
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 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.

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
Such a beautiful place. Lisa was very responsive before and during our trip. The backyard is an oasis and an extra space to have fun and laughs with loved ones. The space felt homey and beautifully decorated. The bathrooms were fully stocked with towels and tissue. And the showers in each bathroom were the right temperature and pressure. It was like being in your own spa. We didn't cook, but if we did, the kitchen was fully stocked with spices, utensils and pots and pans. I loved the coffee bar that was fully stocked with sugar, creamer, and coffee. One of the best airbnbs I've stayed in, in awhile. Thanks again Lisa!

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. 🤭

The Tree House at Old Beach
Really enjoyed the space! The downstairs felt very functional with a spacious kitchen. The upstairs is essentially two hotel suites with the key being two full baths. The spiral staircase is a charming touch and the best part is the front deck. It’s spacious with plenty of seating so you can truly enjoy beach living. The hosts gave clear instructions and it was an easy check-out. The neighborhood is peaceful yet only a short walk to the heart of Virginia Beach’s boardwalk. I highly recommend staying at this home!

Relax! Refreshing 3 bedroom Rancher
E’s place was great for our long weekend getaway. The neighborhood is very quiet and is great to walk around. I have a dog so the place was great for her. Overall, a great place.
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!

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.

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
This place is so amazing from the way its decorated to how clean everything is in every room..it has anything and everything you would need for the beach or in the beach house and a quiet neighborhood i will definitely be staying here again 😊

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
loved our stay. cozy home with everything you need and FANTASTIC host who meets all yours demands without hesitation.

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.

3 Bd Townhome near Historic Waterfront Portsmouth
This was a great property the Host was very responsive and helpful. She ensured that we had a great stay. The house does look like the picture. The neighborhood is an older neighborhood but it is very quiet and peaceful.

The Bird’s Nest
We loved Peggy’s house. It was in a quiet neighborhood, with a nice driveway, good for larger cars. The house was so clean, comfortable, cozy and well equipped with everything. We would certainly come back. Peggy is an excellent host, very flexible and quick to answer any question. I highly recommend her place.

VA Beach-Town Center Escape
This is my 2nd stay in Krystal’s Air BNB. This was the place I knew where I feel safe and comfortable at. The location is close great restaurants and shopping locations. The neighborhood is very quiet. Krystal is responsive, friendly, and respectful. When I do visit VA again I’ll probably be at this particular Air BNB!

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.

Hidden Gem.4/bedroom cozy home fenced in yard
This place is truly a Hidden Gem. It was perfect for our family. We enjoyed the decks, large backyard, and theater room. The host, Camille is so thoughtful. She really went the extra mile with including items for our grandkids and dog (who ended up not being able to make the trip).

Private studio
We had a wonderful stay while visiting with family ! It was perfect for me, my fiancé, and our dog. It’s a clean, cozy space with cute decor. The area was quiet and felt secure. The fenced in yard was perfect for our dog. It was close to a variety of restaurants and stores. Check in was super easy with guided instructions, and there were detailed instructions for checkout too. Aryel was friendly and proactive. We would definitely stay again!
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
Wi-Fi availability
270 properties include access to Wi-Fi
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- Virginia Beach Oceanfront
- Carova Beach
- Resort Beach
- Corolla Beach
- Busch Gardens Williamsburg
- Buckroe Beach
- Bethel Beach
- Water Country USA
- First Landing State Park
- Kingsmill Resort
- Buckroe Beach and Park
- Grandview Beach
- Currituck Beach Lighthouse
- Jamestown Settlement
- Sarah Constant Beach Park
- Haven Beach
- Virginia Beach National Golf Club
- Ocean Breeze Waterpark
- Norfolk Botanical Garden
- Wilkins Beach
- Bonito St. Public Beach Access
- Little Creek Beach
- Outlook Beach
- Kiptopeke Beach