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Holiday Homes in Chester
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Our top choices for Chester holiday homes
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, (43 reviews)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
Stephanie S.
The price is €199
includes taxes & fees
2 Feb - 3 Feb
Charming Coastal/Country Home w/3 Acres & Sauna!
Charming Coastal/Country Home w/3 Acres & Sauna!Stevensville
9.6 out of 10, Exceptional, (32 reviews)
"Great stay, would do it again."
Brandon D.
The price is €225
includes taxes & fees
8 Feb - 9 Feb
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 reviews)
"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.
Walk to Beach! King Bed & Free Beach Passes
Walk to Beach! King Bed & Free Beach PassesNorth Beach
10.0 out of 10, Exceptional, (18 reviews)
"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 €273
includes taxes & fees
2 Feb - 3 Feb
Large 2 bedroom house with private parking in a nice neighborhood
Large 2 bedroom house with private parking in a nice neighborhoodArnold
9.4 out of 10, Exceptional, (36 reviews)
"This house was perfect for my husband and I, plus two daughters! We loved the location and how clean the unit was. The beds were comfortable and there were plenty of towels and all the things we needed for our weekend. We will definitely stay here again!"
Emily B.
The price is €271
includes taxes & fees
4 Feb - 5 Feb
BAYSIDE BUNGALOW
BAYSIDE BUNGALOWRock Hall
10.0 out of 10, Exceptional, (52 reviews)
"Very quaint and quiet place to stay. Very relaxing."
Roger
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 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
Malarkey F.
Annapolis Retreat - 7 mins from downtown Annapolis!
Annapolis Retreat - 7 mins from downtown Annapolis!Hillsmere
10.0 out of 10, Exceptional, (5 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
Paul C.
The price is €435
includes taxes & fees
2 Feb - 3 Feb
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 Chester Hotel Reviews
Hampton Inn & Suites Annapolis
10/10 Excellent
Find out more about Chester
Chester Holiday Homes information
Number of reviews | 296 |
|---|---|
Accommodation | 659 Holiday Homes |
Lowest Price | €199 |
Highest Price | €592 |