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Featured Condo Rentals in Chesapeake Bay

Wyndham Kingsgate - 2 Bedroom Deluxe
10.0 out of 10, Exceptional, (10)
"Property exceeded expectations. Amenities were awesome. Kids loved the game room and pool. Was close to all attractios. Would recommend 10/10"
Wyndham Kingsgate - 2 Bedroom Deluxe
West Taylor Run Hotel
4.0 star property
8.4 out of 10, Very good, (17)
"Very nice clean and well organized living room bathroom,kitchen bedrooms perfect parking outside sitting area I like its a good place for family "
The price is AU$494
includes taxes & fees
30 Sept - 1 Oct
West Taylor Run Hotel
Beautiful 1 bedroom condo with a view!
10.0 out of 10, Exceptional, (31)
"We loved our stay! It is perfectly located to spend time in Colonial Williamsburg, Jamestown and Busch Gardens. So close! Lovely trails to run/walk, beautiful view, short walk to breakfast spot. The place was incredibly clean, comfortable, cozy and beautifully decorated. The bed was comfy, there is a full length mirror which we don't always find in a VRBO place. Kitchen was well stocked! Host was very friendly, responsive and helpful. We will definitely stay here again! "
Beautiful 1 bedroom condo with a view!
Blue Oasis w/private parking close to attractions
The price is AU$302
includes taxes & fees
28 Oct - 29 Oct
Blue Oasis w/private parking close to attractions
5 minutes to Assateague National Seashore!
9.0 out of 10, Wonderful, (11)
"Finding the Inn was like finding Waldo. The address to the Inn leads you to a restaurant parking lot. When we did find the entrance it was a very tiny road and the parking lot was really small. The unit itself needs an upgrade. The carpet had a lot of stains and the air mattress on the sofa bed has a short in the cord. The bedroom has no A/C. The screen door needs to be replaced and the curtains needs an upgrade. The bathroom and kitchen were in pretty good working order. Beautiful view from the...
The price is AU$274
includes taxes & fees
1 Oct - 2 Oct
5 minutes to Assateague National Seashore!
Bliss on the Bay - Perfect Beach Getaway
9.8 out of 10, Exceptional, (6)
"This was a very cute little place with a fantastic view and just minutes away from everywhere I needed to go! I felt safe and had everything I needed for a comfortable stay. Property management was very welcoming and easy to communicate with. I would definitely stay here again! "
Bliss on the Bay - Perfect Beach Getaway
Kingsmill Condo on Golf Course 9th Fairway! Local owner
10.0 out of 10, Exceptional, (69)
"Easy check in Code was easy to use as it was my# Location was great New shower was huge Plenty of towels Large kitchen Golf course sunset views Close to all amenities Very happy family arrived and left so sad vacation was over. That’s when you know things went great. "
Kingsmill Condo on Golf Course 9th Fairway! Local owner
Waterfront on Marsh Island!
9.2 out of 10, Wonderful, (7)
"This was an absolute delight of a vacation. We stayed on Marsh Island, Chincoteague, VA for 6 nights. WOW! What a stay. The Pearl was sensational. Crab traps, a beach bag, umbrella and gobs of other things to make us feel at home did JUST THAT. The team checked in on us frequently to see if we needed anything and to be sure we were enjoying our stay. Out unit was clean, exactly as pictured in digital online views, comfortable and in a great location to enjoy Chincoteague and then get away...
Waterfront on Marsh Island!
Luxury Riverfront Condo w/ sunrise & sunset views
9.6 out of 10, Exceptional, (46)
"The condo was perfect for my husband and I. The view is heavenly and the condo has everything you would need. Communication was great We will definitely be back!"
The price is AU$508
includes taxes & fees
30 Sept - 1 Oct
Luxury Riverfront Condo w/ sunrise & sunset views
Club Wyndham Kingsgate - 1 Bedroom Suite
10.0 out of 10, Exceptional, (3)
"great place to stay in Williamsburg, close to lot attractions, restaurants and food stores, Well maintained and very clean, offers a lot to do"
Club Wyndham Kingsgate - 1 Bedroom Suite
Waterfront on Marsh Island!
9.0 out of 10, Wonderful, (17)
"Very close to the water. Screened in porch overlooking the bay."
Waterfront on Marsh Island!
Downtown Delight Vibrant Oasis in Heart of DC's Bustling Streets
8.8 out of 10, Excellent, (8)
"Lovely property. Cool host"
Downtown Delight Vibrant Oasis in Heart of DC's Bustling Streets
Water-view in Kingsmill, 10 minutes to Busch Gardens & Colonial Williamsburg!
10.0 out of 10, Exceptional, (128)
"Kingsmill is a lovely property, very convenient to local attractions. The condo was clean and well furnished. "
Water-view in Kingsmill, 10 minutes to Busch Gardens & Colonial Williamsburg!
Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!
9.8 out of 10, Exceptional, (116)
"Room was clean and quit. Peaceful neighborhood. Great place to walk or run. "
Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!
Luxury Condo 2br close to Metro & NIH Walter Rees/Sightseeing/Museums/Zoo/shops
9.6 out of 10, Exceptional, (43)
"This was an excellent location for combined work in the area plus ability to host friends with children for a weekend visit."
Luxury Condo 2br close to Metro & NIH Walter Rees/Sightseeing/Museums/Zoo/shops
Lovely Duplex Apartment - Free Garage parking close to DC
9.0 out of 10, Wonderful, (9)
"Overall had a great stay at this property. Was nice to have reserved parking spot in a covered garage. Kids loved the large pool with an 8.5’ deep end. Convenient location to downtown DC or pretty much anything in the NOVA area. Didn’t realize when booking that the property is two floors, but I realize that I overlooked the stairs in one of the photos. That was a plus for us because adults could stay awake downstairs without worrying about disturbing sleeping kids upstairs."
The price is AU$553
includes taxes & fees
30 Sept - 1 Oct
Lovely Duplex Apartment - Free Garage parking close to DC
Beach, beach, beach in historic Cape Charles. Lovely 2BR Apt1Block from beach
9.8 out of 10, Exceptional, (24)
"My daughter was married at Mimosa Barn and my husband and I (from Mass) stayed at the Beach Retreat. It was better than the what the photos portrayed and was perfect for two people (plus my daughter the night before the wedding). The owner was very gracious and we will definitely stay there again if it's available. "
Beach, beach, beach in historic Cape Charles. Lovely 2BR Apt1Block from beach
Sunset Bay 319 - Bella Vista!
10.0 out of 10, Exceptional, (6)
"This condo is well equipped and very comfortable. The pool is lovely. But for us, the highlight was the balcony overlooking the water. The views are stunning. We will be back. "
Sunset Bay 319 - Bella Vista!
Annapolis Condominium in the heart of the historic center
9.8 out of 10, Exceptional, (259)
"We had a wonderful stay, our second at this prime location in the heart of downtown Annapolis. Host was exceptional, and we look forward to future stays! Thanks again!"
Annapolis Condominium in the heart of the historic center
Fun + History! 1BR Suite at Wyndham Kingsgate, Close to Park & Busch Gardens
9.2 out of 10, Wonderful, (15)
"Clean property. Good amenities."
Fun + History! 1BR Suite at Wyndham Kingsgate, Close to Park & Busch Gardens
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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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Other property types in Chesapeake Bay

