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
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
14 Feb - 16 Feb
In two weeks
21 Feb - 23 Feb
In one month
7 Mar - 9 Mar
In two months
4 Apr - 6 Apr

Featured Condo Rentals in Chesapeake Bay and around

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, (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!
Exterior

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!
Property grounds

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
Fridge, microwave, oven, stovetop

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
Signature Condo, 2 Bedrooms | In-room dining

West Taylor Run Hotel

4.0 star property
8.6 out of 10, Excellent, (19)
"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 €322
includes taxes & fees
4 Feb - 5 Feb
West Taylor Run Hotel
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

9.2 out of 10, Wonderful, (13)
"The property itself is great. But I have to agree with other reviewers that the location is indeed sketchy. I know it's not their fault but on one of the days there was literally a shooting a block away that had dozens of police cars coming to. And the people that just.... hang around the liquor store next door harassed the person I was staying with. Again, the property itself is really great. And so is the host; very responsive. But the location is not the greatest. "
Downtown Delight Vibrant Oasis in Heart of DC's Bustling Streets
Wyndham Kingsgate - 2 Bedroom Deluxe
Pool

Wyndham Kingsgate - 2 Bedroom Deluxe

10.0 out of 10, Exceptional, (18)
"Condo met our needs. The amenities are fantastic. "
Wyndham Kingsgate - 2 Bedroom Deluxe
Beautiful Condo - Water View Near City Dock
Outdoor dining

Beautiful Condo - Water View Near City Dock

9.6 out of 10, Exceptional, (139)
"We came up for the bowl game in Annapolis and this place offered a great place to stay near downtown and access to anywhere! The condo offered a clean comfortable place with all you need so close. "
Beautiful Condo - Water View Near City Dock
3-bedroom condo in charming Washington with AC, WiFi. Relax and enjoy
Microwave, oven, stovetop, dishwasher

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
Smart TV, fireplace

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

8.0 out of 10, Very good, (10)
"Checkin didn't go well. Door wouldn't open when we got there. Owner responded fairly quick. Otherwise it was a nice place to stay. Comfortable."
The price is €274
includes taxes & fees
23 Feb - 24 Feb
2-Bdr Condo, Free Parking , Self Check-In
Beautiful 1 bedroom condo with a view!
Property grounds

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!
Beach

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 €186
includes taxes & fees
5 Feb - 6 Feb
Only 5 min. from the Beach!
Waterfront on Marsh Island!
Interior

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
Fridge, microwave, oven, stovetop

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"
Upscale Penthouse Rooftop TV+Capitol+Monument Views+Parking
Waterfront on Marsh Island!
Interior

Waterfront on Marsh Island!

9.4 out of 10, Exceptional, (8)
"I stayed while finding a more permanent place to live. Beautiful space!"
Waterfront on Marsh Island!
Luxurious 3 Bedroom Condo Sleeps 8!
Fridge, microwave, oven, stovetop

Luxurious 3 Bedroom Condo Sleeps 8!

10.0 out of 10, Exceptional, (88)
"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
Property grounds

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
Property grounds

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

9.6 out of 10, Exceptional, (8)
"The space is nice but minimal. It met our basic needs. Could use lamps, luggage racks or some furniture to put luggage on, bath mats, sheets, bedding for couch, higher quality towels and sheets. Dryer didnt seem to be working correctly."
Designer 3-BDR Penthouse+Private Rooftop View of Monument&Capitol+Parking
Roof Top Terrace Condo in DC
Property grounds

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!
Outdoor dining

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
Sign in
Sign up, it's free

Other property types in Chesapeake Bay

ARC HOTEL Washington DC, Georgetown
View from room

ARC HOTEL Washington DC, Georgetown

3.0 star property
8.2 out of 10, Very good, (2194)
"Love the view "
The price is €139
includes taxes & fees
9 Feb - 10 Feb
ARC HOTEL Washington DC, Georgetown
Glover Park - Georgetown
Exterior

Glover Park - Georgetown

4.0 star property
8.8 out of 10, Excellent, (2316)
"Great location and friendly staff, carpet seemed slightly outdated but overall I would recommend this place. "
The price is €176
includes taxes & fees
11 Feb - 12 Feb
Glover Park - Georgetown
Sonder Georgetown C&O
Lobby

Sonder Georgetown C&O

3.5 star property
8.6 out of 10, Excellent, (574)
"Love the room. Thank you so much for everything "
The price is €152
includes taxes & fees
11 Feb - 12 Feb
Sonder Georgetown C&O
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?
Expect to pay from to per night for condos in Chesapeake Bay. No matter your budget, an ideal 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 condos to choose from. Enter your travel dates and destination and get a start on planning your ideal getaway today.
Why book your condo in Chesapeake Bay with Expedia?
Vacays shouldn’t be difficult, so if you’re looking for condos at a great price, Expedia can help. Keep the budget in check and go for something cheap and cheerful, or splurge on 5-star accommodation and treat your loved ones. Our search filters make it a breeze to find an escape in Chesapeake Bay that suits you best.
How can I find cheap condos in Chesapeake Bay?
With Expedia’s helpful filter tool, getting your hands on cheap condos in Chesapeake Bay is a snap. To view properties that’ll make your wallet happy, narrow your search results by star rating, amenities and budget.
What is there to do in Chesapeake Bay near my condo?
One of the best travel accessories for your Chesapeake Bay adventure is an awesome itinerary! National Mall, National Air and Space Museum and Smithsonian’s National Zoo are among the most popular things to do if you’re headed to Washington. Baltimore also offers lots of famous attractions, such as National Aquarium in Baltimore. In the mood to explore more? Pencil in a visit to Baltimore Museum of Art and American Visionary Art Museum too.