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Apartments
Our top choices for Chester holiday 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 €672
includes taxes & fees
9 Nov - 10 Nov

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 €464
includes taxes & fees
8 Dec - 9 Dec

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, (22 reviews)
The price is €133
includes taxes & fees
9 Nov - 10 Nov

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 €625
includes taxes & fees
17 Nov - 18 Nov

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 €422
includes taxes & fees
8 Dec - 9 Dec

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 €631
includes taxes & fees
17 Nov - 18 Nov

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 €133
includes taxes & fees
17 Nov - 18 Nov

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 €1,225
includes taxes & fees
16 Nov - 17 Nov

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 €1,032
includes taxes & fees
17 Nov - 18 Nov

10. Spectacular Historic Mansion w/Pool&Tennis
Spectacular Historic Mansion w/Pool&TennisGoshen
10.0 out of 10, Exceptional, (20 reviews)
The price is €2,255
includes taxes & fees
9 Nov - 10 Nov

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 €460
includes taxes & fees
22 Nov - 23 Nov

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 €122
includes taxes & fees
9 Nov - 10 Nov

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 €439
includes taxes & fees
9 Nov - 10 Nov

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 €492
includes taxes & fees
16 Nov - 17 Nov

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 €394
includes taxes & fees
9 Nov - 10 Nov

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 €361
includes taxes & fees
8 Dec - 9 Dec

17. Lakefront Couples Escape | Dock • Kayaks • Firepit
Lakefront Couples Escape | Dock • Kayaks • FirepitHewitt
9.8 out of 10, Exceptional, (6 reviews)
The price is €404
includes taxes & fees
9 Nov - 10 Nov

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 €859
includes taxes & fees
17 Nov - 18 Nov

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 €766
includes taxes & fees
20 Nov - 21 Nov

20. Perfect 2BR with Free Parking! Walk to West Point!
Perfect 2BR with Free Parking! Walk to West Point!Highland Falls
The price is €310
includes taxes & fees
17 Nov - 18 Nov
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.


































































