Top 12 Airbnb Vacation Rentals In Chesapeake, Virginia - Updated 2023

| 5 min read

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 States
91 reviews Superhost  Wifi Available
Entire townhouse 3 Beds 5 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 5

Top guest reviews
Amenities & Room:
the beds were comfortable the furniture was comfortable and it was in the perfect location for our needs
this house was great tons of room we enjoyed the space having 2
very clean and updated
super clean town home
it was clean and comfortable
traci's place was very clean
the place smelled super clean when we walked in which i appreciated
thank you tracy for your kind hospitality
traci has definitely been a great host
traci is an excellent host
traci was a great host to work with
traci was so responsive to our questions the place was great
very nice condo close to airport and all major highways
great location and well kept property
a busy neighborhood but very quiet and friendly
its in a great location very close to restaurants norfolk & the beach
grocery stores are right around the corner and getting onto the highway was easy
Read more reviews

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 States
32 reviews Superhost  Wifi Available
ENTIRE HOME 3 Beds 6 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Amenities & Room:
the listing was better than the photos very cozy
this place is very nice very clean and there is so many things to do around the area
owners made accommodations for us and left us a sweet basket that the kids enjoyed
this place is breathtaking host was beyond helpful if i could give 6 stars i would
sparks was extremely responsive and helpful when i had questions
neighborhood is quiet and neighbors were friendly
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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 States
420 reviews Superhost  Wifi Available
Entire guest suite 2 Beds 4 Guests 1 Bedroom 1 Bathrooms

Accommodates: 4

Top guest reviews
Amenities & Room:
amenities: pool internet tv snacks and wash were awesome
felt like a real bed and breakfast
comfortable bed and space
- a fridge full of water bottles and sodas a clean kitchen space and a keurig
you won't regret it clean extremely comfortable amazing amenities and awesome extras
it's clean convenient and comfortable
everything was clean and we'll prepared for us
pool was great place was spotless and the welcome was amazing
very clean tammy was very communicative and flexible
the place was beautiful modern and spotless
amazing and wonderful hosts
owners are super responsive
very friendly hosts who go above and beyond
lovely accommodations kind and responsive hosts beautiful neighborhood
tammy and phil were amazing hosts
quiet location beautiful pool area
the location is very quiet great neighborhood to take a walk
it's located in a nice quiet neighborhood
perfect location for my visit with family
wonderful space close to everything you could possibly need
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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 States
160 reviews Superhost  Wifi Available
ENTIRE HOME 5 Beds 10 Guests 4 Bedrooms 2 Bathrooms

Accommodates: 10

Top guest reviews
Amenities & Room:
we all enjoyed the deck pool and hot tub
my kids loved the hammock chairs in the family room
the private pool and hot tub was a wonderful treat for my family
this place is amazing screened in pool hot tub grill and porch in the back yard
everyone loved the screened in porch with the pool hot tub and fire
everything was clean and tidy
clean with everything we needed
place is clean and spacious
house is very clean and well appointed
the house was clean and the kitchen was well equipped
fantastic hosts - exceeded expectations
love the house and owners were great to work with
not a bad thing to say about the hosts
traci and kurt are wonderful hosts
kurt and traci are super quick to respond to any and all questions as well as very friendly
great location only few mins from restaurants and local activities
the house is in a great convenient location
it’s nice to be able to park close and take the little ones to the bayside
definitely a place we would stay again if our travels bring us back near chesapeake
excellent hosts and a wonderful location we had everything we needed
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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 States
509 reviews Superhost  Wifi Available
Private room in guesthouse 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
the views of the lake from the room are stunning
the bed was very comfy sunset view was beautiful amenities were great
we enjoyed all the on site amenities; pool hot tub sauna and lake
they loved the place enjoyed the view of the river and said the bed was very comfortable
pictures can’t do the amazing views justice the tempurpedic bed was very comfortable
super clean and very cozy
all very clean
#1 thing for me was it was clean
the guesthouse was sparkling clean and the beds are very comfortable
very clean and everything looks as pictured
hosts are awesome and informative
excellent hosts always looking to help you throughout the stay
great hosts great house
very kind and generous hosts
chuck and kathyvwere fabulous hosts
great location with a lot of local gems nearby and only 25 minutes to the beach
close to shopping restaurants will definitely go back again
exceeded our expectations great location and a beautiful place
fantastic romantic location with great hosts
the location is a great alternative to the crowded noisy beach environs where most hotels are
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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 States
197 reviews Superhost  Wifi Available
Entire guesthouse 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
the wifi is great along with a tv equipped with roku
the room is a nice size; kitchen is fully furnished; wifi was outstanding
having the full kitchen coffee pot and little extras was wonderful
the bed was super comfy and the bathroom was stocked with extra toiletries in case we forgot something
everything from the hand written welcome sign to the treats to the comfortable studio
everything was very clean and organized
the place is really clean and smell good
very clean with easy check in
the place was amazing very clean and neat
the space was clean and overall very comfortable
wonderful hosts wonderful stay
kevin and mandy were so accommodating and lovely
kevin and mandy are wonderful hosts i would certainly come back again
kevin and mandy were very responsive and pleasant hosts
mandy and kevin - thank you for being such wonderful hosts
the location was also absolutely perfect
charming and very quiet location
good location for visiting norfolk and virginia beach
we would highly recommend this location to anyone
i would definitely reserve this location on my next visit
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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 States
230 reviews Superhost  Wifi Available
Entire guest suite 1 Bed 3 Guests 0 Bedrooms 1 Bathroom

