
Holiday Homes in Chester
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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 AU$1,100
includes taxes & fees
10 Nov - 11 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 AU$739
includes taxes & fees
18 Nov - 19 Nov

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 AU$227
includes taxes & fees
10 Nov - 11 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 AU$1,001
includes taxes & fees
10 Nov - 11 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 AU$681
includes taxes & fees
3 Dec - 4 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 AU$1,034
includes taxes & fees
10 Nov - 11 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 AU$214
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 AU$1,927
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 AU$1,672
includes taxes & fees
10 Nov - 11 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 AU$3,604
includes taxes & fees
12 Nov - 13 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 AU$738
includes taxes & fees
1 Dec - 2 Dec

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 AU$196
includes taxes & fees
10 Nov - 11 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 AU$771
includes taxes & fees
10 Nov - 11 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 AU$776
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 AU$624
includes taxes & fees
10 Nov - 11 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 AU$542
includes taxes & fees
15 Nov - 16 Nov

17. Lakefront Couples Escape | Dock • Kayaks • Firepit
Lakefront Couples Escape | Dock • Kayaks • FirepitHewitt
9.8 out of 10, Exceptional, (6 reviews)
The price is AU$646
includes taxes & fees
9 Dec - 10 Dec

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 AU$1,290
includes taxes & fees
30 Nov - 1 Dec

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 AU$1,170
includes taxes & fees
21 Nov - 22 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 AU$383
includes taxes & fees
10 Nov - 11 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.
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Top Chester Hotel Reviews

Hampton Inn & Suites Mahwah
8/10 Good
Find out more about Chester
Chester Holiday Homes information
Number of reviews | 246 |
|---|---|
Accommodation | 305 Holiday Homes |
Lowest Price | AU$196 |
Highest Price | AU$3,604 |

































































