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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Browse Select Chesapeake Bay Condo Rentals

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
Marina

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

2.5 star property
10.0 out of 10, Exceptional, (10)
"Property was located in heart of Cambridge restaurant district. Easy access to great restaurants. Parking easy and plentiful. Condo was as beautiful as advertised! Stunning penthouse 2 bedroom apartment!"
The price is £308
includes taxes & fees
21 Aug - 22 Aug
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Marina

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

2.0 star property
9.8 out of 10, Exceptional, (9)
"This was such a cozy, comfortable space for a girls weekend away. We loved the charm of the old building paired with thoughtful amenities. "
The price is £298
includes taxes & fees
21 Aug - 22 Aug
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Beautiful 2BR/1BA Renovated Condo near DC w/pool
Fridge, microwave, oven, stovetop

Beautiful 2BR/1BA Renovated Condo near DC w/pool

9.4 out of 10, Exceptional, (49)
"Everything we needed for a great stay and EXCELLENT communication with the host. "
The price is £142
includes taxes & fees
22 Aug - 23 Aug
Beautiful 2BR/1BA Renovated Condo near DC w/pool
Unit #2 Close to Howard University
Fridge, microwave, oven, stovetop

Unit #2 Close to Howard University

2.0 star property
9.2 out of 10, Wonderful, (5)
"This was a great place to stay. Host was great, location is amazing. Would love to stay here again when I come back to Washington DC!"
The price is £242
includes taxes & fees
25 Aug - 26 Aug
Unit #2 Close to Howard University
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Marina

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

9.4 out of 10, Exceptional, (3)
"The place was very clean and in the most perfect spot in downtown Cambridge. We had a wedding walking distance from this place. Jen is a very responsive and accommodating host!"
The price is £226
includes taxes & fees
21 Aug - 22 Aug
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Beautiful 2 Bedroom Apt in downtown silverspring
Fridge, microwave, oven, stovetop

Beautiful 2 Bedroom Apt in downtown silverspring

9.4 out of 10, Exceptional, (13)
"I enjoyed my stay here. Clean place and the location is very convenient.Highly recommended."
The price is £186
includes taxes & fees
26 Aug - 27 Aug
Beautiful 2 Bedroom Apt in downtown silverspring
West Taylor Run Hotel
Signature Condo, 2 Bedrooms | In-room dining

West Taylor Run Hotel

4.0 star property
8.4 out of 10, Very good, (27)
"We had a great stay. The property manager replied very quickly."
The price is £229
includes taxes & fees
21 Aug - 22 Aug
West Taylor Run Hotel
Luxury Riverfront Condo w/ sunrise & sunset views
Marina

Luxury Riverfront Condo w/ sunrise & sunset views

9.6 out of 10, Exceptional, (63)
"Magnificent view, accommodation s and amenities. Highly Recommended "
The price is £272
includes taxes & fees
24 Aug - 25 Aug
Luxury Riverfront Condo w/ sunrise & sunset views
Only 5 min. from the Beach!
Interior

Only 5 min. from the Beach!

9.2 out of 10, Wonderful, (25)
"We were only here for one night, but enjoyed our stay and the cute and cozy accommodations. Great location, and lots of shops and eateries nearby."
The price is £145
includes taxes & fees
8 Sept - 9 Sept
Only 5 min. from the Beach!
Lovely 2 BR Condo in 4💎 Historic Golf Resort
Fridge, microwave, oven, stovetop

Lovely 2 BR Condo in 4💎 Historic Golf Resort

9.6 out of 10, Exceptional, (17)
"great location. easy to get to everything..condo was great"
The price is £359
includes taxes & fees
24 Aug - 25 Aug
Lovely 2 BR Condo in 4💎 Historic Golf Resort
Only 5 min to Assateague National Seashore!
Terrace/patio

Only 5 min to Assateague National Seashore!

9.6 out of 10, Exceptional, (18)
"Nice place. "
The price is £154
includes taxes & fees
9 Sept - 10 Sept
Only 5 min to Assateague National Seashore!
Welcome to "The Happy Haven". Located in the heart of the city.
Outdoor dining

Welcome to "The Happy Haven". Located in the heart of the city.

