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, (133)
"Dream hotel apartment"
The price is $186
$219 total
includes taxes & fees
May 27 - May 28
ROOST Baltimore
Terrace/patio
The Dupont Circle Hotel
4.5 star property
9.4 out of 10, Exceptional, (1235)
"The staff was second to none. Absolutely wonderful and attentive."
The price is $287
$333 total
includes taxes & fees
May 23 - May 24
The Dupont Circle Hotel
Indoor pool
Park Hyatt Washington
5.0 star property
9.4 out of 10, Exceptional, (794)
"Rooms are well kept hotel staff was friendly."
The price is $350
$406 total
includes taxes & fees
Jun 21 - Jun 22
Park Hyatt Washington
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Terrace/patio
The River Inn
3.5 star property
9.4 out of 10, Exceptional, (1420)
"The property is located in a nice neighborhood, a short walk to the Metro and grocery stores. "
The price is $154
$179 total
includes taxes & fees
May 27 - May 28
The River Inn
Meeting facility
Fairmont Washington, D.C., Georgetown
4.0 star property
9.4 out of 10, Exceptional, (1300)
"Walkable to Georgetown. Nice hotel. "
The price is $224
$260 total
includes taxes & fees
Jun 14 - Jun 15
Fairmont Washington, D.C., Georgetown
One Bedroom Apartment | Living area | Flat-screen TV
Coda on Half a Placemakr Experience
4.0 star property
9.2 out of 10, Wonderful, (210)
"loved it it was clean and upscale. I wouldn’t mind living here."
The price is $169
$196 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, (334)
"Great location."
The price is $149
$170 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, (414)
"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 $146
$165 total
includes taxes & fees
Jun 10 - Jun 11
WhyHotel by Placemakr Columbia
Lobby
Georgetown Inn
3.5 star property
9.0 out of 10, Wonderful, (1364)
"Very nice boutique hotel in the heart of Georgetown. Small bathrooms (very), but good stay overall. "
The price is $224
$260 total
includes taxes & fees
May 27 - May 28
Georgetown Inn
Lobby
Embassy Suites by Hilton Washington DC Georgetown
3.5 star property
9.0 out of 10, Wonderful, (1612)
"Very nice place with big suite rooms. Convenient location as well."
The price is $169
$225 total
includes taxes & fees
May 31 - Jun 1
Embassy Suites by Hilton Washington DC Georgetown
Rooftop terrace
Rosewood Washington, D.C.
5.0 star property
9.0 out of 10, Wonderful, (165)
"Check-in was seamless even though we arrived several hours early. The staff was wonderfully attentive, but unobtrusive at the same time. The hotel is small, but charming and located in a great area with many restaurants and fabulous shops nearby."
The price is $593
$688 total
includes taxes & fees
May 28 - May 29
Rosewood Washington, D.C.
View from property
Embassy Suites by Hilton Washington D.C. – Convention Center
3.5 star property
8.8 out of 10, Excellent, (1929)
"Great location! The staff was excellent. Plan to visit this location again soon. "
The price is $180
$208 total
includes taxes & fees
May 28 - May 29
Embassy Suites by Hilton Washington D.C. – Convention Center
Exterior
Glover Park - Georgetown
4.0 star property
8.8 out of 10, Excellent, (2017)
"Friendly staff. Convenient location. "
The price is $172
$200 total
includes taxes & fees
May 26 - May 27
Glover Park - Georgetown
Kayaking
The Melrose Georgetown Hotel
4.0 star property
8.8 out of 10, Excellent, (1769)
"Quiet and nice hotel "
The price is $159
$208 total
includes taxes & fees
May 27 - May 28
The Melrose Georgetown Hotel
Exterior
The Churchill Hotel near Embassy Row
3.5 star property
8.8 out of 10, Excellent, (1460)
"Beautiful property. Building is old and does have a musty smell but great location. Walkable to dupont circle metro and surrounded by wonderful restaurants. Staff was very nice and valet was convenient "
The price is $152
$200 total
includes taxes & fees
May 30 - May 31
The Churchill Hotel near Embassy Row
Exterior
The Graham Georgetown
4.0 star property
8.8 out of 10, Excellent, (1334)
"Your door man is the best!!!"
The price is $287
$333 total
includes taxes & fees
May 26 - May 27
The Graham Georgetown
Reception
Hilton Garden Inn Washington DC Downtown
3.0 star property
8.6 out of 10, Excellent, (1574)
"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 $168
$195 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, (3718)
"Very convenient to the Capitol/Mall area. Located pretty close to Air & Space. McDonald’s just outside the property if you need a quick bite. Hotel was nice and we enjoyed it."
The price is $160
$186 total
includes taxes & fees
May 27 - May 28
Holiday Inn Washington Capitol - Natl Mall, an IHG Hotel
Lobby
Sonder Georgetown C&O
3.5 star property
8.4 out of 10, Very Good, (385)
"The property was great - apart from the air con in our room - so noisy that it kept waking us up. Choice - be super hot or super awake all night. Such a shame as stopped this being a perfect stay."
The price is $269
$312 total
includes taxes & fees
Jun 19 - Jun 20
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

Exterior
State Plaza Hotel
3.5 star property
9.2 out of 10, Wonderful, (1652)
"Could have used a little less humidity in the room and more pressure for bathroom sink Very professional staff and great restaurant."
The price is $128
$148 total
includes taxes & fees
May 27 - May 28
State Plaza Hotel
Property amenity
citizenM Washington DC Capitol
4.0 star property
9.0 out of 10, Wonderful, (1787)
"The hotel was clean, neat and had a new look feel. Room are very small. It felt like I was on a cruise. But it has everything you need. Staff VERY friendly, attentive and helpful. "
The price is $129
$150 total
includes taxes & fees
May 27 - May 28
citizenM Washington DC Capitol
Suite, 1 King Bed (Lapidus) | View from room
Washington Plaza Hotel
4.0 star property
8.8 out of 10, Excellent, (3271)
"I did not enjoy paying a $50 per night parking fee. I think thats insane and i would've never stayed if i was aware of that charge before booking. "
The price is $119
$138 total
includes taxes & fees
May 27 - May 28
Washington Plaza Hotel
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 $132 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

Hamilton Hotel Washington DC

Hamilton Hotel Washington DC

5/5 Excellent
"The staff at the hotel is amazing and the location was perfect."
A verified traveler stayed at Hamilton Hotel Washington DC
Posted 3 hours ago
Hamilton Hotel Washington DC