Photo by Patricia Knorr
Holiday Homes in Chester
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
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 NZ$467
includes taxes & fees
17 Feb - 18 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 NZ$479
includes taxes & fees
17 Feb - 18 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.
The price is NZ$687
includes taxes & fees
9 Feb - 10 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 NZ$529
includes taxes & fees
11 Feb - 12 Feb
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady SideShady Side
10.0 out of 10, Exceptional, (4 reviews)
"Would stay here again "
Thomas D.
The price is NZ$729
includes taxes & fees
9 Feb - 10 Feb
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 NZ$849
includes taxes & fees
9 Feb - 10 Feb
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Bay Ridge unit by Downtown Annapolis and Quiet Waters ParkAnnapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
William
The price is NZ$793
includes taxes & fees
9 Feb - 10 Feb
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.
The price is NZ$669
includes taxes & fees
11 Feb - 12 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.
Find holiday rentals that suit your style
Private holiday homes
Apartments
Save an average of 15% on thousands of hotels when you're signed in
Top Chester Hotel Reviews
Crowne Plaza Annapolis by IHG
10/10 Excellent
Find out more about Chester
Chester Holiday Homes information
Number of reviews | 254 |
|---|---|
Accommodation | 659 Holiday Homes |
Lowest Price | NZ$467 |
Highest Price | NZ$1,194 |