
Chesapeake vacation rentals
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in Chesapeake
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chesapeake vacation rentals
House rentals in Chesapeake

Beautiful home in Chesapeake
This home was very clean, accurate to the photos, and very comfortable. We really appreciated the fully fenced in backyard for our dog. The location was close to a mall, restaurants, supermarkets, and Virginia Beach. The neighborhood was very family friendly and safe. We would definitely stay here again if in the area.

R & R River House
Our stay was really nice. The townhouse was beautiful and very clean. It had all the necessary amenities anyone could ask for. It was centrally located to all the places we wanted to see and we enjoyed how we felt at home from the minute we walked in. We would definitely stay there again.

Chesapeake Haven - Relaxing Space + Lux Kitchen
My family and I had a wonderful stay at this lovely Airbnb! The house was spotless, cozy, and felt just like home. Everything was thoughtfully prepared, from the comfortable bed to the little touches that made the space warm and inviting. The host was kind and responsive, making the whole experience easy and relaxing. I’d definitely stay here again—highly recommend!

Ghent on the Corner: Cozy 3 bed 2.5 bath home
If you're looking for a thoughtful host, a well-run place and a cozy stay, Abel's place is the place to go! The house is so beautiful, well taken care of and fully equipped. Abel is so friendly, a reliable host and quick to respond if you ever have any questions regarding the house. My stay here was above my expectations. Abel is absolutely an amazing host, and I had a great time at this place! It was perfect and I really enjoyed my time here. I would definitely go back to this place again, and I highly recommend it.

@Whit’s End? Come in and Relax
the house and fenced yard worked perfectly for our family vacation. We brought our 2 English cream retrieversand the set up for the back yard was perfect. Our son plays piano so having a piano in the house made it extra special. I would definitely stay here again.

Quilted Quarters by the Bay with Private Entrance
Audrey’s quilted corners by the bay was perfect for a peaceful, relaxation vacation with my sister. We enjoyed being close to the quiet, peaceful beachfront and the bike/walking path into the state park. Highly recommend for a relaxing virginia beach experience. When we experienced issues with bugs entering the room (which is a very normal occurrence in the southern climate especially in the rain), Audrey quickly contacted us and eased our minds by spraying for bugs inside the room and outside the house. Audrey did everything she could to help. Be aware of the possibility of bugs given the nature of the climate and more wooded, residential area. Overall, we really enjoyed our stay.

Picture Worthy Spanish Style Casita! 2 BR/ 2BA
Adam's place was a great find! Beautiful home..loved the decorations. Made our stay in Norfolk just like home and enjoyable..will be back again soon!

Simply Amazing in Chesapeake
Sereva made us feel welcome and valued from the moment we first contacted her. The home was beautiful, sparkling clean, and lovely. We enjoyed every minute of our stay and she was always available to answer questions. Thank you for being a wonderful, welcoming host!
Other great vacation rentals in Chesapeake

2 BR With King. ⚡️Fast Wifi. 🔐 Easy Self Check-In.
We had a wonderful stay! The house was spotless and comfortable. Our hosts provided some snacks and water which was so appreciated after a long drive with our baby. We have family in the area and would absolutely stay again next time we visit!

Country Escape - Next DOOR - Hidden Gem
The lodging was great! Very clean, and so tastfully and creatively decorated. Tracy had "everything" you would need, extra batteries, spices, blankets, toiletries, and much much more....oh and games of course. We stayed 2 nights for a grandaughter's wedding. Stayed with our daughter, husband, and 2 children. It even has laundry detergent for the washer and dryer. The beds were comfortable and temperature controls worked great. We loved it. Thank you.

Country Living Guest House (Upstairs/Downstairs)
We booked Willis's guest house for my friend's birthday celebration. She wanted a laid back, relaxing weekend & that's exactly what we experienced! The hot tub was amazing. We enjoyed walking the land & seeing all the chicken. We used the full kitchen to cook a wonderful dinner. And the hosts were sooo welcoming. We felt right at home. We hope to come back soon!

Entire Apartment - No Cleaning Fees!
Listen, this house is the house you want to stay at instead of a hotel lol me & my 2 year old stayed here & it just felt like home. The house looks exactly like the pictures, and don’t get me started on the bed, I slept like a baby, it was like being on a cloud, I kid you not lol. Jamey was so nice & answered and responded quickly. it’s a quiet neighborhood, everything is close far as food & shopping. I would definitely recommend staying here to anyone.

Blissful Nook @ Washington
This was an extremely satisfying stay. The place looks like the photos, but arriving in person really shows the coziness of the rooms. Great atmosphere within a private space with all the amenities necessary during an extended stay. Absolutely loved and would recommend.

