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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Featured Condo Rentals in Chesapeake Bay and around

Historic DC Firehouse Penthouse Loft
Interior

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
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, (278)
"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
West Taylor Run Hotel
Signature Condo, 2 Bedrooms | In-room dining

West Taylor Run Hotel

4.0 star property
8.4 out of 10, Very good, (26)
"We had a great stay. The property manager replied very quickly."
West Taylor Run Hotel
Only 5 minutes to Assateague National Seashore!
2 bedrooms, Internet, bed sheets

Only 5 minutes to Assateague National Seashore!

8.8 out of 10, Excellent, (9)
"Enjoyed very much, will definitely come back!!"
The price is €218
includes taxes & fees
17 Aug - 18 Aug
Only 5 minutes to Assateague National Seashore!
Delmarva - Brand new condo in downtown Cape Charles!
Property grounds

Delmarva - Brand new condo in downtown Cape Charles!

Delmarva - Brand new condo in downtown Cape Charles!
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, (27)
"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 €327
includes taxes & fees
3 Aug - 4 Aug
Lovely Duplex Apartment - Free Garage parking close to DC
5 minutes to Assateague National Seashore!
Flat-screen TV

5 minutes to Assateague National Seashore!

8.8 out of 10, Excellent, (15)
"There was enough space for 3 adults and to children. The bathroom in the hall has not been updated. The shower was crudy and no towel rack. The spicket for shower/bath in the 2nd bathroom was almost impossible to use. The rental was okay."
The price is €209
includes taxes & fees
18 Aug - 19 Aug
5 minutes to Assateague National Seashore!
Only 5 min. from the Beach!
Microwave, stovetop, coffee/tea maker, toaster

Only 5 min. from the Beach!

8.6 out of 10, Excellent, (28)
"It’s a good location. Property is clean. We enjoyed our visit. "
The price is €207
includes taxes & fees
18 Aug - 19 Aug
Only 5 min. from the Beach!
"Pura Vida" Fabulous 4 Bed Home near H St & Union Market
Private kitchen

"Pura Vida" Fabulous 4 Bed Home near H St & Union Market

9.6 out of 10, Exceptional, (24)
"Super clean, quick walk to the train and downtown DC. Great for family trip would stay again! "
The price is €445
includes taxes & fees
10 Aug - 11 Aug
"Pura Vida" Fabulous 4 Bed Home near H St & Union Market
Luxury Riverfront Condo w/ sunrise & sunset views
Marina

Luxury Riverfront Condo w/ sunrise & sunset views

9.6 out of 10, Exceptional, (62)
"Amazing views and beautiful property."
The price is €318
includes taxes & fees
3 Aug - 4 Aug
Luxury Riverfront Condo w/ sunrise & sunset views
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, (3)
"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, (144)
"Enjoyed our long weekend at the kingsmill resort. The unit was clean and spacious. Check in was easy and the hosts were friendly and way to communicate with We took advantage of the tennis and the beautiful location. "
Water-view in Kingsmill, 10 minutes to Busch Gardens & Colonial Williamsburg!
Downtown Delight Vibrant Oasis in Heart of DC's Bustling Streets
Fridge, microwave, oven, stovetop

Downtown Delight Vibrant Oasis in Heart of DC's Bustling Streets

8.4 out of 10, Very good, (17)
"This place is very conveniently located in downtown DC, where everything you can want to see, do or experience is just a short distance away. This was perfect for our short visit the owner was super nice, super responsive and vey helpful"
Downtown Delight Vibrant Oasis in Heart of DC's Bustling Streets
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, (84)
"Overall satisfied with the stay. Location was great, not crowded and easy to get around. "
Kingsmill Condo on Golf Course 9th Fairway! Local owner
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, (199)
"Very nice, spacious place in a great area!"
3 Bedroom, 3 Bath Condo on the James River in gated Kingsmill
Only 5 min to Assateague National Seashore!
Terrace/patio

Only 5 min to Assateague National Seashore!

9.6 out of 10, Exceptional, (17)
"Nice place. "
Only 5 min to Assateague National Seashore!
Only 5 min from Assateague National Seashore!
Property grounds

Only 5 min from Assateague National Seashore!

8.0 out of 10, Very good, (1)
"We had short trip for the oyster festival but really enjoyed our stay. It was quiet and cozy. Beautiful views off the deck. "
The price is €226
includes taxes & fees
12 Aug - 13 Aug
Only 5 min from Assateague National Seashore!
Unit #1 - 1-bedroom condo in amazing Washington Close to Howard University,
Exterior

Unit #1 - 1-bedroom condo in amazing Washington Close to Howard University,

9.0 out of 10, Wonderful, (2)
"Thank you for accommodating our resident. If we ever have any recommendations for winter or stay, I will recommend your property. Thanks for all your help."
The price is €221
includes taxes & fees
4 Aug - 5 Aug
Unit #1 - 1-bedroom condo in amazing Washington Close to Howard University,
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
Luxurious 3 Bedroom Condo Sleeps 8!
Fridge, microwave, oven, stovetop

Luxurious 3 Bedroom Condo Sleeps 8!

10.0 out of 10, Exceptional, (93)
"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!
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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Top Chesapeake Bay Hotel Reviews

Sheraton Pentagon City Hotel

Sheraton Pentagon City Hotel

10/10 Excellent
"The price is good, and the shuttle bus is convinient to the city."
Dawei 1-night trip
Posted 7 hours ago
Sheraton Pentagon City Hotel

Frequently asked questions

How much do condos in Chesapeake Bay cost?
Expect to pay from €207 to €445 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 84 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.