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Check prices for these dates

Next weekend
20 Jun - 22 Jun
In two weeks
27 Jun - 29 Jun
In one month
11 Jul - 13 Jul
In two months
8 Aug - 10 Aug

Featured Condo Rentals in Chesapeake Bay and around

West Taylor Run Hotel
Signature Condo, 2 Bedrooms | In-room dining

West Taylor Run Hotel

4.0 star property
8.6 out of 10, Excellent, (24)
"This is a well-kept place with all of the things we needed. Extremely comfortable beds, good kitchen and easy access."
West Taylor Run Hotel
Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!
Property grounds

Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!

9.8 out of 10, Exceptional, (133)
"My parents stayed at this condo so that they could be close to us during the Thanksgiving holiday. It was nicely decorated and very clean! They loved the location and view off of the back patio. Great place to stay!"
Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!
3 Bedroom, 3 Bath Condo on the James River in gated Kingsmill
Beach nearby

3 Bedroom, 3 Bath Condo on the James River in gated Kingsmill

10.0 out of 10, Exceptional, (193)
"We loved our stay at Fred’s condo! Perfect location with a great view. Absolutely wonderful!"
3 Bedroom, 3 Bath Condo on the James River in gated Kingsmill
Only 5 min. from the Beach!
Interior

Only 5 min. from the Beach!

9.2 out of 10, Wonderful, (19)
"Quiet, convenient location. Nicely decorated. Great price."
The price is €211
includes taxes & fees
7 Jul - 8 Jul
Only 5 min. from the Beach!
Waterfront on Marsh Island!
Interior

Waterfront on Marsh Island!

8.8 out of 10, Excellent, (25)
"Small Cozy condo for couples. Very quiet and relaxing with great sunrises and sunsets! Great location with being on the water!"
Waterfront on Marsh Island!
Only 5 min. from the Beach!
Beach

Only 5 min. from the Beach!

8.6 out of 10, Excellent, (25)
"Great time. Nice accomodations, easy access. Beautiful area."
Only 5 min. from the Beach!
Luxurious 3 Bedroom Condo Sleeps 8!
Fridge, microwave, oven, stovetop

Luxurious 3 Bedroom Condo Sleeps 8!

10.0 out of 10, Exceptional, (92)
"We enjoyed our stay at Kingsmill. Property was neat and clean, not to mention conveniently located. Would definitely stay again! "
Luxurious 3 Bedroom Condo Sleeps 8!
Luxury Riverfront Condo w/ sunrise & sunset views
Property grounds

Luxury Riverfront Condo w/ sunrise & sunset views

9.6 out of 10, Exceptional, (57)
"Our stay was amazing. The condo was immaculate, the kitchen was well stocked and the Riverview was outstanding. "
The price is €323
includes taxes & fees
11 Jun - 12 Jun
Luxury Riverfront Condo w/ sunrise & sunset views
Waterfront on Marsh Island!
Interior

Waterfront on Marsh Island!

9.4 out of 10, Exceptional, (10)
"Spent a long weekend with the wife. Location was perfect. Property manager was very communicative. Easy check in process. Unit is small, like an efficiency, but perfect for our needs. Nothing fancy, but has everything you need."
Waterfront on Marsh Island!
Annapolis Condominium in the heart of the historic center
Terrace/patio

Annapolis Condominium in the heart of the historic center

9.8 out of 10, Exceptional, (273)
"The location and amenities are great. The host are very friendly, helpful and easy to make contact with. My family used this location for commission week and could not have asked for more. "
Annapolis Condominium in the heart of the historic center
Lovely Duplex Apartment - Free Garage parking close to DC
Fridge, microwave, oven, stovetop

Lovely Duplex Apartment - Free Garage parking close to DC

9.0 out of 10, Wonderful, (24)
"A friend and I were in town for a conference and the place was perfect. Obtaining the keys was an interesting but fun process. It was like a treasure hunt. Plenty of towels, comfy beds, coffee, great area. Thank you for a great stay!"
The price is €367
includes taxes & fees
19 Jun - 20 Jun
Lovely Duplex Apartment - Free Garage parking close to DC
Cape Haven - Condo 1.5 Blocks from Beach
Miscellaneous

Cape Haven - Condo 1.5 Blocks from Beach

9.8 out of 10, Exceptional, (44)
"This place was amazing. Spacious and beautifully decorated and the location was perfect!!!"
Cape Haven - Condo 1.5 Blocks from Beach
Beautiful 1 bedroom condo with a view!
Property grounds

Beautiful 1 bedroom condo with a view!