Glover Park - Georgetown
4.0 star property
8.8 out of 10, Excellent, (2197)
"Nice spacious hotel in Georgetown . Little dated but god value . Don’t desk receptionists are all amazing. "
The price is AU$335
includes taxes & fees
30 Oct - 31 Oct
Glover Park - Georgetown
Embassy Suites by Hilton Washington D.C. – Convention Center
3.5 star property
8.8 out of 10, Excellent, (2263)
"Would definitely return."
The price is AU$400
includes taxes & fees
6 Oct - 7 Oct
Embassy Suites by Hilton Washington D.C. – Convention Center
Holiday Inn Washington Capitol - Natl Mall, an IHG Hotel
3.0 star property
8.4 out of 10, Very good, (4120)
"Proximity to the Monuments and Museums"
The price is AU$334
includes taxes & fees
3 Oct - 4 Oct
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.

Frequently asked questions

How much do condos in Chesapeake Bay cost?
You’ll pay from AU$274 to AU$553 per night for condos in Chesapeake Bay. No matter your budget, you’ll find the perfect stay on Expedia. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many condos are there in Chesapeake Bay?
Take a peek at our 58 condos in Chesapeake Bay and then book your favourite. Whether you’re embarking on a family getaway or kicking back with your pals, your perfect stay is just a few clicks away with Expedia.
What is there to do in Chesapeake Bay near my condo?
Whether you enjoy shopping, dining, history or culture, Chesapeake Bay promises something for everyone! The awesome city of Washington has tons of attractions, including National Mall, Smithsonian Institution and National Museum of African American History and Culture. If you’re holidaying in Baltimore, National Aquarium in Baltimore, Baltimore Museum of Art and American Visionary Art Museum have to be on your itinerary.