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Pet-friendly vacation rentals in Chesapeake

Find and book unique pet-friendly homes on Airbnb

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Popular amenities for Chesapeake pet-friendly home rentals

Pet-friendly home rentals with a pool

Top guest favorite
An aerial view showcases a private beach beside a rectangular saltwater pool, surrounded by open grassy areas, perfect for outdoor activities. The landscape features a clear path leading from the property to the beach, with residential buildings on one side.
Cottage in Norfolk
4.97 out of 5 average rating, 241 reviews

Positano Villa

DanicaRating, 5 stars1 week ago
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.
Guest favorite
A three-story beach house is shown during sunset, with soft orange and pink hues in the sky. The exterior features multiple balconies and large staircases. A private pool is illuminated within a fenced area, surrounded by outdoor seating for relaxation.
Home in Corolla
4.91 out of 5 average rating, 22 reviews

LUX Oceanview•Heated Pool•2-Min Walk to Beach

BridgetRating, 5 stars6 days ago
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
Guest favorite
Aerial view of the property showcasing a fenced backyard with a sparkling blue pool surrounded by concrete. A seating area with lounge chairs and various floatation devices is visible beside the pool. Lush greenery from surrounding trees frames the scene, providing a sense of privacy.
Home in Portsmouth
4.94 out of 5 average rating, 108 reviews

Wooded Wonderland Miniature Golf Hot tub Pool

JustinRating, 5 stars5 days ago
We rented this property to visit the Virginia Tattoo and the beach and had a great trip!
Superhost
An aerial view of a private pool surrounded by a concrete patio. Several white lounge chairs are positioned around the pool, and a hot tub is visible near the corner. The water is clear, reflecting a vibrant blue, inviting relaxation.
Home in Corolla
4.83 out of 5 average rating, 48 reviews

The Moor House

MeganRating, 5 stars7 months ago
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!
Guest favorite
A spacious pool area is presented, featuring a large, inviting blue swimming pool with a built-in hot tub. Several lounge chairs and umbrellas provide shaded seating around the pool, while sliding glass doors lead to the interior of the house.
Guesthouse in Virginia Beach
4.72 out of 5 average rating, 115 reviews

POOL, Pool House, Hot Tub, Grill, 2 bedroom

John DavidRating, 5 stars1 month ago
He was so nice and everything!!
Guest favorite
The pool area is showcased with a clear blue water feature and adjacent Jacuzzi. Surrounding lounge furniture and a nearby seating arrangement provide space for relaxation. The backdrop features a low, stone wall and buildings with a warm color palette, enhancing the community atmosphere.
Condo in Sandbridge
4.87 out of 5 average rating, 233 reviews

Ocean Escape

DebbieRating, 5 stars1 week ago
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!
Superhost
Home in Virginia Beach
4.89 out of 5 average rating, 132 reviews

Beach Home, Upscale Croatan Resort + Private Pool

BetsyRating, 5 stars4 months ago
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.
Guest favorite
The open-concept living space is shown, featuring a comfortable seating area with a queen sleeper sofa and two armchairs. A wood-burning fireplace is adjacent to the large TV, while a dining table is set for six. Wall-to-wall glass doors provide views of the outdoors.
Condo in Williamsburg
4.95 out of 5 average rating, 123 reviews

Kingsmill 2bd2ba Condo on Golf Course 9th Fairway!

KristenRating, 5 stars1 month ago
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

Guest favorite
A charming blue beach house features a multi-level design with large windows that invite natural light. A spacious deck offers unobstructed views of the surrounding sandy landscape. Steps lead up to the entrance, enhancing accessibility to the home. Wild grasses frame the property.
Cottage in Corolla
4.88 out of 5 average rating, 146 reviews

Horses-Views-Dog Friendly-4WD Area

MaggieRating, 5 stars4 weeks ago
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.
Superhost
Home in Cape Charles
4.67 out of 5 average rating, 3 reviews

Hot Tub - Massage Chair - Golf Cart - Beach Gear

DanielleRating, 5 stars1 week ago
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!
Guest favorite
A private hot tub is enclosed within a screened area, featuring steps for easy access. A plastic chair is located nearby, and the walls are finished in soft yellow, providing a bright and airy atmosphere. Natural light filters through the surrounding screens, enhancing the space.
Townhouse in Corolla
4.87 out of 5 average rating, 31 reviews

4 bedroom T/H, Hot tub, short walk to beach

StephanieRating, 5 stars2 weeks ago
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!
Top guest favorite
Home in Corolla
4.99 out of 5 average rating, 84 reviews

