
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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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 stars2 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, 61 reviewsSleeps 6-8, King bed, 2.5 baths
DeborahRating, 5 stars2 weeks ago
This is my fourth stay at one of Monica's properties and it never disappoints. My visits are consistently pleasant and comfortable. Monica is a great host. I look forward to many returns when visiting my granddaughters in the area.
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, 58 reviewsBeautiful 3 bedroom riverfront home
FrannyRating, 5 stars1 week ago
I wish we had more time here! I hesitate to say it felt “homey” because sometimes that’s a euphemism for something else. But this place is truly homey; you instantly feel at ease and welcome! I would highly recommend staying here if you’re in the area!
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, 210 reviewsGR8 Family Vacation Rental
KayteRating, 5 stars2 weeks ago
Even though he was out of town when we arrived, Spence was available by phone and quick to respond. We were charmed by the tangible history of the house, and surprised by how private it is, in spite of its proximity to the street. For us, the vintage upstairs bathroom was an added pleasure, and well worth the signs of age. This is a truly beautiful house for visitors who can appreciate it, and Spence is a great host!
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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