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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 Norfolk
4.92 out of 5 average rating, 138 reviews

3 bedroom private home a block from the beach!

JessicaRating, 5 stars2 weeks ago
I had a wonderful stay at Kate’s home, it was easily 3 minutes to the beach, she had all the needed cooking utensils and even more! And even had some bathroom essentials that was really appreciated
Superhost
Home in Norfolk
5 out of 5 average rating, 4 reviews

The Blue Octopus~Private Pool~HotTub~Beach~FirePit

AngelaRating, 5 stars6 days ago
Family vacation for almost a week and everyone loved it! We definitely recommend families to come to the Blue Octopus for their next visit to Ocean View-Willoughby Spit. Friendly, clean and with all the amenities for the whole family.
Guest favourite
Home in Portsmouth
5 out of 5 average rating, 24 reviews

The Bartlett Inn

NatalieRating, 5 stars2 weeks ago
Stayed here was a family event it was spacious with a well equipped kitchen . The neighborhood was very quiet and safe could walk for miles without seeing a car or busy street .
Superhost
Home in Williamsburg
4.83 out of 5 average rating, 241 reviews

Colonial Retreat

JocelynRating, 5 stars1 month ago
We stayed at this AirBnB during the weekend of our son’s graduation. It’s only 10 minutes away from campus but it seemed like a different world as it was almost rural! The house is extremely quiet and has a lovely large backyard. There is ample parking. Every thing is well labeled and the kitchen is well stocked with utensils and crockery.
Guest favourite
Home in Norfolk
4.95 out of 5 average rating, 104 reviews

Gorgeous Vacation House

AlexisRating, 5 stars1 week ago
The house was super clean when we got there, the temperature of the house was great the entire stay. The pool was certainly clean, but since we went early, June the water was a little bit cold, but it felt really nice and refreshing honestly. There were three beach chairs and a wagon there that were helpful for traveling to the beach. There were available cups plate, utensils, and all the necessities that you would need, they even had shampoo and conditioner bottles there for us. We weren’t aware that there was a code to get into the house so instructions for check-in were a little bit unclear, but all I had to do is message and they responded. Overall, I would recommend staying here because even though the area surrounding isn’t the nicest, I felt safe the entire time at that house!
Guest favourite
Home in Norfolk
5 out of 5 average rating, 7 reviews

Backyard Bungalow | Near Beach

JoshuaRating, 5 stars6 days ago
Awesome hosts, great communication and very nice home
Guest favourite
Home in Portsmouth
4.93 out of 5 average rating, 29 reviews

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

DeidraRating, 5 stars3 weeks ago
Had a great girls weekend. It was peaceful and such a cute and quiet neighborhood. We would stay again. It’s located close to everything. The hot water was wonderful. 🤭
Guest favourite
Home in Hampton
4.84 out of 5 average rating, 362 reviews

Family Holiday House. Events and Beaches Nearby

FlemmingRating, 5 stars2 days ago
Great stay in Hampton! We were close to Captain George’s and Busch Gardens and the host was super helpful with our needs. Highly recommend if you’re traveling with a family and plan on staying awhile!

Pet-friendly home rentals with a pool

Top guest favourite
Cottage in Norfolk
4.97 out of 5 average rating, 250 reviews

Positano Villa

RhondaRating, 5 stars1 week ago
We had an amazing time. The house was perfect for us. We really enjoyed the pool and short walk to the beach. We could hear the ocean from the master suite. The upstairs deck had view of the water. Everything about our stay was perfect. The area was nice and was quiet and peaceful. We will definitely go back and stay longer next year. Thank you!!!
Top guest favourite
Apartment in Williamsburg
4.95 out of 5 average rating, 164 reviews

Kingsmill 1bed/1ba on Golf Course 9th Fairway

AmyRating, 5 stars5 days ago
Crystal's condo was spotless and an easy place to stay. Crystal was very proactive and made us feel welcome. her dinner suggestions were superb too! perfect for a weekend getaway in a resort atmosphere. Thank you so much, we highly recommend!
Guest favourite
Flat in Williamsburg
4.85 out of 5 average rating, 169 reviews

Westgate Historic Williamsburg One Bedroom

JordanRating, 5 stars2 months 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!
Top guest favourite
Home in Virginia Beach
4.94 out of 5 average rating, 65 reviews

Paint The Beach Pink! Full House | Private Pool

WyattRating, 5 stars3 days ago
Check in was super easy, the AC was on when we arrived which was great after a long Uber. The pool felt nice and the whole backyard area was fantastic. We ended up using the bikes a lot more than we thought which was a lot of fun. It's a quick bike ride to the boardwalk and walking didn't take too much longer. Bradley was very quick to respond whenever I had a question about anything. If we come back to Virginia Beach we will definitely be checking the availability of this house!
Guest favourite
Guest house in Virginia Beach
4.73 out of 5 average rating, 120 reviews

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

BryanneRating, 5 stars3 weeks ago
This was perfect for my family of four and dog. We stayed two nights and would have loved to been able to stay longer. Ron was an excellent host. This felt like a private spa trip with the massive pool, hot tub, dry sauna, and steam room. We are local to the area and would definitely stay again!
Top guest favourite
Home in East Ocean View
4.98 out of 5 average rating, 55 reviews

