Chesapeake Bay Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    one key icon
    Treat yourself
    Save instantly and earn perks with One Key
    Learn about One Key
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Chesapeake Bay

Rooftop terrace
ROOST Baltimore
4.5 star property
9.6 out of 10, Exceptional, (131)
"Large rooms. Nice appliances. "
The price is $203
$239 total
includes taxes & fees
May 23 - May 24
ROOST Baltimore
Terrace/patio
The Dupont Circle Hotel
4.5 star property
9.4 out of 10, Exceptional, (1226)
"Perfect spot for a special graduation weekend! The location is beautiful, the staff very accommodating, the room extremely clean and comfortable and the bar and restaurant cozy and delicious! Nice way to celebrate our daughter’s college graduation!"
The price is $248
$288 total
includes taxes & fees
May 24 - May 25
The Dupont Circle Hotel
Terrace/patio
The River Inn
3.5 star property
9.4 out of 10, Exceptional, (1415)
"The unusual thing about the River Inn is literally every employee, front desk, bellman, food service & room cleaning go out of their way to be friendly and extremely helpful. Even the small things, heading toward the elevator? They push the call button. Need hot water? Here it is. Need a recommendation? They ask a couple of questions and you get all the details. Heading for the door? Anybody in the vicinity opens it. Don't see this as consistently at the Four Seasons or Ritz Carlton!"
The price is $142
$165 total
includes taxes & fees
May 27 - May 28
The River Inn
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Meeting facility
Fairmont Washington, D.C., Georgetown
4.0 star property
9.4 out of 10, Exceptional, (1297)
"Everything was nice, we had an enjoyable stay."
The price is $269
$312 total
includes taxes & fees
May 24 - May 25
Fairmont Washington, D.C., Georgetown
Indoor pool
Park Hyatt Washington
5.0 star property
9.4 out of 10, Exceptional, (793)
"Rooms are well kept hotel staff was friendly."
The price is $352
$408 total
includes taxes & fees
May 26 - May 27
Park Hyatt Washington
One Bedroom Apartment | Living area | Flat-screen TV
Coda on Half a Placemakr Experience
4.0 star property
9.2 out of 10, Wonderful, (208)
"Staff was phenomenal and worked with me when my flight was delayed and made me miss my initial reservation. Room was super clean and cozy as well"
The price is $154
$179 total
includes taxes & fees
May 27 - May 28
Coda on Half a Placemakr Experience
Premium Two Bedroom Apartment with Balcony | Iron/ironing board, free WiFi, bed sheets
Placemakr Marymount Ballston
4.0 star property
9.2 out of 10, Wonderful, (328)
"Wonderful "
The price is $145
$166 total
includes taxes & fees
May 27 - May 28
Placemakr Marymount Ballston
Terrace/patio
AKA White House
4.0 star property
9.2 out of 10, Wonderful, (667)
"Very nice suite, quiet, and clean. The staff on site is excellent. "
The price is $225
$290 total
includes taxes & fees
Jun 9 - Jun 10
AKA White House
Studio Apartment | Private kitchen | Fridge, microwave, oven, stovetop
WhyHotel by Placemakr Columbia
4.0 star property
9.0 out of 10, Wonderful, (406)
"Awesome greeter at check in. Very impressive Apt! Very affordable! Please note, you will have to pay for parking, but there is a free parking lot in the back. I will definitely stay again!"
The price is $155
$175 total
includes taxes & fees
May 20 - May 21
WhyHotel by Placemakr Columbia
Lobby
Georgetown Inn
3.5 star property
9.0 out of 10, Wonderful, (1362)
"Easy check in"
The price is $237
$275 total
includes taxes & fees
Jun 2 - Jun 3
Georgetown Inn
Lobby
Embassy Suites by Hilton Washington DC Georgetown
3.5 star property
9.0 out of 10, Wonderful, (1611)
"Very nice place with big suite rooms. Convenient location as well."
The price is $169
$225 total
includes taxes & fees
May 27 - May 28
Embassy Suites by Hilton Washington DC Georgetown
View from property
Embassy Suites by Hilton Washington D.C. – Convention Center
3.5 star property
8.8 out of 10, Excellent, (1923)
"Súper lindo! Limpio y buena atención. "
The price is $178
$206 total
includes taxes & fees
May 31 - Jun 1
Embassy Suites by Hilton Washington D.C. – Convention Center
Exterior
Glover Park - Georgetown
4.0 star property
8.8 out of 10, Excellent, (2008)
"Comfortable boutique hotel with easy parking ($45 per day) but has unlimited in and out privileges, easy access from garage to room totally indoors so no worries about moving bags in bad weather. Beds comfortable, bathrooms modern, reasonably priced accommodation."
The price is $172
$200 total
includes taxes & fees
May 27 - May 28
Glover Park - Georgetown
Exterior
The Churchill Hotel near Embassy Row
3.5 star property
8.8 out of 10, Excellent, (1458)
"We have stayed at this hotel multiple times in the past and have never been disappointed. For an older hotel, it is kept up nicely. The rooms are a little small but are clean. The beds are extremely comfortable! The front desk staff was very friendly and helpful. Please note that there is no free parking (it is D.C.), and the valet was expensive at $55/day."
The price is $145
$191 total
includes taxes & fees
May 24 - May 25
The Churchill Hotel near Embassy Row
Kayaking
The Melrose Georgetown Hotel
4.0 star property
8.8 out of 10, Excellent, (1759)
"I had an amazing stay. The rooms are beautiful and very, very comfortable. Staff is helpful and friendly."
The price is $152
$200 total
includes taxes & fees
May 27 - May 28
The Melrose Georgetown Hotel
Exterior
The Graham Georgetown
4.0 star property
8.8 out of 10, Excellent, (1328)
"Excellent location, friendly staff, comfortable but small room. "
The price is $279
$323 total
includes taxes & fees
May 23 - May 24
The Graham Georgetown
Reception
Hilton Garden Inn Washington DC Downtown
3.0 star property
8.6 out of 10, Excellent, (1573)
"The property was in a great location for all of the iconic attractions in downtown Washington. The breakfast was great we ate there everyday. Only problem was the air conditioning and heating did not work properly. We could not set the temperature in the room it was either too warm or too cool."
The price is $151
$175 total
includes taxes & fees
May 27 - May 28
Hilton Garden Inn Washington DC Downtown
Exterior
Holiday Inn Washington Capitol - Natl Mall, an IHG Hotel
3.0 star property
8.4 out of 10, Very Good, (3706)
"Nice location!"
The price is $160
$186 total
includes taxes & fees
May 27 - May 28
Holiday Inn Washington Capitol - Natl Mall, an IHG Hotel
Indoor pool
Hyatt Regency Washington on Capitol Hill
4.0 star property
8.4 out of 10, Very Good, (1460)
"Extremely helpful staff! "
The price is $173
$224 total
includes taxes & fees
May 27 - May 28
Hyatt Regency Washington on Capitol Hill
Lobby
Sonder Georgetown C&O
3.5 star property
8.4 out of 10, Very Good, (380)
"The property location was great, very close most shops in Georgetown. The condition could have been a little bit better, but overall it was very very good and I enjoyed staying at the property and will most definitely be staying there again and would recommend it."
The price is $269
$312 total
includes taxes & fees
Jun 9 - Jun 10
Sonder Georgetown C&O
Don't see what you're looking for?
See all available properties in Chesapeake Bay
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.

