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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
A private saltwater pool is depicted, surrounded by a spacious patio area. The pool's clear blue water is inviting, with a ladder providing easy access. Lush greenery and a white fence frame the background, enhancing the serene ambiance near the Chesapeake Bay.
Cottage in Bayview
4.97 out of 5 average rating, 248 reviews

Villa Positano

Emily RobbinsRating, 5 stars1 week ago
Wow! We had such a wonderful time at Mr. Roger’s place! The house was just beautiful and clean. The weather caused us not to be able to enjoy the pool and beach, but thats no fault of Mr. Roger! We will definitely book here again. Thanks again!
Top guest favorite
A cozy bedroom features a king-size bed with crisp white linens and decorative pillows. A large window offers a view of a green space beyond, with a sitting area including a chair and small table. A 50" TV and coffee station are positioned on a wooden dresser.
Condo in Williamsburg
4.94 out of 5 average rating, 163 reviews

Kingsmill 1bed/1ba on Golf Course 9th Fairway

ShelmanRating, 5 stars2 weeks ago
The stay was perfect for what we needed during our stay in Williamsburg. It was nice to walk to the nearby marina and restaurant in the evenings.
Guest favorite
A resort pool area is depicted, featuring a vibrant blue swimming pool surrounded by lounge chairs. The brick building in the background is characterized by rows of windows and a variety of green umbrellas, set against a clear blue sky.
Apartment in Williamsburg
4.85 out of 5 average rating, 169 reviews

Westgate Historic Williamsburg One Bedroom

JordanRating, 5 stars2 months ago
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!
Top guest favorite
A private pool area features comfortable lounge chairs with floral cushions, surrounded by a clean concrete patio. A screened-in porch is visible in the background, with two inviting chairs for relaxing. The fenced yard offers additional privacy and space for outdoor enjoyment.
Home in Virginia Beach
4.94 out of 5 average rating, 63 reviews

Paint The Beach Pink! Full House | Private Pool

MarybethRating, 5 stars2 weeks ago
Our stay was amazing and the house fit our needs perfectly. It was super clean and decorated beautifully. The walk to the beach was quick and easy and the location of the house is nice and quiet and away from the crowds and traffic! It's also a quick drive to the convention center and many restaurants and shops. It was also nice not having to pack so much extra beach stuff to bring along (chairs, wagon, etc) because they had it all available to use. My kids loved the pool, playing Jenga on the porch and corn hole outside. My husband and older son took the bikes out for a spin too. We had a few questions before and during the stay and Bradley was very responsive and helpful every time. We will definitely stay here again if we head back to Virginia Beach next year! Thank you for an amazing stay!!!
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, 118 reviews

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

MichaelRating, 5 stars1 month ago
Ron was great with communication. And the place was exactly as described.
Top guest favorite
The image captures a serene beach scene at sunset, with soft waves lapping at the shore. A figure playfully splashes in the water, while another stands in the distance. The sky displays vibrant shades of orange and pink, reflecting on the water's surface.
Home in East Ocean View
4.98 out of 5 average rating, 54 reviews

The Seaglass Cottage

LandrumRating, 5 stars4 days ago
Nancy was super kind and friendly during our stay! She gave a great seafood restaurant recommendation that was both delicious, affordable, and right down the road. The cottage is quaint and a charming place to stay for a young couple. We had plenty of space, and the cottage was accurately represented by the photos available. We would definitely stay here again if we are in the area!
Top guest favorite
A spacious backyard features a saltwater inground pool surrounded by manicured grass. A two-level deck is visible with patio furniture, offering comfortable seating options. The exterior of the two-story house is seen in the background, under a partly cloudy sky.
Home in Suffolk
4.85 out of 5 average rating, 93 reviews

Perfect Getaway!

JimRating, 5 stars3 days ago
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!
Top guest favorite
An aerial view of a beach cottage reveals its elevated structure surrounded by natural foliage. A swimming pool is visible on the right, while a spacious deck with hammocks provides an inviting outdoor space. The cottage features a light green exterior with white accents.
Home in Carova Beach
5 out of 5 average rating, 19 reviews

Splash of Lime Carova 4x4 Beach Cottage

MichaelaRating, 5 stars2 weeks ago
We absolutely loved A Splash of Lime! The house was great for us and our 2 dogs! The kitchen had everything we could have asked for. The pool and hot tub were also a huge plus. Easy walk to the beach and you may even pass a few wild horses on the way! Thank you, Martin, for an excellent vacation home!

