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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 Norfolk
4.97 out of 5 average rating, 250 reviews

Villa Positano

RhondaRating, 5 stars1 week ago
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!!!
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
4.95 out of 5 average rating, 164 reviews

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

AmyRating, 5 stars4 days ago
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!
Superhost
A private pool is surrounded by a spacious patio area, featuring lounge chairs and shaded seating. The clear water reflects the blue sky, while a white fence offers privacy. Decorative elements such as lights and tropical decor enhance the leisure space.
Home in Norfolk
5 out of 5 average rating, 4 reviews

The Blue Octopus~Private Pool~HotTub~Beach~FirePit

AngelaRating, 5 stars5 days ago
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.
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, 65 reviews

Paint The Beach Pink! Full House | Private Pool

WyattRating, 5 stars2 days ago
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!
Guest favorite
A well-appointed backyard patio features a dining table accompanied by several chairs. A swimming pool is situated nearby, surrounded by a wooden fence and trees. Sunlight illuminates the area, creating a bright and inviting outdoor space.
Home in Norfolk
4.95 out of 5 average rating, 104 reviews

Gorgeous Vacation House

AlexisRating, 5 stars1 week ago
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!
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
4.84 out of 5 average rating, 94 reviews

Perfect Getaway!

JimRating, 5 stars1 week 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!
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, 237 reviews

Ocean Escape

JamesRating, 5 stars4 days ago
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

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
4.89 out of 5 average rating, 150 reviews

Horses-Views-Dog Friendly-4WD Area

RamonaRating, 5 stars3 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 Norfolk
5 out of 5 average rating, 63 reviews

Stylish Beach House, Hot Tub, Pet Friendly

AdamRating, 5 stars2 weeks 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 Corolla
5 out of 5 average rating, 30 reviews

Aloha Beaches OBX

DavidRating, 5 stars2 weeks 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!
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, 80 reviews

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

KathleenRating, 5 stars2 weeks 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.
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 Corolla
5 out of 5 average rating, 20 reviews

Splash of Lime Carova 4x4 Beach Cottage

KristenRating, 5 stars4 days ago
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.
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!
Guest favorite
A cozy living area is furnished with two light blue sofas and a light-colored area rug. A ceiling fan hangs above, providing air circulation. In the background, a dining area with a wooden table and blue chairs is visible through an arched entryway, framed by bright natural light from window blinds.
Cottage in Norfolk
4.91 out of 5 average rating, 113 reviews

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

NinaRating, 5 stars1 month ago
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.
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 stars1 week 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.

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, 132 reviews

Water Oaks at Chic's Beach

EmmaRating, 5 stars1 month ago
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!
Superhost
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, 138 reviews

3 bedroom private home a block from the beach!

JessicaRating, 5 stars2 weeks 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
4.9 out of 5 average rating, 40 reviews

Beautiful home in Chesapeake

MelissaRating, 5 stars1 week ago
⭐️⭐️⭐️⭐️⭐️ 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!
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, 24 reviews

The Bartlett Inn

NatalieRating, 5 stars2 weeks 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 .
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, 47 reviews

Beach Stay

TylerRating, 5 stars2 weeks ago
Fantastic hosts and the place was spotless. The hosts thought of everything to make us feel at home.
Guest favorite
An outdoor seating area is presented on a wooden deck, featuring a table surrounded by rattan chairs and an additional bench. Colorful floral murals embellish the wooden fence, while a black umbrella offers shade. Lush grass surrounds the area, creating a serene environment.
Home in Norfolk
5 out of 5 average rating, 7 reviews

Backyard Bungalow | Near Beach

JoshuaRating, 5 stars5 days ago
Awesome hosts, great communication and very nice home
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, 29 reviews

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

DeidraRating, 5 stars3 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. 🤭
Guest favorite
A spacious home is depicted with a welcoming front porch featuring a gentle ramp for accessibility. Lush greenery surrounds the exterior, and the peaceful atmosphere is enhanced by the colorful sunset sky. The house showcases a combination of brick and siding with large windows.
Home in Hampton
4.84 out of 5 average rating, 362 reviews

Family Holiday House. Events and Beaches Nearby

FlemmingRating, 5 stars1 day ago
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

Destinations to explore