Quiet Neighborhood 7 Miles From the Beaches
Had a wonderful stay at Mona's place. We were in town for a softball tournament and her place was perfect for our visit. Close to fields, beaches, and restaurants. Mona was so nice and helpful. Wish we could have stayed longer her place was so peaceful, spacious and super clean. We would definitely return.

Beautiful Cottage Waterfront Near Downtown Norfolk
My wife and I have been using Airbnb for about 10 years now. This is our absolute favorite place. The cottage is very clean. It is in a great location (between downtown Norfolk and Virginia Beach) in a quiet neighborhood right on the Elizabeth River. Michael and Andy a very quick to respond to any questions with great recommendations. It is the little things, like leaving snacks and drinks (which came in handy after long hikes) to Andy greeting us at check-in that made us feel welcomed and comfortable. We cannot wait to come back again

Guest Suite Studio w/ Kitchenette & Private bath.
It was exactly as depicted and perfect for a quick getaway.
Quick stats about vacation rentals in Chesapeake
Total rentals
970 properties
Total number of reviews
32K reviews
Family-friendly rentals
440 properties are a good fit for families
Pet-friendly rentals
280 properties allow pets
Rentals with a pool
130 properties have a pool
Rentals with dedicated workspaces
510 properties have a dedicated workspace
Frequently Asked Questions
Where should I stay in Chesapeake?
Make yourself at home in Chesapeake by choosing from our most frequently booked neighborhoods. We have over 110 vacation rentals in Salem, over 110 vacation rentals in Lynnhaven, over 500 vacation rentals in Downtown Norfolk, over 270 vacation rentals in Ghent, and over 500 vacation rentals in Olde Towne.
Are there vacation rentals with a dedicated workspace in Chesapeake?
Yes! Work meets play with ease at over 510 vacation rentals in Chesapeake featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Chesapeake?
Four-legged friends are welcome in Chesapeake. Choose from more than 280 vacation rentals for guests traveling with pets.
Are there Chesapeake vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 130 vacation homes with pools in Chesapeake, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in guesthouse rentals in Chesapeake?
Experience the best of Chesapeake with our guesthouse rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do townhouse rentals in Chesapeake have a gym?
Absolutely! We offer over 10 townhouse rentals with a gym in Chesapeake. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Chesapeake have self check-in?
Absolutely! We offer over 40 apartment rentals with self check-in in Chesapeake. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly condo rentals in Chesapeake?
Chesapeake has more than 10 family-friendly condo rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Destinations to explore
- Virginia Beach Vacation rentals
- Williamsburg Vacation rentals
- Richmond Vacation rentals
- Shanghai Vacation rentals
- Myrtle Beach Vacation rentals
- Charlotte Vacation rentals
- Outer Banks Vacation rentals
- Washington Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Jersey Shore Vacation rentals
- New York Vacation rentals
- Kid-friendly rentals Chesapeake
- Rentals with a patio Chesapeake
- Pet-friendly rentals Chesapeake
- Rentals with pools Chesapeake
- Condo rentals Chesapeake
- Beach house rentals Chesapeake
- Rentals with a fire pit Chesapeake
- Rentals with a kayak Chesapeake
- Rentals with lake access Chesapeake
- Mansion rentals Chesapeake
- Private suite rentals Chesapeake
- House rentals Chesapeake
- Rentals with a fireplace Chesapeake
- Waterfront rentals Chesapeake
- Rentals with breakfast Chesapeake
- Family-friendly rentals Chesapeake
- Fitness-friendly rentals Chesapeake
- Cottage rentals Chesapeake
- Rentals with beach access Chesapeake
- Rentals with outdoor seating Chesapeake
- Rentals with an EV charger Chesapeake
- Rentals with a hot tub Chesapeake
- Beachfront rentals Chesapeake
- Rentals with a washer and dryer Chesapeake
- Apartment rentals Chesapeake
- Townhouse rentals Chesapeake
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Virginia Beach Oceanfront
- Carova Beach
- Resort Beach
- Corolla Beach
- Busch Gardens Williamsburg
- Bethel Beach
- Buckroe Beach
- First Landing State Park
- Kingsmill Resort
- Water Country USA
- Buckroe Beach and Park
- Grandview Beach
- Currituck Beach Lighthouse
- Virginia Beach National Golf Club
- Jamestown Settlement
- Sarah Constant Beach Park
- Wilkins Beach
- Haven Beach
- Ocean Breeze Waterpark
- Norfolk Botanical Garden
- Bonito St. Public Beach Access
- Grove Beach
- Golden Horseshoe Golf Club
- Little Creek Beach