
Pet-friendly vacation rentals in Chesapeake
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in Chesapeake
Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Chesapeake pet-friendly home rentals
Pet-friendly home rentals with a pool

Positano Villa
Roger’s beach house was charming. It was an older-style home with many modern updates. Quick and easy walking path to the beach. The pool in the backyard was lovely. It was a little dirty upon arriving and Roger came right over and got it all cleaned up for us during our stay. The neighborhood was a little rough we did have a few uncomfortable encounters with homeless people being two girls alone it was a little unsettling. Overall, I would definitely come back again. The weather was absolutely beautiful for our stay.

LUX Oceanview•Heated Pool•2-Min Walk to Beach
This was a beautiful place with lots of room. The host was super responsive to any questions and also offered up local adventures to enjoy. House was clean and in great shape. I would recommend this vacation home to anyone and would use again. The kitchen was stocked perfect with all plates and cookware you need to host meals for a large family

Wooded Wonderland Miniature Golf Hot tub Pool
We rented this property to visit the Virginia Tattoo and the beach and had a great trip!

The Moor House
This home is an absolutely FANTASTIC getaway location! My family enjoyed every moment of our vacation. The house was as pictured and as described and then more. It is a quick ride back to the water where we spent most our day. We would finish each day with a dip in the pool and hot tub. The back yard view is fantastic as well. My kids spent so much time fishing off the dock on the canal catching crabs, and white perch fish. We loved all the horse views at all random times of the day. I could go on, and on! The hosts were very responsive to all my questions and so accommodating. I would give this home 10 stars if I could!

POOL, Pool House, Hot Tub, Grill, 2 bedroom
He was so nice and everything!!

Ocean Escape
This was a great place to stay in Sandbridge! We loved that we had a view of both the beach and the bay. It's an easy quick walk to the beach, which is beautiful and not crowded. There is a restaurant right on the premises and another one across the street, plus very close to a public park and the wildlife refuge. Randy and Tracy's place was so well-stocked - they had everything from sponges and soap in the kitchen to tissues and shampoo in the bathroom - it was so nice that we didn't have to go buy any of those items, especially for a short weekend! They also have a great storage closet packed with chairs, beach toys and bikes. The beds were very comfortable and the place itself was very nice and spacious. The hosts were super responsive whenever we had a question. We were very happy with our stay and would highly recommend it if you need a condo in Sandbridge!

Beach Home, Upscale Croatan Resort + Private Pool
This is a wonderful beach home within walking distance of the oceanfront. Our extended family enjoyed a fantastic visit. The house is set up perfectly for multiple families with a large gathering space on the top floor next to the kitchen. There are several decks throughout the home to catch the sea breeze and air. Beverly was a great host and responsive to our needs.

Kingsmill 2bd2ba Condo on Golf Course 9th Fairway!
I had a fantastic stay in Williamsburg! The room was exactly as described—clean, comfortable, and had all the comforts of home. The hosts were incredibly communicative and helpful, making the entire experience seamless. Their attention to detail and hospitality really stood out. I would absolutely love to return for another visit. Highly recommend!
Pet-friendly home rentals with a hot tub

Horses-Views-Dog Friendly-4WD Area
Thanks again for another relaxing stay at “Breakin’ Wind”! It’s been 5 years since our last trip here and we loved coming back to Terra’s place. We especially loved the hot tub, shelling and walks on the beach and seeing the horses again.

Hot Tub - Massage Chair - Golf Cart - Beach Gear
The house was wonderful, the location was beautiful. We enjoyed watching the sunrise and listening to the birds on the back deck. So peaceful! We were away from the crowds but could easily bike or ride the golf cart into town to walk, shop, or visit the restaurants and bars. Highly recommend!

4 bedroom T/H, Hot tub, short walk to beach
We needed a last minute rental after our first spot fell through & we were already in Corolla. Jennifer was amazing and quick to respond to our request to rent her place. Despite the same day rental & check-in, the house was clean & ready for visitors. Jennifer knew of our previous rental situation and that we had 2 children with us and even offered earlier check-in if we needed it. The welcome info had great restaurant recommendations and other helpful info. She was always quick to respond to any questions. The location is great and the hot tub was nice to relax in at the end of the day. We would definitely rent this spot again!

