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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

Guest favorite
A spacious sleeping area features a white metal bed with a striped blue and white comforter accented by vibrant pillows. Light floods the room through a large window, with sheer white curtains allowing for natural light. A ceiling fan and modern wall sconces provide additional illumination.
Home in Sandbridge
4.99 out of 5 average rating, 70 reviews

Pool Opens May 2nd at The Golden Hour

AshleyRating, 5 stars7 months ago
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!
Top guest favorite
A colorful living area features a green sofa adorned with bright cushions. A round wooden coffee table is positioned in front, displaying a stack of books and a small decorative item. The walls are painted in vibrant colors, creating a cheerful atmosphere.
Home in Virginia Beach
4.93 out of 5 average rating, 54 reviews

Paint The Beach Pink! Full House | Private Pool

MelissaRating, 5 stars1 week ago
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!
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 stars3 weeks ago
He was so nice and everything!!
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, 97 reviews

Gorgeous Vacation House

Phillip HakyeonRating, 5 stars1 month ago
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.
Guest favorite
An outdoor deck area is visible, featuring a wooden table surrounded by six chairs, a grill nearby, and two lounge chairs positioned for relaxation. The space is enclosed by a wooden fence, with greenery providing a natural backdrop.
Place to stay in Virginia Beach
4.93 out of 5 average rating, 76 reviews

North End Home with pool, beach & state park.

MelissaRating, 5 stars7 months ago
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.
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, 87 reviews

Perfect Getaway!

PatriciaRating, 5 stars1 month ago
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.
Superhost
Home in Virginia Beach
4.89 out of 5 average rating, 132 reviews

Beach Home, Upscale Croatan Resort + Private Pool

BetsyRating, 5 stars3 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, 122 reviews

Kingsmill 2bd2ba Condo on Golf Course 9th Fairway!

KristenRating, 5 stars3 weeks 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, 145 reviews

Horses-Views-Dog Friendly-4WD Area

MaggieRating, 5 stars2 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.
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, 105 reviews

Wooded Wonderland Miniature Golf Hot tub Pool

KeelinRating, 5 stars1 day ago
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.
Superhost
A multi-level house is set against a clear blue sky, featuring a light-colored exterior with multiple windows. A paved pathway leads to the entrance, lined with greenery, while a sandy area extends alongside, reflecting the property's coastal location.
Home in Corolla
4.83 out of 5 average rating, 48 reviews

The Moor House

MeganRating, 5 stars6 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 wide, sandy beach is outlined by spacious condos in soft pastel colors against a clear blue sky. Fishing rods are positioned in the sand near beach carts, indicating a relaxed atmosphere. Waves gently lap at the shoreline, creating a tranquil coastal setting.
Condo in Sandbridge
4.87 out of 5 average rating, 232 reviews

Ocean Escape

DebbieRating, 5 stars2 days 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!
Guest favorite
Cabin in Smithfield
4.88 out of 5 average rating, 139 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
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, 108 reviews

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

MonicaRating, 5 stars3 weeks ago
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! 💯
Superhost
A hot tub with bubbling water is illuminated by a warm pendant light. The area is enclosed by wooden posts and a privacy fence, with hints of colorful decor in the background set against a serene atmosphere.
Home in Sandbridge
4.86 out of 5 average rating, 43 reviews

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

BrandonRating, 5 stars6 days ago
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!
Guest favorite
A sunset casts warm hues over the calm waters of the bay, with silhouettes of a shaded gazebo and a hammock. Weathered pilings and a single bird in flight can be seen against the vibrant sky, enhancing the tranquil atmosphere.
Home in Knotts Island
4.95 out of 5 average rating, 111 reviews

Island Lotus Yoga & Spa

CallieRating, 5 stars5 days ago
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

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, 129 reviews

Water Oaks at Chic's Beach

ClaireRating, 5 stars1 month ago
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!
Superhost
Home in East Ocean View
4.88 out of 5 average rating, 60 reviews

Walk to Beach! Large Fenced Yard, Dogs Welcome!

JasminRating, 5 stars3 months ago
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.
Superhost
Home in East Ocean View
4.82 out of 5 average rating, 28 reviews

New! Clean + Affordable + Central!

AnaRating, 5 stars1 week ago
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!
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 stars4 days 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.
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 stars3 weeks 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 stars1 month 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 stars2 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!

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