
Vacation rentals in Chesapeake
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Chesapeake
Guests agree: these stays are highly rated for location, cleanliness, and more.

Quiet Neighborhood 7 Miles From the Beaches
Be sure to read about the pricing using both bedrooms below in 2nd paragraph. My house is in a quiet neighborhood by a creek of the Lynnhaven River 7 miles from the Oceanfront/Chesapeake Bay with easy access to the interstate and surrounding cities in Hampton Roads. Only minutes from Town Center and local malls. Your private area is the 1st level with your own private entrance, but no kitchen. There is small microwave and a coffee machine in the unit , & a small fridge on the screened-in-porch.

Purple Room- Rare Luxury Ste w/prkg - 1 of a kind!
Welcome to The Purple Room, get ready for an AirBnB experience unlike any others. This one of a kind AirBnB not only offers a memorable staying experience, but will be a welcome end to an exciting day at the beach, dinner and drinks at a local restaurant or bar, or an adventurous day exploring all the culture and history the area has to offer. We are centrally located, offer free parking, wifi and kitchenette. We have local art, free wine and food samples. Come see what the excitement is about!

The Little House on Park Avenue
Our cottage is a quiet get-away. Sit on the front porch and enjoy the birds and a cup of coffee. Small kitchen provides everything you may need for your stay, including a local yummy treat. A desk in the bedroom gives you a place to work while others in your group utilize the spaces in the living room or dining room. You can leisurely stroll by the Ruritan Park to Studio 32 Gallery and Gift shop on weekends. In 10 minutes drive to Merchants Millpond State Park. Historic Edenton only30 minutes.

Beautiful Cottage Waterfront Near Downtown Norfolk
A Beautiful Secluded Paradise! We respond quickly This spacious Non-Smoking cozy cottage has a great view of the Elizabeth River. It's 5 miles from downtown Norfolk and a 5 minute walk to a lightrail stop nearby. A day pass is $4.50 including a ferry to Portsmouth. Great amenities Renovated interior Beautiful Fireplace New floor/fully equipped kitchen Fresh organic eggs/yogurt/snacks/juice/coffee included WiFi-CableTV/HBO Bluetooth sound bar Luxury linens New waterview sunroom Washer/dryer

Private Guesthouse, Ghent/Downtown near ODU, EVMS
Legally licensed and permitted with the City of Norfolk! We did it right here! European-style guesthouse between Ghent and the Heart of Downtown. Walking access to many restaurants and hotspots, and across from “The Tide” light rail, and YMCA, Chrysler Museum of Art, Granby St, Colley Ave, EVMS, Town Point Park! 15-min from the ocean. FREE PRIVATE PARKING: designated driveway parking spot; Kitchenette includes– cooktop, sink, microwave, coffee, fridge; Wifi, separate HVAC, bath, FREE laundry.

Wooded Wonderland Miniature Golf Hot tub Pool
Make yourself at home! This property offers a warm and welcoming environment for guests, located in a quiet and established neighborhood in the middle of Portsmouth, VA. Guests should expect a clean space equipped with modern technology and appliances. Attractions aren’t too far; 41mi from Busch Gardens, 24 mi from Virginia Beach Ocean Front, 7.3 mi from Waterside District Norfolk, and 2.9 mi from Rivers Casino Portsmouth. Peaceful mornings and a comfortable stay awaits at Wooded Wonderland!

Salty Willow-a “suite retreat” in the heart of VB!
We love welcoming people to our home in the heart of Virginia Beach! Come and go as you please in our guest suite with a separate entrance and privacy latches-no one will enter your space. You will also have the added convenience of having the host family on site. We do our best to provide the comforts of home. -fridge/freezer -beach essentials -toaster -coffee bar -extra essentials We want you to make yourself at home with us. Maybe we’ll enjoy a summer night together on the porch soon!

Modern Luxury Peace & Quiet.
Covered parking with EV Charger. With one acre fenced in yard. 1000+ sq ft Modern Second Floor Guest House apartment with separate private entrance attached to a 10,000+ sq ft Mansion on 3 acres in a very safe, quiet and private neighborhood. Free private parking. Minutes from restaurants, shopping centers, and a beautiful 30 minute drive to oceanfront. Free Netflix, High Speed WiFi, washer, dryer, full kitchen. With Keurig. Brand new Heat and Air Condition! Plus 2 dedicated parking spots.

