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Our top choices for Chester vacation homes

1. Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8
Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8Chester
9.0 out of 10, Wonderful, (2 reviews)
The price is CA $390
CA $1,061 total
includes taxes & fees
Nov 9 - Nov 10

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, (69 reviews)
The price is CA $398
CA $733 total
includes taxes & fees
Nov 18 - Nov 19

3. 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
8.8 out of 10, Excellent, (23 reviews)
The price is CA $127
CA $208 total
includes taxes & fees
Nov 9 - Nov 10

4. 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)
The price is CA $584
CA $985 total
includes taxes & fees
Nov 9 - Nov 10

5. 3-bedroom house in marvelous Goshen. Luxury cabin vibes for your getaway.
3-bedroom house in marvelous Goshen. Luxury cabin vibes for your getaway.Goshen
8.0 out of 10, Very good, (1 review)
The price is CA $389
CA $671 total
includes taxes & fees
Dec 3 - Dec 4

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)
The price is CA $494
CA $996 total
includes taxes & fees
Nov 9 - Nov 10

7. 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, (28 reviews)
The price is CA $123
CA $210 total
includes taxes & fees
Nov 16 - Nov 17

8. Lakefront Paradise Pool + Paddle Boats Sleeps 12
Lakefront Paradise Pool + Paddle Boats Sleeps 12Monroe
10.0 out of 10, Exceptional, (5 reviews)
The price is CA $665
CA $1,938 total
includes taxes & fees
Nov 16 - Nov 17

9. Lakefront • 7BR Retreat • Sleeps 12 • Massage Chair
Lakefront • 7BR Retreat • Sleeps 12 • Massage ChairMonroe
10.0 out of 10, Exceptional, (5 reviews)
The price is CA $834
CA $1,632 total
includes taxes & fees
Nov 9 - Nov 10

10. Spectacular Historic Mansion w/Pool&Tennis
Spectacular Historic Mansion w/Pool&TennisGoshen
10.0 out of 10, Exceptional, (20 reviews)
The price is CA $2,258
CA $3,606 total
includes taxes & fees
Nov 9 - Nov 10

11. Waterfront Home with Hot Tub, Firepit, and Kayaks
Waterfront Home with Hot Tub, Firepit, and KayaksGreenwood Lake
10.0 out of 10, Exceptional, (47 reviews)
The price is CA $314
CA $730 total
includes taxes & fees
Dec 1 - Dec 2

12. A Cozy Private Suite in a Country Home near New Paltz
A Cozy Private Suite in a Country Home near New PaltzWallkill
9.2 out of 10, Wonderful, (20 reviews)
The price is CA $102
CA $188 total
includes taxes & fees
Nov 9 - Nov 10

13. Latitude Lake House | Lake Access • Fire Pit
Latitude Lake House | Lake Access • Fire PitGreenwood Lake
10.0 out of 10, Exceptional, (8 reviews)
The price is CA $222
CA $672 total
includes taxes & fees
Nov 9 - Nov 10

14. La Victoria 5-bedroom estate in the heart of Warwick, an Hour away from NYC
La Victoria 5-bedroom estate in the heart of Warwick, an Hour away from NYCWarwick
9.6 out of 10, Exceptional, (7 reviews)
The price is CA $426
CA $766 total
includes taxes & fees
Nov 17 - Nov 18

15. 3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point
3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West PointCornwall
10.0 out of 10, Exceptional, (16 reviews)
The price is CA $321
CA $619 total
includes taxes & fees
Nov 9 - Nov 10

16. Panoramic Fall Foliage Escape, Fire Pit, Wood Stove
Panoramic Fall Foliage Escape, Fire Pit, Wood StoveGreenwood Lake
10.0 out of 10, Exceptional, (3 reviews)
The price is CA $293
CA $534 total
includes taxes & fees
Nov 15 - Nov 16

17. Lakefront Couples Escape | Dock • Kayaks • Firepit
Lakefront Couples Escape | Dock • Kayaks • FirepitHewitt
9.8 out of 10, Exceptional, (6 reviews)
The price is CA $258
CA $632 total
includes taxes & fees
Nov 9 - Nov 10

18. Entire Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ 2 Decks
Entire Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ 2 DecksGreenwood Lake
10.0 out of 10, Exceptional, (12 reviews)
The price is CA $631
CA $1,192 total
includes taxes & fees
Nov 9 - Nov 10

19. Dock Holiday | Lakefront • Boathouse Bar • Kayaks
Dock Holiday | Lakefront • Boathouse Bar • KayaksGreenwood Lake
10.0 out of 10, Exceptional, (2 reviews)
The price is CA $464
CA $1,186 total
includes taxes & fees
Nov 20 - Nov 21

20. Perfect 2BR with Free Parking! Walk to West Point!
Perfect 2BR with Free Parking! Walk to West Point!Highland Falls
The price is CA $201
CA $377 total
includes taxes & fees
Nov 9 - Nov 10
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.
Learn more about Chester
Lace up your hiking boots and hit the trails at Goosepond Mountain State Park for stunning views. After working up an appetite, head to Castle Fun Centre for go-karts, mini-golf, and arcade games.

Top reviews in Chester

Holiday Inn Express Hotel & Suites Chester by IHG
Holiday Inn Express Hotel & Suites Chester by IHGChester
















































































































