
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

5-Acre Getaway close to Historic Triangle
This place was great for our golf trip to Williamsburg! This was our second time renting it.

Water Oaks at Chic's Beach
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!

3 bedroom private home a block from the beach!
We had a beautiful family vacation to the beach at Kate’s place. She was so responsive and kind, we had a great time.

Quiet family location and close to BEACH!
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 ❤️

Castaway 2 bed cottage by the beach
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!!

Bamboo Bungalo Duplex Near Busch Gardens
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.

Gorgeous Vacation House
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!

Family Holiday House. Events and Beaches Nearby
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

Villa Positano
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!!!

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

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

Paint The Beach Pink! Full House | Private Pool
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!

The Seaglass Cottage
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 :)

Perfect Getaway!
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!

Ocean Escape
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+

Epic Sunsets | Waterfront Cottage | Pet Friendly
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

August Suite | Beach | Balcony | Fire Pit
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.

Timeless Norfolk Escape
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.

The Bartlett Inn
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 .

Beach Stay
Fantastic hosts and the place was spotless. The hosts thought of everything to make us feel at home.

Backyard Bungalow | Near Beach
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!

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

Hidden Gem.4/bedroom cozy home fenced in yard
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

Private studio
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
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- Virginia Beach Oceanfront
- Carova Beach
- Resort Beach
- Corolla Beach
- Busch Gardens Williamsburg
- Buckroe Beach
- First Landing State Park
- Water Country USA
- Buckroe Beach and Park
- Kingsmill Resort
- Grandview Beach
- Currituck Beach Lighthouse
- Outlook Beach
- Jamestown Settlement
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- Ocean Breeze Waterpark
- Sarah Constant Beach Park
- Virginia Beach National Golf Club
- Norfolk Botanical Garden
- Wilkins Beach
- Bonito St. Public Beach Access
- Little Creek Beach
- Kiptopeke Beach
- Golden Horseshoe Golf Club