Search Vacation Homes in Chesapeake Bay

    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

Compare 449 Vacation Homes in Chesapeake Bay with updated reviews, rates, and availability.

Smart TV
Newly Remodeled Historic Home 2 Blocks from the Beach, Downtown, and the Park
10.0 out of 10, Exceptional, (1)
"House was perfect for our group of four, with a bedroom for each of us. House was well equipped, clean and in a perfect location just a block and 1/2 to the beach and shopping/dining. The house has been remodeled beautifully. Host was very responsive and very helpful. Would highly recommend!"
Newly Remodeled Historic Home 2 Blocks from the Beach, Downtown, and the Park
Fridge, microwave, oven, stovetop
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (3)
"Wonderful place to stay and Erin was great. Asked about a Grill on the property and the next day we had a grill. The young adults loved the pool and water activities while the older adults enjoyed sitting on the docks watching the sunrise with a cuppa coffee. Would highly recommend this property."
The price is ¥98,250
per night
Jun 4 - Jun 5
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Terrace/patio
Near JHU & Downtown - Luxury Modern 4bd/3.5bath Rowhome w/ Outdoor Lounge
2.0 star property
10.0 out of 10, Exceptional, (2)
"Beautifully decorated row home with thoughtful amenities. Hosts were very communicative, offering suggestions on things to do as well as local restaurants. Very pleasant stay."
Near JHU & Downtown - Luxury Modern 4bd/3.5bath Rowhome w/ Outdoor Lounge
Save an average of 15% on thousands of hotels when you're signed in
TV, Netflix, Hulu, streaming services
Top of the Town!Perfectly Private w Pking & Access Downtown
10.0 out of 10, Exceptional, (10)
"The place was great. Even as presented online! Very spacious. Very clean and updated furnishing. Lots of options for television entertainment. Kindness and helpfulness of the owner was much appreciated. Our only suggestion is to get a railing for the steps going to the lower level."
Top of the Town!Perfectly Private w Pking & Access Downtown
Property grounds
DC Rowhome + HUGE Roofdeck & Parking ✲ 4br | 3.5ba
10.0 out of 10, Exceptional, (12)
"This property was in excellent condition. A wonderful place to go “home” to every night after our day in DC. Public transportation is nearby so you can just park your vehicle and ride. One of the best places we have stayed."
The price is ¥63,261
per night
May 28 - May 29
DC Rowhome + HUGE Roofdeck & Parking ✲ 4br | 3.5ba
Fridge, microwave, oven, stovetop
Hampton Centrally Located Oasis
10.0 out of 10, Exceptional, (3)
"Extras were a delightful touch, didn't need anything during our stay. Host was quick to respond, location was close to stores and everything we needed."
The price is ¥17,807
per night
May 23 - May 24
Hampton Centrally Located Oasis
Fridge, microwave, oven, stovetop
Entire home in Washington, District of Columbia, United States
10.0 out of 10, Exceptional, (1)
"Great location and just an overall great place to stay"
The price is ¥18,275
per night
Jun 17 - Jun 18
Entire home in Washington, District of Columbia, United States
Fridge, microwave, oven, stovetop
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (180)
"Charming spot in the heart of Annapolis, just a few moments walk from anything you might need."
Directly Across from Gate One & Steps from the Waterfront
Fridge, microwave, oven, stovetop
Chincoteague Island House "Sir Whelk-A-Lot" Bikes/Kayaks Included! DT Location!
10.0 out of 10, Exceptional, (27)
"The house is a character in itself, loved the stay."
The price is ¥25,003
per night
May 23 - May 24
Chincoteague Island House "Sir Whelk-A-Lot" Bikes/Kayaks Included! DT Location!
1 bedroom, desk, blackout drapes, iron/ironing board
Hotel-style Accommodation - large private room
10.0 out of 10, Exceptional, (22)
"Was a great place and suited my needs perfectly."
Hotel-style Accommodation - large private room
Property grounds
Fabulous 1890 Victorian home on Capitol Hill, only 100 steps to subway station!
10.0 out of 10, Exceptional, (118)
"This location was amazing, so close to some awesome bars and restaurants and super close to the metro to easy access to anywhere. The neighborhood was so cute and the house was super clean."
Fabulous 1890 Victorian home on Capitol Hill, only 100 steps to subway station!
Smart TV, stereo
Rooftop Deck Escape! Free Parking!
10.0 out of 10, Exceptional, (3)
