Search Chesapeake Bay Condo Rentals

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Featured Condo Rentals in Chesapeake Bay

Annapolis Condominium in the heart of the historic center

9.8 out of 10, Exceptional, (269)
"This property is just steps from Main Street. It was the perfect location for exploring town and enjoying all that Annapolis had to offer during the holiday season. "
Annapolis Condominium in the heart of the historic center

Contemporary Condo in Quiet Locale!

10.0 out of 10, Exceptional, (27)
"Nice, quiet, place inside the Belt Way. Works for me!"
Contemporary Condo in Quiet Locale!

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

9.8 out of 10, Exceptional, (123)
"Great experience "
Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!

Luxury Pied-a-Terre Penn Quarter Downtown Washington DC

9.6 out of 10, Exceptional, (7)
"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

West Taylor Run Hotel

4.0 star property
8.6 out of 10, Excellent, (20)
"My family and I stayed here for jusy over a week while between homes and really loved it. My kids and cats were comfortable and we had enough space that we weren’t on top of each other like we would be in other hotel suites. "
The price is AU$517
includes taxes & fees
5 Mar - 6 Mar
West Taylor Run Hotel

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

9.2 out of 10, Wonderful, (14)
"It was great staying here, everything close by, the neighborhood is great n would definitely stay here again next time im in DC"
Downtown Delight Vibrant Oasis in Heart of DC's Bustling Streets

Wyndham Kingsgate - 2 Bedroom Deluxe

10.0 out of 10, Exceptional, (19)
"A lovely property and staff…highly recommend!"
Wyndham Kingsgate - 2 Bedroom Deluxe

Beautiful Condo - Water View Near City Dock

9.6 out of 10, Exceptional, (140)
"I currently live in this complex, and I rented this condo for my parents to come stay a few days while I recovered from surgery. Joe and Beth were extremely accommodating and kept communication with my parents while they stayed (but also didn't bug them!). I was thankful to have such an easy process for my older parents and they are already talking about coming back down again because they enjoyed their stay so much!"
Beautiful Condo - Water View Near City Dock

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

2.0 star property
10.0 out of 10, Exceptional, (2)
"Both the host (CJ) and the property were phenomenal!! From smooth lining the experience for checking in to getting around the city the stay felt very personal and welcoming aside from only being aesthetically pleasing. There was plenty of room to stretch out, the directions to the location were easy to follow, and the pictures for the property were as posted. Our only regret was not staying another day. To make up for it, we just boasted about the stay to all our friends to at least consider...
3-bedroom condo in charming Washington with AC, WiFi. Relax and enjoy

2-Bdr Condo, Free Parking , Self Check-In

8.0 out of 10, Very good, (10)
"The condo was very clean and nicely set up. It was perfect for me. Just a short Lyft ride into DC. "
2-Bdr Condo, Free Parking , Self Check-In

Beautiful 1 bedroom condo with a view!

10.0 out of 10, Exceptional, (38)
"Crysty was very accommodating and a great host! The place was very clean and had all the main essentials! We enjoyed our stay and highly recommend the space."
Beautiful 1 bedroom condo with a view!

Only 5 min. from the Beach!

9.0 out of 10, Wonderful, (19)
"We were pleased with what we found! The space was exactly as advertised and we really liked the fact that the bedroom was completely separate from the kitchenette and second bed. The two bathrooms we also great since it was my wife and I, our daughter and her best friend. The separate space for the adults was super! The cost of the room per night was very reasonable for it being the off season. "
The price is AU$310
includes taxes & fees
6 Mar - 7 Mar
Only 5 min. from the Beach!

Waterfront on Marsh Island!

8.8 out of 10, Excellent, (21)
"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!

Upscale Penthouse Rooftop TV+Capitol+Monument Views+Parking

9.4 out of 10, Exceptional, (27)
"The property was exactly as stated. It was a quiet neighborhood. Plenty of parking. Close to H street for theater restaurants and night life. We will return"
The price is AU$1,153
includes taxes & fees
27 Mar - 28 Mar
Upscale Penthouse Rooftop TV+Capitol+Monument Views+Parking

Waterfront on Marsh Island!

9.4 out of 10, Exceptional, (9)
"Spent a long weekend with the wife. Location was perfect. Property manager was very communicative. Easy check in process. Unit is small, like an efficiency, but perfect for our needs. Nothing fancy, but has everything you need."
Waterfront on Marsh Island!

Luxurious 3 Bedroom Condo Sleeps 8!

10.0 out of 10, Exceptional, (89)
"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!

Wyndham Kingsgate - 1 Bedroom Suite

10.0 out of 10, Exceptional, (7)
"We had a very good stay. Property was very clean and comfortable. "
Wyndham Kingsgate - 1 Bedroom Suite

Designer 3-BDR Penthouse+Private Rooftop View of Monument&Capitol+Parking

9.6 out of 10, Exceptional, (9)
"I loved everything about the apartment and the host.The only problem we had was at check in. The host hadn't told us ANYTHING about when she planned to send us the key information, so when it was 2 min after check in time, and I still hadn't heard ANYTHING, I panicked. Then, at 4 min after check in time, the key information arrived via email. All was well after that.Great apartment! Comfy beds! Thanks!"
Designer 3-BDR Penthouse+Private Rooftop View of Monument&Capitol+Parking

Roof Top Terrace Condo in DC

10.0 out of 10, Exceptional, (5)
"The location is really convenient , clean and charming place "
Roof Top Terrace Condo in DC

Book A Piece of History at Kingsmill Resort in Williamsburg Virginia!

9.4 out of 10, Exceptional, (26)
"The property was perfect for our family. The location was near all the attractions. My only disappointment was that we couldn’t use Kingsmill Resort pools. We also had to tell a white lie so that we could dine on-site."
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.
Don't see what you're looking for?
See all available properties in Chesapeake Bay
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Chesapeake Bay

The Melrose Georgetown Hotel

4.0 star property
8.8 out of 10, Excellent, (2102)
"Beautiful decor, excellent service and amenities for a very reasonable price. Also love how walkable it is. "
The price is AU$470
includes taxes & fees
15 Mar - 16 Mar
The Melrose Georgetown Hotel

Glover Park - Georgetown

4.0 star property
8.8 out of 10, Excellent, (2336)
"Comfortable room, friendly staff, would stay again. "
The price is AU$312
includes taxes & fees
5 Mar - 6 Mar
Glover Park - Georgetown

The River Inn

4.0 star property
9.4 out of 10, Exceptional, (1611)
"I’ve stayed here many times now. Can’t beat their very pet friendly policies as well as their ever accommodating staff. Although the hotel rooms could use a bit of a refresh, the staff, location and pricing really can’t be beat."
The price is AU$252
includes taxes & fees
7 Mar - 8 Mar
The River Inn
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.

Frequently asked questions

How much do condos in Chesapeake Bay cost?
You’ll pay from AU$310 to AU$1,153 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 57 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.