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 Carova Beach
4.89 out of 5 average rating, 150 reviews

Horses-Views-Dog Friendly-4WD Area

RamonaRating, 5 stars2 weeks ago
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.
Guest favorite
A hot tub is set on a concrete patio, surrounded by lush green grass. Wooden steps lead up to the deck area, which features seating and a sandy play area. The backyard is framed by wooden fencing, providing a private outdoor retreat.
Home in Willoughby Spit
5 out of 5 average rating, 63 reviews

Stylish Beach House, Hot Tub, Pet Friendly

AdamRating, 5 stars1 week ago
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.
Guest favorite
A two-story beach house features a light blue exterior with a spacious deck. A private pool is enclosed by a white fence, providing an area for relaxation. The surrounding landscape showcases sandy terrain and beach access, emphasizing a pet-friendly environment.
Home in Carova Beach
5 out of 5 average rating, 29 reviews

Aloha Beaches OBX

DavidRating, 5 stars1 week ago
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!
Superhost
The beach house is showcased in the evening light, featuring a three-story structure with multiple balconies. Sturdy steps lead to the entrance, framed by surrounding trees. Soft lighting illuminates the exterior, creating a welcoming presence against the night sky.
Home in Carova Beach
5 out of 5 average rating, 4 reviews

Salty Breeze 4x4 section

RebeccaRating, 5 stars9 months ago
Much needed retreat and the ponies showed off for us!!! Sunrise in Carova is like no other!!!
Guest favorite
A spacious hot tub is situated on the deck, overlooking the vast expanse of the water. The tranquil surface ripples under the cloudy sky, creating a serene ambiance. A black lounge chair is positioned nearby, inviting relaxation while enjoying the captivating views.
Home in Buckroe Beach
4.96 out of 5 average rating, 79 reviews

Exclusive Beachfront Home w/ 180° Views & Hot Tub!

KathleenRating, 5 stars1 week ago
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.
Guest favorite
A charming log cabin features a front porch with a wooden railing and seating area. Surrounding the cabin are landscaped flower beds, tall trees, and a well-kept lawn. The cabin's rustic design is complemented by its natural setting, offering a peaceful view of the waterfront.
Cabin in Smithfield
4.89 out of 5 average rating, 142 reviews

Wickline Cabin on Moon Creek

AshleighRating, 5 stars1 month ago
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!
Superhost
A vibrant outdoor space features a private saltwater pool surrounded by lounge chairs and umbrellas. An orange daybed sits next to the water, while a colorful mural with the text 'SANDBRIDGE, VA' adds a cheerful touch to the backdrop.
Home in Sandbridge
4.85 out of 5 average rating, 48 reviews

Designer 7BR w/ Pool and Hot Tub. Pets welcome!

RobertRating, 5 stars2 days ago
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.
Top guest favorite
The house is situated among lush greenery, featuring multiple levels with extensive balconies. A private pool is visible in the foreground, while the sunset casts a warm glow across the sky, enhancing the serene setting. Adjacent properties offer a glimpse of the local architecture.
Home in Carova Beach
4.98 out of 5 average rating, 64 reviews

Carova beach home w/ ocean view, pool & hot tub!

KelleyRating, 5 stars2 weeks ago
Our stay at this place was absolutely incredible! The highlight was undoubtedly the breathtaking 360-degree views that greeted us every morning and evening. It was truly a slice of paradise! The property’s dog-friendly policy was a big plus for us, allowing our furry friends to join in on the vacation fun! The accommodation was not only pet-friendly but also exceptionally well stocked. From kitchen essentials to beach gear, everything we needed was conveniently available, making our stay comfortable and stress-free. We couldn’t have asked for a better retreat. The combination of stunning views, pet-friendly amenities and thoughtful provisions made our stay unforgettable! We will definitely be staying here again in the future!

