Popular all over Virginia for its delicious seafood fare and proximity to the beach while still being an economically reasonable city to live in, Chesapeake is an amazing hidden gem for travellers of all kinds. The city also has a rich American culture that is evident in its food scene, cultural events, and thrilling things to do. If you are interested in a cosy suburban city with plenty of parks and playgrounds and welcoming locals, this is the best place to be. While there are several extended stay hotels in Chesapeake, why not choose to stay in your very own home-away-from-home with all the comforts and cosiness of your own house? Read on to check out our awesome list of the top Airbnb vacation rentals in Chesapeake, Virginia.
1. Cosy townhouse ideal for families (from USD 162)
For the entire family to enjoy a comfy holiday, why not spend your days in this cosy townhouse in a suburban neighbourhood? Your group can huddle in the spacious living room, which is guaranteed to be a popular spot for movie nights. But before everyone gets hooked on to the screen, make sure to whip up some snacks in the well-equipped kitchen. This short-term rental in Chesapeake is also readily equipped with WiFi to keep you in touch with life back home.
Stepping outside the back patio, you’ll be greeted with a fenced outdoor space perfect for alfresco lounging. If you feel like hitting nearby hotspots, you can include Portsmouth Naval Shipyard Museum, along with many restaurants and shops, in your itinerary.
Chesapeake, Virginia, United StatesSuperhost
Accommodates: 5
Top guest reviews
Amenities & Room:
the beds were comfortable the furniture was comfortable and it was in the perfect location for our needsthis house was great tons of room we enjoyed the space having 2Cleanliness:
very clean and updatedsuper clean town homeit was clean and comfortabletraci's place was very cleanthe place smelled super clean when we walked in which i appreciatedHost:
thank you tracy for your kind hospitalitytraci has definitely been a great hosttraci is an excellent hosttraci was a great host to work withtraci was so responsive to our questions the place was greatRead more reviewsLocation:
very nice condo close to airport and all major highwaysgreat location and well kept propertya busy neighborhood but very quiet and friendlyits in a great location very close to restaurants norfolk & the beachgrocery stores are right around the corner and getting onto the highway was easy
2. The Sparks Home (from USD 292)
Sitting in Chesapeake, the Sparks Home captures the sparkle of a homey yet modern vacation rental pretty well. Split across two floors, the interior features conveniences such as restful bedrooms, a fully stocked kitchen, and a roomy living space with a smart TV along with your favourite streaming services. Of course, reliable WiFi is provided for an uninterrupted viewing experience. And for those who prefer classic entertainment, board games and cards are made available.
The location is also a winner as it caters to a variety of thrills. There is a community pond five minutes away on foot should you want to cast your fishing rod. Virginia Beach and The Downtown Waterside District are also excellent nearby diversions to add more spark to your trip.
Chesapeake, Virginia, United StatesAccommodates: 6
Top guest reviews
Amenities & Room:
the listing was better than the photos very cozyCleanliness:
this place is very nice very clean and there is so many things to do around the areaHost:
owners made accommodations for us and left us a sweet basket that the kids enjoyedthis place is breathtaking host was beyond helpful if i could give 6 stars i wouldsparks was extremely responsive and helpful when i had questionsRead more reviewsLocation:
neighborhood is quiet and neighbors were friendly
3. Pet-friendly suite with a leafy lawn (from USD 125)
Very highly rated among the vacation rentals in Virginia, this Airbnb with a pool is right in the midst of Chesapeake. Featuring lush green lawns outside, private parking, a swimming pool to enjoy, and barbecue facilities for you to arrange your own cookout, this is an ideal home for a small family. The kitchen is fully equipped, with all the cookware and amenities you need to make a wonderful meal and other gadgets that adorn the living area such as a large-screen television set.
The hosts are extremely welcoming and committed to ensuring your stay at this pretty home as comfortable as possible.
