
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

3 bedroom private home a block from the beach!
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

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.

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 .

Colonial Retreat
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.

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!

Backyard Bungalow | Near Beach
Awesome hosts, great communication and very nice home

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. 🤭

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

Positano Villa
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!

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!

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!

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

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+
Private, pet-friendly home rentals

The "Bison" contemporary retreat (King Bed)+
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 :)

Beautiful home in Chesapeake
⭐️⭐️⭐️⭐️⭐️ 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!

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.

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

BaysideBungalow | 5 Beds, King Suite, Walkable
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!

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

Chesapeake Retreat
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.

Lux Elegance
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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- 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
- Haven Beach
- 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