Assateague Island vacation rentals
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Top-rated vacation rentals in Assateague Island
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Condo in Ocean City
4.88 out of 5 average rating, 89 reviewsLuxurious Oceanfront Retreat with Amazing Views!
“I recently stayed at this condo and had an absolutely wonderful experience! The space was immaculate, well-furnished, and thoughtfully equipped with everything needed for a comfortable stay. The kitchen had modern appliances, making it easy to prepare meals, and the living area was cozy yet spacious, perfect for relaxing after a day out. The location was fantastic – close to great restaurants, shopping, and public transportation, which made getting around a breeze. I also loved the view from the balcony; it was the perfect spot for morning coffee or an evening unwind. The host was incredibly responsive and helpful, providing clear instructions I would highly recommend this condo to anyone looking for a great place to stay
Home in Chincoteague
5 out of 5 average rating, 38 reviewsCentral Location-Walk to Restaurants & Activities!
Chip was very responsive and answered anything I asked. We'll kept place and had lots of extras that you wouldn't expect. I will definitely look to stay there during peak season, this was just a quick trip.
Home in Ocean City
4.78 out of 5 average rating, 23 reviewsThe Oliver House
Stayed for Ocean’s calling festival 2024. Would do it again. Great place!
Cottage in Rehoboth Beach
4.9 out of 5 average rating, 109 reviewsDog friendly, Close to outlets, fire pit, Sleeps 6
This house was great for us. Traveling with 2 dogs (one senior with mobility issues), this home was all one level and made it easy to navigate for our senior boy. The location was great too because you’re within 15 mins of beaches and great restaurants.
Condo in Ocean City
4.95 out of 5 average rating, 167 reviewsModern Oceanside 42nd st 2bed 2bath sleeper sofa
Enjoyed our stay at Paul’s condo everything was provided that we would need including sheets blankets toilet paper etc.. most places charge extra. Host was very responsive and condo very clean and great location. walking distance to beach perfect thanks again for having us we will definitely be booking again.
Home in Chincoteague
4.87 out of 5 average rating, 105 reviewsSunny Claire-Beautiful Downtown Cottage w/Hot Tub
The house is nice and spacious, centrally located and good for walking around town. Kitchen is stocked with all the necessary to make any meal. Sufficient parking for two vehicles. Only downside is having to pick up and drop off the house keys at a rental office.
Townhouse in Bethany Beach
4.93 out of 5 average rating, 109 reviewsLakefront slps 6; beach, pools, tennis, gym, view!
Sherri’s place is awesome and the community and surroundings are beautiful. The kitchen is furnished with everything you need for cooking. The deck is such a plus, with the view of the pond and the ducks, as well as the private little beach. The community is very friendly and walkable, and the different options for pools were very fun for us to explore. Taking walks in the morning was amazing. It is very close to Bethany “downtown” and 6 min drive to the beach. You can also walk or take the tram. I had a great time with my kids and would definitely recommend and come back!
Condo in Rehoboth Beach
4.96 out of 5 average rating, 156 reviewsClassy Beach Getaway
The place was at a great location. Easy drive to boardwalk, beaches, restaurants, and entertainment. The house had all things needed for a restful vacation. The trails were great for walking and bike riding. It is a five star Airbnb.
Home in Chincoteague
4.9 out of 5 average rating, 111 reviewsChincoteague Island Creekside Cottage
We thoroughly enjoyed our weekend stay. We liked that the home was in a quieter area in Chincoteague but within close proximity to restaurants, activities and especially to Assateague. There were only two of us, but the house could have easily accomodated a family. It was well laid out, clean and amply stocked with all the essentials. It was also tastefully furnished and had comfy couches. My only wish was that the house had cable or one of the movie channels, so that in the evening, we might have relaxed with a show before bedtime. One day, we took Captain Dan's boat tour, a recommendation from Kathleen, and it was an exciting and interesting outing. We traveled the back channels in the marshes where we saw lots of ponies and a bald eagle soared overhead in one area. Captain Dan had lots of stories to share which kept us entertained the whole trip. Since it was our anniversary, we splurged on a five course dinner at the Channel Bass Inn and Restaurant. Food was excellent.
Condo in Rehoboth Beach
4.93 out of 5 average rating, 102 reviewsCozy condo, 3 pools, and 4 beds in Rehoboth Beach
We had a great time staying at the condo! It was close to the beach, close to local restaurants, very cozy, clean, and Timothy left great suggestions for places to visit and eat at. Checking in and checking out was effortless. Greatly recommend staying with Timothy, and when we come back we hope to get the chance to stay here again!
