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Check prices for these dates

Next weekend
18 July - 20 July
In two weeks
25 July - 27 July
In one month
8 Aug - 10 Aug
In two months
5 Sept - 7 Sept

Featured Condo Rentals in Chesapeake Bay

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, (135)
"Location was excellent. "
Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!
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, (276)
"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
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
Waterfront on Marsh Island!
Interior

Waterfront on Marsh Island!

8.8 out of 10, Excellent, (28)
"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!
Kingsmill Condo on Golf Course 9th Fairway! Local owner
Sun-loungers, beach towels

Kingsmill Condo on Golf Course 9th Fairway! Local owner

10.0 out of 10, Exceptional, (83)
"The accommodation was great. It was so comfortable. Being on the ground level made it so easy with our dog. She loved sitting on the porch watching the golfers. "
Kingsmill Condo on Golf Course 9th Fairway! Local owner
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, (25)
"We had a great stay. The property manager replied very quickly."
The price is AU$683
includes taxes & fees
11 July - 12 July
West Taylor Run Hotel
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
Only 5 min to Assateague National Seashore!
TV, DVD player

Only 5 min to Assateague National Seashore!

9.6 out of 10, Exceptional, (16)
"Nice place. "
Only 5 min to Assateague National Seashore!
Only 5 min. from the Beach!
Beach

Only 5 min. from the Beach!

8.6 out of 10, Excellent, (27)
"Great time. Nice accomodations, easy access. Beautiful area."
The price is AU$368
includes taxes & fees
27 July - 28 July
Only 5 min. from the Beach!
Luxury Riverfront Condo w/ sunrise & sunset views
Property grounds

Luxury Riverfront Condo w/ sunrise & sunset views

9.6 out of 10, Exceptional, (60)
"Our stay was amazing. The condo was immaculate, the kitchen was well stocked and the Riverview was outstanding. "
The price is AU$556
includes taxes & fees
22 July - 23 July
Luxury Riverfront Condo w/ sunrise & sunset views
Historic DC Firehouse Penthouse Loft
Smart TV, fireplace

Historic DC Firehouse Penthouse Loft

8.6 out of 10, Excellent, (23)
"It’s a great place with lots of space for everyone. We enjoyed our stay. Close to the Metro and awesome restaurants. Highly recommended "
Historic DC Firehouse Penthouse Loft
Beautiful Condo - Water View Near City Dock
Outdoor dining

Beautiful Condo - Water View Near City Dock

9.6 out of 10, Exceptional, (145)
"Clean, quiet, and very close to both downtown and Eastport restaurants."
Beautiful Condo - Water View Near City Dock
Beautiful 1 bedroom condo with a view!
Property grounds

Beautiful 1 bedroom condo with a view!

10.0 out of 10, Exceptional, (48)
"Great condo, great location, nice view, extremely clean, nice area to walk around. "
Beautiful 1 bedroom condo with a view!
Wyndham Kingsgate - 2 Bedroom Deluxe
Pool

Wyndham Kingsgate - 2 Bedroom Deluxe

9.4 out of 10, Exceptional, (20)
"Great complex in Williamsburg for families. Will definitely go back."
Wyndham Kingsgate - 2 Bedroom Deluxe
"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, (21)
"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
Williamsburg Condo Rental: 3 Mi to Busch Gardens!
Pool

Williamsburg Condo Rental: 3 Mi to Busch Gardens!

9.0 out of 10, Wonderful, (14)
"Great place! Extremely clean and had anything you needed…shampoo, body wash, great internet, tvs in every room, and very spacious! The neighborhood is beautiful and offers a community pool and gated. Only minutes from Busch Gardens, Water Park USA, grocery stores and more! Great communication with contact. Highly recommend!"
Williamsburg Condo Rental: 3 Mi to Busch Gardens!
Rendezvous at the Bay, Resort Condo in charming Cape Charles. Relaxation awaits
Sun-loungers

Rendezvous at the Bay, Resort Condo in charming Cape Charles. Relaxation awaits

10.0 out of 10, Exceptional, (2)
"We had an amazing time for a family getaway. There was ample room for six adults and two kids to and under the host were great and super accommodating and helpful with helping us to get everything set up so that we were able to enjoy the golf course and the pool we would love to come again"
Rendezvous at the Bay, Resort Condo in charming Cape Charles. Relaxation awaits
Water-view in Kingsmill, 10 minutes to Busch Gardens & Colonial Williamsburg!
Beach nearby, beach towels

Water-view in Kingsmill, 10 minutes to Busch Gardens & Colonial Williamsburg!

10.0 out of 10, Exceptional, (140)
"Good"
Water-view in Kingsmill, 10 minutes to Busch Gardens & Colonial Williamsburg!
Lovely 2 BR Condo in 4💎 Historic Golf Resort
Fridge, microwave, oven, stovetop

Lovely 2 BR Condo in 4💎 Historic Golf Resort

9.4 out of 10, Exceptional, (15)
"great location. easy to get to everything..condo was great"
The price is AU$734
includes taxes & fees
23 July - 24 July
Lovely 2 BR Condo in 4💎 Historic Golf Resort
Only 5 min. from the Beach!
Interior

Only 5 min. from the Beach!

9.2 out of 10, Wonderful, (23)
"The property is just the right size if you're looking to get away on your own or with a significant other. It's a cozy space that's decorated tastefully. It's also very quiet at this property (though I was here during the off-season). It's centrally located on Chincoteague so close to everything. "
The price is AU$479
includes taxes & fees
2 Aug - 3 Aug
Only 5 min. from the Beach!
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?
You'll pay from AU$368 to AU$734 per night for condos in Chesapeake Bay. No matter your budget, you'll find the perfect stay on Expedia. This price was 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?
Take a peek at our 82 condos in Chesapeake Bay and then book your favourite. Whether you're embarking on a family getaway or kicking back with your pals, your perfect stay is just a few clicks away with Expedia.
What is there to do in Chesapeake Bay near my condo?
Whether you enjoy shopping, dining, history or culture, Chesapeake Bay promises something for everyone! The awesome city of Washington has tons of attractions, including National Mall, Smithsonian Institution and National Museum of African American History and Culture. If you're holidaying in Baltimore, National Aquarium in Baltimore, Baltimore Museum of Art and American Visionary Art Museum have to be on your itinerary.