
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.

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!

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.

Historic Hideaway Private Apartment/Suite
You will be comfortable in this spacious, one bedroom suite. You have your own kitchen, washer/dryer, and living room space with large tvs in the bedroom and the living room. To wind down from your day step into your large beautiful shower that has endless hot water. Try living room sofa pulls out to a sleeper lay down while watching tv, or to use as an extra bed. Enter/exit thru a private entrance. Only you will have access to your space. Clean and inviting. Stay a day, or stay a while!

Wooded Wonderland Miniature Golf Hot tub Pool
Make yourself at home! This property offers a warm and welcoming environment for guest, 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!

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.

THE POINT! Private waterfront Oasis!
Enjoy breath taking views & a fully equipped home w/ many amenities. Looking for a private & intimate experience of quality time & a relaxing retreat w/ nature & ample spacw to spread out, this is IT! Convenient to Virginia Beach Oceanfront, Downtown Norfolk, Rivers Casino, Waterside District & a host of popular attractions. Wheelchair accessible, Tesla charging stations 3 minutes away, perfect for holiday family & group trips, 12 minutes from Carnival Cruise Half Moon port.🛳🌊🚢🏠😊!

The Cozy Cottage Two Bedroom, King bed House
This is a charming and cozy Cape Cod style house. It’s decorations are eclectic and comfortable. There is a king size bed in the master bedroom and a queen size bed in the second bedroom. There are smart TV’s in each bedroom and the living room. This home has brand new central heat and air conditioning, new stainless steel refrigerator and smooth top stove, microwave, and new carpeting. It’s centrally located and there is plenty of space for parking. This is truly a home away from home.

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

Gorgeous Olde Towne historic home - modern updates
Full of historic charm, modern in all the right places! This 1880s home is located in the heart of Olde Towne Portsmouth, just one block from the Elizabeth River harbor. Walk 3 minutes to the ferry stop and ride across the river to Norfolk's downtown and waterfront restaurants, or walk 5 minutes to Portsmouth's High Street to enjoy Olde Towne's charming coffee shops, restaurants, museums, and theaters. This location is unbeatable!
Popular amenities for Chesapeake vacation rentals
Other great vacation rentals in Chesapeake

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

Entire Apartment - No Cleaning Fees!

Cozy Home Near Hospitals & Beach

Blissful Nook @ Washington

The Main House

Modern Cottage 2 Blocks to Beach

Hidden Gem.4/bedroom cozy home fenced in yard

Quiet 3/2 beautiful Chesapeake
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 86 | € 86 | € 90 | € 95 | € 99 | € 101 | € 105 | € 103 | € 92 | € 86 | € 86 | € 86 |
| 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 110 vacation rentals in Salem, over 50 vacation rentals in Great Bridge, and over 110 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 apartment rentals in Chesapeake?
Experience the best of Chesapeake with our apartment rentals, starting at about $20 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 apartment rentals in Chesapeake have a gym?
Absolutely! We offer over 40 apartment rentals with a gym in Chesapeake. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Chesapeake have wifi?
Absolutely! We offer over 540 house rentals with wifi 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 townhouse rentals in Chesapeake?
Chesapeake has more than 50 family-friendly townhouse 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 € 9 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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- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Carova Beach
- Buckroe Beach
- Corolla Beach
- Water Country USA
- First Landing State Park
- Haven Beach
- Buckroe Beach and Park
- Grandview Beach
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- Chrysler Museum of Art
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