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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Condo Rentals in Chesapeake Bay

Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!
Enjoy waterfront views from the deck with benches and picnic tables, surrounded by a marina and pier.

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

9.8 out of 10, Exceptional, (137)
"The place was in a great location to see our Son and grandson. "
Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!
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. "
The price is NZ$394
includes taxes & fees
8 Sept - 9 Sept
Only 5 min to Assateague National Seashore!
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, (279)
"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
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, (16)
"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 NZ$368
includes taxes & fees
18 Aug - 19 Aug
5 minutes to Assateague National Seashore!
Perfect Cozy Vacation Rental on the Eastern Shore
Relax in this inviting living space with a sofa, table, and ceiling fan.

Perfect Cozy Vacation Rental on the Eastern Shore

8.2 out of 10, Very good, (26)
"Dated and not modern, clean but not a getaway or vacation rental, stove and oven dirty, only a few dishwater items available. "
Perfect Cozy Vacation Rental on the Eastern Shore
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."
The price is NZ$533
includes taxes & fees
10 Aug - 11 Aug
West Taylor Run Hotel
A Beach Bargain in Chincoteague!
Mini-fridge, microwave, stovetop, coffee/tea maker

A Beach Bargain in Chincoteague!

8.8 out of 10, Excellent, (3)
"Simple. Did not use kitchen. View from door was beautiful."
A Beach Bargain in Chincoteague!
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!
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, (28)
"Apartment was very clean. With a grocery store & restaurants close by."
The price is NZ$628
includes taxes & fees
1 Sept - 2 Sept
Lovely Duplex Apartment - Free Garage parking close to DC
Wyndham Kingsgate - 2 Bedroom Deluxe
Relax by the pool surrounded by lush greenery and comfortable lounge chairs.

Wyndham Kingsgate - 2 Bedroom Deluxe

10.0 out of 10, Exceptional, (13)
"We stay at different locations frequently due to kid's activities and this was BY FAR the best stay we've had. It was honestly better than the listing. Incredibly clean, beautiful location, tons of fun activities. We were actually googling other places we could stay at the same resorts! Absolutely amazing and would stay again in a heartbeat "
Wyndham Kingsgate - 2 Bedroom Deluxe
"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 NZ$879
includes taxes & fees
26 Aug - 27 Aug
"Pura Vida" Fabulous 4 Bed Home near H St & Union Market
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 NZ$603
includes taxes & fees
10 Aug - 11 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, (145)
"Property was clean, comfortable and close to many amenities! Perfect for a weekend getaway. Would absolutely stay again!"
Water-view in Kingsmill, 10 minutes to Busch Gardens & Colonial Williamsburg!
Lovely 2 BR Condo in 4💎 Historic Golf Resort
Compact kitchen with a classic design, featuring a refrigerator, microwave, oven, and sink.

Lovely 2 BR Condo in 4💎 Historic Golf Resort

9.4 out of 10, Exceptional, (16)
"great location. easy to get to everything..condo was great"
The price is NZ$796
includes taxes & fees
10 Aug - 11 Aug
Lovely 2 BR Condo in 4💎 Historic Golf Resort
Luxe 3BDR Penthouse Rooftop TV+Capitol+Monument Views+Parking Free Cancellation
Enjoy cooking in this well-equipped kitchen with a central island, gas stove, oven, and dishwasher.

Luxe 3BDR Penthouse Rooftop TV+Capitol+Monument Views+Parking Free Cancellation

9.4 out of 10, Exceptional, (32)
"Very clean and well maintained.We enjoyed the large space and roof top deck with tv.Kitchen was well stocked with coffee and dishes etc.Primary has a large tv.Easy drive to local attractions. Host was very responsive."
The price is NZ$1,056
includes taxes & fees
31 Aug - 1 Sept
Luxe 3BDR Penthouse Rooftop TV+Capitol+Monument Views+Parking Free Cancellation
Beautiful 1 bedroom condo with a view!
Property grounds

Beautiful 1 bedroom condo with a view!

10.0 out of 10, Exceptional, (51)
"Had a great time during our stay! Love every minute of it! "
Beautiful 1 bedroom condo with a view!
3-bedroom condo in charming Washington with AC, WiFi. Relax and enjoy
Enjoy cooking in this well-lit kitchen with sleek cabinetry, a refrigerator, and oven.

3-bedroom condo in charming Washington with AC, WiFi. Relax and enjoy

2.0 star property
10.0 out of 10, Exceptional, (9)
"CJ, our host, was communicative and informative at ALL stages of trip. From booking to check-in, during the stay and even at check out, CJ was quick to respond with questions and help. The house was beautiful, and the extra little touches were well thought out and sweet. The location was perfect for what we needed! Thank you so, so much CJ!"
3-bedroom condo in charming Washington with AC, WiFi. Relax and enjoy
Waterfront on Marsh Island!
Enjoy the serene view of the water and distant bridge from this spacious balcony with a glass door leading out to the ocean.

Waterfront on Marsh Island!

8.8 out of 10, Excellent, (32)
"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 Assateague National Seashore!
Relax in the comfort of this cozy seating area, featuring a sofa and chairs.

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 NZ$386
includes taxes & fees
8 Sept - 9 Sept
Only 5 min from 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 "
4206 Washington Blvd Condos
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 beds were comfortable, breakfast had a variety of choices. "
colesha k 3-night trip
Posted 20 hours ago
Sheraton Pentagon City Hotel

Frequently asked questions

How much do condos in Chesapeake Bay cost?
Expect to pay from NZ$368 to NZ$1,056 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 91 condos on offer. Enter your destination and travel dates and get a head start on planning your perfect trip today.
What is there to do in Chesapeake Bay near my condo?
Whatever you're into, there are almost endless things to keep you entertained in Chesapeake Bay. If you're off to Washington, stop by Arlington House-The Robert E. Lee Memorial, Cady's Alley and Francis Scott Key Memorial Park. Escaping to Baltimore? Geppi's Entertainment Museum, Union Soldiers and Sailors Monument and Edgar Allan Poe's Gravesite and Memorial are some major attractions in this city.