Other types of properties in Chesapeake Bay you may be interested in

Suite, 1 King Bed (Lapidus) | View from room
Washington Plaza Hotel
4.0 star property
8.8 out of 10, Excellent, (3254)
"Everything was good! Excellent employees!"
The price is $119
$138 total
includes taxes & fees
May 27 - May 28
Washington Plaza Hotel
Exterior
Renaissance Baltimore Harborplace Hotel
4.0 star property
8.4 out of 10, Very Good, (2081)
"The staff needs to do better with guest request, I made a request for extra blanket and it never came."
The price is $161
$189 total
includes taxes & fees
Jun 9 - Jun 10
Renaissance Baltimore Harborplace Hotel
Exterior
Capital Hilton
4.0 star property
8.2 out of 10, Very Good, (1003)
"Excellent stay"
The price is $135
$186 total
includes taxes & fees
Jun 1 - Jun 2
Capital Hilton
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.

Everything you need to know about Chesapeake Bay vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chesapeake Bay vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesapeake Bay vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chesapeake Bay vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesapeake Bay. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chesapeake Bay in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $125 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chesapeake Bay rentals

At Expedia, we put the best Chesapeake Bay vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chesapeake Bay rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesapeake Bay vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesapeake Bay. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Recent reviews of Chesapeake Bay properties
Expedia verified reviews

Club Quarters Hotel in Washington DC

Club Quarters Hotel in Washington DC

5/5 Excellent
"Staff was very friendly and helpful. Hotel conveniently located by the Metro blue line. Great restaurants within walking distance. "
A verified traveler stayed at Club Quarters Hotel in Washington DC
Posted 18 hours ago
Club Quarters Hotel in Washington DC