Chester Vacation Rentals
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 vacation homes
1. Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of TownWarwick
8.6 out of 10, Excellent, (19 reviews)
"I absolutely loved my stay. A beautiful place with Victorian inspired, a big comfy bed, a really nice cozy reading nook with stone glass windows, and had an enjoyable stay!!
Very easy check-in and check-out process. Great air conditioning during a heat wave!!"
Daisy
The price is CA $130
CA $223 total
includes taxes & fees
Sep 22 - Sep 23
2. Country House w/Hot Tub, Deck, Grill & Fire Pit
Country House w/Hot Tub, Deck, Grill & Fire PitGoshen
9.8 out of 10, Exceptional, (67 reviews)
"We had a nice weekend at the Country House. I would recommend this property to friends and family. "
Mike T.
The price is CA $460
CA $841 total
includes taxes & fees
Sep 27 - Sep 28
3. The Columbus Hotel - The Courtyard Suite - 89-303
The Columbus Hotel - The Courtyard Suite - 89-303Middletown
The price is CA $138
CA $296 total
includes taxes & fees
Sep 23 - Sep 24
4. Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of TownWarwick
8.8 out of 10, Excellent, (23 reviews)
"Great value and beautiful room and In ."
Paul E.
The price is CA $137
CA $231 total
includes taxes & fees
Oct 19 - Oct 20
5. Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space
Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor SpaceGoshen
10.0 out of 10, Exceptional, (35 reviews)
"Great house, as advertised!"
Steven K.
The price is CA $789
CA $1,275 total
includes taxes & fees
Sep 22 - Sep 23
6. Amazing Home Near West Point, Shopping, Skiing and Legoland
Amazing Home Near West Point, Shopping, Skiing and LegolandMonroe
9.8 out of 10, Exceptional, (17 reviews)
"Very nice property in a nice neighborhood . Had all the amenities we needed and Ruth was super responsive. If we are in the area again, we will def stay at this location. "
Kimberly R.
The price is CA $490
CA $1,024 total
includes taxes & fees
Sep 22 - Sep 23
7. Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Waterfront Home with Hot Tub, Kayaks, and Fast WifiGreenwood Lake
10.0 out of 10, Exceptional, (41 reviews)
"We have stayed here a few times and the house is always perfect. Will stay here again in the future! "
Lex S.
The price is CA $326
CA $781 total
includes taxes & fees
Sep 23 - Sep 24
8. Charming 2-bedroom house in Greenwood Lake with Central AC/Heat
Charming 2-bedroom house in Greenwood Lake with Central AC/HeatGreenwood Lake
10.0 out of 10, Exceptional, (7 reviews)
"Very clean and really cute place. "
Katie C.
The price is CA $283
CA $639 total
includes taxes & fees
Sep 28 - Sep 29
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 vacation rentals that suit your style
Aparthotels
Apartments
Save an average of 15% on thousands of hotels when you're signed in
Top Chester Hotel Reviews
Hilton Garden Inn Nanuet
10/10 Excellent
Find out more about Chester
Chester Vacation Homes information
Number of reviews | |
|---|---|
Accommodation | 322 Vacation Homes |
Lowest Price | CA $2,167 |
Highest Price | CA $2,167 |
Explore a world of travel with Expedia
- Hilton Hotels in Goshen
- Americas Best Value Inn at Central Valley
- Cabin Rentals in Woodbury
- B&B in Walden
- Motels in Middletown
- Hotels near LEGOLAND® New York
- B&B in Beaverdam Lake-Salisbury Mills
- Hotels near Woodbury Common Premium Outlets
- Brooklyn Hotels
- Condo Rentals in West Point
- Apartments in Buchanan
- Motels in Mount Hope
- Middletown Hotels
- Motels in Newburgh
- B&B in Mount Ivy
- B&B in Woodbury
- Rv Parks in Philipstown
- Soho Hotels
- Hotels near Central Park
- B&B in Monroe
- Stagecoach Inn
- B&B in Newburgh
- Motels in New York
- Hostels in New York
- Resorts in Monroe
- 4 Star Hotels in Goshen
- B&B in Cornwall
- Holiday Inn Express Hotel & Suites Chester by IHG
- Cabin Rentals in Wallkill
- Cheap Hotels in New York
- Fairfield Inn & Suites by Marriott Goshen Middletown
- Apartments in New York
- Hampton Inn Harriman Woodbury
- Chelsea Hotels
- Florida Hotels
- Midtown Hotels
- Sleep Inn & Suites Monroe
- Cabin Rentals in Scotchtown
- Monroe Hotels
- Villas in West Point
- New York Hotels
- The Dominion House Bed & Breakfast
- Chester Hotels
- Motels in Highland Falls
- Motels in Bear Mountain
- Cabin Rentals in Greenwood Lake
- Villas in Woodbury
- Goshen Hotels
- Motels in Orange County
- Motels in Salisbury Mills
- B&B in Warwick
- Beach Hotel Hotels in Goshen
- Cheap Hotels in Manhattan
- 5 Star Hotels in Goshen
- Hotels near Times Square
- B&B in Hillburn
- Manhattan Hotels
- Inns in West Point
- Flights from Ottawa (YOW) to New York (NYC)
- Flights from London (LON) to New York (NYC)
- Flights from Hamilton (YHM) to New York (LGA)
- Flights from Detroit (DTW) to New York (LGA)
- Flights from Halifax (YHZ) to New York (LGA)
- Flights from Los Angeles (LAX) to New York (NYC)
- Westjet Toronto (YYZ) to New York (LGA) flights
- Flights from Toronto (YTO) to New York (NYC)
- Flights from Ottawa (YOW) to New York (LGA)
- Flights from Toronto (YYZ) to New York (JFK)
- Flights from Buffalo (BUF) to New York (JFK)
- Flights from Québec (YQB) to New York (NYC)
- Flights from Toronto (YYZ) to Newburgh (SWF)
- Flights from Calgary (YYC) to New York (JFK)
- Flights from Edmonton (YEG) to New York (LGA)
- Flights from Boston (BOS) to New York (NYC)
- Flights from Toronto (YYZ) to New York (NYC)
- Flights to New York
- Flights from Vancouver (YVR) to New York (JFK)
- Flights from Stewart Intl.
- Flights from Montreal (YUL) to New York (LGA)
- Flights from Toronto (YYZ) to New York (LGA)
- Flights from Vancouver (YVR) to New York (NYC)
- Flights from Winnipeg (YWG) to New York (LGA)
- Flights from Toronto (YTZ) to New York (NYC)