. A lot of delicate artwork and intentional decor- (if traveling with a young child, one needs to watch them closely :) Re: the beds- my 7 year old described it as “sleeping on clouds!” - very comfy! The area is close (2-3 min) to outlet shops and a bunch of restaurants on Costal Highway 1 and about a 6 min drive to the Rehoboth pier. It’s also a central location to other neighboring beach towns.
Top guest favorite
Home in Lewes
4.98 out of 5 average rating, 188 reviews

Beautiful Waterfront Home-Private, Clean, Relaxing

PatriciaRating, 5 stars1 week ago
My husband and I went to this "home" with another couple for several days of peace and quiet. The home and its location were definitely what we were looking for during our short stay. The kitchen was fully stocked which was great since I forgot certain spices for our planned meals. Our initial excursion was to Fort Miles at Camp Henlopen for a tour of the defensive setup along the coast during WWII. The tour was excellent, and with Laura's recommendation we returned to Camp Henlopen's beach for two days of sun and relaxation. This location is close to Lewes and Rehoboth Beach with plenty of restaurants and things to do on the boardwalk if that is something you are interested in doing. Laura was responsive to all emails we sent during our stay. We would definitely return to this home if our travels took us that way.
Superhost
Home in Ocean City
4.91 out of 5 average rating, 11 reviews

Sunkissed Ocean Haven

GenevaRating, 5 stars1 week ago
I loved the location, the condo, and everything about it. I enjoyed hearing the ocean waves crashing at night. The entertainment on the boardwalk was wonderful. I loved seeing the Clydesdale horses walk down the boardwalk. Looking out, you can watch the parasailers as they glide over the ocean. The condo was huge with separate full bathrooms for each room. The showers were large and roomy. I would definitely recommend this condo for large families as well as couples just just getting together for vacation. Steve the host was fantastic and communicated very quickly to our questions. Definitely a five star and would love to go back again.
Top guest favorite
Home in Accomac
4.98 out of 5 average rating, 266 reviews

Heartsong Farmhouse , a nature lover's retreat.

HarliRating, 5 stars1 week ago
Sarah’s place is AMAZING! Sarah went above and beyond being they didn’t have time with the weather to set up the new pool but went and dropped off a sprinkler and water hose for my daughter to use even though the weather never quite cooperated for us to use! Sarah was very responsive and helpful with anything we needed as well as gave great recommendations for local things! We will definitely be returning & staying here!

Weekly house rentals

Guest favorite
Home in Reedville
4.95 out of 5 average rating, 41 reviews

Sunnybank Getaway - Waterfront w/Pier & Kayaks

SandyRating, 5 stars2 weeks ago
We love our stay here! The house had everything we needed and more. It was easy to find, and the views were amazing. We spent the whole time outside in the nature, and we loved how quiet it was. Kevin was easy to reach for any questions we had, and we appreciated his help. We would definitely come back here in the future.
Top guest favorite
Home in Willards
5 out of 5 average rating, 19 reviews

Quiet country getaway

AshleyRating, 5 stars2 weeks ago
We were in for our nieces graduation from SU and this was the perfect place to stay. It reminded me so much of home! It was peaceful and relaxing. It was so nice I wish we had been able to spend more time there! Susan was an exceptional host. She was very informative, gave us helpful tips, and was very friendly. I would recommend this place to stay to anyone. Best AIR BnB I’ve been to so far!
Top guest favorite
Home in Chincoteague
4.98 out of 5 average rating, 63 reviews

Saltwater Cowgirls' Cottage

BethRating, 5 stars1 month ago
I chose Chincoteague and the Saltwater Cowgirls' cottage to celebrate a birthday - it was PERFECT. The cottage had character and charm in a nice and quiet neighborhood. The view of the creek was a plus, and we enjoyed watching the families of geese while having coffee on the deck in the mornings. The sunroom was a favorite place for us to chill. The kitchen was well equipped and lacked nothing. We especially loved that our furbabies were welcome - the fully fenced backyard was perfect for our active pups. We absolutely loved the wildlife refuge, the charm of the downtown shops, library and waterfront park. An added bonus - we were within walking distance of the seafood festival! April was very responsive, friendly, and accommodating - We loved staying at the cottage and hope to stay again! It will be the FIRST place we'll check for availability for our next visit to the island.
Top guest favorite
Home in Selbyville
5 out of 5 average rating, 71 reviews

Lighthouse Cottage- Pet Friendly & Close to beach

DarinRating, 5 stars1 week ago
This cottage is absolutely beautiful! Perfect for a couple or family. Honestly it’s so much nicer than the pictures, it’s bigger than I thought. Such a clean place to stay also. The deck is absolutely beautiful, we sat out there every morning and evening and watched deer! They even had a water bowl for our fur baby. It is so close to ocean city and Bethany beach!. You will not be sorry staying here, I’ll just say that!! Thank you Jay for letting us stay at the Lighthouse Cottage, we will always Remember our experience there, we will be back!❤️
Top guest favorite
Home in Reedville
5 out of 5 average rating, 68 reviews

