House holiday rentals in Chesapeake Bay

Find and book unique houses on Airbnb

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Popular amenities for Chesapeake Bay house rentals

House rentals with a pool

Guest favourite
Home in Cape May
4.82 out of 5 average rating, 131 reviews

Beautiful 5BR house with inground salt water pool

JanitaRating, 5 stars8 months ago
We loved our stay! We had a great time as a family. one thing we thought of was we were very thankful our children were at the ages (5,3,2, 7 months) they were since there was lots and lots of glass stuff sitting around.
Guest favourite
Home in Edgewater
4.92 out of 5 average rating, 143 reviews

House in Edgewater Maryland

NancyRating, 5 stars3 weeks ago
Leisa’s home suited our needs to a T!! We were in town to attend a wedding at the London Town and Gardens, which was just a half mile away. The rehearsal dinner in downtown Annapolis was also a short distance away. Everything was fresh and clean, the beds were comfortable, and the showers were really great. The lack of seating in the main room wasn’t a problem for us as we didn’t spend much time there during the day. The area around the pool looked really comfortable and inviting for guests staying during the summer season! Would stay there again.
Superhost
Home in Rehoboth Beach
4.75 out of 5 average rating, 4 reviews

New property with private pool! Sleeps 10

KimberlyRating, 5 stars6 months ago
Exactly as described, great space! Bedrooms, bathrooms and kitchen brand new and super high end appliances. Living room space comfortable and well appointed. Highly recommend!
Guest favourite
Home in Rock Hall
4.95 out of 5 average rating, 37 reviews

Rockfish Keeper

Mary JaneRating, 5 stars1 week ago
It was a great stay after a long day roaming around Washington DC and Maryland. The accommodation was clean and nicely decorated with very inspiring words of wisdom providing a cozy and comfortable retreat throughout our stay. Kelly has been very informative and detailed on the instructions to help us on a very smooth check in and check out process. The location was fantastic and quiet neighborhood. Overall, we had a wonderful time and would highly recommend this place to anyone looking for a memorable Airbnb experience!"
Top Guest favourite
Home in Villas
4.99 out of 5 average rating, 126 reviews

Hot Tub Backyard Oasis, Private Beach, Local Pool

KaylaRating, 5 stars2 weeks ago
The house was even nicer than it appeared in the pictures. The living area is spacious and the bedrooms and bathrooms comfortable for our family's needs. The outdoor area was very enjoyable as well. It is evident that Heather has put a lot of care into creating a welcoming vacation home.
Guest favourite
Home in Severn
4.88 out of 5 average rating, 164 reviews

Large Home with Pool & 7 bedrooms; sleeps 21

LoisRating, 5 stars1 week ago
Staying here made our family wedding stay away from home, a very memorable and fun weekend for the whole family. Muvh better than being stuck in a hotel with lots of kids!!
Guest favourite
Home in Fort Washington
4.91 out of 5 average rating, 150 reviews

5 BEDR, Inground Pool+Billiard Table, Close To D.C

CurtRating, 5 stars2 days ago
Simple, clean and well organized place .. would definitely recommend.
Superhost
Home in Newark
4.82 out of 5 average rating, 74 reviews

Spacious 4-bedroom house with a private pool.

CaroleRating, 5 stars4 months ago
We had a lovely week staying at George's place. The location was convenient for visiting nearby family, as well as attractions such as the Brandywine River Museum and Bombay Hook for birding. We even took the train into Philly one day, and that was easy and fun. The house itself is very clean and comfortable, and well-stocked with the basics. Our bed may have been the most comfortable I've ever experienced as an Air BnB renter! Thanks, George, for sharing your home!

Weekly house rentals

Top Guest favourite
Home in Wildwood
4.97 out of 5 average rating, 271 reviews

Unique Wildwood 3 BR 1,5 BA House -Heart of town-

SallyRating, 5 stars1 week ago
Great stay for our family! The house was beautiful, clean, and comfortable, we were walkable to a lot of dining options (and the beach, but we were there during a cold snap). We’d highly recommend it!
Guest favourite
Home in Dewey Beach
4.96 out of 5 average rating, 164 reviews

McAvoy B & B

JaimeeRating, 5 stars3 weeks ago
Great spot, responsive host, overall great experience!
Guest favourite
Home in Dewey Beach
4.94 out of 5 average rating, 211 reviews

Cozy Home at 109 Swedes St

KelleyRating, 5 stars6 months ago
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.
Guest favourite
Home in Rehoboth Beach
4.87 out of 5 average rating, 229 reviews

Dodd House Beach Home w/private pool and hot tub

MorganRating, 5 stars1 week ago
Lynn and Brian’s house was amazing. It was perfect for our large group! The house had everything we needed and more. The hot tub and outdoor area were a huge plus! The house was very clean and they supplied us with sheets and towels which was a huge help. Brian was very responsive and super easy to communicate with. Couldn’t have asked for a better house or hosts!
Guest favourite
Home in Rehoboth Beach
4.82 out of 5 average rating, 172 reviews

IN-TOWN - WALK/BIKE/DRIVE TO BEACH/DINING & STORES

GeorgiaRating, 5 stars8 months ago
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.
Guest favourite
Home in Chincoteague
4.94 out of 5 average rating, 18 reviews

