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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

Guest favourite
Home in Toano
4.92 out of 5 average rating, 105 reviews

5-Acre Getaway close to Historic Triangle

DanRating, 5 stars2 weeks ago
This place was great for our golf trip to Williamsburg! This was our second time renting it.
Guest favourite
Home in Chic's Beach
4.96 out of 5 average rating, 132 reviews

Water Oaks at Chic's Beach

EmmaRating, 5 stars1 month ago
Tommy and Janet were very responsive! They were extremely friendly and went above and beyond to make our wedding weekend special. The house was a wonderful experience!
Superhost
Home in Norfolk
4.92 out of 5 average rating, 139 reviews

3 bedroom private home a block from the beach!

BethanyRating, 5 stars2 weeks ago
We had a beautiful family vacation to the beach at Kate’s place. She was so responsive and kind, we had a great time.
Top guest favourite
Home in Virginia Beach
4.99 out of 5 average rating, 152 reviews

Quiet family location and close to BEACH!

GinaRating, 5 stars2 weeks ago
I can’t begin to describe our recent visit!! We stayed from Sunday 6-1 to Thursday 6-5. My husband and I had our 10 year old daughter and 3 of her best friends along w our 3 small furry babies. The house is “nestled” on a sweet friendly street. The house lake view SURROUNDS the house along with the outside balcony. It was beautiful to see the ducks and various birds every day. The house was extremely clean! I didn’t have to do any cleaning before we unpacked. The garage had everything!!! Bikes, beach stuff along w anything u can think of. There was plenty of outside sitting areas with a private outside shower. I used it!! Water was nice! The beach was literally a 10 mins walk! We rode the bikes and walked to the beach, a couple of times a day. The boardwalk is very dog friendly so we were able to bring them. The pier from the boardwalk has people fishing. I rode 1 of the bikes around the every day! W have been using Airbnb for years and this was the best experience! Bob is the best ❤️
Superhost
Home in East Ocean View
4.77 out of 5 average rating, 105 reviews

Castaway 2 bed cottage by the beach

CourtRating, 5 stars1 week ago
Sam is very accommodating to her guests, we had change of plans and needed to check in earlier, she made a way to accommodate us, we had very pleasant stay at her cozy place. It is walking distance from the beach. Highly recommended!!
Guest favourite
Home in Williamsburg
4.86 out of 5 average rating, 264 reviews

Bamboo Bungalo Duplex Near Busch Gardens

JanekRating, 5 stars1 week ago
Very comfortable and well-priced home, very easy to find, check in and felt a good location for the sights in DC - even without a car you can get a tram or bus into the centre, and the Metro was not too far a walk away either. The neighbourhood felt fine and safe. Parking situation was fine - it's only 2 hours during weekdays right outside but there's free parking with no time limit just a street away (2 min walk). Would recommend as somewhere to stay for a trip to DC.
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 Hampton
4.84 out of 5 average rating, 362 reviews

Family Holiday House. Events and Beaches Nearby

FlemmingRating, 5 stars3 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

Villa Positano

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 stars6 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!
Superhost
Home in Norfolk
5 out of 5 average rating, 4 reviews

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

AngelaRating, 5 stars1 week 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.
Top guest favourite
Home in Virginia Beach
4.94 out of 5 average rating, 66 reviews

Paint The Beach Pink! Full House | Private Pool

WyattRating, 5 stars4 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!
Top guest favourite
Home in East Ocean View
4.98 out of 5 average rating, 55 reviews

The Seaglass Cottage

BarbaraRating, 5 stars5 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 stars2 weeks 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 stars6 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+
Guest favourite
Cottage in Sandbridge
5 out of 5 average rating, 23 reviews

Epic Sunsets | Waterfront Cottage | Pet Friendly

CateRating, 5 stars1 week ago
This place was the most charming airbnb I have ever stayed in. Badria and Jay made every detail of our stay perfect with all of their extra touches, including saltwater taffy and a box of croissants, slippers and a lavender mask, and a fully stocked coffee station with syrups. We instantly felt at home and in vacation mode at their place and literally laid out on the dock the entire time. A perfect spot for kayaking, laying out in the sun, and I even brought out my mat and did some yoga on the dock. The views were unreal. The couch was so comfortable I accidentally fell asleep there the whole night and woke up to the gorgeous window views. Amazing hosts and location!

Private, pet-friendly home rentals

Superhost
Apartment in Norfolk
4.79 out of 5 average rating, 34 reviews

August Suite | Beach | Balcony | Fire Pit

RebeccaRating, 5 stars3 days ago
I honestly couldn’t get this place a better review. You get exactly what you expect and it is priced well for the area, location, and Hadley is a great host. The host is very responsive and communicates well of her expectations and fulfilling yours.
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 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 .
Guest favourite
Home in Norfolk
5 out of 5 average rating, 47 reviews

Beach Stay

TylerRating, 5 stars2 weeks ago
Fantastic hosts and the place was spotless. The hosts thought of everything to make us feel at home.
Guest favourite
Home in Norfolk
5 out of 5 average rating, 7 reviews

Backyard Bungalow | Near Beach

AileenRating, 5 starstoday
The house was spotless, cozy, and exactly what we needed for a relaxing stay. We felt right at home and truly enjoyed every moment. We’d definitely love to return!
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. 🤭
Top guest favourite
Home in Portsmouth
5 out of 5 average rating, 55 reviews

Hidden Gem.4/bedroom cozy home fenced in yard

JulieRating, 5 stars1 week ago
Truly a “hidden gem”! This place was perfect and was more like a home away from home. We felt comfortable and welcomed here. The next time we are in Va Beach we will definitely be checking to see the availability of this place. Thank you, again, Camille
Guest favourite
Flat in Portsmouth
4.95 out of 5 average rating, 59 reviews

Private studio

TaylorRating, 5 stars1 week 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

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