Accommodates: 3

Top guest reviews
Amenities & Room:
super fast wifi with netflix was great for the kids 10/10
the check-in was seamless and the room features a lot of great amenities
the space was large and comfortable and i especially liked the touchscreen lock on the door
the bathroom was a good size
expect a warm and comfortable stay
very clean and quiet
the bathroom was very clean and spacious
room was very clean
really clean comfy and cozy place to stay at
clean space and the bed was heavenly
karla was a great host
hosts are super responsive
very very nice host
karla was an amazing host
hosts are also extremely kind and friendly
very nice neighborhood and convenient location
nice neighborhood everything is so close
check in was smooth and easy and the location was very nice as well
karla’s place was perfect for a quick trip
quiet and nice neighborhood
Read more reviews

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 States
108 reviews  Wifi Available
Entire townhouse 1 Bed 3 Guests 1 Bedroom 1 Bathrooms

Accommodates: 3

Top guest reviews
Amenities & Room:
the bed is super comfy
convenient location clean and comfortable
sarah was a good host
sarah was a wonderful host but the townhome did not meet our expectations for cleanliness
located in a great space close to my family and very clean
the house had all that we could’ve asked for and the location was perfect with everything in fair distance
very quiet neighborhood with a lot of good restaurants nearby
sarah’s home was close to a lot of places comfortable bed and safe neighborhood
it's a great place to stay
Read more reviews

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 States
96 reviews  Wifi Available
Entire townhouse 3 Beds 8 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
the ceiling fan in the common space wasn’t working
beds chairs and couches are comfy and welcoming
it had all the amenities one would need to be comfortable during their use of the house
the house in all is cute and cozy looks the same in the photos
having said that the house was comfortable clean had nice new furniture and a very good value
everything is very clean and well maintained
nice and clean place for the family
a clean home kitchen a bit small
lovely spacious house that was sparkling clean upon arrival
it was neat and tidy and very clean and comfortable
host was very responsive
the host was very responsive and considerate
overall the owner is very responsive
great host who was always available at any time
i loved the decor and the management staff was quite responsive
the location was good
walking distance to the grocery store and a park so super convenient
very nice space in a great location that is walking distance from lake trails
it was in a great location for us
good location - lots of highway noise
Read more reviews

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 States
104 reviews Superhost  Wifi Available
Private room in residential home 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
the amenities in both the room and bathroom were a huge help
the bed was comfortable and the small amenities and personal touches were perfect
rebecca was amazing the room was as described
she had complimentary waters in the room which was also a nice touch
the room lets in some great natural light and the room is clean and feels peaceful and private
particularly clean and loved the decoration
very clean stylish and comfortable setting
the space was impeccably clean just as listed
the space was clean and the backyard was great for our dog
everything was clean and we were highly satisfied
she was a great host
rebecca was a great host
very friendly hosts and they made us feel welcome
she was a fantastic host who responded quickly to my messages
outstanding hosts so kind and welcoming you feel right at home
fabulous place to stay only 15 minutes from the airport
it was a great location close to the beach and restaurants
we highly recommend and will be returning to this location in the future thanks again rebecca
nice place in good neighborhood
i would definitely recommend booking this place
Read more reviews

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 States
65 reviews
Entire apartment 1 Bed 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
very thoughtful on the games in the living room toothpaste in the bathroom and bottled water
clean comfortable and convenient
the place is extremely clean and quiet
it was very spacious and impeccably clean
great stay very clean stylish and organized
sparkling clean lots of room and local tips to places nearby
great host with amazing hospitality
all around this place was nice and the host went above and beyond
great place to stay at glad i chose this location
huge apt in a safe quiet neighborhood
Read more reviews

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 States
77 reviews Superhost  Wifi Available
Entire residential home 3 Beds 5 Guests 2 Bedrooms 1 Bathroom

Accommodates: 5

Top guest reviews
Amenities & Room:
also the cottage has very strong air conditioners as well
it was very quiet there and the window air conditioners were very effective
clean comfortable and well positioned for shops restaurants and access to interstatethanks les
i highly suggest the huddle house - just around the corner - delicious breakfast
very clean and spacious
it was super clean and the communication was perfect
very clean and well kept up
the space was clean overall
but other than that the bathroom itself was sparkling clean
the host is a nice person
les was a great host super friendly awesome recommendations and cozy place
the owner was very quick to respond and very helpful with suggestions and questions
great place to stay great host
the host leslie was very friendly attentive accommodating and responsive
very cute cottage in a great location in greenbrier
located near the city park and shopping items needed for daily life were easy to find
also very good location with lots of things around and near
the location was great and overall it was an amazing deal
great value for great stay it was close and the center to all the things we wanted to do
Read more reviews

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 .

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Being a military kid, Shamika has lived and travelled all over India, and her nomadic childhood has fueled an immense hunger and fascination for new cultures and languages (she's a polyglot!)...Read more

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