Pet-friendly house rentals

Guest favorite
An aerial view captures the surrounding area, featuring a mix of residential homes and lush greenery with sandy beach access visible. The Chesapeake Bay Bridge-Tunnel stretches toward the horizon over calm waters, providing a scenic backdrop to the coastal neighborhood.
Home in Chic's Beach
4.96 out of 5 average rating, 131 reviews

Water Oaks at Chic's Beach

NewRating, 5 stars1 month ago
We stayed here over spring break with our young kids. Tommy and Janet were very friendly and responsive. The location is great! Literally right across the street from the beach, and close to our all time favorite brewery :) we'd love to come back again in the summer months!
Guest favorite
A spacious living room features a comfortable sectional sofa, a wooden entertainment center with a large TV, and a decorative console table. Light-colored walls complement the area rug, and framed artwork adds interest. A staircase is visible, leading to the upper level.
Home in Norfolk
4.92 out of 5 average rating, 137 reviews

3 bedroom private home a block from the beach!

JessicaRating, 5 stars1 week ago
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
Guest favorite
A light-filled living area features a comfortable sectional sofa and a coffee table centered on a textured rug. Adjacent, a dining table accommodates several chairs, while a wall-mounted television is positioned above a decorative fireplace. Windows provide views of the outdoor space.
Home in Chesapeake
4.92 out of 5 average rating, 38 reviews

Beautiful home in Chesapeake

MelindaRating, 5 stars3 weeks ago
This home was very clean, accurate to the photos, and very comfortable. We really appreciated the fully fenced in backyard for our dog. The location was close to a mall, restaurants, supermarkets, and Virginia Beach. The neighborhood was very family friendly and safe. We would definitely stay here again if in the area.
Guest favorite
A classic Cape Cod home is surrounded by well-maintained greenery. The brick exterior is complemented by a gravel pathway leading to the front steps. A concrete driveway provides access to an attached garage, while flags are displayed on the front porch, enhancing the home's welcoming appearance.
Home in Portsmouth
5 out of 5 average rating, 23 reviews

The Bartlett Inn

NatalieRating, 5 stars5 days ago
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 .
Top guest favorite
A modern living room is showcased with light hardwood flooring and elegant furnishings. A large flat-screen TV is mounted on a marble feature wall, while a plush sofa is positioned nearby. Natural light flows in through large windows adorned with sheer curtains.
Home in Norfolk
5 out of 5 average rating, 46 reviews

Beach Stay

DeannaRating, 5 stars1 week ago
Immediately felt right at home. Short drive to the Navel Base and short walk to OceanView Beach. Well equipped kitchen as well as every convenient that I typically have at home. In my opinion nothing was forgotten, you have everything needed. Nick and Marjana are fantastic hosts!!
Top guest favorite
A circular fire pit is surrounded by stone blocks, with logs burning brightly in the center. Smoke gently rises into the air, and the area is bordered by grass and a quiet wooded backdrop.
Home in Surry
4.99 out of 5 average rating, 105 reviews

Surry Homeplace

ShellyRating, 5 stars2 weeks ago
We really enjoyed our stay! Check-in was easy and they left the lights on for us, so it was easy to find in the dark! We were looking for a place to stay near the Surry Seafood Marina and this was very convenient. The fenced in back yard was so great to have for our dogs! They loved all of the different terrains within the fence. The refrigerator and freezer are a nice size to bring your own food and make your own meals. And there is a Dollar Tree, Dollar General, and Family Dollar right around the corner if you forget anything. We will be renting this place, 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
4.86 out of 5 average rating, 262 reviews

Bamboo Bungalo Duplex Near Busch Gardens

StevenRating, 5 stars3 days ago
The house was very comfortable and well furnished. it was very conveniently located for our exploration of Yorktown Battlefield and Jamestown Settlement.
Guest favorite
The kitchen features a modern design with white cabinetry and stainless steel appliances. A large island provides seating for several guests, complemented by industrial-style pendant lighting. Brick accents add warmth to the space, while a dining area is also visible, designed for casual meals.
Home in Portsmouth
4.93 out of 5 average rating, 27 reviews

Quiet & Private, Comfy Beds, Fire Pit, & Bikes

DeidraRating, 5 stars2 weeks ago
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. 🤭

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