Chesapeake, Virginia, United StatesAccommodates: 4
Top guest reviews
Amenities & Room:
amenities: pool internet tv snacks and wash were awesomefelt like a real bed and breakfastcomfortable bed and space- a fridge full of water bottles and sodas a clean kitchen space and a keurigyou won't regret it clean extremely comfortable amazing amenities and awesome extrasCleanliness:
it's clean convenient and comfortableeverything was clean and we'll prepared for uspool was great place was spotless and the welcome was amazingvery clean tammy was very communicative and flexiblethe place was beautiful modern and spotlessHost:
amazing and wonderful hostsowners are super responsivevery friendly hosts who go above and beyondlovely accommodations kind and responsive hosts beautiful neighborhoodtammy and phil were amazing hostsRead more reviewsLocation:
quiet location beautiful pool areathe location is very quiet great neighborhood to take a walkit's located in a nice quiet neighborhoodperfect location for my visit with familywonderful space close to everything you could possibly need
4. Well-maintained ranch home best for families (from USD 399)
Perfect for a group of friends or a large family, this beautiful and well-maintained ranch home is a hidden gem in Chesapeake. Guests loved how child-friendly the space is, filled with books and toys, a private swimming pool for the little ones’ enjoyment, as well as a cot for them to sleep in. The location is very good too, close to all the tourist attractions you might wish to check out. For adults, there is a hot tub facility that you can access for free, as well as a propane-powered barbecue facility to grill some steaks and hot dogs for an all-American meal.
Chesapeake, Virginia, United StatesAccommodates: 10
Top guest reviews
Amenities & Room:
we all enjoyed the deck pool and hot tubmy kids loved the hammock chairs in the family roomthe private pool and hot tub was a wonderful treat for my familythis place is amazing screened in pool hot tub grill and porch in the back yardeveryone loved the screened in porch with the pool hot tub and fireCleanliness:
everything was clean and tidyclean with everything we neededplace is clean and spacioushouse is very clean and well appointedthe house was clean and the kitchen was well equippedHost:
fantastic hosts - exceeded expectationslove the house and owners were great to work withnot a bad thing to say about the hoststraci and kurt are wonderful hostskurt and traci are super quick to respond to any and all questions as well as very friendlyRead more reviewsLocation:
great location only few mins from restaurants and local activitiesthe house is in a great convenient locationit’s nice to be able to park close and take the little ones to the baysidedefinitely a place we would stay again if our travels bring us back near chesapeakeexcellent hosts and a wonderful location we had everything we needed
5. Riverside studio best for couples (from USD 185)
Situated right on the banks of the river, this beautiful studio apartment is ideal for couples looking for economical accommodations without compromising on the amenities and views. Enjoy the perks of living in a small home, complete with a proper kitchenette with cookware and dinnerware, as well as a lovely terrace where you can sip your morning coffee. In addition, you have access to free WiFi as well as cable television for your enjoyment. The decor is very masculine, with hardwood floors and a subtle colour palette designed to soothe the senses.
Chesapeake, Virginia, United StatesAccommodates: 2
Top guest reviews
Amenities & Room:
the views of the lake from the room are stunningthe bed was very comfy sunset view was beautiful amenities were greatwe enjoyed all the on site amenities; pool hot tub sauna and lakethey loved the place enjoyed the view of the river and said the bed was very comfortablepictures can’t do the amazing views justice the tempurpedic bed was very comfortableCleanliness:
super clean and very cozyall very clean#1 thing for me was it was cleanthe guesthouse was sparkling clean and the beds are very comfortablevery clean and everything looks as picturedHost:
hosts are awesome and informativeexcellent hosts always looking to help you throughout the staygreat hosts great housevery kind and generous hostschuck and kathyvwere fabulous hostsRead more reviewsLocation:
great location with a lot of local gems nearby and only 25 minutes to the beachclose to shopping restaurants will definitely go back againexceeded our expectations great location and a beautiful placefantastic romantic location with great hoststhe location is a great alternative to the crowded noisy beach environs where most hotels are
6. Centrally located apartment with river views (from USD 80)
Situated strategically near the peninsula where the two rivers, Indian River and Elizabeth River, meet, this home boasts an unmatched location close to all the tourist attractions without the crowds and noises. Wake up to the sound of the rippling river and birds chirping, and enjoy the recently refurbished interiors of the studio apartment, complete with beautiful granite kitchen surfaces and hardwood floors as well as pretty decor that lends a homey feel to the space. Guests highly compliment the cleanliness and maintenance of the premises, as well as the hospitality.
Chesapeake, Virginia, United StatesAccommodates: 2
Top guest reviews
Amenities & Room:
the wifi is great along with a tv equipped with rokuthe room is a nice size; kitchen is fully furnished; wifi was outstandinghaving the full kitchen coffee pot and little extras was wonderfulthe bed was super comfy and the bathroom was stocked with extra toiletries in case we forgot somethingeverything from the hand written welcome sign to the treats to the comfortable studioCleanliness:
everything was very clean and organizedthe place is really clean and smell goodvery clean with easy check inthe place was amazing very clean and neatthe space was clean and overall very comfortableHost:
wonderful hosts wonderful staykevin and mandy were so accommodating and lovelykevin and mandy are wonderful hosts i would certainly come back againkevin and mandy were very responsive and pleasant hostsmandy and kevin - thank you for being such wonderful hostsRead more reviewsLocation:
the location was also absolutely perfectcharming and very quiet locationgood location for visiting norfolk and virginia beachwe would highly recommend this location to anyonei would definitely reserve this location on my next visit
7. Romantic retreat near Virginia Beach Oceanfront (from USD 90)
This beautiful and well-decorated guest suite is close to some really amazing attractions, including farmers’ markets, woods and the Chesapeake Bay in Virginia Beach. The rental has keyless entry and previous guests lauded the fast and easy check-in.
