
Pet-friendly holiday rentals in Chesapeake
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Top-rated pet-friendly home rentals in Chesapeake
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Popular amenities for Chesapeake pet-friendly home rentals
Pet-friendly house rentals

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

2 BR Family & Pet Friendly House - Williamsburg
Charlene is a wonderful and very responsive host. This was our second time staying there when we visit Williamsburg. The location is great and only a few minutes from everything. The house was comfortable and had everything we needed to enjoy our week. We look forward to staying again in the future.

@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

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!!!

Historic Capitol Landing 3BR/2Ba home
This house and property is really special. It is a beautifully maintained and renovated old house, and has great views of the woods and the creek. We enjoyed evenings on the beautiful porch taking in the views. The house itself was well appointed and clean, with minimal/essential furnishings. A few other reviews did mention the noise from the highway and it is true—though it did not disturb us except for in the night, when an occasional loud truck might pass. It was a great base for my family and two small dogs to explore the local sights. Would definitely consider staying here again.

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!

Fun Family Friendly 3 BR Home Close to Everything
Our stay at this place was amazing for a family of 5. Joseph is a wonderful host. The place was exactly as described. Joseph responded extremely quick and helpful with every question we had prior to arrival. Though traffic did not work in our favor, he even let us know that we had an earlier checkin time should we had arrived earlier. He was even willing to work with us prior to booking for a slightly later checkout that our family needed. We felt at home having a bbq, bonfire, enjoying the massage chair, and playing several rounds of pool in this nice quiet neighborhood. Love that we were able to bring our dog along too! Would definitely stay here again!
Pet-friendly home rentals with a pool

Villa Positano
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.

Pets OK, Private Pool, Hot Tub, Close to beach!
Rental home was very clean with updated amenities and very close to the beach access. Beautiful pool and hot tub and of course our two dogs were allowed to accompany us on this vacation. A very memorable vacation. Definitely would choose this rental property again!
Private, pet-friendly home rentals

Quaint Apartment By the Sea
Clean, safe, easy to get to. Did the job we needed it to for the weekend.

New! Clean + Affordable + Central!
Host was very responsive and very helpful! The house was clean and close to stores if we needed something! A wonderful stay; and, would stay again!

Home-Sweet-Home
Nice clean home with everything you need in a great location close to the beach, enjoyed my stay and would definitely come back.

Relaxing on the bay/Relocation Special/Close beach
The house was just what we asked for. Host was very responsive and very nice it snowed she had her people come out and shovel the walk way and porch of the house and even offered to clean our cars for us. The view is just amazing would definitely book again.

Seaglass Cottage
This spot was perfect for a few days right in Virginia Beach. We walked to the beach with our dog in the morning after we chose from several nearby spots for coffee and treats. The neighborhood was walkable, friendly, with things to do and see. The house itself is cozy, with everything you could want or need while traveling. A home away from home.

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.

S&S Hideaway
This is a clean, cozy accommodation with lots of privacy. I loved it and would stay again!

Quiet Suite with Private Entrance
If you have the option to book this place DO IT!!! This is one of the nicest places I’ve stayed and is an absolute gem in Virginia Beach. This was the most peaceful and secluded location I have ever seen in this area. You don’t find many places like this one. The bed was super comfortable and the unit was extremely spacious and cozy. I will definitely be looking to stay here again!
Quick stats about holiday 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
Destinations to explore
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- Virginia Beach Oceanfront
- Carova Beach
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- Busch Gardens Williamsburg
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- Currituck Beach Lighthouse
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- Norfolk Botanical Garden
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- Red Wing Lake Golf Course
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