Search Condos Rentals in Chesapeake Bay from CA $149

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Browse Select Chesapeake Bay Condo Rentals

Exterior
Contemporary Condo in Quiet Locale!
10.0 out of 10, Exceptional, (21)
"Very clean 1 bedroom property. Had lots of great amenities that made my stay very comfortable. 10 minute walk to Metro, which was what I needed to be a tourist and go to my conference. Nice outside table that I enjoyed in the evening. Wonderful street nearby with great restaurants and stores. Helpful hosts. I would stay here again 😀"
Contemporary Condo in Quiet Locale!
Fridge, microwave, oven, stovetop
Luxurious 3 Bedroom Condo Sleeps 8!
10.0 out of 10, Exceptional, (76)
"Kingsmill Resort was a beautiful setting. The location was great - very close to major attractions. The condo was very clean with comfortable, lovely furnishings. The en suite bedrooms and common area were a perfect fit for our 3 adult couples. The kitchen was well stocked and we appreciated the complimentary coffee. The host was responsive and friendly. I highly recommend this unit for a very pleasant stay."
Luxurious 3 Bedroom Condo Sleeps 8!
Pool
Wyndham Kingsgate - 2 Bedroom Deluxe
10.0 out of 10, Exceptional, (3)
"Very nice apartment. Well outfitted. Close to many restaurants , all price levels. Children upstairs were noisy but they quieted down around 9:00 pm. We enjoyed having room to spread out. I’d stay here again."
Wyndham Kingsgate - 2 Bedroom Deluxe
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Beach nearby, beach towels
Water-view in Kingsmill, 10 minutes to Busch Gardens & Colonial Williamsburg!
10.0 out of 10, Exceptional, (119)
"Comfortable, clean and the location was great."
Water-view in Kingsmill, 10 minutes to Busch Gardens & Colonial Williamsburg!
2 bedrooms, in-room safe, desk, iron/ironing board
Magnificent DC Getaway Deluxe 2BR Work Space/Gym/ Near Met Park/DC/Metro/Mall
10.0 out of 10, Exceptional, (2)
"Pretty place, close to metro, lots of restaurants and shops"
Magnificent DC Getaway Deluxe 2BR Work Space/Gym/ Near Met Park/DC/Metro/Mall
Property grounds
Walk to Main Street from Waterfront Condo with pool and parking
10.0 out of 10, Exceptional, (7)
"In an older apartment building, this condo is situated over the creek with views to the bridge and beyond. Everything is new and I would highly recommend."
Walk to Main Street from Waterfront Condo with pool and parking
TV
Bliss on the Bay - Perfect Beach Getaway
10.0 out of 10, Exceptional, (2)
"Clean, quaint, quiet! Just what we wanted!"
Bliss on the Bay - Perfect Beach Getaway
Property grounds
Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!
9.8 out of 10, Exceptional, (102)
"The unit was very nice and perfect for what we needed. Cute community with scenic grounds and plenty of food options nearby. Check in was easy and check out time was generous. It was a perfect centrally located spot for us to do some regional college visits! Would definitely stay here again when we come back for Busch Gardens."
Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!
Property grounds
Only 5 min to Assateague National Seashore!
9.8 out of 10, Exceptional, (6)
"Property was clean and in a great location on the island. The GPS did not take us all the way to the end of the road where the inn was, so coming in after dark made it tricky for us to find. We came to go crabbing and the water level is low off the dock in the back so we had to go elsewhere to crab."
The price is CA $137
CA $256 total
includes taxes & fees
May 21 - May 22
Only 5 min to Assateague National Seashore!
Property grounds
Luxury Riverfront Condo w/ sunrise & sunset views
9.8 out of 10, Exceptional, (41)
"We had a wonderful week long stay at this peaceful location overlooking the James River."
The price is CA $271
CA $524 total
includes taxes & fees
May 20 - May 21
Luxury Riverfront Condo w/ sunrise & sunset views
Property grounds
Annapolis Condominium in the heart of the historic center
9.8 out of 10, Exceptional, (248)
"Great location right in the heart of town!! We enjoyed the long weekend. Wish the rain had held off more so we could have really enjoyed the nice rooftop deck!"
Annapolis Condominium in the heart of the historic center
Property grounds
Cape Haven -Condo 1.5 Blocks from Beach, New Roof Top Deck!
9.8 out of 10, Exceptional, (30)
"If you want a great location with walking access to downtown Cape Charles, then this is the place. We arrived in town and easily found the place following the directions we were given. The condo was very clean and equipped with everything we needed. Lots of thoughtful touches, those details set Cape Haven apart from just another condo. Would definitely recommend and looking forward to staying there again!"
Cape Haven -Condo 1.5 Blocks from Beach, New Roof Top Deck!
Beach
