
Pet-friendly holiday rentals in Chesapeake
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Top-rated pet-friendly home rentals in Chesapeake
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Popular amenities for Chesapeake pet-friendly home rentals
Pet-friendly house rentals

Walk to Beach! Large Fenced Yard, Dogs Welcome!
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.

Home-Sweet-Home
My family came into town to take our kiddos to Busch Gardens for spring break, and Ford’s place in Hampton was perfect. Quiet neighborhood right next to a big school with open fields to run your dogs, with easy access to restaurants and amenities just minutes down the road. The shower water pressure was fantastic and the hot water never ran out. Comfortable and cozy stay, exactly what we needed. Thank you! Would totally stay again.

The Captains Cottage KAYAK/FISH on Elizabeth River
Janine was very responsive and accommodating. Would stay here again.

@Whit’s End? Come in and Relax
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!

The Moor House
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!

Cozy Country Cottage
Nice quite location

Picture Worthy Spanish Style Casita! 2 BR/ 2BA
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!

Bamboo Bungalo Duplex Near Busch Gardens
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!!!
Pet-friendly home rentals with a pool

Villa Positano
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.

LUX Oceanview•Heated Pool•2-Min Walk to Beach
We really enjoyed our time at OVR Beach House. The location is perfect—just a short walk to the beach, which made it so easy to relax and enjoy the ocean. The house was large very clean, the beds were super comfortable, and everything was well taken care of. Shilpa was a great host, always responsive and helpful. We’d definitely love to come back! Thanks for making our vacation special.

Wooded Wonderland Miniature Golf Hot tub Pool
I can’t recommend this Airbnb enough! If you’re looking for comfort, style, and an unbeatable location paired with a wonderful host, look no further. I can't wait to return!

Westgate Historic Williamsburg One Bedroom
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!

Perfect Getaway!
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.

Ocean Escape
We've stayed at this resort before but this is the first in this condo. It was easy to get our packed and get checked in. We loved the condo, the view is great, the beds comfortable, and clean.

Beach Home, Upscale Croatan Resort + Private Pool
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.

Kingsmill 2bd2ba Condo on Golf Course 9th Fairway!
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!
Private, pet-friendly home rentals

New! Clean + Affordable + Central!
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!

Private and Cozy Bungalow Loaded with Amenities
Great stay with responsive, kind hosts. Accommodations were as described and very clean! Would stay there again!

Relaxing on the bay/Relocation Special/Close beach
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.

Seaglass Cottage
This house was fantastic and met all of our needs. Very clean and convenient to so many great places to eat. The vibe district is awesome. Highly recommend.

Coral Cove- Backyard-Hot Tub-Walk to beach-Dogs ok
Hot tub was wonderful and clean. The house was very baby friendly, lots of room and little clutter. Loved that a high chair and pack and play were available, it really helped make the vacation spot feel like home.

Quiet & Private, Comfy Beds, Fire Pit, & Bikes
We were locals needing a place to stay while our home was on the market, and this was our perfect home away from home. The decor and furnishings are modern and tasteful. It's conveniently located near highways, Coast Guard Base Portsmouth, and a nice Harris Teeter three minutes away for groceries. We appreciated that it was pet-friendly and had a fenced yard for our dog. We also enjoyed walking our dog in the subdivision across the street. We took full advantage of the LG washer and dryer, the comfy couch and huge Roku TV (easy to log into our streaming accounts), and a working kitchen with nice seating. Excellent local take-out spots are just three minutes away, too! The host was very proactive, friendly, and responsive with all communication. Kitchen supplies, dinnerware, etc. for cooking and eating are a bit sparse, so we supplemented with our own from home. The street the house is located on can be busy, and you can hear traffic inside. Check-in and check-out were a breeze.

Chesapeake Retreat
Susan made our stay wonderful. The camper was immaculate and cozy. Susan and Ed went beyond to make our stay comfortable. They assisted us to obtain a tire when ours went flat and even helped when I forgot a shirt for my husband to wear with his suit for a wedding. It was a retreat. The fish pond and birds were so relaxing. We highly recommend this location and Susan and Ed are excellent hosts.

Ultimate Cabin Farm Stay Cape Charles
From the greeting of Buddy and farm friends upon arrival it was made known that we were welcomed and invited into their home ! It offered exactly what I was seeking for our getaway trip - Peace, Relaxation and Nature! It’s a great escape from the normal busy life and allowed us to slow down and enjoy the harmony of nature and its surroundings! We loved every minute of being in our little cabin, walking the trails, feeding the animals, watching my grand girls play so carefree, fishing, boat paddles, swinging on swing. Lastly, hearing Paul’s fireside stories and meeting other people were an extra bonus! It was difficult leaving and returning home; however we will return soon! :)
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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- Virginia Beach Oceanfront
- Carova Beach
- Resort Beach
- Corolla Beach
- Busch Gardens Williamsburg
- Buckroe Beach and Park
- Buckroe Beach
- Kingsmill Resort
- First Landing State Park
- Virginia Beach National Golf Club
- Currituck Beach Lighthouse
- Norfolk Botanical Garden
- Cape Charles Beachfront
- Red Wing Lake Golf Course
- Jungle Golf
- Little Creek Beach
- Outlook Beach
- Dog Beach
- Kiptopeke Beach
- Water Country USA
- Ocean Breeze Waterpark
- Bonito St. Public Beach Access
- Currituck County Southern Public Beach Access
- The Grass Course