Coral Cove- Backyard-Hot Tub-Walk to beach-Dogs ok
This was the perfect place for our family of 4 to stay. The host was very kind and helpful with instructions. The space was clean, comfortable, and had everything we needed. We were impressed by the accommodations that were included for small children (pack-n-play, high chair, etc)! We would definitely stay here again.

MillerLight
It was the ideal retreat for our two families, with six children ranging in age from 3 to 13. From the moment we arrived, we felt completely at home. There was ample space for everyone to relax and enjoy themselves. The location was fantastic—just under five minutes’ drive to the beach and local shops, nestled in a peaceful neighborhood surrounded by trees. It felt wonderfully private and serene. Cindy was incredibly responsive and helpful throughout our stay. We were genuinely disappointed not to have booked for longer and will absolutely be returning in the future.

Wickline Cabin on Moon Creek
Spent the weekend up here for a quick getaway. It’s a beautiful cabin - location is great, it’s very quiet, and it was the perfect place to escape life for a couple of days. Loved it!!

Haley Kona Paradise 4 BR|Hot Tub|2 Dogs|7 beds
What a wonderful house! My family and I came to the OBX for a wedding and this house was exactly what we needed. The right spot for all the wedding events that we had. The house was so homie! Perfect for relaxing after a long day. The community pool was an awesome addition to have. Great hosts! Very responsive!

Cozy Cottage - NEW hot tub, dogs OK, fenced yard
The house was super clean, comfortable and walking distance to some delicious restaurants! I highly recommend this spot if you have dogs; the yard is fully fenced with privacy fencing, is clean and spacious enough for large dogs to run around. It’s in a very quiet neighborhood as well. I’ve stayed in some other Airbnb’s that had a chore list a mile long, with complicated check in/out instructions but this place was the total opposite. The whole process and stay was super easy and worry free. We’ll definitely be booking again in the future! :)
Pet-friendly house rentals

Cozy and Modern Beach House
The Airbnb was very neat and clean and it looked just like the pictures.The location was perfect and the weather was great.Would love to come back for another visit.

Home-Sweet-Home
We were very happy with our stay and felt that it was a great value. The house itself matched the pictures and description. It was clean, it had all the supplies we needed, and it had enough space for our family of 4 and dogs. We found checking in and out to be simple as the host provided easy to follow instructions and even if we did run into any trouble, the host was friendly and responsive over messaging. Location wise, the house was in a residential area that had a lot of homes but the neighborhood was quiet during the day and at night and the neighbors were friendly. The best part about the location was the convenience that it offered. A nice beach, a grocery store, a local coffee shop, and more were all within a 5 minute drive. Busch Gardens and the zoo took under 30 minutes to get to. The aquarium was 40 minutes away. Being centrally located and being more affordable than other areas allowed us to do a lot more fun activities than we could have done someplace else.

The Captains Cottage KAYAK/FISH on Elizabeth River
Janine was very responsive and accommodating. Would stay here again.

@Whit’s End? Come in and Relax
Travelling with our dog, the fenced yard and pet amenities were definitely appreciated! The space was clean and comfortable, and very much met all of our travel needs. Thanks!

Cozy Country Cottage
Nice quite location

Picture Worthy Spanish Style Casita! 2 BR/ 2BA
The house is very comfortable and spacious with a nice kitchen and big bathroom. The living room and bedrooms are big. The beds are very comfortable and the backyard was a nice addition. The house is located within 10 minutes driving on local roads to many of the attractions that Norfolk has to offer and also within a 10 minutes drive to amazing restaurants. Adam is a great host and we would stay at this house again!

Bamboo Bungalo Duplex Near Busch Gardens
Accessible to all that williamsburg has to offer. close to gas stations, groceries, homemade donuts, and a diner!! the space was so perfect for our family. we really appreciated having our own rooms and my 13 year old loved the privacy of the bed tent. thank you so much for sharing your space. we hope to return next year!!!

Relax! Refreshing 3 bedroom Rancher
Our stay was very nice. The home is in a quiet neighborhood and the house smelled amazing when we walked through the door. The keyless lock was very convenient, considering we arrived in the middle of the night. It had everything we needed for our stay. Thank you!
Quick stats about vacation rentals that are pet-friendly in Chesapeake
Total rentals
280 properties
Total number of reviews
9.4K reviews
Family-friendly rentals
160 properties are a good fit for families
Rentals with a pool
40 properties have a pool
Rentals with dedicated workspaces
160 properties have a dedicated workspace
Wifi availability
270 properties include access to wifi
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