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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

Featured Condo Rentals in Chesapeake Bay

Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!
Property grounds

Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!

9.8 out of 10, Exceptional, (138)
"Great location very clean and cozy room. Beautiful area!!"
Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!
Water-view in Kingsmill, 10 minutes to Busch Gardens & Colonial Williamsburg!
Beach nearby, beach towels

Water-view in Kingsmill, 10 minutes to Busch Gardens & Colonial Williamsburg!

10.0 out of 10, Exceptional, (146)
"We enjoyed our stay! Very nice place."
Water-view in Kingsmill, 10 minutes to Busch Gardens & Colonial Williamsburg!
Lovely Duplex Apartment - Free Garage parking close to DC
Fridge, microwave, oven, stovetop

Lovely Duplex Apartment - Free Garage parking close to DC

9.0 out of 10, Wonderful, (30)
"Apartment was very clean. With a grocery store & restaurants close by."
The price is AU$601
includes taxes & fees
2 Sept - 3 Sept
Lovely Duplex Apartment - Free Garage parking close to DC
"Pura Vida" Fabulous 4 Bed Home near H St & Union Market
Private kitchen

"Pura Vida" Fabulous 4 Bed Home near H St & Union Market

9.6 out of 10, Exceptional, (25)
"Super clean, quick walk to the train and downtown DC. Great for family trip would stay again! "
The price is AU$782
includes taxes & fees
25 Aug - 26 Aug
"Pura Vida" Fabulous 4 Bed Home near H St & Union Market
Kingsmill Condo on Golf Course 9th Fairway! Local owner
Sun-loungers, beach towels

Kingsmill Condo on Golf Course 9th Fairway! Local owner

10.0 out of 10, Exceptional, (86)
"Overall satisfied with the stay. Location was great, not crowded and easy to get around. "
Kingsmill Condo on Golf Course 9th Fairway! Local owner
Beautiful 1 bedroom condo with a view!
Property grounds

Beautiful 1 bedroom condo with a view!

10.0 out of 10, Exceptional, (51)
"Had a great time during our stay! Love every minute of it! "
Beautiful 1 bedroom condo with a view!
5 minutes to Assateague National Seashore!
Flat-screen TV

5 minutes to Assateague National Seashore!

8.8 out of 10, Excellent, (16)
"There was enough space for 3 adults and to children. The bathroom in the hall has not been updated. The shower was crudy and no towel rack. The spicket for shower/bath in the 2nd bathroom was almost impossible to use. The rental was okay."
The price is AU$310
includes taxes & fees
17 Sept - 18 Sept
5 minutes to Assateague National Seashore!
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 AU$319
includes taxes & fees
9 Sept - 10 Sept
Only 5 min to Assateague National Seashore!
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 AU$547
includes taxes & fees
4 Sept - 5 Sept
Luxury Riverfront Condo w/ sunrise & sunset views
Only 5 min to Assateague National Seashore!
Microwave, stovetop, coffee/tea maker, toaster

Only 5 min to Assateague National Seashore!

9.0 out of 10, Wonderful, (13)
"As usual we had a wonderful stay at the Assateague Inn and cannot wait for our next visit. "
The price is AU$310
includes taxes & fees
17 Sept - 18 Sept
Only 5 min to Assateague National Seashore!
Beautiful Condo - Water View Near City Dock
Marina

Beautiful Condo - Water View Near City Dock

9.6 out of 10, Exceptional, (145)
"Clean, quiet, and very close to both downtown and Eastport restaurants."
Beautiful Condo - Water View Near City Dock
A Beach Bargain in Chincoteague!
Mini-fridge, microwave, stovetop, coffee/tea maker

A Beach Bargain in Chincoteague!

8.8 out of 10, Excellent, (3)
"Simple. Did not use kitchen. View from door was beautiful."
A Beach Bargain in Chincoteague!
Waterfront on Marsh Island!
Interior

Waterfront on Marsh Island!

9.6 out of 10, Exceptional, (13)
"Enjoy the location and the clean, attractive accommodations."
Waterfront on Marsh Island!
Downtown Loft & Close to EVERYTHING!
Microwave, dishwasher, coffee/tea maker, cookware/dishes/utensils

Downtown Loft & Close to EVERYTHING!

7.2 out of 10, Good, (5)
"Nice place, but not for the older people like us. Central location to everything the harbor, bars and shopping."
The price is AU$404
includes taxes & fees
22 Aug - 23 Aug
Downtown Loft & Close to EVERYTHING!
Waterfront on Marsh Island!
Interior

Waterfront on Marsh Island!

8.8 out of 10, Excellent, (32)
"We stayed in the "Lovers Lane" unit which is on the lower level of this small condo unit. It had access to a secure laundry room, private deck with picnic table, BBQ grill and awesome lighting for night crabbing or fishing right from your private dock! Couldn't ask for more. The unit was very clean. This location has great access to Chincoteague with easy egress and ingress from the Island. If your looking for a quiet stay away from the commercial hustle, this is the place, though the room...
Waterfront on Marsh Island!
Perfect Cozy Vacation Rental on the Eastern Shore
Smart TV

Perfect Cozy Vacation Rental on the Eastern Shore

8.2 out of 10, Very good, (27)
"Dated and not modern, clean but not a getaway or vacation rental, stove and oven dirty, only a few dishwater items available. "
Perfect Cozy Vacation Rental on the Eastern Shore
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 AU$477
includes taxes & fees
25 Aug - 26 Aug
Unit #2 Close to Howard University
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 AU$300
includes taxes & fees
8 Sept - 9 Sept
Only 5 min. from the Beach!
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 AU$657
includes taxes & fees
22 Aug - 23 Aug
West Taylor Run Hotel
Luxurious 3 Bedroom Condo Sleeps 8!
Fridge, microwave, oven, stovetop

Luxurious 3 Bedroom Condo Sleeps 8!

10.0 out of 10, Exceptional, (93)
"Perfect base of operations for our group."
Luxurious 3 Bedroom Condo Sleeps 8!
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

Hotel Lombardy

Hotel Lombardy

10/10 Excellent
"Very comfortable and roomy accommodations. Perfect location convenient to GWU as we were dropping off child for college. Opted for nearby lot parking which saved some $. Inadvertently left laptop at hotel; called and mailed it promptly back to me. Would happily stay there again."
Ira 3-night trip
Posted 15 hours ago
Hotel Lombardy

Frequently asked questions

How much do condos in Chesapeake Bay cost?
You'll pay from AU$300 to AU$782 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 96 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.