Tiny home in Salisbury
4.83 out of 5 average rating, 120 reviewsCattail's Branch
Thoroughly enjoyed this is my second time staying here to visit my friend and it’s always a great time, perfect for sitting outside and having a small fire.
Condo in Tangier
5 out of 5 average rating, 17 reviewsThe Tarryn Elizabeth Unit A
Great spot close to the docks, affordable price and very responsive!
Vacation rentals for every style
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Popular amenities for Assateague Island vacation rentals
Assateague Island beach vacation rentals
Townhouse in Ocean City
4.98 out of 5 average rating, 42 reviewsUnique Direct Oceanfront 3-Level w/a Private Beach
Our third year staying here. Wonderful as always. Easy access to the beach and all the beach accessories that Meri provides make the trips so fun!
Condo in Rehoboth Beach
4.9 out of 5 average rating, 77 reviewsCOZY 3BR BEACH LOFT - pool/tennis court
Absolutely satisfied, for the price you can’t find better. Everything was exactly as stated and I had no issues, the owner made sure we were comfortable and always responded fast, I would definitely recommend and look forward to booking again.
Condo in Ocean City
4.95 out of 5 average rating, 19 reviewsBeach Bliss - A Modern Ocean City Rental
I have stayed at Melonie’s place before. I love the short walk to the beach. There is plenty of space for families to come together. Lots of restaurants close. Property is on a street with very few cars driving by.
Condo in Ocean City
4.85 out of 5 average rating, 13 reviewsExperience a Seashore Adventure! Book today!
The stay was literally amazing. Each room was amazing. My Favorite part about the property was each room has access to the balcony so I was able to move a chair down to sit outside my room and watch the ocean at night. The view was great and it was in the most perfect area. The boardwalk is literally right Outside downstairs, so we never had to go too far to get anywhere. It was also super close to the carnival area so that was great for rides and quick fun. Also the room is at the end of the hallway and perfectly the parking spots are right by the door with the elevator that is right outside the room so you never have to take the long hallway walk. Also, that same elevator leads directly to the pool on the 4th floor. Perfection! I would definitely stay here again. …and no worries if you have guests over there’s a bathroom in the hallway so you don’t have to share either of the personal ones.
Cottage in Ocean City
4.85 out of 5 average rating, 27 reviewsSandy sheets cozy beach cottage
This is the second time we’ve stayed there so that should tell you something. There are plenty of bedrooms and beds. A wonderful size porch, where the family can gather. The location is the best.
Condo in Ocean City
4.85 out of 5 average rating, 55 reviewsFul Dek - Family Casual Condo-Midtown-Ocean Block!
Really have no complaints about Jen’s place!!! There is so much space, it’s very cozy and homie. TVs in every room. The deck is so cute to sit outside and play some games or eat breaker/dinner. You have two parking spots, access to the beach and many restaurants around you. The bus stop to take you to the boardwalk is not a far walk either so you have unlimited access to everything you need. This was my first time back to OC MD in a long time and Jen’s place was the right place. 10/10 and will hopefully be staying again soon 😁
Villa in Ocean City
4.93 out of 5 average rating, 29 reviewsCheery & Cozy Beach Villa - Walk to Beach
This is a really great place. Highly recommend. Host is wonderful. Very responsive. Place was great. Has everything you need. Will definitely be renting this place again.
Apartment in Ocean City
5 out of 5 average rating, 6 reviewsLuxury Beach Front Vista on the OCMD Boardwalk
We really can’t say enough about this place. The location was perfect, the place was amazing and the host & property manager were the best! They have thought of EVERYTHING - from beach chairs to family games to things like can openers. They provide it all! And if you ever need anything the hostess’ son (Sean) is right there to lend a helping hand. We definitely plan to go back!
Assateague Island house rentals
Home in Crisfield
4.78 out of 5 average rating, 130 reviewsBayTime
It worked to support our holiday family gathering.
Home in Dewey Beach
4.94 out of 5 average rating, 211 reviewsCozy Home at 109 Swedes St
Eileen’s place did not disappoint. It was as beautiful as the pictures. The kitchen was well appointed. We enjoyed the outdoors space. It was a great place for some rest and relaxation. Thank you Eileen for sharing you house with us and being a great host.
Home in Ocean City
4.89 out of 5 average rating, 18 reviewsNew 5 Bdrm/Bayside Home/Prime Spot/Private Parking
The house was huge and super clean! It was great for our large group.
Home in Rehoboth Beach
4.95 out of 5 average rating, 191 reviewsPet friendly cottage 4 blocks to Beach
This is a great spot for a getaway, especially with dogs with the fenced in backyard. The house is in a great location, is clean, spacious and inviting. Highly recommend staying here. It’s a gem.