Coastal Daze Cottage

CatherineRating, 5 stars7 months ago
Christine was a wonderful and very responsive host. The stay was really wonderful for a last minute trip with my husband. The house is walking distance to many restaurants on the island and you can walk a short distance to the sound side of the island. The shower is on the main floor and the bedrooms are on the second. Theres a small bathroom on the second floor which was very convenient. The house was incredibly charming and well air conditioned. The bed was incredibly comfortable - we would stay here again!
Superhost
Home in Cape May County
4.89 out of 5 average rating, 28 reviews

Cozy Beach Cottage

ValerieRating, 5 stars2 weeks ago
Beautifully designed beach cottage. Small, but had everything you needed for comfort. The deck was such a plus for relaxing and enjoying the quiet outdoor space. The beds were super comfortable and decor impeccable! It was a quick 8 minute walk to the beach. Loved staying here and so wonderful that Daniel graciously invited dogs into his home. Thank you!
Superhost
Home in Lewes
4.92 out of 5 average rating, 59 reviews

Modern Comfort in Historic Lewes

DonRating, 5 stars6 months ago
Mark's house was perfect for my son's in-laws who came into town for his wedding this past weekend. They didn't have a car, so the location was important - walking distance to downtown Lewes and walking distance to our home. The house was clean and well equipped. Other than a musty smell from being closed when we first arrived, it was perfect.

Private house rentals

Top Guest favourite
Home in Selbyville
4.9 out of 5 average rating, 173 reviews

Country Private Vacation House

ElizabethRating, 5 stars7 months ago
This was a great place to stay while we went to the Ocean’s Calling music festival in Ocean City. The location was great, away from everything but still only a short drive. As someone who easily gets grossed out by air bnbs, it was so clean and comfortable, with plenty of space! Thanks for an incredible stay, will definitely want to stay again if we come back to the area!
Guest favourite
Home in Harpers Ferry
4.89 out of 5 average rating, 113 reviews

Hot Tub, Wi-fi, Rural Setting, Smrtv, Convenient

MeganRating, 5 stars3 weeks ago
Lovely area close to the cute town of Harpers Ferry. Loved the Hot Tub.
Guest favourite
Home in Norfolk
4.92 out of 5 average rating, 131 reviews

3 bedroom private home a block from the beach!

JennRating, 5 stars3 weeks ago
Kate’s place was perfect for our family’s first trip to Norfolk! The beach is literally less than a 5 minute walk away. Her home is adorable and her neighbors are the sweetest people! My kids loved their little dog. We felt very comfortable in the house — very nice neighborhood and the home had everything we needed! We were very close to downtown as well. We will definitely be coming back if we make it back to Norfolk! Thank you Kate!
Guest favourite
Home in Montross
4.93 out of 5 average rating, 202 reviews

The Glebe

Irma VRating, 5 stars2 weeks ago
We loved the open space concept in the house. It has beautiful views and a fire pit. Beds were clean and comfortable. Very well supplied kitchen. We will come back. Thanks,
Guest favourite
Home in Virginia Beach
4.94 out of 5 average rating, 114 reviews

Lakefront House @ Oceanfront

CelestineRating, 5 stars8 months ago
Responsive even before I booked. As pictured. Accommodated 5 of us very comfortably. Friends stayed one half block up I liked our place much better!
Superhost
Home in Rehoboth Beach
4.9 out of 5 average rating, 110 reviews

Secluded Beach Cottage, 9 min from the beach

JarrettRating, 5 stars1 week ago
We had a great time at Sergiu’s place! Our two dogs had an excellent time and there was a perfect amount of space where both us and our other two friends felt like we had plenty of privacy and each couple had their own bathroom to use. We grilled out back and used the fire pit too and really enjoyed the location. Short drive to the beach and to all the restaurants and stores in Rehoboth. Sergiu was very easy to communicate with and responded quickly. Highly recommend!
Top Guest favourite
Home in Cape Charles
4.96 out of 5 average rating, 144 reviews

Hidden Treasure

BriannaRating, 5 stars2 weeks ago
The name says it all! My week at Sandi’s place felt like a slice of heaven. Beautiful lot, peaceful, quiet, but also just a quick drive to anything you need or would want to see! Immaculately cleaned. Stocked with everything you need! I cooked nearly every meal and all the basics were there, which was great after long days on a job site. That covered porch is THE BOMB! Comfy, clean beds, too. Great wifi! Sandi is extremely response, so friendly, and any instructions were crystal clear! She put her heart and soul into this home & it shows! My dogs loved the little walking trail behind the house & napping on the porch! 110% will be back! Thank you Sandi!!
Top Guest favourite
Home in Virginia Beach
4.99 out of 5 average rating, 192 reviews

Play by the Bay 1 MIN TO WATER

AmyRating, 5 stars1 day ago
I had a wonderful stay at this beautiful home right next to the beach. The location couldn’t be better, steps from the ocean, yet incredibly quiet and peaceful. The home itself was spotless and well-maintained, offering a very comfortable and relaxing environment. Diana and Tom were exceptionally kind and went out of their way to help with a need I had during my stay, which I truly appreciated. Highly recommend this place for anyone looking for a serene beach getaway with thoughtful, responsive hosts.

Destinations to explore