Pet-friendly holiday 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 house rentals

Top guest favourite
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 favourite
Home in Williamsburg
4.84 out of 5 average rating, 80 reviews

2 BR Family & Pet Friendly House - Williamsburg

DavidRating, 5 stars8 months ago
Charlene is a wonderful and very responsive host. This was our second time staying there when we visit Williamsburg. The location is great and only a few minutes from everything. The house was comfortable and had everything we needed to enjoy our week. We look forward to staying again in the future.
Guest favourite
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 favourite
Home in Moyock
4.86 out of 5 average rating, 113 reviews

Cozy Country Cottage

CrystalRating, 5 stars2 months ago
Nice quite location
Guest favourite
Home in Williamsburg
4.87 out of 5 average rating, 252 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 favourite
Home in Williamsburg
4.79 out of 5 average rating, 107 reviews

Historic Capitol Landing 3BR/2Ba home

JessicaRating, 5 stars2 weeks ago
This house and property is really special. It is a beautifully maintained and renovated old house, and has great views of the woods and the creek. We enjoyed evenings on the beautiful porch taking in the views. The house itself was well appointed and clean, with minimal/essential furnishings. A few other reviews did mention the noise from the highway and it is true—though it did not disturb us except for in the night, when an occasional loud truck might pass. It was a great base for my family and two small dogs to explore the local sights. Would definitely consider staying here again.
Guest favourite
Home in Newport News
4.9 out of 5 average rating, 123 reviews

Relax! Refreshing 3 bedroom Rancher

HeatherRating, 5 stars3 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!
Guest favourite
Home in Newport News
4.95 out of 5 average rating, 147 reviews

Fun Family Friendly 3 BR Home Close to Everything

KristaRating, 5 stars1 week ago
Our stay at this place was amazing for a family of 5. Joseph is a wonderful host. The place was exactly as described. Joseph responded extremely quick and helpful with every question we had prior to arrival. Though traffic did not work in our favor, he even let us know that we had an earlier checkin time should we had arrived earlier. He was even willing to work with us prior to booking for a slightly later checkout that our family needed. We felt at home having a bbq, bonfire, enjoying the massage chair, and playing several rounds of pool in this nice quiet neighborhood. Love that we were able to bring our dog along too! Would definitely stay here again!

Pet-friendly home rentals with a pool

Top guest favourite
Cottage in Norfolk
4.97 out of 5 average rating, 241 reviews

Villa Positano

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 favourite
Home in Corolla
4.91 out of 5 average rating, 22 reviews

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

BridgetRating, 5 stars5 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 favourite
Home in Portsmouth
4.94 out of 5 average rating, 108 reviews

Wooded Wonderland Miniature Golf Hot tub Pool

JustinRating, 5 stars4 days ago
We rented this property to visit the Virginia Tattoo and the beach and had a great trip!
Superhost
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 favourite
Guest house in Virginia Beach
4.72 out of 5 average rating, 115 reviews

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

John DavidRating, 5 stars4 weeks ago
He was so nice and everything!!
Guest favourite
Apartment 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.
Superhost
Home in Corolla
5 out of 5 average rating, 3 reviews

Pets OK, Private Pool, Hot Tub, Close to beach!

BarbaraRating, 5 stars7 months ago
Rental home was very clean with updated amenities and very close to the beach access. Beautiful pool and hot tub and of course our two dogs were allowed to accompany us on this vacation. A very memorable vacation. Definitely would choose this rental property again!

Private, pet-friendly home rentals

Guest favourite
Flat in Norfolk
4.86 out of 5 average rating, 35 reviews

Quaint Apartment By the Sea

AlexRating, 5 stars1 month ago
Clean, safe, easy to get to. Did the job we needed it to for the weekend.
Superhost
Home in East Ocean View
4.77 out of 5 average rating, 30 reviews

New! Clean + Affordable + Central!

AnaRating, 5 stars2 weeks 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!
Guest favourite
Home in Buckroe Beach
4.87 out of 5 average rating, 79 reviews

Home-Sweet-Home

IsmaelRating, 5 stars1 week ago
Nice clean home with everything you need in a great location close to the beach, enjoyed my stay and would definitely come back.
Superhost
Townhouse in East Ocean View
4.7 out of 5 average rating, 53 reviews

Relaxing on the bay/Relocation Special/Close beach

FaythRating, 5 stars2 months ago
The house was just what we asked for. Host was very responsive and very nice it snowed she had her people come out and shovel the walk way and porch of the house and even offered to clean our cars for us. The view is just amazing would definitely book again.
Top guest favourite
Cottage in Virginia Beach
4.95 out of 5 average rating, 387 reviews

Seaglass Cottage

LatchmiRating, 5 stars1 week ago
This spot was perfect for a few days right in Virginia Beach. We walked to the beach with our dog in the morning after we chose from several nearby spots for coffee and treats. The neighborhood was walkable, friendly, with things to do and see. The house itself is cozy, with everything you could want or need while traveling. A home away from home.
Top guest favourite
Home in Corolla
4.99 out of 5 average rating, 84 reviews

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

TriciaRating, 5 stars4 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.
Superhost
Campervan/Motorhome in Shawboro
4.77 out of 5 average rating, 22 reviews

S&S Hideaway

JanetRating, 5 stars6 months ago
This is a clean, cozy accommodation with lots of privacy. I loved it and would stay again!
Top guest favourite
Guest suite in Virginia Beach
4.98 out of 5 average rating, 147 reviews

Quiet Suite with Private Entrance

TravisRating, 5 stars1 week ago
If you have the option to book this place DO IT!!! This is one of the nicest places I’ve stayed and is an absolute gem in Virginia Beach. This was the most peaceful and secluded location I have ever seen in this area. You don’t find many places like this one. The bed was super comfortable and the unit was extremely spacious and cozy. I will definitely be looking to stay here again!

Quick stats about holiday 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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