Holiday Homes in Chesapeake Bay

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Featured Holiday Homes in Chesapeake Bay

Fridge, microwave, oven, stovetop
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (2)
"My rugby team traveled down for a competition. Erin met us there walked us around the property and gave us great recommendations for food in the area. She was an amazing manager, always answering questions and getting us anything we needed. The property was beautiful and fit our entire team comfortably. The large slace and outdoor activity allowed for a lot of team building and we had a blast llaying pickle ball and basketball with each other. We wish we coukd have spent more time there."
The price is AU$2,151
per night
6 May - 7 May
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Fridge, microwave, oven, stovetop
Hampton Centrally Located Oasis
10.0 out of 10, Exceptional, (2)
"Stay was nice. Property is close to Amenities and interstate."
The price is AU$328
per night
6 May - 7 May
Hampton Centrally Located Oasis
TV, books, offices
Cherry Blossom Charm
10.0 out of 10, Exceptional, (7)
"Everything was pretty much perfect and as we expected. Real nice place, nice neighborhood. Thank you."
Cherry Blossom Charm
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Terrace/patio
Near JHU & Downtown - Luxury Modern 4bd/3.5bath Rowhome w/ Outdoor Lounge
2.0 star property
10.0 out of 10, Exceptional, (1)
"Great for 4-6 people. Location in Remington is convenient. Very nicely appointed; our trip was old school friends who hadn't seen each other for a while, so we did a lot of chilling in the house. Would stay again!"
Near JHU & Downtown - Luxury Modern 4bd/3.5bath Rowhome w/ Outdoor Lounge
Pool
Cozy Home away from Home-10mins from National Harbor
10.0 out of 10, Exceptional, (3)
"It is a room in a house Shared bath Commo. Area"
The price is AU$201
per night
5 May - 6 May
Cozy Home away from Home-10mins from National Harbor
Fridge, microwave, oven, stovetop
Cheerful 3-Bedroom House in Downtown Annapolis
10.0 out of 10, Exceptional, (10)
"We were looking for a place to spend our Thanksgiving and this was perfect! Great location close to downtown Annapolis. Marina was awesome - she was super responsive and took time during the holiday weekend to answer our questions. We loved that there were two places to hang out. Kitchen was well stocked. Lots of extra towels and blankets. General notes: The sofa bed in the basement is not a pull out as expected but is technically a twin bed and the bunk bed is actually a twin with a trundle...
Cheerful 3-Bedroom House in Downtown Annapolis
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!
Fridge, microwave, oven, stovetop
Sojourn | Capitol Hill Home on The Park | 3 BR
10.0 out of 10, Exceptional, (46)
"Property served as an excellent Hill base camp for exploring DC. Walkable to grocery store, playgrounds, parks, museums, metro, Mall, Pennsylvania Ave. Well-equipped kitchen allowed for some “home” cooking. The price is high, considering the condition of the house, though it’s not in poor shape. Had a great weekend."
Sojourn | Capitol Hill Home on The Park | 3 BR
Beach
The Crows Nest. <br>Sunsets at the Harbor. Enjoy bird’s eye view. Unique location!
10.0 out of 10, Exceptional, (121)
"We love this spot and love the location. It was nice to have the golf cart because we did not have that last year. However, we still couldn't get the stove working (again), the lock box to get the golf cart out was the incorrect code and the tire on the golf cart had a leak. Luckily, we got an air compressor, so we were able to fill it up a couple of times and still use the cart."
The Crows Nest. <br>Sunsets at the Harbor. Enjoy bird’s eye view. Unique location!
Fridge, microwave, oven, stovetop
Modern Condo, 2 bed/ 2 bath, Rooftop - 6 PPL!
10.0 out of 10, Exceptional, (26)
"The property owner is great! When we got there, the blow dryer was on its last leg to say the least. I messaged the property owner and a new one was at the front door when we got back from dinner! The house has all the kitchen stuff you need … even a Britta water filter in the refrigerator. The owner also left us a bottle of wine. If you’re a foodie the location is an easy walk to some great restaurants. Get the Michelin Guide and know you can’t go wrong with any of the Bib Gourmand rated...
The price is AU$768
