
Pet-friendly vacation 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 home rentals with a pool

Villa Positano
We had an amazing time. The house was perfect for us. We really enjoyed the pool and short walk to the beach. We could hear the ocean from the master suite. The upstairs deck had view of the water. Everything about our stay was perfect. The area was nice and was quiet and peaceful. We will definitely go back and stay longer next year. Thank you!!!

Kingsmill 1bed/1ba on Golf Course 9th Fairway
Crystal's condo was spotless and an easy place to stay. Crystal was very proactive and made us feel welcome. her dinner suggestions were superb too! perfect for a weekend getaway in a resort atmosphere. Thank you so much, we highly recommend!

The Blue Octopus~Private Pool~HotTub~Beach~FirePit
Family vacation for almost a week and everyone loved it! We definitely recommend families to come to the Blue Octopus for their next visit to Ocean View-Willoughby Spit. Friendly, clean and with all the amenities for the whole family.

Westgate Historic Williamsburg One Bedroom
We had a great stay at Eddie's place! Very close to restaurants, Colonial Williamsburg, and Busch Gardens. The unit we stayed in was spotless and had all of the amenities that we needed during our stay. Highly recommended!

Paint The Beach Pink! Full House | Private Pool
Check in was super easy, the AC was on when we arrived which was great after a long Uber. The pool felt nice and the whole backyard area was fantastic. We ended up using the bikes a lot more than we thought which was a lot of fun. It's a quick bike ride to the boardwalk and walking didn't take too much longer. Bradley was very quick to respond whenever I had a question about anything. If we come back to Virginia Beach we will definitely be checking the availability of this house!

Gorgeous Vacation House
The house was super clean when we got there, the temperature of the house was great the entire stay. The pool was certainly clean, but since we went early, June the water was a little bit cold, but it felt really nice and refreshing honestly. There were three beach chairs and a wagon there that were helpful for traveling to the beach. There were available cups plate, utensils, and all the necessities that you would need, they even had shampoo and conditioner bottles there for us. We weren’t aware that there was a code to get into the house so instructions for check-in were a little bit unclear, but all I had to do is message and they responded. Overall, I would recommend staying here because even though the area surrounding isn’t the nicest, I felt safe the entire time at that house!

Perfect Getaway!
We had a great family visit at this house. We really enjoyed the pool and whole house was very comfortable and clean! It was nice to just hang all day by the pool or top for a sanctuary from a long day of events. Sabrina was very attentive and responsive with questions and situations, appreciate her flexibility as a host!

Ocean Escape
My family really enjoyed our vacation. It was a great location to the beach and a private pool. It was our first vavation w/ an 18month old and 1 on the way. Randy was very quick to respond to any questions. A+
Pet-friendly home rentals with a hot tub

Horses-Views-Dog Friendly-4WD Area
The place was perfect. Very well stocked and pet friendly. We saw horses daily by the rental. Very easy access to the beach. Only thing it needs is a sign out by the entrance of the driveway with house #. We came in at night during a storm and it took us a few minutes to find the drive. I definitely recommend.

Stylish Beach House, Hot Tub, Pet Friendly
We traveled to Norfolk with our 2 young children and dog, the house couldn't have been better. Everything we needed was provided, including high chair and pack-n-play. We loved being able to travel to the zoo, aquarium, carousel, and great nearby library while we dealt with the rain and unfortunate beach closure. However, we were able to use the convenient beach access provided by the hosts and it was a great alternative. Great communication from the hosts and comfortable stay. Echo what others said about the road noise and construction but we came prepared thanks to the other reviews with blackout curtains and white noise machines.

Aloha Beaches OBX
This was our second year in a row we stayed here, and we love it. It’s right next to the beach, and accommodates or group perfectly. The pool/hot tub are perfect for after the beach. Sarah is super responsive and a great host for any needs we reached out with! We are already looking forward to next year’s trip!

Exclusive Beachfront Home w/ 180° Views & Hot Tub!
I could not wait to write a review about our stay. So much so that we are not even home yet. We had a glorious week at Bay Bliss! Bliss is the perfect description. Anywhere in this beautiful home you can hear the waves of the ocean. There was nothing better than listening to that while falling asleep on the comfiest bed in the master bedroom. Hosts were extremely responsive, helpful with local recommendations and extremely friendly. I have stayed at lot of AirBnb’s and hotels. Honestly, I have never felt so at home and I felt that way from the second I walked in the door. We will definitely be back.