You have access to a variety of amenities for your comfort and enjoyment including a king-sized bed, a fully equipped kitchen area, a private bathroom with complimentary toiletries, and more. The home is very pretty and is sure to charm you the moment you step in. Large windows and a light colour palette give the space a bright and airy feel.
Chesapeake, Virginia, United StatesAccommodates: 3
Top guest reviews
Amenities & Room:
super fast wifi with netflix was great for the kids 10/10the check-in was seamless and the room features a lot of great amenitiesthe space was large and comfortable and i especially liked the touchscreen lock on the doorthe bathroom was a good sizeexpect a warm and comfortable stayCleanliness:
very clean and quietthe bathroom was very clean and spaciousroom was very cleanreally clean comfy and cozy place to stay atclean space and the bed was heavenlyHost:
karla was a great hosthosts are super responsivevery very nice hostkarla was an amazing hosthosts are also extremely kind and friendlyRead more reviewsLocation:
very nice neighborhood and convenient locationnice neighborhood everything is so closecheck in was smooth and easy and the location was very nice as wellkarla’s place was perfect for a quick tripquiet and nice neighborhood
8. Traditional townhouse in a quiet neighbourhood
Do you wish to stay in a more traditional townhouse, decorated in a homey yet stylish colour palette, offering all the basic amenities you need for a relaxing and enjoyable stay? Look no further than this rental, located close to city parks in a quiet neighbourhood. You can use the well-equipped kitchen to cook your own meals, and your bedroom comes with an ensuite for your convenience and privacy. In addition, you can also use the complimentary WiFi in the home to watch movies on your device.
Chesapeake, Virginia, United StatesAccommodates: 3
Top guest reviews
Amenities & Room:
the bed is super comfyCleanliness:
convenient location clean and comfortableHost:
sarah was a good hostsarah was a wonderful host but the townhome did not meet our expectations for cleanlinessRead more reviewsLocation:
located in a great space close to my family and very cleanthe house had all that we could’ve asked for and the location was perfect with everything in fair distancevery quiet neighborhood with a lot of good restaurants nearbysarah’s home was close to a lot of places comfortable bed and safe neighborhoodit's a great place to stay
9. Stylish home ideal for families or friends
This modern and stylish home is perfect for a group of friends or a family. Featuring three bedrooms and two bathrooms, along with all the amenities of a well-furnished home, and perks like a fenced backyard, smart television, barbecue facilities and board games, guests loved how cost-effective it was compared to a hotel room. The space is large enough to have your own privacy while still being with your family or friends.
Chesapeake, Virginia, United StatesAccommodates: 8
Top guest reviews
Amenities & Room:
the ceiling fan in the common space wasn’t workingbeds chairs and couches are comfy and welcomingit had all the amenities one would need to be comfortable during their use of the housethe house in all is cute and cozy looks the same in the photoshaving said that the house was comfortable clean had nice new furniture and a very good valueCleanliness:
everything is very clean and well maintainednice and clean place for the familya clean home kitchen a bit smalllovely spacious house that was sparkling clean upon arrivalit was neat and tidy and very clean and comfortableHost:
host was very responsivethe host was very responsive and considerateoverall the owner is very responsivegreat host who was always available at any timei loved the decor and the management staff was quite responsiveRead more reviewsLocation:
the location was goodwalking distance to the grocery store and a park so super convenientvery nice space in a great location that is walking distance from lake trailsit was in a great location for usgood location - lots of highway noise
10. Fascinating single-room accommodation
Enjoy the security and comfort of having your hosts staying right with you, taking care of your every need! Situated on a beautiful and sprawling family ranch home, this accommodation gives you access to a single bedroom where you can stay with another person or just by yourself. You have access to comfortable facilities including a smart television, a kitchen, laundry facility, and a lovely backyard to relax in. The biggest perk is that the host, Rebecca, has two adorable dogs that you can play with, or bring your own pups to make new dog friends!
