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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

Historic DC Firehouse Penthouse Loft
Enjoy meals in the kitchen with a central island, sink, and stove, and dine in the adjacent seating area with a sofa and coffee table.

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
West Taylor Run Hotel
Enjoy cooking in this well-equipped kitchen with an oven, microwave, and stainless steel appliances.

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!
Cozy retreat with a kitchenette, featuring a bed, seating area, and views of lush greenery.

Only 5 minutes to Assateague National Seashore!

8.8 out of 10, Excellent, (9)
"Enjoyed very much, will definitely come back!!"
The price is AU$390
includes taxes & fees
17 Aug - 18 Aug
Only 5 minutes to Assateague National Seashore!
Delmarva - Brand new condo in downtown Cape Charles!
Relax on the balcony with a chair and enjoy the view.

Delmarva - Brand new condo in downtown Cape Charles!

Delmarva - Brand new condo in downtown Cape Charles!
Only 5 min. from the Beach!
Compact kitchen with refrigerator, microwave, sink, and oven, offering ample storage and cooking facilities.

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 AU$375
includes taxes & fees
18 Aug - 19 Aug
Only 5 min. from the Beach!
Rendezvous at the Bay, Resort Condo in charming Cape Charles. Relaxation awaits
Guests can enjoy the beach with umbrellas and calm waters surrounded by lush greenery and a rocky breakwater.

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
Luxury Riverfront Condo w/ sunrise & sunset views
Enjoy waterfront views from the covered patio area, surrounded by lush trees and a marina with moored boats.

Luxury Riverfront Condo w/ sunrise & sunset views

9.6 out of 10, Exceptional, (62)
"Amazing views and beautiful property."
The price is AU$564
includes taxes & fees
3 Aug - 4 Aug
Luxury Riverfront Condo w/ sunrise & sunset views
Water-view in Kingsmill, 10 minutes to Busch Gardens & Colonial Williamsburg!
Relax on the beach with a view of the water and access to a dock.

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

10.0 out of 10, Exceptional, (143)
"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!
5 minutes to Assateague National Seashore!
Relax in this inviting living room with a comfortable sofa, side table, and stunning deck views.

5 minutes to Assateague National Seashore!

8.8 out of 10, Excellent, (15)
"Very nice stay, no complaints "
5 minutes to Assateague National Seashore!
Downtown Delight Vibrant Oasis in Heart of DC's Bustling Streets
Enjoy cooking in this well-equipped kitchen with a spacious countertop, modern cabinetry, and a refrigerator.

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
Lovely Duplex Apartment - Free Garage parking close to DC
Enjoy a meal in the kitchen with an oven and stainless steel sink, then step out to a balcony with a sliding glass door.

Lovely Duplex Apartment - Free Garage parking close to DC

9.0 out of 10, Wonderful, (26)
"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 AU$581
includes taxes & fees
3 Aug - 4 Aug
Lovely Duplex Apartment - Free Garage parking close to DC
Annapolis Condominium in the heart of the historic center
Enjoy the city view from this balcony with a sofa and wicker chairs.

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
3 Bedroom, 3 Bath Condo on the James River in gated Kingsmill
Enjoy lakeside picnics at a tranquil setting with picnic tables and benches, perfect for fishing or boating.

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

10.0 out of 10, Exceptional, (198)
"Very nice, spacious place in a great area!"
3 Bedroom, 3 Bath Condo on the James River in gated Kingsmill
Kingsmill Condo on Golf Course 9th Fairway! Local owner
Relax on the beach with comfortable seating areas and a picturesque pier.

Kingsmill Condo on Golf Course 9th Fairway! Local owner

10.0 out of 10, Exceptional, (83)
"Overall satisfied with the stay. Location was great, not crowded and easy to get around. "
Kingsmill Condo on Golf Course 9th Fairway! Local owner
"Pura Vida" Fabulous 4 Bed Home near H St & Union Market
Enjoy cooking in this well-equipped kitchen with a central island, oven, and microwave.

"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 AU$767
includes taxes & fees
26 Aug - 27 Aug
"Pura Vida" Fabulous 4 Bed Home near H St & Union Market
Only 5 min to Assateague National Seashore!
Guests can enjoy seating on the deck with comfortable chairs and a bench, offering a safe boundary and a view of the surrounding field.

Only 5 min to Assateague National Seashore!

9.6 out of 10, Exceptional, (17)
"Nice place. "
Only 5 min to Assateague National Seashore!
4206 Washington Blvd Condos
Relax in this serene bedroom with a large bed, adorned with pillows, and a small table with a vase of flowers.

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 "
The price is AU$558
includes taxes & fees
1 Aug - 2 Aug
4206 Washington Blvd Condos
Bliss on the Bay - Perfect Beach Getaway
Enjoy the serene sea view from the comfort of this stylish room, featuring a sofa, stool, and wicker lamp.

Bliss on the Bay - Perfect Beach Getaway

9.8 out of 10, Exceptional, (8)
"Great view over the bay, small space but efficient use. Great fridge and comfortable bed"
Bliss on the Bay - Perfect Beach Getaway
Luxury Pied-a-Terre Penn Quarter Downtown Washington DC
Enjoy cooking in this well-equipped kitchen with a stove, microwave, and sink.

Luxury Pied-a-Terre Penn Quarter Downtown Washington DC

9.0 out of 10, Wonderful, (13)
"Wonderful areas with lots of amazing restaurants nearby and close to the action in DC. Perfect for my short business stay. "
Luxury Pied-a-Terre Penn Quarter Downtown Washington DC
Book A Piece of History at Kingsmill Resort in Williamsburg Virginia!
Enjoy al fresco dining at our outdoor bar, surrounded by comfortable seating and a stunning ocean view.

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?
You'll pay from AU$375 to AU$767 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.