9.8 out of 10, Exceptional, (20)
"My wife and I had a blast staying at this beautiful property and definitely reccomend it"
The price is £154
includes taxes & fees
26 Aug - 27 Aug
Welcome to "The Happy Haven". Located in the heart of the city.
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, (9)
"CJ, our host, was communicative and informative at ALL stages of trip. From booking to check-in, during the stay and even at check out, CJ was quick to respond with questions and help. The house was beautiful, and the extra little touches were well thought out and sweet. The location was perfect for what we needed! Thank you so, so much CJ!"
The price is £415
includes taxes & fees
25 Aug - 26 Aug
3-bedroom condo in charming Washington with AC, WiFi. Relax and enjoy
Quiet, Remodeled 1BR/1BA Condo in Annandale, VA w/pool near DC
Outdoor pool

Quiet, Remodeled 1BR/1BA Condo in Annandale, VA w/pool near DC

8.6 out of 10, Excellent, (8)
"The location was close to my family, which I was visiting. Also not far from stores and the place was clean, which is a plus. I would stay there again when visiting."
The price is £159
includes taxes & fees
2 Sept - 3 Sept
Quiet, Remodeled 1BR/1BA Condo in Annandale, VA w/pool near DC
Cozy Mid-Century Apartment Steps From Restaurants
2 bedrooms, desk, iron/ironing board, travel cot

Cozy Mid-Century Apartment Steps From Restaurants

10.0 out of 10, Exceptional, (3)
"Great location and the place was beautiful. A lot of thought went into making our stay a great experience If you’re driving parking is challenging! "
The price is £267
includes taxes & fees
21 Aug - 22 Aug
Cozy Mid-Century Apartment Steps From Restaurants
Station House East: Upscale Loft in the Historic District Cambridge, MD
Marina

Station House East: Upscale Loft in the Historic District Cambridge, MD

The price is £277
includes taxes & fees
21 Aug - 22 Aug
Station House East: Upscale Loft in the Historic District Cambridge, MD
Only 5 minutes to Assateague National Seashore!
2 bedrooms, Internet, bed sheets

Only 5 minutes to Assateague National Seashore!

8.8 out of 10, Excellent, (9)
"Enjoyed very much, will definitely come back!!"
The price is £158
includes taxes & fees
14 Sept - 15 Sept
Only 5 minutes to Assateague National Seashore!
Only 5 min from Assateague National Seashore!
Property grounds

Only 5 min from Assateague National Seashore!

8.0 out of 10, Very good, (1)
"We had short trip for the oyster festival but really enjoyed our stay. It was quiet and cozy. Beautiful views off the deck. "
The price is £149
includes taxes & fees
16 Sept - 17 Sept
Only 5 min from Assateague National Seashore!
DC Retreat in Capitol Hill—Pets, Parking & Metro
Interior

DC Retreat in Capitol Hill—Pets, Parking & Metro

10.0 out of 10, Exceptional, (2)
"Super cozy apartment with a warm, homey feel! The host was responsive and helpful throughout our stay. The free parking is a huge bonus. Definitely not something you find often in D.C.! Highly recommend!"
The price is £322
includes taxes & fees
21 Aug - 22 Aug
DC Retreat in Capitol Hill—Pets, Parking & Metro
Lovely 1-Bedroom Condo with Pool and City View
Interior

Lovely 1-Bedroom Condo with Pool and City View

9.6 out of 10, Exceptional, (21)
"My wife and I wanted a place near the Metro for ease of access to the city. This apartment was perfect. Very short walk to the Metro, and a parking space in the garage included. The apartment was stocked with toiletries, which was a very nice touch. Communication with the host was easy, with very prompt replies to our questions. Would definitely stay again. "
The price is £130
includes taxes & fees
30 Aug - 31 Aug
Lovely 1-Bedroom Condo with Pool and City View
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.
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Top Chesapeake Bay Hotel Reviews

Hilton Vacation Club The Historic Powhatan Williamsburg

Hilton Vacation Club The Historic Powhatan Williamsburg

10/10 Excellent
"Check in & check out was super easy. A staff member checked in periodically throughout our stay via text which was great. Staff was incredibly friendly & helpful. Property was beautiful. Amenities great. Location perfect:) Thank you!"
Meaghan 4-night trip
Posted 9 hours ago
Hilton Vacation Club The Historic Powhatan Williamsburg