Splash of Lime Carova 4x4 Beach Cottage
What a great place to stay. Splash of lime worked great for our group. The house is set up nicely and has lots of storage available. We were lucky enough to get daily visits from the wild horses throughout the day. Martin is an excellent host and responded very quickly to answer any questions we had.

Wickline Cabin on Moon Creek
We loved this cabin, and Caleb was such a gracious host! Arriving to a dozen farm fresh eggs was such a treat. We grabbed some bacon (Smithfield brand, of course) at the local Kroger and had eggs and bacon every day of our trip. The cabin is so quite and peaceful. It literally feels like you are in the middle of nowhere, but it's a 5 minute drive to all kinds of shops and activities. The povided kayaks were a major selling point for us. It was a very relaxing and beginner friendly paddle up the creek to the river. We saw all kinds of wildlife including otters playing in the creek! It is true that the hot tub is a little glitchy, but it was plenty warm and didn't impact our enjoyment of it at all. Caleb was kind enough to stack wood in the fire pit for us, making our evening campfire easy and streamline. The cabin is really close to great hiking, boutique and antique shops, the brewery, winery and restaurants. I wish we would have taken him up on the offer to bring our dogs. Next time!

Cozy Cottage - NEW hot tub, dogs OK, fenced yard
This was a great stay. I loved being close to the airport, walmart and places to grab food. We had a fun time in the hot tub which was pristine, and the back yard was dreamy and well-manicured. the bathroom and kitchen had everything you need and the beds were comfortable. The entire house was pretty and bright.

Designer 7BR w/ Pool and Hot Tub. Pets welcome!
This rental property was the ideal spot for our family reunion of 16, ages 8 to 78. This was one of the most well-equipped properties we have stayed at. We have stayed at several rental properties in Sandbridge Beach, VA in previous years, and this is our favorite. The kitchen was well equipped and stocked with essentials (coffee, sugar, creamers, paper towels, toilet paper, regular and beach towels, etc.) The kids loved the game room and outdoor pool. The adults enjoyed the hot tub and ping pong room. Two big dining tables easily accommodated our group size (8 adults at one and 8 kids at the other). The beds and pillows were all comfortable. Amy, the Operations Manager, was most helpful and very responsive to any of our questions. We plan to return to this property sometime in the future. Definitely a 5-star experience for everyone in our family.
Pet-friendly house rentals

Water Oaks at Chic's Beach
Tommy and Janet were very responsive! They were extremely friendly and went above and beyond to make our wedding weekend special. The house was a wonderful experience!

3 bedroom private home a block from the beach!
I had a wonderful stay at Kate’s home, it was easily 3 minutes to the beach, she had all the needed cooking utensils and even more! And even had some bathroom essentials that was really appreciated

Beautiful home in Chesapeake
⭐️⭐️⭐️⭐️⭐️ We had a wonderful stay! The location was perfect—close to everything we needed and in a neighborhood that had such a nostalgic, charming feel to it. The home itself was spotless and well cared for, and Keyonna was incredibly friendly and welcoming, which made the experience even better. It truly felt like a home away from home. We’d definitely stay here again!

The Bartlett Inn
Stayed here was a family event it was spacious with a well equipped kitchen . The neighborhood was very quiet and safe could walk for miles without seeing a car or busy street .

Beach Stay
Fantastic hosts and the place was spotless. The hosts thought of everything to make us feel at home.

Backyard Bungalow | Near Beach
Awesome hosts, great communication and very nice home

Quiet & Private, Comfy Beds, Fire Pit, & Bikes
Had a great girls weekend. It was peaceful and such a cute and quiet neighborhood. We would stay again. It’s located close to everything. The hot water was wonderful. 🤭

Family Holiday House. Events and Beaches Nearby
Great stay in Hampton! We were close to Captain George’s and Busch Gardens and the host was super helpful with our needs. Highly recommend if you’re traveling with a family and plan on staying awhile!
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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- Virginia Beach Oceanfront
- Carova Beach
- Resort Beach
- Corolla Beach
- Busch Gardens Williamsburg
- Buckroe Beach
- First Landing State Park
- Water Country USA
- Buckroe Beach and Park
- Kingsmill Resort
- Grandview Beach
- Currituck Beach Lighthouse
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- Jamestown Settlement
- Haven Beach
- Ocean Breeze Waterpark
- Sarah Constant Beach Park
- Virginia Beach National Golf Club
- Norfolk Botanical Garden
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- Bonito St. Public Beach Access
- Little Creek Beach
- Kiptopeke Beach
- Golden Horseshoe Golf Club