per night
8 May - 9 May
Modern Condo, 2 bed/ 2 bath, Rooftop - 6 PPL!
Property grounds
Tiki bar jacuzzy and rooftop close to M&T stadium
10.0 out of 10, Exceptional, (5)
"Loved it , when we walked up the steps to the main bedroom the railing fell. Also i was taking a jucuzzi bath and the tiling fell off the side. Other than those little things the property is amazing "
The price is AU$707
per night
15 May - 16 May
Tiki bar jacuzzy and rooftop close to M&T stadium
Fridge, microwave, oven, stovetop
Cozy House in DC with FREE Private Parking & Yard Space
10.0 out of 10, Exceptional, (11)
"Enjoyed the stay"
Cozy House in DC with FREE Private Parking & Yard Space
Fridge, microwave, oven, stovetop
Gorgeous designer home in Capital Hill
10.0 out of 10, Exceptional, (83)
"We enjoyed the welcome amenities and clear instructions and communication from the host. Clean, and comfortable accommodations."
Gorgeous designer home in Capital Hill
Property grounds
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
10.0 out of 10, Exceptional, (62)
"I’ve reviewed this home several times, still 5/5"
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
Smart TV, books
The Greenhouse: A peaceful retreat minutes from all Williamsburg has to offer
10.0 out of 10, Exceptional, (17)
"This was a nice quiet location for a weekend getaway.The home was clean and comfortable, the backyard delightful (if only it were a touch warmer, we would have enjoyed the pool!), the kitchen well-stocked with tools,the beds comfortable. We were a touch worried about the dog boarding facility, but you can really only hear the dogs barking around meal time and it stops pretty quickly. The only caveat I give is be sure to read the description carefully, because they're upfront that the fourth...
The Greenhouse: A peaceful retreat minutes from all Williamsburg has to offer
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 AU$1,072
per night
7 May - 8 May
DC Rowhome + HUGE Roofdeck & Parking ✲ 4br | 3.5ba
Fridge, microwave, oven, stovetop
Entire Cozy 3 bedrooms Single Bungalow House in Arlington Near DC
10.0 out of 10, Exceptional, (29)
"Clean and includes all features listed"
Entire Cozy 3 bedrooms Single Bungalow House in Arlington Near DC
Fridge, microwave, oven, stovetop
Chincoteague Island House "Sir Whelk-A-Lot" Bikes/Kayaks Included! DT Location!
10.0 out of 10, Exceptional, (26)
"Hi we stayed at the beach house and loved it. Easy booking process, great host, great accommodations and location was perfect!"
The price is AU$447
per night
6 May - 7 May
Chincoteague Island House "Sir Whelk-A-Lot" Bikes/Kayaks Included! DT Location!
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!
Private kitchen
Great 3 bedroom, 2.5 bath with attached garage close to everything!
9.8 out of 10, Exceptional, (101)
"The property is beautifully decorated and very clean. It was very nice for a long weekend in DC. It does have a lot of stairs. Would not recommend for someone who has difficulty climbing stairs. For those who plan to use the metro there was not a metro station within walking distance."
Great 3 bedroom, 2.5 bath with attached garage close to everything!
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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, (1195)
"Lovely hotel in a beautiful neighborhood. Walkable to DC highlights, restaurants and more."
The price is AU$525
per night
24 May - 25 May
The Dupont Circle Hotel
Exterior
The Churchill Hotel near Embassy Row
3.5 star property
8.8 out of 10, Excellent, (1449)
"The Churchill is a landmark hotel where the ghosts and spirits of the worlds greats, who have stayed there, make you feel that you have been invited to an Inaugural ball."
The price is AU$220
per night
5 May - 6 May
The Churchill Hotel near Embassy Row
View from property
Embassy Suites by Hilton Washington D.C. – Convention Center
3.5 star property
8.8 out of 10, Excellent, (1898)
"Getting to the property is expensive since it's downtown but it's worth it. I haven't had a 12 hr good sleep like what i had there"
The price is AU$312
per night
1 June - 2 June
Embassy Suites by Hilton Washington D.C. – Convention Center
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 Holiday Homes information

Number of reviews
632
Accommodation
445 Holiday Homes
Lowest Price
AU$201
Highest Price
AU$2,151

Recent Reviews in Chesapeake Bay
Expedia verified reviews