Chesapeake, Virginia, United StatesAccommodates: 2
Top guest reviews
Amenities & Room:
the amenities in both the room and bathroom were a huge helpthe bed was comfortable and the small amenities and personal touches were perfectrebecca was amazing the room was as describedshe had complimentary waters in the room which was also a nice touchthe room lets in some great natural light and the room is clean and feels peaceful and privateCleanliness:
particularly clean and loved the decorationvery clean stylish and comfortable settingthe space was impeccably clean just as listedthe space was clean and the backyard was great for our dogeverything was clean and we were highly satisfiedHost:
she was a great hostrebecca was a great hostvery friendly hosts and they made us feel welcomeshe was a fantastic host who responded quickly to my messagesoutstanding hosts so kind and welcoming you feel right at homeRead more reviewsLocation:
fabulous place to stay only 15 minutes from the airportit was a great location close to the beach and restaurantswe highly recommend and will be returning to this location in the future thanks again rebeccanice place in good neighborhoodi would definitely recommend booking this place
11. Quaint apartment ideal for solo travellers or couples
This home is sure to charm you the minute you step inside. With plenty of room for a small family to comfortably stay, and decorated using a subdued and quaint colour palette, this space is great for couples or even solo travellers. The accommodation is equipped with a proper kitchen space featuring all the amenities you need to make your own meals, laundry facilities, and a comfortable sitting room. The biggest perk is that it allows dogs, so you need not leave your furry friend behind while on vacation!
Chesapeake, Virginia, United StatesTop guest reviews
Amenities & Room:
very thoughtful on the games in the living room toothpaste in the bathroom and bottled waterCleanliness:
clean comfortable and convenientthe place is extremely clean and quietit was very spacious and impeccably cleangreat stay very clean stylish and organizedsparkling clean lots of room and local tips to places nearbyRead more reviewsHost:
great host with amazing hospitalityall around this place was nice and the host went above and beyond
12. Luxurious two-bedroom accommodation
This adorable and beautiful cottage is sure to bowl you over with amenities. Known as Jubilee Cottage, this is a private home that you have all to yourself. It is situated close to all the awesome attractions that you can check out, such as beaches, museums, city parks, nature trails, zoos and more. Why share walls with anyone else when you are on a vacation? Enjoy two bedrooms, a private bathroom, a private backyard, smart television and WiFi, and a fully equipped kitchen, all at the cost of a single hotel room. It really doesn’t get better than this!
Chesapeake, Virginia, United StatesAccommodates: 5
Top guest reviews
Amenities & Room:
also the cottage has very strong air conditioners as wellit was very quiet there and the window air conditioners were very effectiveclean comfortable and well positioned for shops restaurants and access to interstatethanks lesi highly suggest the huddle house - just around the corner - delicious breakfastCleanliness:
very clean and spaciousit was super clean and the communication was perfectvery clean and well kept upthe space was clean overallbut other than that the bathroom itself was sparkling cleanHost:
the host is a nice personles was a great host super friendly awesome recommendations and cozy placethe owner was very quick to respond and very helpful with suggestions and questionsgreat place to stay great hostthe host leslie was very friendly attentive accommodating and responsiveRead more reviewsLocation:
very cute cottage in a great location in greenbrierlocated near the city park and shopping items needed for daily life were easy to findalso very good location with lots of things around and nearthe location was great and overall it was an amazing dealgreat value for great stay it was close and the center to all the things we wanted to do
Enjoy your stay at Chesapeake
Chesapeake is a beautiful suburban dream, with a lot to explore and enjoy than what meets the eye. So what are you waiting for? Be sure to book your accommodations as soon as possible!
Frequently asked questions about the Airbnb vacation rentals in Chesapeake, Virginia
1. Which Airbnb vacation rentals in Chesapeake have a pool?
If you’re keen to enjoy a splashing time in your vacation rental in Chesapeake, you can consider staying at one of these lovely accommodations with pools: i) pet-friendly suite with a leafy lawn, ii) well-maintained ranch home best for families, and iii) centrally located apartment with river views.
2. Which vacation rentals in Chesapeake have parking?
To secure a guaranteed parking space at your accommodation, make sure to book a stay at any of these properties with car parking facilities i) cosy townhouse ideal for families, ii) pet-friendly suite with a leafy lawn, iii) riverside studio best for couples, and iv) romantic retreat near Virginia Beach Oceanfront .
Get Trip101 in your inbox
Unsubscribe in one click. See our Privacy Policy for more information on how we use your data
Create an account to bookmark our articles, like local expert tips, receive great stories in your inbox, and follow writers and topics that you love.
Log in with Google ×