Sweet Suite!
Private attached MOTHER IN LAW suite (not the whole house) in a quiet neighborhood in the heart of Hampton Roads. We offer keyless entry and a private parking space, private pool and backyard grill area. All are welcome here, including pets. We ask that you tell us if you are bringing a pet(s) and I'll message you about the added pet fee. We are minutes away from all major attractions and less than 5 minutes from major highways. Our location gives you easy access to the Outer Banks.

Island Lotus Yoga & Spa
A nature lover’s dream! Waterfront, ample natural light, serene beauty, and privacy can be all yours at our charming ranch right on the bay. The bay faces east, giving you the most breathtaking views of the sunrise and moonrise. Relax in the spa, adventure on kayaks, and chill and grill over the fire-pit. You’ll also local fresh eggs, and a private yoga class. Check us out on insta @islandlotusyoga! PS we’re not actually an island. Reach us by driving through Virginia Beach!

Family friendly townhouse
A perfect place to stay when you can't be at home!Townhouse located in lovely family friendly neighborhood. Only a 20-30 min drive to NOB, Portsmouth Naval Shipyard and Oceana. Bright open kitchen with everything you need. Large living room with new comfortable couch and large Smart TV to hang out and watch tv. Privacy fenced back yard to sit and enjoy the evening or a morning cup of coffee. Large primary bedroom with private bathroom and shower. Washer and dryer in t

Blissful Nook @ Washington
This is a beautiful modern, comfortable, and cozy one bedroom apartment located on the second floor above the car garage. While relaxing or vacationing just know that this apartment is centrally located to Virginia Beach Oceanfront, Outer banks N.C. museums, Colonial Williamsburg, Busch garden, Water Country USA and many restaurant. This apartment is attached to the main home with a dedicated private entrance. This location is safe and private for our guest.
Popular amenities for Chesapeake vacation rentals
Other great vacation rentals in Chesapeake

Serene Tree House Retreat | Spacious 1br/1bth Home

Peaceful beach @Courtyard Cottage+No Cleaning Fee!

Chesapeake Haven - Relaxing Space + Lux Kitchen

Entire Apartment - No Cleaning Fees!

Quilted Quarters by the Bay with Private Entrance

King Guest Suite - A Family Vacation Rental

Quiet 3/2 beautiful Chesapeake

Cowbell Cottage
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ367 | ﺩ.ﺇ367 | ﺩ.ﺇ386 | ﺩ.ﺇ404 | ﺩ.ﺇ422 | ﺩ.ﺇ430 | ﺩ.ﺇ448 | ﺩ.ﺇ441 | ﺩ.ﺇ393 | ﺩ.ﺇ367 | ﺩ.ﺇ367 | ﺩ.ﺇ367 |
| Avg. temp | 6°C | 7°C | 10°C | 16°C | 20°C | 25°C | 27°C | 26°C | 23°C | 18°C | 12°C | 8°C |
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 270 vacation rentals in Ghent, over 110 vacation rentals in Salem, and over 100 vacation rentals in Lynnhaven.
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 300 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 private suite rentals in Chesapeake?
Experience the best of Chesapeake with our private suite rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Chesapeake have a bbq area?
Absolutely! We offer over 110 house rentals with a bbq area in Chesapeake. Enjoy a tailored experience with all the comforts you desire.
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 wifi?
Absolutely! We offer over 150 apartment rentals with wifi in Chesapeake. Enjoy a tailored experience with all the comforts you desire.
Do condo rentals in Chesapeake have self check-in?
Absolutely! We offer over 10 condo rentals with self check-in in Chesapeake. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly apartment rentals in Chesapeake?
Chesapeake has more than 50 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Quick stats about vacation rentals in Chesapeake

Total vacation rentals
Explore 970 vacation rentals in Chesapeake

Nightly prices starting at
Chesapeake vacation rentals start at ﺩ.ﺇ37 per night before taxes and fees

Verified guest reviews
Over 35,620 verified reviews to help you choose

Family-friendly vacation rentals
440 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 300 rentals that welcome pets

Vacation rentals with a pool
130 properties feature pools

Rentals with dedicated workspaces
510 properties have a dedicated workspace

Wi-Fi availability
930 of Chesapeake vacation rentals include wi-fi access

Popular amenities for guests
Guests love Self check-in, Gym, and BBQ grill across Chesapeake rentals

4.8 Average rating
Chesapeake stays are highly rated by guests—averaging 4.8 out of 5!

Nearby attractions
Chesapeake's top spots, include Chrysler Museum of Art, Nauticus, and Cinemark Chesapeake Square
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