
Pet-friendly holiday rentals in Chesapeake
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Top-rated pet-friendly home rentals in Chesapeake
Guests agree: These pet-friendly homes are highly rated for location, cleanliness and more.
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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

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
Fantastic place! Very close to Colonial Williamsburg. Place is a bit secluded which is great after a full day of sightseeing. Nice to come back to a little oasis. Very clean, well stocked. Host very responsive, pleasant and flexible. Recommend it highly!

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!
Pet-friendly home rentals with a pool

Villa Positano
💯 your money worth and the interaction with Roger was amazing .good location good fishing right of tha beach . safe and clean environment and gorgeous views

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!

Sound View! Dogs OK! Pool&Spa, Sound&Beach Access
Lisa was absolutely an incredible host! The home was beautiful and it was in a quiet family friendly neighborhood which we loved! It truly was perfect but I do think the beds could use a little updating they are a bit hard and unsupportive but other than that it was an amazing stay and we would love to come back again!

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!

Perfect Getaway!
First off! Sabrina is one of the most nicest, considerate, kind-hearted, caring , responsive host that I’ve come across. Her house is BEAUTIFUL, clean, spacious and cozy. The bed that I splept in was so comfortable! The house is technology ready!! “SMART HOUSE” “ absolutely loved it!! Beautiful pool and backyard. I enjoyed my stay! 😁

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.
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
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.

Seaglass Cottage
We came here for a quick few nights and it was absolutely perfect. Susan was a great host. It was in a great location and there was lots in walking distance to do! We had a great time and would definitely come back and stay here 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.

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
5 stars. I will be staying here again when we come back to Virginia Beach!

East Beach Bungalow, 1 block to the beach!
Adorable place - great location and plenty of parking.
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
Wi-Fi availability
270 properties include access to Wi-Fi
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- Virginia Beach Oceanfront
- Carova Beach
- Resort Beach
- Corolla Beach
- Busch Gardens Williamsburg
- Bethel Beach
- Buckroe Beach
- First Landing State Park
- Kingsmill Resort
- Currituck Beach Lighthouse
- Virginia Beach National Golf Club
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- Grove Beach
- Buckroe Beach and Park
- Golden Horseshoe Golf Club
- Wilkins Beach
- Haven Beach
- Cape Charles Beachfront
- Norfolk Botanical Garden
- Grandview Beach
- Kiptopeke Beach
- Jamestown Settlement
- Ocean Breeze Waterpark