Search Condo Rentals in Chesapeake Bay

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
27 Jun - 29 Jun
In two weeks
4 Jul - 6 Jul
In one month
18 Jul - 20 Jul
In two months
15 Aug - 17 Aug

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, (134)
"Location was excellent. "
Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!
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, (273)
"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
Waterfront on Marsh Island!
Interior

Waterfront on Marsh Island!

8.8 out of 10, Excellent, (26)
"Small Cozy condo for couples. Very quiet and relaxing with great sunrises and sunsets! Great location with being on the water!"
Waterfront on Marsh Island!
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, (82)
"The accommodation was great. It was so comfortable. Being on the ground level made it so easy with our dog. She loved sitting on the porch watching the golfers. "
Kingsmill Condo on Golf Course 9th Fairway! Local owner
West Taylor Run Hotel
Signature Condo, 2 Bedrooms | In-room dining

West Taylor Run Hotel

4.0 star property
8.6 out of 10, Excellent, (25)
"We had a great stay. The property manager replied very quickly."
The price is AEDĀ 654
AEDĀ 1,503 total
includes taxes & fees
17 Jun - 18 Jun
West Taylor Run Hotel
Only 5 min to Assateague National Seashore!
TV, DVD player

Only 5 min to Assateague National Seashore!

9.6 out of 10, Exceptional, (16)
"Nice place. "
The price is AEDĀ 452
AEDĀ 797 total
includes taxes & fees
30 Jun - 1 Jul
Only 5 min to Assateague National Seashore!
Only 5 min. from the Beach!
Beach

Only 5 min. from the Beach!

8.6 out of 10, Excellent, (25)
"Great time. Nice accomodations, easy access. Beautiful area."
The price is AEDĀ 597
AEDĀ 974 total
includes taxes & fees
6 Jul - 7 Jul
Only 5 min. from the Beach!
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, (23)
"Great location, close to town, beach, fishing spots. very clean, safe and spacious parking for boats."
Perfect Cozy Vacation Rental on the Eastern Shore
Luxury Riverfront Condo w/ sunrise & sunset views
Property grounds

Luxury Riverfront Condo w/ sunrise & sunset views

9.6 out of 10, Exceptional, (58)
"Our stay was amazing. The condo was immaculate, the kitchen was well stocked and the Riverview was outstanding. "
The price is AEDĀ 658
AEDĀ 1,320 total
includes taxes & fees
22 Jun - 23 Jun
Luxury Riverfront Condo w/ sunrise & sunset views
Beautiful 1 bedroom condo with a view!
Property grounds

Beautiful 1 bedroom condo with a view!

10.0 out of 10, Exceptional, (47)
"Crysty was very accommodating and a great host! The place was very clean and had all the main essentials! We enjoyed our stay and highly recommend the space."
The price is AEDĀ 808
AEDĀ 1,653 total
includes taxes & fees
22 Jun - 23 Jun
Beautiful 1 bedroom condo with a view!
Beautiful Condo - Water View Near City Dock
Outdoor dining

Beautiful Condo - Water View Near City Dock

9.6 out of 10, Exceptional, (145)
"This is our second time at this property and it is just perfect for us. Quiet, great location, comfortable, great host!!!!"
Beautiful Condo - Water View Near City Dock
Wyndham Kingsgate - 2 Bedroom Deluxe
Pool

Wyndham Kingsgate - 2 Bedroom Deluxe

9.4 out of 10, Exceptional, (18)
"Property and condo were very clean, location was close to pools and game room and many local shops and restaurants. "
Wyndham Kingsgate - 2 Bedroom Deluxe
"La Casa Bianca" Fabulous 3 Bed Home next to H St & Union Market
Interior

"La Casa Bianca" Fabulous 3 Bed Home next to H St & Union Market

9.8 out of 10, Exceptional, (19)
"Beautifully maintained and comfortable. There was six of us and taking the Uber everywhere we wanted to go was super easy and inexpensive. We would stay here again!"
"La Casa Bianca" Fabulous 3 Bed Home next to H St & Union Market
Williamsburg Condo Rental: 3 Mi to Busch Gardens!
Pool

Williamsburg Condo Rental: 3 Mi to Busch Gardens!

9.4 out of 10, Exceptional, (12)
"We really enjoyed our stay here. It was neat and clean. There was plenty of space and was well stocked. Would love to come again."
Williamsburg Condo Rental: 3 Mi to Busch Gardens!
4206 Washington Blvd Condos
Exclusive Condo, 3 Bedrooms | 3 bedrooms, individually decorated, individually furnished, desk

4206 Washington Blvd Condos

4.0 star property
4.8 out of 10, (3)
"No hot water for the first 3 days, we have to boil our own water to shower . When we try to contact no one answer for a while. Very confusing instructions to how to get in the house "
The price is AEDĀ 618
AEDĀ 1,335 total
includes taxes & fees
17 Jun - 18 Jun
4206 Washington Blvd Condos
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, (138)
"Lovely forested area with lots of walking trails"
Water-view in Kingsmill, 10 minutes to Busch Gardens & Colonial Williamsburg!
Lovely 2 BR Condo in 4šŸ’Ž Historic Golf Resort
Fridge, microwave, oven, stovetop

Lovely 2 BR Condo in 4šŸ’Ž Historic Golf Resort

9.4 out of 10, Exceptional, (14)
"great location. easy to get to everything..condo was great"
The price is AEDĀ 988
AEDĀ 1,731 total
includes taxes & fees
17 Jun - 18 Jun
Lovely 2 BR Condo in 4šŸ’Ž Historic Golf Resort
Only 5 min. from the Beach!
Interior

Only 5 min. from the Beach!

9.2 out of 10, Wonderful, (20)
"Great location; cute renovation of room at Assateague Inn."
The price is AEDĀ 531
AEDĀ 888 total
includes taxes & fees
7 Jul - 8 Jul
Only 5 min. from the Beach!
Luxurious 3 Bedroom Condo Sleeps 8!
Fridge, microwave, oven, stovetop

Luxurious 3 Bedroom Condo Sleeps 8!

10.0 out of 10, Exceptional, (92)
"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!
Rendezvous at the Bay, Resort Condo in charming Cape Charles. Relaxation awaits
Sun loungers

Rendezvous at the Bay, Resort Condo in charming Cape Charles. Relaxation awaits

10.0 out of 10, Exceptional, (1)
"Rendezvous was a perfect location and a wonderful proeperty. Immaculate, fully stocked with whatever you might need. Would definitely ret8rn."
Rendezvous at the Bay, Resort Condo in charming Cape Charles. Relaxation awaits
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Frequently asked questions

How much do condos in Chesapeake Bay cost?
Expect to pay from AED 452 to AED 988 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 58 condos on offer. Enter your destination and travel dates and get a head start on planning your perfect trip today.
Why book your condo in Chesapeake Bay with Expedia?
We think that vacations should be a piece of cake, so if youā€™re in search of condos at an affordable rate, Expedia delivers. Keep the budget in check and pick something cheap and cheerful, or book 5-star accommodations and treat your loved ones. Take advantage of our search filters to find an escape in Chesapeake Bay that suits your needs.