Home in Rehoboth Beach
4.95 out of 5 average rating, 106 reviewsIn-Town Rehoboth Beach, Walk to Everything!
I’ve been coming to Rehoboth for almost a decade now with family and friends. Angela’s place was perfect for our stay. The house was clean and comfortable. The location was also exactly what we wanted. Angela is very thorough and very helpful and makes the whole process seamless. Thank you for being so detailed! Would definitely stay here again!
Home in Salisbury
4.98 out of 5 average rating, 195 reviewsBeautiful Renovated Home, Perfect Getaway!
Ann was very responsive to any of my questions and responded very quickly, house was as described and enjoyed our stay even though it was only one night. If we’re ever in that area again I would not hesitate to stay there again!!
Home in Rehoboth Beach
4.92 out of 5 average rating, 61 reviewsSalt Forest RB Home - Centrally Located
My parents, myself, and my 2 youngest kids (9, 11) thoroughly loved the house. We felt right at home. You can tell the owners actually use the house as it has everything that you may need. No need to bring towels, sheets, blankets, or towels. They have it. Plenty of dishes and glasses. Games! Wine opener. Awesome refrigerator. Huge washer and dryer. Back porch is screened in. The 2 zones for HVAC were much appreciated as my parents are older and get cold. They were able to have the downstairs area a little warmer while we had the upstairs comfortable for us. My mom uses a cane. We really appreciated the ease of one floor living for her once we were in the house. Easy instructions to follow. A binder full of helpful local tips and info. We didn’t have any issues but based on my prior experiences with them, I know the owners would have responded. It was so nice to not deal with a property mgt comp. Neighborhood was nice. Everyone waves. Felt safe. Close to all. We hope to return!
Home in Rehoboth Beach
4.82 out of 5 average rating, 172 reviewsIN-TOWN - WALK/BIKE/DRIVE TO BEACH/DINING & STORES
We had a great stay at Rhonda’s house. She’s an excellent communicator and instructions were very clear. We had a small issue and she responded right away she walked us through how to correct it. As for house it was very clean and updated. Plenty of space for 5 people. The beds were very comfortable (attested to by my 9 year old son). The location was great as it was less than a 10 minute walk to the Main Street with restaurants, coffee shops and stores.About a 20 -25 minute to the boardwalk. We did drive to the beach and my husband rode his bike but you could walk the 20-25 minutes. We would definitely stay here again on our next trip to Rehoboth.
Assateague Island condo rentals
Condo in Ocean City
5 out of 5 average rating, 11 reviewsCondo on the Canal 13th Street (Aronimink)
Great location. Close to boardwalk and restaurants. Close to bus stops for further trips. Clean and comfortable.
Condo in Ocean City
4.91 out of 5 average rating, 273 reviewsWight Bay Unit 245
Jenna’s place is great, very clean and spacious. And a super relaxing space, I highly recommend it
Condo in Ocean City
4.98 out of 5 average rating, 113 reviewsAhoy Condo! Great ocean view just steps to beach!
This was a great place to stay. It's on the north end of Ocean City, so we'll removed from a lot of the touristy stuff. Really great access to the beach that had lots of open space and absolutely no crowding. The place was well appointed and very comfortable.
Condo in Ocean City
4.78 out of 5 average rating, 105 reviewsSpacious Direct Oceanfront 1BR Condo w/Balconies
An amazing place! Double balconies for sunrise and sunset views. Very peaceful and friendly neighbors. Everything within walking distance. Would highly recommend! Natasha was very quick to respond to any questions or needs you may have.
Condo in Ocean City
4.82 out of 5 average rating, 265 reviews🏖 *Ocean *Ocean *Ocean* 🏖 Beautiful Condo!!
We had a wonderful stay here for a few days. Peaceful home, GREAT view and all you need for a quiet relaxing getaway. I highly recommend!
Condo in Ocean City
4.93 out of 5 average rating, 44 reviews2BR/2BA/ 5 Bed condo with 2 private balconies!
Another great stay. The location can't be any better, central OC at it's best. Easy walk to the beach. We tried Barrio Taco this time, it's huge, recently remodeled. Dead Freddie's across the street is a plus. Plenty of room for our family. We'll be back! Raif went above and beyond with his hospitality - thank you.
Condo in Ocean City
4.87 out of 5 average rating, 101 reviewsCharming Remodeled 2 level condo w/ amazing views
Great stay for me and my family while we were down for Thanksgiving. The host was wonderful and the place was beautiful. Definitely recommend staying here
Condo in Ocean City
4.74 out of 5 average rating, 19 reviewsMallard condo’s A
Perfect location! Easy check-in. Melinda is very quick to respond to any questions! Definitely recommend this place!
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