The Haven On The Chesapeake Bay

CriselyRating, 5 stars6 days ago
We love the Haven on the Bay! This was our third year staying here, and we can't rave enough about how perfect a space it is for us. The waterfront view is incredibly peaceful, the sunrise is gorgeous, and the physical space invites great quality time for the group. Ashley was a very gracious host, and was very quick to respond anytime we reached out with a question. We even had the joy of seeing dolphins while we were roasting s'mores around the fire pit!
Top guest favorite
Home in Onancock
5 out of 5 average rating, 64 reviews

Egret’s Point on the Creek

WilliamRating, 5 stars1 week ago
My wife and I were celebrating our 35th wedding anniversary and we couldn't have picked a better place to stay. We felt right at home and the house was decorated perfectly for us. The location was great, a quiet street but plenty of things to do in the area. We would recommend Karen's place to anyone traveling in that area. Only wish we had more time to stay.
Top guest favorite
Home in Ocean City
4.98 out of 5 average rating, 49 reviews

Luxurious Bay Front Condo

AbbyRating, 5 starstoday
Perfect Beach Getaway! We had an amazing stay at this condo! It was incredibly clean and spacious, with plenty of room for our family to relax. The views were stunning, and we loved being just a short walk from the beach and boardwalk—super convenient, especially with kids. The space is definitely kid-friendly, and the overall vibe was comfortable and welcoming. On top of it all, the host was extremely responsive and friendly, making the entire experience smooth and stress-free. Highly recommend for anyone visiting Ocean City!
Superhost
Home in Westover
4.94 out of 5 average rating, 34 reviews

Private beach with comfort

RosalieRating, 5 stars1 week ago
We were able to check in earlier which was great tho some of us weren’t able to get there right away… we enjoyed our stay very peaceful and were wishing we could have one more day! 😊 we were going to grill burgers but couldn’t find grill utensils so just did our best inside and still turned out great!!! Thank you for your house and allowing us to stay there!

Private house rentals

Top guest favorite
Home in Chincoteague
5 out of 5 average rating, 21 reviews

Magnolia House ~Available June 15-18~

BarbaraRating, 5 stars3 weeks ago
Beautiful house, clean, neat, and very well-appointed, just as advertised. Good location...I enjoyed being able to walk to get ice cream, while also being close to road to the beach. Jess was very responsive via e-mail.
Superhost
Home in Westover
4.95 out of 5 average rating, 80 reviews

Beachfront Chesapeake Bay Retreat

SarahRating, 5 stars2 weeks ago
Fantastic airbnb experience! The house is cozy and comfortable, fits a lot of people, and has so many amenities. You can have a peaceful time without going stir crazy and I didn't have any concerns about anything while there because of the great hosts! Will be back the next time I find myself in the area!
Top guest favorite
Home in Reedville
5 out of 5 average rating, 64 reviews

Spacious waterfront family retreat. Dogs welcome!

PaulRating, 5 stars2 weeks ago
What an amazing place! The photos did not do it justice. We had beautiful weather and the back patio/deck was the perfect hangout. We went kayaking, caught a lot of crabs, and enjoyed being by the water. We had the firepit going while one of us was grilling food and the vibes were perfect. The detached game room saw plenty of heated pool games with a great selection of music and sound system. Bedrooms were comfortable and the kitchen was a joy to cook in. Dawn provided very detailed instructions so that you know all that you need to do. All-in-all, great spot that is a perfect group getaway!
Guest favorite
Home in Salisbury
4.9 out of 5 average rating, 60 reviews

Bury Oasis: Pool, Hottub, Movie Theatre, Game Room

DavidRating, 5 stars5 months ago
The Oasis was perfect for our needs . We will definitely book it again in the future!
Guest favorite
Home in Princess Anne
4.93 out of 5 average rating, 14 reviews

countryside home in Princess Anne

AlexisRating, 5 stars5 days ago
Katlynn was a phenomenal host, she was quickly responsive whenever I had a question and was super flexible with me and my stay. If you’re looking for something peaceful and to feel right on at home, this is the place to go.
Top guest favorite
Home in Saxis
5 out of 5 average rating, 10 reviews

Island Jewell Near Chincoteague

MichelleRating, 5 stars7 months ago
My husband and I booked a last minute anniversary trip and Denise's home was absolutely perfect. This little home was everything that you could want and more for peace and relaxation. Denise was helpful and responsive and accomodated a very late night check in with no problems!
Guest favorite
Home in Rehoboth Beach
5 out of 5 average rating, 14 reviews

Gorgeous 5BR, 4.5BA, in town, pool, hot tub, beach

TammyRating, 5 stars2 weeks ago
We had a wonderful stay during our first visit to Rohoboth. The house was beautiful, spacious, and clean. The host was quick to respond to any question or need. The kitchen had everything we needed to cook and the dining area was great for playing our group games. We loved the pool and hot tub area as well. We would definitely come back!
Guest favorite
Home in Deal Island Historic District
4.94 out of 5 average rating, 32 reviews

House of the Setting Sun/Deal Island Bayfront Home

DawnRating, 5 stars1 week ago
Once again, our family had an awesome stay in this beautiful home. Definitely will be back..

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