"Myself and a few friends were down for a conference, The location was perfect especially for a group of guys. Easy to walk to the convention center or to Camden yards or m&t bank. Plenty of local restaurants and bars. Great communication by the host."
The price is ¥17,182
per night
Jun 3 - Jun 4
Rooftop Deck Escape! Free Parking!
Exterior
Historic Victorian Duplex Brownstone Steps To The White House & Georgetown
10.0 out of 10, Exceptional, (65)
"The property was beautiful, comfortable and clean! Location was great, 10 min walk to the White House and so many great restaurants. We were a group of 6….5 adults and one teen, and we fit comfortably in the house. Anand and Lisa are wonderful hosts, so gracious and welcoming, they even changed the sheets for us after a minor medical issue. Highly recommend this property!"
Historic Victorian Duplex Brownstone Steps To The White House & Georgetown
TV, fireplace
WFH-Friendly Washington DC Vacation Rental!
10.0 out of 10, Exceptional, (12)
"My family had a great stay here! We came to see the sites in DC and it was wonderful to have a comfortable, clean place to stay after long days! The kitchen was awesome if you plan to cook! The sofa was so comfortable as well as the beds! We felt welcome and everything was easy! Thanks for letting us stay here! We would book again!!"
WFH-Friendly Washington DC Vacation Rental!
Property grounds
A block to the beach!
9.8 out of 10, Exceptional, (38)
"We were at a different location than we originally booked. I am not sure how to rate the place shown since we weren't there. The alternative home we did stay in was very nice, on the beach and easy to get to everywhere."
A block to the beach!
Beach
The Crows Nest. <br>Sunsets at the Harbor. Enjoy bird’s eye view. Unique location!
9.8 out of 10, Exceptional, (123)
"I think I said this in my last review but if you like boats this is the place for you. We love sitting outside watching the boats come and go. Walking to the Shanty is quick and easy. We would much rather stay here than right in the town. The property was clean enough but I feel like it really can use a deep cleaning. There’s lots of lovely decorations that seem to catch a lot of dust and hair. We plan on coming back in a few years and staying here again. Thanks for the great family memories."
The Crows Nest. <br>Sunsets at the Harbor. Enjoy bird’s eye view. Unique location!
Exterior
Close to Old Town Alexandria And All Things DC
9.8 out of 10, Exceptional, (33)
"This property was truly a comfy, cozy stay. With delicious coffee and espressos provided, the dining table was very comfortable to sit around with the six of us and enjoy a tasty breakfast from the Junction Bakery which is a convenient short walk. Mark, the host, was on top of things and was even there when we arrived. The beds were super comfortable after a long day of sightseeing. It is a great location and very quiet. One note, just make sure you can climb stairs rather easily as both...
Close to Old Town Alexandria And All Things DC
Beach
Petit Cozy Beach Bungalow— 5 min walk to the beach
9.8 out of 10, Exceptional, (9)
"Nice quaint bungalow. Beds were nice and comfortable and the bathroom was also quite nice. It's close to the beach area and an easy walk. All positive about our stay there."
Petit Cozy Beach Bungalow— 5 min walk to the beach
Exterior
Quaint Cottages Near Everything on Beach Road
9.6 out of 10, Exceptional, (25)
"Jimmy worked hard to meet our ever need. Location is very central fir restaurants and getting to Assateague Island. Unit is basic with all the essentials, comfortable bed."
Quaint Cottages Near Everything on Beach Road
Exterior
Hunt's Home -off H Street Corridor.
9.6 out of 10, Exceptional, (90)
"You need a hand-rail for the basement stairs."
Hunt's Home -off H Street Corridor.
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 property types in Chesapeake Bay

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 ¥46,704
per night
May 25 - May 26
The Dupont Circle Hotel
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 ¥26,687
per night
May 28 - May 29
Embassy Suites by Hilton Washington D.C. – Convention Center
Exterior
Holiday Inn Washington Capitol - Natl Mall, an IHG Hotel
3.0 star property
8.4 out of 10, Very Good, (3719)
"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 ¥24,992
per night
May 27 - May 28
Holiday Inn Washington Capitol - Natl Mall, an IHG 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.

Chesapeake Bay Vacation Homes information

Number of reviews
451
Accommodation
449 Vacation Homes
Lowest Price
¥15,620
Highest Price
¥98,250

Recent reviews of Chesapeake Bay hotels
Expedia verified reviews