Golf Course View - Kingsmill, Minutes to Busch Gardens and Colonial Williamsburg
9.6 out of 10, Exceptional, (54)
"Perfect 2 bedroom spot in Kingsmill community. Kitchen was well stocked with coffee to get you started. Great back patio to watch golfers come up the fairway. Cant access Kingsmill golf courses and amenities, but great to walk around the beautiful community. Perfect for a couples trip. The unit was very clean and updated. Wonderful for a quick weekend away!"
Golf Course View - Kingsmill, Minutes to Busch Gardens and Colonial Williamsburg
Property grounds
Beautiful Condo - Water View Near City Dock
9.6 out of 10, Exceptional, (127)
"Location location location! This comfortable condo is in our favorite part of Annapolis, Eastport, just across the drawbridge from Main Street, Ego Alley, and the USNA. It is a great destination for walkers (and others - free easy parking). We made use of the kitchen for a couple of dinners. There are also amazing views from the rooftop. Thanks!"
Beautiful Condo - Water View Near City Dock
Property grounds
Book A Piece of History at Kingsmill Resort in Williamsburg Virginia!
9.4 out of 10, Exceptional, (23)
"The condo was well kept and clean. The furniture was comfortable and in great shape. The condo was close to Busch Gardens and Williamsburg. I would definitely recommend it to friends and family. "
Book A Piece of History at Kingsmill Resort in Williamsburg Virginia!
Beach
Golf Course Studio - Kingsmill, Minutes to Busch Gardens & Colonial Williamsburg
9.2 out of 10, Wonderful, (46)
"For the price this is a very nice deal for a get away. The bed was comfy and the location was ideal for our purpose. Would recommend for a great deal. We will be back. Thank you."
Golf Course Studio - Kingsmill, Minutes to Busch Gardens & Colonial Williamsburg
Indoor pool, a heated pool
Fun + History! 1BR Suite at Wyndham Kingsgate, Close to Park & Busch Gardens
9.2 out of 10, Wonderful, (9)
"The suite was very clean & quiet, convenient to the historical area. They try to sell the time share."
Fun + History! 1BR Suite at Wyndham Kingsgate, Close to Park & Busch Gardens
Microwave, stovetop, coffee/tea maker, toaster
Only 5 min. from the Beach!
9.2 out of 10, Wonderful, (5)
"The suite was cute and well stocked!"
The price is CA $142
CA $260 total
includes taxes & fees
May 29 - May 30
Only 5 min. from the Beach!
Outdoor dining
Waterfront on Marsh Island!
9.0 out of 10, Wonderful, (6)
"Property was clean, all advertised amenities were provided, quiet area (off season). Only negatives was the constant humming coming from the attached utility room that shared a wall with the bedroom. Humming was loud enough to wake us up at night. Also, that same side of the building is starting to settle and slopes down 1+ inch."
Waterfront on Marsh Island!
Beach
Picture Frame Beach n Bed
9.0 out of 10, Wonderful, (6)
"Even though the weather was cold, we still managed to take a walk on the beach. Enjoy being able to step out and be a few steps from the beach. Great restaurants are a long walk or short drive away."
Picture Frame Beach n Bed
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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, (1225)
"All good. On my way out I had a quick lunch at Pembroke. To my surprise, a corner table - with the sofa - has water dripping on the couch, from the ceiling, probably A/C. It didn’t affect me but judging by the damage on the cushion surface, it’s been there for a while "
The price is CA $407
CA $472 total
includes taxes & fees
May 24 - May 25
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, (1920)
"Modern property and saps opus suites. It’s in the perfect location. Walking distance to the capital one arena, White House and the Washington monument. Breaks is pretty good and is included. "
The price is CA $243
CA $281 total
includes taxes & fees
Jun 1 - Jun 2
Embassy Suites by Hilton Washington D.C. – Convention Center
Exterior
Glover Park - Georgetown
4.0 star property
8.8 out of 10, Excellent, (2008)
"I enjoyed my stay at Glover Park Hotel. The staff were nice and even allowed me to check in early. My main issue was that the restaurant’s kitchen closed down an hour before the restaurant did, but that information was not made available until I showed up for dinner. However the bartender was very nice and the service was great. Also, the walls are a little thin but nothing that could disturb my sleep. Overall, I recommend this property. Well priced and great location, with easy access to...
The price is CA $260
CA $301 total
includes taxes & fees
May 26 - May 27
Glover Park - Georgetown
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 Condo Rentals information

Number of reviews
849
Accommodation
54 Condo Rentals
Lowest Price
CA $149
Highest Price
CA $271

Recent Reviews in Chesapeake Bay
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