The Seaglass Cottage

BarbaraRating, 5 stars4 days ago
The host was so kind and made sure we had a comfortable stay! The AC ended up not working due to an accidental mishap when she was working on her yard! She was able to get the AC fixed as we arrived to the Air BNB and we had the coolest room ever ( which we love) especially on a hot day! We are thankful for the time she took to get that done ASAP! She also had a wonderful cute cottage with all that you’d need for a short stay! It was equipped with great dishes and all the things you’d need for a perfect stay in a home :) it was extremely clean and decorated nicely for your small family! It also has a beautiful back yard oasis to sit out and relax or go for a swim :) you won’t want to miss this Airbnb!! Located near the beach and a great park and walking paths for you kiddos!! All you need nearby just a short walk away!! It was a great getaway for the weekend with a very kind host who is always there to help if needed :)
Guest favourite
Home in Suffolk
4.84 out of 5 average rating, 94 reviews

Perfect Getaway!

JimRating, 5 stars1 week ago
We had a great family visit at this house. We really enjoyed the pool and whole house was very comfortable and clean! It was nice to just hang all day by the pool or top for a sanctuary from a long day of events. Sabrina was very attentive and responsive with questions and situations, appreciate her flexibility as a host!
Guest favourite
Apartment in Sandbridge
4.87 out of 5 average rating, 237 reviews

Ocean Escape

JamesRating, 5 stars5 days ago
My family really enjoyed our vacation. It was a great location to the beach and a private pool. It was our first vavation w/ an 18month old and 1 on the way. Randy was very quick to respond to any questions. A+

Private, pet-friendly home rentals

Superhost
Home in Hampton
4.82 out of 5 average rating, 92 reviews

The "Bison" contemporary retreat (King Bed)+

NyjahaRating, 5 stars1 week ago
The place was beautiful inside and out. My family and I felt like we’re at home. I love the outdoor space. Most of the times, my parents and I chilled outside enjoying the weather and chitchatting with each other. My family and I came down from Pennsylvania to visit my sisters who live about 10-15 mins away from the home. My family and I had a great time during our weekend stay. Hopefully one day we’ll come back and stay at this beautiful home again. I highly recommend this beautiful home. Definitely 5 stars :)
Guest favourite
Home in Chesapeake
4.9 out of 5 average rating, 40 reviews

Beautiful home in Chesapeake

MelissaRating, 5 stars1 week ago
⭐️⭐️⭐️⭐️⭐️ We had a wonderful stay! The location was perfect—close to everything we needed and in a neighborhood that had such a nostalgic, charming feel to it. The home itself was spotless and well cared for, and Keyonna was incredibly friendly and welcoming, which made the experience even better. It truly felt like a home away from home. We’d definitely stay here again!
Guest favourite
Flat in Downtown Norfolk
4.86 out of 5 average rating, 14 reviews

Timeless Norfolk Escape

TjRating, 5 stars1 week ago
Ventura’s place was great, very clean and tidy. Very quiet with a good vibe. Enjoyed being able to walk to several restaurants in the area.
Guest favourite
Home in Norfolk
4.99 out of 5 average rating, 92 reviews

Newport Nook: 5/2.5 Home in Norfolk - Sleeps 10!

KathyRating, 5 stars1 week ago
This home stands out among the many air B&B’s I have stayed it. Emily and Abel provided many extras such as cold water and snacks when we arrived, beach towels for our use, dog food bowls for our dog, soft beds with plush throws to use at our leisure. The neighborhood is walkable filled with southern charm. Our family used this home as a gathering place for my son’s wedding. It exceeded my expectations.
Guest favourite
Bungalow in East Ocean View
4.99 out of 5 average rating, 77 reviews

BaysideBungalow | 5 Beds, King Suite, Walkable

AnnRating, 5 stars2 weeks ago
Andria was an accommodating host who communicated and assisted to our needs. The home is beautiful and well stocked for a comfortable stay. Great location to restaurants and the beach within walking distance. Our dog loved the fenced in backyard. We cannot wait to book again!
Guest favourite
Flat in Portsmouth
4.95 out of 5 average rating, 59 reviews

Private studio

TaylorRating, 5 stars6 days ago
My bf and I stayed here for our anniversary and we loved it everything was just a 10/10 very private very beautiful we are definitely booking again within the next few weeks
Top guest favourite
Campervan/Motorhome in Chesapeake
4.96 out of 5 average rating, 28 reviews

Chesapeake Retreat

RobertRating, 5 stars1 week ago
Susan has a hidden gem which shines beyond what you'd expect. Beautiful yard, beautiful location and super hosts. I wish they were both managers of the last La Quinta I stayed. Goodness.
Top guest favourite
Home in Hampton
5 out of 5 average rating, 26 reviews

Lux Elegance

ChereseRating, 5 stars2 weeks ago
Well what can I say! We all gathered from Atlanta and Maryland to attend a family members graduation. This property blew our mind and it was well worth our travels and the cost. It was spotless, extremely clean, and very spacious and the aroma was breathtaking with a plethora of amenities. Most important, Ivan the host… was exceptionally hospitable. Not to mention the neighbors were also nice to my family and I. We also traveled with our two little dogs who felt right at home in their two cages. This property is number one on our list for Hampton,Virginia! ❤️❤️❤️

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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