10.0 out of 10, Exceptional, (47)
"Crysty was very accommodating and a great host! The place was very clean and had all the main essentials! We enjoyed our stay and highly recommend the space."
Beautiful 1 bedroom condo with a view!
Walk to beaches, large beautiful 2bdrm two bath, "Kingsmill on the James"
Beach nearby, sun-loungers

Walk to beaches, large beautiful 2bdrm two bath, "Kingsmill on the James"

10.0 out of 10, Exceptional, (44)
"We enjoyed are short stay at the Kingsmill. Place was perfect for our family!"
Walk to beaches, large beautiful 2bdrm two bath, "Kingsmill on the James"
"La Casa Bianca" Fabulous 3 Bed Home next to H St & Union Market
Interior

"La Casa Bianca" Fabulous 3 Bed Home next to H St & Union Market

9.8 out of 10, Exceptional, (18)
"Beautifully maintained and comfortable. There was six of us and taking the Uber everywhere we wanted to go was super easy and inexpensive. We would stay here again!"
"La Casa Bianca" Fabulous 3 Bed Home next to H St & Union Market
Paradise by Busch Gardens, walk to beach! Lovely large 3bedroom/3 full bathrooms
Beach

Paradise by Busch Gardens, walk to beach! Lovely large 3bedroom/3 full bathrooms

10.0 out of 10, Exceptional, (8)
"My family and I were very comfortable during our stay here. Gayle, the host was very responsive and the condo was well stocked with everything we needed. The location was great. We would stay here again!"
Paradise by Busch Gardens, walk to beach! Lovely large 3bedroom/3 full bathrooms
The Gallery Unit 101
Interior

The Gallery Unit 101

3.5 star property
9.6 out of 10, Exceptional, (5)
"Very clean"
The Gallery Unit 101
4206 Washington Blvd Condos
Exclusive Condo, 3 Bedrooms

4206 Washington Blvd Condos

4.0 star property
4.8 out of 10, (3)
"No hot water for the first 3 days, we have to boil our own water to shower . When we try to contact no one answer for a while. Very confusing instructions to how to get in the house "
4206 Washington Blvd Condos
Perfect Cozy Vacation Rental on the Eastern Shore
Smart TV

Perfect Cozy Vacation Rental on the Eastern Shore

8.2 out of 10, Very good, (23)
"Great location, close to town, beach, fishing spots. very clean, safe and spacious parking for boats."
Perfect Cozy Vacation Rental on the Eastern Shore
Book A Piece of History at Kingsmill Resort in Williamsburg Virginia!
Outdoor dining

Book A Piece of History at Kingsmill Resort in Williamsburg Virginia!

9.4 out of 10, Exceptional, (28)
"Traveled to Kingsmill for a golf tournament. Excellent accommodations and easy access to the resort. Owner very responsive."
Book A Piece of History at Kingsmill Resort in Williamsburg Virginia!
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.
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Frequently asked questions

How much do condos in Chesapeake Bay cost?
Expect to pay from €211 to €367 per night for condos in Chesapeake Bay. No matter your budget, a terrific stay is a click away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many condos are there in Chesapeake Bay?
Chesapeake Bay has 58 condos on offer. Enter your destination and travel dates and get a head start on planning your perfect trip today.
Why book your condo in Chesapeake Bay with Expedia?
We think that holidays should be a piece of cake, so if you’re in search of condos at an affordable rate, Expedia delivers. Keep the budget in check and pick something cheap and cheerful, or book 5-star accommodation and treat your loved ones. Take advantage of our search filters to find an escape in Chesapeake Bay that suits your needs.