Search Chesapeake Bay Condo Rentals

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
24 Oct - 26 Oct
In one month
7 Nov - 9 Nov
In two months
5 Dec - 7 Dec
In three months
2 Jan - 4 Jan

Featured Condo Rentals in Chesapeake Bay

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Marina

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

2.0 star property
9.8 out of 10, Exceptional, (9)
"This was such a cozy, comfortable space for a girls weekend away. We loved the charm of the old building paired with thoughtful amenities. "
The price is AU$546
includes taxes & fees
20 Oct - 21 Oct
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
Marina

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

2.5 star property
10.0 out of 10, Exceptional, (10)
"Just a beautiful place. I would stay here again. Everything was walking distance. "
The price is AU$584
includes taxes & fees
20 Oct - 21 Oct
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Marina

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

8.8 out of 10, Excellent, (5)
"The place was very clean and in the most perfect spot in downtown Cambridge. We had a wedding walking distance from this place. Jen is a very responsive and accommodating host!"
The price is AU$476
includes taxes & fees
8 Oct - 9 Oct
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Unit #2 Close to Howard University
Fridge, microwave, oven, stovetop

Unit #2 Close to Howard University

2.0 star property
9.2 out of 10, Wonderful, (5)
"This was a great place to stay. Host was great, location is amazing. Would love to stay here again when I come back to Washington DC!"
The price is AU$549
includes taxes & fees
21 Oct - 22 Oct
Unit #2 Close to Howard University
Beautiful 2BR/1BA Renovated Condo near DC w/pool
Fridge, microwave, oven, stovetop

Beautiful 2BR/1BA Renovated Condo near DC w/pool

9.4 out of 10, Exceptional, (50)
"Everything we needed for a great stay and EXCELLENT communication with the host. "
The price is AU$287
includes taxes & fees
19 Oct - 20 Oct
Beautiful 2BR/1BA Renovated Condo near DC w/pool
Beautiful 2 Bedroom Apt in downtown silverspring
Fridge, microwave, oven, stovetop

Beautiful 2 Bedroom Apt in downtown silverspring

9.4 out of 10, Exceptional, (13)
"I enjoyed my stay here. Clean place and the location is very convenient.Highly recommended."
The price is AU$378
includes taxes & fees
12 Oct - 13 Oct
Beautiful 2 Bedroom Apt in downtown silverspring
Only 5 min to Assateague National Seashore!
Terrace/patio

Only 5 min to Assateague National Seashore!

9.4 out of 10, Exceptional, (20)
"Stay at Assateague Inn was clean, comfy, cozy, and convenient. "
The price is AU$290
includes taxes & fees
9 Oct - 10 Oct
Only 5 min to Assateague National Seashore!
Luxury Riverfront Condo w/ sunrise & sunset views
Marina

Luxury Riverfront Condo w/ sunrise & sunset views

9.6 out of 10, Exceptional, (65)
"Enjoyed my stay at this condo..I hope it becomes available again this year, "
The price is AU$532
includes taxes & fees
9 Oct - 10 Oct
Luxury Riverfront Condo w/ sunrise & sunset views
Only 5 min from Assateague National Seashore!
Property grounds

Only 5 min from Assateague National Seashore!

7.4 out of 10, Good, (3)
"Low-quality furniture. needs to be updated"
The price is AU$290
includes taxes & fees
14 Oct - 15 Oct
Only 5 min from Assateague National Seashore!
Quiet, Remodeled 1BR/1BA Condo in Annandale, VA w/pool near DC
Outdoor pool

Quiet, Remodeled 1BR/1BA Condo in Annandale, VA w/pool near DC

8.8 out of 10, Excellent, (9)
"The location was close to my family, which I was visiting. Also not far from stores and the place was clean, which is a plus. I would stay there again when visiting."
The price is AU$305
includes taxes & fees
21 Oct - 22 Oct
Quiet, Remodeled 1BR/1BA Condo in Annandale, VA w/pool near DC
Lovely condo with water & golf course view
Terrace/patio

Lovely condo with water & golf course view

9.6 out of 10, Exceptional, (8)
"We greatly enjoyed our stay at this condo. It was super clean and very well appointed with everything we needed. The hosts were very responsive and easy to get in touch with to coordinate our stay. The location was convenient to everything we wanted to do, both inside and outside of the resort. We loved this condo and will definitely stay there again in the future."
The price is AU$549
includes taxes & fees
8 Oct - 9 Oct
Lovely condo with water & golf course view
Welcome to "The Happy Haven". Located in the heart of the city.
Outdoor dining

Welcome to "The Happy Haven". Located in the heart of the city.

9.8 out of 10, Exceptional, (20)
"Great visit!"
The price is AU$309
includes taxes & fees
20 Oct - 21 Oct
Welcome to "The Happy Haven". Located in the heart of the city.
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, (10)
"Enjoyed very much, will definitely come back!!"
The price is AU$290
includes taxes & fees
9 Oct - 10 Oct
Only 5 minutes to Assateague National Seashore!
Bayside Getaways Oyster Oasis - Chesapeake Properties
TV, offices

Bayside Getaways Oyster Oasis - Chesapeake Properties

10.0 out of 10, Exceptional, (3)
"Clean, nicely decorated, comfortable bed, and excellent location. "
The price is AU$666
includes taxes & fees
3 Nov - 4 Nov
Bayside Getaways Oyster Oasis - Chesapeake Properties
Station House East: Upscale Loft in the Historic District Cambridge, MD
Marina

Station House East: Upscale Loft in the Historic District Cambridge, MD

The price is AU$388
includes taxes & fees
22 Oct - 23 Oct
Station House East: Upscale Loft in the Historic District Cambridge, MD
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, (32)
"Apartment was very clean. With a grocery store & restaurants close by."
The price is AU$501
includes taxes & fees
14 Oct - 15 Oct
Lovely Duplex Apartment - Free Garage parking close to DC
Only 5 min. from the Beach!
Interior

Only 5 min. from the Beach!

9.2 out of 10, Wonderful, (27)
"Great location that was very clean, kid friendly, and good amenities! Liked how close it was to everything, very walkable."
The price is AU$294
includes taxes & fees
4 Nov - 5 Nov
Only 5 min. from the Beach!
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
Indoor pool

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

10.0 out of 10, Exceptional, (1)
"Very clean , great location. Will stay there again!!!"
The price is AU$300
includes taxes & fees
4 Nov - 5 Nov
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
Lovely 2 BR Condo in 4💎 Historic Golf Resort
Fridge, microwave, oven, stovetop

Lovely 2 BR Condo in 4💎 Historic Golf Resort

9.2 out of 10, Wonderful, (20)
"You can't beat the location if you are visiting Busch Gardens! Literally minutes away! It was so nice to be able to easily go back and rest during the day. The condo is just as described and in great condition. Owner very responsive to messages. Well kept, clean, and quiet! Perfect for families!"
The price is AU$725
includes taxes & fees
13 Oct - 14 Oct
Lovely 2 BR Condo in 4💎 Historic Golf Resort
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chesapeake Bay Hotel Reviews

Sheraton Pentagon City Hotel

Sheraton Pentagon City Hotel

10/10 Excellent
"Very good personal "
Violetta 3-night trip
Posted 1 day ago
Sheraton Pentagon City Hotel

Find out more about Chesapeake Bay

Find out more about Chesapeake Bay

Chesapeake Bay Condo Rentals information

Number of reviews
Accommodation
 Condo Rentals
Lowest Price
Highest Price

Frequently asked questions

How much do condos in Chesapeake Bay cost?
You'll pay from to 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 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia