
Pet-friendly vacation 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.
Vacation rentals for every style
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Popular amenities for Chesapeake pet-friendly home rentals
Pet-friendly home rentals with a pool

Pool Opens May 2nd at The Golden Hour
We really enjoyed staying at the golden hour! The hosts were very responsive and helpful! They had sound machines in every bedroom which if you have kids is a big deal. The toys and kids activities there were a big hit! The pools are pristine and the whole outdoor area is very nice! Very short walk to beach which was also convenient! They literally thought of everything, if you forgot something chances are they had it! Definitely recommend staying here if you have children and want a nice low key place to stay!

Paint The Beach Pink! Full House | Private Pool
This is our second stay at Bradley’s. It feels like our home away from home. Bradley is a great host and his place is lovely, comfortable, and a great location. We will definitely be back!

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

Gorgeous Vacation House
What a fantastic place! LARGE and clean house, best bang for your buck, and 5 min walk to the beach. Couldn't ask for a better place to stay around the area. my wife and my dog also loved the home. 11/10, would absolutely come back for another stay.

North End Home with pool, beach & state park.
Lovely home in a great location . Very clean, nicely decorated, well appointed and cozy with a beautiful pool area. John-Leon is a great host and was very responsive with any questions I had. Would definitely stay here again.

Perfect Getaway!
We met Sabrina upon our arrival and she was very kind and caring and made us feel right at home. We were present with a lovely home to stay in and enjoy our family. Thank you, Sabrina.

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.

Wooded Wonderland Miniature Golf Hot tub Pool
We travelled with kids, the backyard was like a paradise for them. This house was convenient to activities and shopping around Norfolk and was an awesome place to return to at the end of a full day of exploring.

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!

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!

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!!

Cozy Cottage - NEW hot tub, dogs OK, fenced yard
We had a wonderful stay here! The house was clean & had everything we could have needed for the week, even a few things we didn't think of ourselves. The hot tub was amazing. Highly recommend staying here! 💯

Designer 7BR w/ Pool and Hot Tub. Pets welcome!
Great location - a walkable block from the beach. We had a great time and the house was large with ample space for our families. We had 5 kids with us (3-7) and it was super comfortable. The house was fantastic! The only downside was they were paving roads that week all throughout. The town was hard to get out of as a result. Upside is for anyone staying, you’ll have great newly paved roads!

Island Lotus Yoga & Spa
Stop searching for a place and book this one. Right now. If you're looking for a tranquil oasis to get away from it all, this is the property for you. The house itself was relaxing and spectacular. I never wanted to leave the sunroom! Yoga with Mari was so much fun and we even got to visit baby goats on the farm with Kristen. The only warning I have is- be prepared to never want to leave. I'm already excited to return! There were fresh eggs left for us, as well as freshly baked blueberry bread. The soap from the goat farm was divine! Be sure to spend plenty of time in the hot tub and get out and look at all of the stars. Nature is truly beautiful in this place. If I could give it ten stars, I would. Thank you, Quang and Mari for such an incredible stay!
Pet-friendly house rentals

Water Oaks at Chic's Beach
I could not recommend this place and these hosts enough! The place was warm and welcoming and I absolutely love the location. A very peaceful neighborhood with easy bay access. The hosts were amazing and responsive. The house had some maintenance problems but at no fault of theirs…just typical house problems and they handled everything extremely well and we were not inconvenienced at all! Also our dog loved the place and they were stocked will all the dog necessities which was very helpful!

Walk to Beach! Large Fenced Yard, Dogs Welcome!
This was an AMAZING SPACE!!. Great floorplan, great amenities, and it will be a perfect space for your family. It was clean, spacious, and had everything we needed and more.. The beds, pillows, and linens were very comfortable, and the kitchen had PLENTY of tableware and utensils for the family. My family and I will certainly return.

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!

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.

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!
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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