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Our top choices for Chester vacation homes
Adorable two-bedroom retreat close to Easton, Denton, Centreville
Adorable two-bedroom retreat close to Easton, Denton, CentrevilleQueen Anne
10.0 out of 10, Exceptional, (26)
"Quiet, quaint....perfect"
Catherine M.
The price is AED 694
AED 1,316 total
includes taxes & fees
22 Dec - 23 Dec
Charming Coastal/Country Home w/3 Acres & Sauna!
Charming Coastal/Country Home w/3 Acres & Sauna!Stevensville
9.6 out of 10, Exceptional, (32)
"Very nice house! We had 3 people in our party and didn't want to rent 2 hotel rooms, this is a great way to save money and enjoy time together. "
Pamela
The price is AED 377
AED 1,061 total
includes taxes & fees
21 Dec - 22 Dec
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Relax on Kent Island in a 4 Bedroom Home w/Waterview!Stevensville
9.8 out of 10, Exceptional, (42)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
Stephanie S.
The price is AED 194
AED 825 total
includes taxes & fees
14 Dec - 15 Dec
HGTV quality, private guest suite, country getaway with hot tub & fire pit
HGTV quality, private guest suite, country getaway with hot tub & fire pitCentreville
10.0 out of 10, Exceptional, (8)
"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"
Renee P.
The price is AED 724
AED 1,628 total
includes taxes & fees
17 Dec - 18 Dec
Walk to Beach! King Bed & Free Beach Passes
Walk to Beach! King Bed & Free Beach PassesNorth Beach
10.0 out of 10, Exceptional, (17)
"We loved our stay! The property was just as advertised and had everything we needed. Quiet area and felt very safe. The owners provided excellent communication as well!"
Jennifer B.
The price is AED 298
AED 1,161 total
includes taxes & fees
4 Jan - 5 January 2026
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.Grasonville
9.6 out of 10, Exceptional, (12)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
Joe C.
The price is AED 918
AED 1,538 total
includes taxes & fees
22 Dec - 23 Dec
Chesapeake Bay Harbor View in a central location to events/restaurants
Chesapeake Bay Harbor View in a central location to events/restaurantsRock Hall
10.0 out of 10, Exceptional, (2)
"House was clean, great location. Furniture needs a little updating but overall our stay was great! Would definitely stay here again."
Todd W.
The price is AED 826
AED 1,001 total
includes taxes & fees
23 Dec - 24 Dec
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, RestaurantsNorth Beach
10.0 out of 10, Exceptional, (31)
"Perfect place to spend quality time with our three adult children and their significant others. "
Malarkey F.
The price is AED 543
AED 1,720 total
includes taxes & fees
8 Jan - 9 January 2026
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.
Top Chester Hotel Reviews
DoubleTree by Hilton Hotel Annapolis
10/10 Excellent
