
Vacation rentals in Chesapeake
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Top-rated vacation rentals in Chesapeake
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Popular amenities for Chesapeake vacation rentals
Other great vacation rentals in Chesapeake
Top guest favourite

Home in Corolla
5 out of 5 average rating, 17 reviews*May specials LUX, Firepit pool/hot tub,ocean view
Chrissy Rating, 5 stars3 weeks ago
fantastic hosts! the house was absolutely amazing! made us all feel at home. the amenities were fabulous. wish I could rate a 10 because it is worth every star! perfect fit for our large family. the memories we made will never be forgotten. thank you to our host, who made everything so easy. defiantly will reserve this gorgeous house in the future.
Guest favourite

Home in Chesapeake
4.98 out of 5 average rating, 63 reviewsSleeps 6-8, King bed, 2.5 baths
RebekahRating, 5 stars1 week ago
This place was wonderful! Perfect for visiting Virginia! Monica was very friendly! Would stay again!
Guest favourite

Home in Corolla
5 out of 5 average rating, 16 reviewsLazy Palm Carova 4x4 Beach
MichelleRating, 5 stars7 months ago
The horses stopped by several times a day. It was magical. Just a short drive to the ocean where we conveniently parked our car on the beach. We had plenty of room on the beach. People were not on top of each other. It was a wonderful vacation! The house was spacious and nicely decorated. the kitchen was well stocked.
Guest favourite

Home in Norfolk
4.95 out of 5 average rating, 38 reviewsFamily Getaway | 1 Block from Beach | Game Room
KimberlyRating, 5 stars1 week ago
This was a wonderful location with personal touches and thoughtful planning. The kitchen and bathroom were stocked, yard was perfect for our dog and beds were clean and comfortable. Our dog loved the beach which was a quick walk away. Brian was responsive on the two occasions I had to reach him. The home was close to Little Creek base which was convenient to see our son. Parking was terrific and the home is on a street that is not too busy. The only negative that I’d have is that (as a middle aged woman who sleeps HOT) we were unable to adjust the home’s temperature below 68. Ceiling fans and oscillating fans were available which was helpful. Overall would recommend this home and its host and will likely be back in the future!
Guest favourite

Home in Cofield
4.78 out of 5 average rating, 59 reviewsBeautiful 3 bedroom riverfront home
ChessieRating, 5 stars2 days ago
This was my 2nd time staying here and again it didn't disappoint!! The kitchen was well stocked, and everything you could need is there! You just can't beat that view!
Top guest favourite

Home in Surry
5 out of 5 average rating, 69 reviewsWaterfront on the James 4,100 SF near Williamsburg
DelRating, 5 stars2 weeks ago
Really nice quiet place on the James River. Kitchen and living room/breakfast area served our family really well. The house is close to the Jamestown ferry which allowed us easy access to the historical sights of Jamestown, Williamsburg and Yorktown and some great restaurants in Williamsburg. A great place.
Guest favourite

Home in Sandbridge
5 out of 5 average rating, 24 reviewsPool, hot tub, walk to beach, family friendly home
JeromyRating, 5 stars1 month ago
The place had plenty of sleeping spaces which is what we needed it was a great stay. Communication went well and there was plenty to entertain everyone
Superhost

Home in Williamsburg
4.6 out of 5 average rating, 211 reviewsGR8 Family Vacation Rental
DanielleRating, 5 stars2 weeks ago
The house is a perfect location for visiting all the historical landmarks in the area. We enjoy having our morning coffee out on the back deck. The kitchen had everything you could need and more in a vacation rental. I would much rather have a smaller kitchen and not have to buy any cooking gear while on vacation. It even had a crockpot. We would highly recommend this place to any one looking to stay in the Williamsburg area.
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
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- Virginia Beach Oceanfront
- Carova Beach
- Resort Beach
- Corolla Beach
- Busch Gardens Williamsburg
- Bethel Beach
- Buckroe Beach
- First Landing State Park
- Kingsmill Resort
- Currituck Beach Lighthouse
- Virginia Beach National Golf Club
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- Grove Beach
- Buckroe Beach and Park
- Golden Horseshoe Golf Club
- Wilkins Beach
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- Norfolk Botanical Garden
- Grandview Beach
- Kiptopeke Beach
- Jamestown Settlement
- Ocean Breeze Waterpark