Search Chesapeake Bay Condo Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

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

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
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
Only 5 minutes to Assateague National Seashore!
2 bedrooms, Internet, bed sheets

Only 5 minutes to Assateague National Seashore!

8.6 out of 10, Excellent, (8)
"Enjoyed very much, will definitely come back!!"
The price is AU$502
includes taxes & fees
3 Aug - 4 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!
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!
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
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
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!
5 minutes to Assateague National Seashore!
Miscellaneous

5 minutes to Assateague National Seashore!

9.2 out of 10, Wonderful, (13)
"Very nice stay, no complaints "
5 minutes to Assateague National Seashore!
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

8.6 out of 10, Excellent, (16)
"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"
The price is AU$349
includes taxes & fees
28 July - 29 July
Downtown Delight Vibrant Oasis in Heart of DC's Bustling Streets
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, (25)
"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$555
includes taxes & fees
27 July - 28 July
Lovely Duplex Apartment - Free Garage parking close to DC
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
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, (196)
"Our family had a wonderful time - beautiful location and so close to everything! "
3 Bedroom, 3 Bath Condo on the James River in gated Kingsmill
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
"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, (23)
"Clean, new property. Convenient to DC and Maryland shore. Would definitely book again"
The price is AU$793
includes taxes & fees
13 July - 14 July
"Pura Vida" Fabulous 4 Bed Home near H St & Union Market
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!
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
Bliss on the Bay - Perfect Beach Getaway
TV

Bliss on the Bay - Perfect Beach Getaway

9.8 out of 10, Exceptional, (7)
"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
Fridge, microwave, oven, stovetop

Luxury Pied-a-Terre Penn Quarter Downtown Washington DC

9.6 out of 10, Exceptional, (12)
"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!
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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.