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

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.
Guest favourite
Home in Buckroe Beach
4.87 out of 5 average rating, 78 reviews

Home-Sweet-Home

CatherineRating, 5 stars1 week ago
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.
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 stars3 weeks ago
Janine was very responsive and accommodating. Would stay here again.
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!
Superhost
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 favourite
Home in Moyock
4.86 out of 5 average rating, 113 reviews

Cozy Country Cottage

CrystalRating, 5 stars1 month 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 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!
Guest favourite
Home in Williamsburg
4.87 out of 5 average rating, 251 reviews

Bamboo Bungalo Duplex Near Busch Gardens

LindsayRating, 5 stars6 days 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!!!

Pet-friendly home rentals with a pool

Top guest favourite
Cottage in Norfolk
4.97 out of 5 average rating, 240 reviews

Villa Positano

DanicaRating, 5 starstoday
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
4.9 out of 5 average rating, 21 reviews

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

RobertRating, 5 stars2 months ago
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.
Guest favourite
Home in Portsmouth
4.94 out of 5 average rating, 104 reviews

Wooded Wonderland Miniature Golf Hot tub Pool

DerrickaRating, 5 stars5 days ago
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!
Guest favourite
Flat
4.85 out of 5 average rating, 169 reviews

Westgate Historic Williamsburg One Bedroom

JordanRating, 5 stars3 weeks 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!
Guest favourite
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.
Guest favourite
Apartment in Sandbridge
4.87 out of 5 average rating, 231 reviews

Ocean Escape

Kevin & KarenRating, 5 stars1 month ago
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.
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 favourite
Apartment in Williamsburg
4.95 out of 5 average rating, 122 reviews

Kingsmill 2bd2ba Condo on Golf Course 9th Fairway!

KristenRating, 5 stars2 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!

Private, pet-friendly home rentals

Superhost
Home in East Ocean View
4.82 out of 5 average rating, 28 reviews

New! Clean + Affordable + Central!

AnaRating, 5 stars6 days 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
Bungalow in Chesapeake
4.95 out of 5 average rating, 99 reviews

Private and Cozy Bungalow Loaded with Amenities

JessicaRating, 5 stars2 months ago
Great stay with responsive, kind hosts. Accommodations were as described and very clean! Would stay there again!
Superhost
Townhouse in East Ocean View
4.69 out of 5 average rating, 52 reviews

Relaxing on the bay/Relocation Special/Close beach

FaythRating, 5 stars1 month 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, 385 reviews

Seaglass Cottage

BillRating, 5 stars5 days ago
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.
Top guest favourite
Home in Corolla
4.99 out of 5 average rating, 83 reviews

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

Rita CharityRating, 5 stars3 weeks ago
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.
Guest favourite
Home in Portsmouth
4.9 out of 5 average rating, 20 reviews

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

RebekahRating, 5 stars4 weeks ago
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.
Top guest favourite
Campervan/Motorhome in Chesapeake
4.96 out of 5 average rating, 25 reviews

Chesapeake Retreat

JeanRating, 5 stars2 weeks ago
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.
Guest favourite
Cabin in Cape Charles
4.96 out of 5 average rating, 168 reviews

Ultimate Cabin Farm Stay Cape Charles

NovaRating, 5 stars3 weeks ago
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

Destinations to explore