Pet-friendly holiday rentals in Chesapeake

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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 Norfolk
4.84 out of 5 average rating, 153 reviews

Picture Worthy Spanish Style Casita! 2 BR/ 2BA

ZelaRating, 5 stars4 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 favourite
Home in Williamsburg
4.87 out of 5 average rating, 254 reviews

Bamboo Bungalo Duplex Near Busch Gardens

AgnieszkaRating, 5 stars1 day ago
Fantastic place! Very close to Colonial Williamsburg. Place is a bit secluded which is great after a full day of sightseeing. Nice to come back to a little oasis. Very clean, well stocked. Host very responsive, pleasant and flexible. Recommend it highly!
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, 124 reviews

Relax! Refreshing 3 bedroom Rancher

HeatherRating, 5 stars1 month 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!

Pet-friendly home rentals with a pool

Top Guest favourite
Cottage in Norfolk
4.97 out of 5 average rating, 242 reviews

Villa Positano

MichelleRating, 5 starstoday
💯 your money worth and the interaction with Roger was amazing .good location good fishing right of tha beach . safe and clean environment and gorgeous views
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 stars1 week 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 stars1 week ago
We rented this property to visit the Virginia Tattoo and the beach and had a great trip!
Guest favourite
Home in Corolla
4.91 out of 5 average rating, 11 reviews

Sound View! Dogs OK! Pool&Spa, Sound&Beach Access

DoreenRating, 5 stars6 months ago
Lisa was absolutely an incredible host! The home was beautiful and it was in a quiet family friendly neighborhood which we loved! It truly was perfect but I do think the beds could use a little updating they are a bit hard and unsupportive but other than that it was an amazing stay and we would love to come back again!
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
Home in Suffolk
4.84 out of 5 average rating, 88 reviews

Perfect Getaway!

KimRating, 5 stars2 weeks ago
First off! Sabrina is one of the most nicest, considerate, kind-hearted, caring , responsive host that I’ve come across. Her house is BEAUTIFUL, clean, spacious and cozy. The bed that I splept in was so comfortable! The house is technology ready!! “SMART HOUSE” “ absolutely loved it!! Beautiful pool and backyard. I enjoyed my stay! 😁
Guest favourite
Condo in Sandbridge
4.87 out of 5 average rating, 233 reviews

Ocean Escape

DebbieRating, 5 stars2 weeks 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.

Private, pet-friendly home rentals

Guest favourite
Apartment 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
4.88 out of 5 average rating, 81 reviews

Home-Sweet-Home

ThomasRating, 5 stars5 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 favourite
Cottage in Virginia Beach
4.95 out of 5 average rating, 388 reviews

Seaglass Cottage

AllisonRating, 5 stars2 days ago
We came here for a quick few nights and it was absolutely perfect. Susan was a great host. It was in a great location and there was lots in walking distance to do! We had a great time and would definitely come back and stay here again.
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 stars1 week 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/RV in Shawboro
4.77 out of 5 average rating, 22 reviews

S&S Hideaway

JanetRating, 5 stars7 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, 148 reviews

Quiet Suite with Private Entrance

CallistaRating, 5 starstoday
5 stars. I will be staying here again when we come back to Virginia Beach!
Top Guest favourite
Home in East Ocean View
4.99 out of 5 average rating, 79 reviews

East Beach Bungalow, 1 block to the beach!

JackieRating, 5 stars4 weeks ago
Adorable place - great location and plenty of parking.

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

  • Wi-Fi availability

    270 properties include access to Wi-Fi

Destinations to explore