Villas in Chesapeake

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Compare Villas in Chesapeake with updated reviews, rates, and availability.

Old-World Retreat at 1860s Manor: Luxury Amenities - Tennis Court & Nature Trail
10.0 out of 10, Exceptional, (43)
"This stay definitely exceeded our expectations. We had a total of 5 adults (all immediate family) and everyone was comfortable. The woodburning fireplace was wonderful on the chilly mornings. The host, Tyler was very quick and responsive for the couple of request we had. We will stay there again for sure."
The price is $165
$384 total
includes taxes & fees
May 20 - May 21
Old-World Retreat at 1860s Manor: Luxury Amenities - Tennis Court & Nature Trail
One Bedroom Suite Ocean View
10.0 out of 10, Exceptional, (2)
"I wasn’t happy that there wasn’t too much leniency on early or late check ins or check outs. Most other hotels I have used in the past have allowed checkins as early as 2am day of as well as 2pm for check outs. This includes Hilton, Marriott and best western. The diamond resort was just purchased by Hilton so hopefully in the future they will be lenient for request from guest. I also understand if they said yes to everyone that ask… it would be tough as well to turn/flip a room. Other than...
One Bedroom Suite Ocean View
The Boat House on the Bay - On the water; Pet Friendly; WiFi
8.2 out of 10, Very Good, (17)
"The positives first the property manager was very friendly and helpful the check in process was easy property was clean had an nice time especially loved the wildlife in the bay! Something's I wish I knew before I booked the pictures are pretty outdated so the dock that we were hoping to fish on was in complete dis repair it was not safe to go on at all a little disappointing but it is off season. We did also have a random couple ask us on our first day what we were doing there because he said...
The price is $209
$388 total
includes taxes & fees
Jun 10 - Jun 11
The Boat House on the Bay - On the water; Pet Friendly; WiFi
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Diamond Resorts Beach Quarters Resort - Studio Accessible Roll in Shower
Diamond Resorts Beach Quarters Resort - Studio Accessible Roll in Shower
Diamond Resorts Turtle Cay Resort - Studio
Diamond Resorts Turtle Cay Resort - Studio
Diamond Resorts Ocean Beach Club - Studio
Diamond Resorts Ocean Beach Club - Studio
Diamond Resorts Ocean Beach Club - Studio - Ocean View
Diamond Resorts Ocean Beach Club - Studio - Ocean View
Diamond Resorts Turtle Cay Resort - Studio Accessible No Roll in Shower
Diamond Resorts Turtle Cay Resort - Studio Accessible No Roll in Shower
Diamond Resorts Turtle Cay Resort - 1 Bedroom Accessible No Roll in Shower
Diamond Resorts Turtle Cay Resort - 1 Bedroom Accessible No Roll in Shower
Diamond Resorts Oceanaire Resort - 2 Bedroom Ocean Front Suite
Diamond Resorts Oceanaire Resort - 2 Bedroom Ocean Front Suite
Diamond Resorts Beach Quarters Resort - 1 Bedroom Ocean Front Max 4
Diamond Resorts Beach Quarters Resort - 1 Bedroom Ocean Front Max 4
Diamond Resorts Ocean Beach Club - Studio - Ocean Front
Diamond Resorts Ocean Beach Club - Studio - Ocean Front
Diamond Resorts Oceanaire Resort - 1 Bedroom Accessible No Roll in Shower OceanView
Diamond Resorts Oceanaire Resort - 1 Bedroom Accessible No Roll in Shower OceanView
Diamond Resorts Turtle Cay Resort - 1 Bedroom
Diamond Resorts Turtle Cay Resort - 1 Bedroom
Diamond Resorts Boardwalk Resort and Villas - 2 Bedroom Ocean Front
Diamond Resorts Boardwalk Resort and Villas - 2 Bedroom Ocean Front
Diamond Resorts Turtle Cay Resort - 1 Bedroom
Diamond Resorts Turtle Cay Resort - 1 Bedroom
Diamond Resorts Boardwalk Resort and Villas - Studio - City View
Diamond Resorts Boardwalk Resort and Villas - Studio - City View
Luxury, Beach-Casual Villa: Walking distance to beach and The Cavalier!
Luxury, Beach-Casual Villa: Walking distance to beach and The Cavalier!
Diamond Resorts Beach Quarters Resort - 1 Bedroom Ocean Front Max 6
Diamond Resorts Beach Quarters Resort - 1 Bedroom Ocean Front Max 6
Diamond Resorts Oceanaire Resort - 3 Bedroom Ocean Front Suite
Diamond Resorts Oceanaire Resort - 3 Bedroom Ocean Front Suite
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other property types in Chesapeake

Beach Condo 2 Min Walk From The Beach
9.2 out of 10, Wonderful, (91)
"This condo was absolutely fabulous. It is literally 2 minute walk to the beach access. The rooms were comfortable and I've never stayed at a Vrbo with such an impressively stocked kitchen. The host responded quickly and answered all our questions. They were also very responsive. It was a lovely stay."
Beach Condo 2 Min Walk From The Beach
The Atrium Resort by VSA Resorts
3.5 star property
8.2 out of 10, Very Good, (1077)
"The property staff was very nice and tentative to our needs during our stay. We had an issue with our room and they changed our room that was more suitable."
The price is $108
$178 total
includes taxes & fees
May 29 - May 30
The Atrium Resort by VSA Resorts
The Ocean Sands Resort by VSA Resorts
3.0 star property
8.0 out of 10, Very Good, (1269)
"View was immaculate. Room was accommodating. Some major amenities were not available during entire duration of stay (wi fi) and some ice machines. The ocean view made it worth the stay."
The price is $122
$199 total
includes taxes & fees
May 16 - May 17
The Ocean Sands Resort by VSA Resorts
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Why book your villa in Chesapeake with Expedia?
We think organizing a vacation should be stress-free, so if you’re on the lookout for villas at an affordable rate, Expedia delivers. Keep costs down and go for an all-inclusive stay, or book a luxury villa to surprise your loved ones. Our search filters make it simple to find a place in Chesapeake that fits your needs.
How can I find cheap villas in Chesapeake?
With Expedia’s helpful filter tool, booking cheap villas in Chesapeake is a piece of cake. To find accommodations that are gentle on your bank balance, narrow your search results by budget, star rating and amenities.
What is there to do near my villa in Chesapeake?
You’ll find loads of fabulous things to see and do in Chesapeake. Head for leading attractions like Portlock Galleries at SoNo, Jillians Billiards and Chesapeake City Park. Oak Grove Lake Park, Cahoon Plantation Golf Course and Chesapeake Golf Club also lure many visitors.