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Check prices for these dates

In two weeks
10 Oct - 12 Oct
In two months
21 Nov - 23 Nov
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16 Jan - 18 Jan

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, (144)
"Great location very clean and cozy room. Beautiful area!!"
Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!
Perfectly located minutes from the Inner Harbor, Ravens and Orioles stadium.
Children’s area

Perfectly located minutes from the Inner Harbor, Ravens and Orioles stadium.

10.0 out of 10, Exceptional, (3)
"Great location .. we walked to Camden Yards, coffee and lunch in Federal Hill and to inner Harbor. Nice street parking w your permits and very quiet. Would stay again for sure!"
The price is NZ$577
includes taxes & fees
28 Sept - 29 Sept
Perfectly located minutes from the Inner Harbor, Ravens and Orioles stadium.
"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, (28)
"Great property! Clean and spacious!"
The price is NZ$849
includes taxes & fees
29 Sept - 30 Sept
"Pura Vida" Fabulous 4 Bed Home near H St & Union Market
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, (149)
"We enjoyed our stay! Very nice place."
Water-view in Kingsmill, 10 minutes to Busch Gardens & Colonial Williamsburg!
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, (88)
"Overall satisfied with the stay. Location was great, not crowded and easy to get around. "
Kingsmill Condo on Golf Course 9th Fairway! Local owner
Waterfront on Marsh Island!
Interior

Waterfront on Marsh Island!

8.4 out of 10, Very good, (36)
"The location is close to everything, but secluded and quiet for when you just want to relax. We loved the closed in porch where we sat for hours on end talking and watching the water. We really felt comfortable and at home. "
Waterfront on Marsh Island!
Luxury Riverfront Condo w/ sunrise & sunset views
Marina

Luxury Riverfront Condo w/ sunrise & sunset views

9.6 out of 10, Exceptional, (64)
"Enjoyed my stay at this condo..I hope it becomes available again this year, "
The price is NZ$593
includes taxes & fees
24 Sept - 25 Sept
Luxury Riverfront Condo w/ sunrise & sunset views
Only 5 min to Assateague National Seashore!
Terrace/patio

Only 5 min to Assateague National Seashore!

9.4 out of 10, Exceptional, (19)
"Nice place. "
The price is NZ$326
includes taxes & fees
30 Sept - 1 Oct
Only 5 min to Assateague National Seashore!
Downtown Loft & Close to EVERYTHING!
Microwave, dishwasher, coffee/tea maker, cookware/dishes/utensils

Downtown Loft & Close to EVERYTHING!

6.8 out of 10, (6)
"The apartment was nice & in a convenient location. Parking was easy, with a parking garage literally around the corner. "
Downtown Loft & Close to EVERYTHING!
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
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."
West Taylor Run Hotel
5 minutes to Assateague National Seashore!
Flat-screen TV

5 minutes to Assateague National Seashore!

9.0 out of 10, Wonderful, (20)
"The condo was perfect for my girlfriend and I, very private location and nice boardwalk by the creek"
The price is NZ$326
includes taxes & fees
24 Sept - 25 Sept
5 minutes to Assateague National Seashore!
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 NZ$465
includes taxes & fees
27 Sept - 28 Sept
Lovely 1-Bedroom Condo with Pool and City View
Annapolis Condominium in the heart of the historic center
Terrace/patio

Annapolis Condominium in the heart of the historic center

9.8 out of 10, Exceptional, (283)
"The location and amenities are great. The host are very friendly, helpful and easy to make contact with. My family used this location for commission week and could not have asked for more. "
Annapolis Condominium in the heart of the historic center
Don't miss this! Fabulous Powhatan 2BDR/2BA. Great amenities. Near Busch Gardens
Exterior detail

Don't miss this! Fabulous Powhatan 2BDR/2BA. Great amenities. Near Busch Gardens

Don't miss this! Fabulous Powhatan 2BDR/2BA. Great amenities. Near Busch Gardens
Beautiful 1 bedroom condo with a view!
Property grounds

Beautiful 1 bedroom condo with a view!

10.0 out of 10, Exceptional, (56)
"Very pleased! Clean, nicely decorated. "
Beautiful 1 bedroom condo with a view!
Stunning Private Rooftop Penthouse in DC! Modern Luxury with Breathtaking Views!
Terrace/patio

Stunning Private Rooftop Penthouse in DC! Modern Luxury with Breathtaking Views!

2.0 star property
4.0 out of 10, (2)
"I was really excited to stay at this property. It looks so nice! However the beautiful new building is situated in a very rough area of DC. We arrived in the late afternoon and a party was just getting started next door. Medium sized crowd, loud music with strong bass line. I ordered some DoorDash and the driver got out, looked at me, looked around, and asked "Are you okay?" But I was still hopeful that everything would be fine. It wasn't. The party went until nearly 4am with escalating yelling...
Stunning Private Rooftop Penthouse in DC! Modern Luxury with Breathtaking Views!
Lovely 2 BR Condo in 4💎 Historic Golf Resort
Fridge, microwave, oven, stovetop

Lovely 2 BR Condo in 4💎 Historic Golf Resort

9.2 out of 10, Wonderful, (20)
"You can't beat the location if you are visiting Busch Gardens! Literally minutes away! It was so nice to be able to easily go back and rest during the day. The condo is just as described and in great condition. Owner very responsive to messages. Well kept, clean, and quiet! Perfect for families!"
The price is NZ$809
includes taxes & fees
24 Sept - 25 Sept
Lovely 2 BR Condo in 4💎 Historic Golf Resort
Luxurious 3 Bedroom Condo Sleeps 8!
Fridge, microwave, oven, stovetop

Luxurious 3 Bedroom Condo Sleeps 8!

10.0 out of 10, Exceptional, (96)
"We enjoyed our stay at Kingsmill. Property was neat and clean, not to mention conveniently located. Would definitely stay again! "
Luxurious 3 Bedroom Condo Sleeps 8!
Beautiful Condo - Water View Near City Dock
Outdoor pool

Beautiful Condo - Water View Near City Dock

9.6 out of 10, Exceptional, (147)
"Clean, quiet, and very close to both downtown and Eastport restaurants."
Beautiful Condo - Water View Near City Dock
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

Holiday Inn Baltimore BWI Airport by IHG

Holiday Inn Baltimore BWI Airport by IHG

10/10 Excellent
"EVERYTHING WAS WONDERFUL AND THE STAFF AMAZING!"
Janette 1-night trip
Posted 3 days ago
Holiday Inn Baltimore BWI Airport by IHG

Find out more about Chesapeake Bay

Find out more about Chesapeake Bay

Chesapeake Bay Condo Rentals information

Number of reviews
1,153
Accommodation
91 Condo Rentals
Lowest Price
NZ$326
Highest Price
NZ$849

Frequently asked questions

How much do condos in Chesapeake Bay cost?
Expect to pay from NZ$326 to NZ$849 per night for condos in Chesapeake Bay. No matter your budget, a terrific stay is a click away on Expedia. These prices were 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?
Chesapeake Bay has 91 condos on offer. Enter your destination and travel dates and get a head start on planning your perfect trip today.
What is there to do in Chesapeake Bay near my condo?
Whatever you're into, there are almost endless things to keep you entertained in Chesapeake Bay. If you're off to Washington, stop by Arlington House-The Robert E. Lee Memorial, Cady's Alley and Francis Scott Key Memorial Park. Escaping to Baltimore? Geppi's Entertainment Museum, Union Soldiers and Sailors Monument and Edgar Allan Poe's Gravesite and Memorial are some major attractions in this city.

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