Coral Cove- Backyard-Hot Tub-Walk to beach-Dogs ok

TriciaRating, 5 stars5 days ago
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.
Guest favorite
A three-story beach house is nestled amid greenery, featuring a light blue exterior and a front porch with outdoor seating. A gravel path leads to the house, surrounded by lush grass and flowering plants. Sun umbrellas and lounge chairs are visible in the yard.
Home in Corolla
4.86 out of 5 average rating, 96 reviews

MillerLight

LeaRating, 5 stars2 weeks ago
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.
Guest favorite
Cabin in Smithfield
4.89 out of 5 average rating, 140 reviews

Wickline Cabin on Moon Creek

DanRating, 5 stars1 month ago
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!!
Guest favorite
The three-story beach house, painted in shades of blue, features multiple decks and a wide staircase leading to the entrance. Lush greenery surrounds the property, enhancing the welcoming exterior. A white vehicle is parked in the driveway, adding to the home-like atmosphere.
Home in Corolla
4.92 out of 5 average rating, 13 reviews

Haley Kona Paradise 4 BR|Hot Tub|2 Dogs|7 beds

EmmaRating, 5 stars9 months ago
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!
Guest favorite
A new six-person hot tub is featured, equipped with 48 jets and two pumps. Water is illuminated, and a cover is positioned nearby. A wooden fence provides privacy around the hot tub, creating a secluded outdoor space for relaxation.
Cottage in Norfolk
4.91 out of 5 average rating, 109 reviews

Cozy Cottage - NEW hot tub, dogs OK, fenced yard

GraceRating, 5 stars5 days ago
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

Top guest favorite
A cozy living space features a green armchair with a patterned cushion, along with a small dining table and four chairs. The kitchen area is visible, showcasing wooden cabinetry and modern appliances. Natural light floods in through blinds on the windows, enhancing the inviting atmosphere.
Home in Virginia Beach
4.93 out of 5 average rating, 42 reviews

Cozy and Modern Beach House

ErikaRating, 5 stars1 week ago
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.
Guest favorite
A ranch-style home is presented, featuring a light-colored exterior with black shutters and a welcoming blue front door. A concrete pathway leads up to the entrance, surrounded by a grassy lawn. Mature trees and a wooden fence are visible in the background.
Home in Buckroe Beach
4.88 out of 5 average rating, 80 reviews

Home-Sweet-Home

ThomasRating, 5 stars2 days ago
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.
Top guest favorite
A panoramic view showcases a serene riverfront setting with lush green grass and a fenced backyard. A fire pit with seating is positioned in the foreground, while docks and a pier extend into the calm water, framed by trees and grasses along the shore.
Home in Portsmouth
4.96 out of 5 average rating, 109 reviews

The Captains Cottage KAYAK/FISH on Elizabeth River

ReynaldoRating, 5 stars1 month ago
Janine was very responsive and accommodating. Would stay here again.
Guest favorite
A living area features a dark sectional sofa with a decorative pillow and a coffee table with a patterned surface. A soft area rug covers the hardwood floor. Light flows in through glass doors that lead to an outdoor space, while ceiling fans provide additional comfort.
Home in East Ocean View
4.91 out of 5 average rating, 188 reviews

@Whit’s End? Come in and Relax

NicholeRating, 5 stars1 month ago
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!
Guest favorite
The covered porch features a seating area with two white chairs and a small table, surrounded by hanging flower baskets. The front door is framed by large windows, allowing natural light into the space. Lush trees are visible in the background.
Home in Moyock
4.86 out of 5 average rating, 113 reviews

Cozy Country Cottage

CrystalRating, 5 stars2 months ago
Nice quite location
Guest favorite
A spacious outdoor patio area is visible, featuring a combination of stone paving and green grass. Two turquoise chairs and a white table provide seating options. A wooden fence surrounds the area, offering privacy, while various plants add natural beauty to the setting.
Home in Norfolk
4.84 out of 5 average rating, 153 reviews

Picture Worthy Spanish Style Casita! 2 BR/ 2BA

ZelaRating, 5 stars3 weeks ago
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!
Guest favorite
A dining area is set with a round table surrounded by eight upholstered chairs. The walls are painted in a calming blue, and large windows allow natural light to fill the space. In the background, a kitchen can be seen, featuring a modern layout.
Home in Williamsburg
4.87 out of 5 average rating, 253 reviews

Bamboo Bungalo Duplex Near Busch Gardens

LindsayRating, 5 stars2 weeks ago
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!!!
Guest favorite
A light-colored leather sofa is positioned in a cozy seating area, accompanied by two matching side tables with soft green lamps. A decorative clock is mounted on the wall, and a coffee table with magazines sits in the center, enhancing the inviting space.
Home in Newport News
4.9 out of 5 average rating, 124 reviews

Relax! Refreshing 3 bedroom Rancher

HeatherRating, 5 stars4 weeks ago
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

Destinations to explore