Chester Vacation Rentals

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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 8
Chester
9.0 out of 10, Wonderful, (2 reviews)
"Host was very nice and accommodating. The house was clean and comfortable. There is a beautiful tub in the master bath but I was wishing there was a shower there. Master bed was very comfortable but also very tall for a shorter person like myself. Overall very nice."
United States
jolene j.
The price is CA $390
CA $1,061 total
includes taxes & fees
Nov 9 - Nov 10
Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8

2. Country House w/Hot Tub, Deck, Grill & Fire Pit

Country House w/Hot Tub, Deck, Grill & Fire Pit
Goshen
9.8 out of 10, Exceptional, (69 reviews)
"We had a nice weekend at the Country House. I would recommend this property to friends and family. "
United States
Mike T.
The price is CA $398
CA $733 total
includes taxes & fees
Nov 18 - Nov 19
Country House w/Hot Tub, Deck, Grill & Fire Pit

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 Town
Warwick
8.8 out of 10, Excellent, (22 reviews)
"Great place, but you can hear red everything going on outside your room with the restaurant downstairs and other people in the common area. But I’d definitely come back here"
United States
Joseph
The price is CA $127
CA $208 total
includes taxes & fees
Nov 9 - Nov 10
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town

4. Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space

Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space
Goshen
10.0 out of 10, Exceptional, (35 reviews)
"Great house, as advertised!"
United States
Steven K.
The price is CA $584
CA $985 total
includes taxes & fees
Nov 9 - Nov 10
Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space

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 check-in process went smoothly. The property was very clean and comfortable. Location was close to many different small towns. "
United States
Kelly M.
The price is CA $389
CA $671 total
includes taxes & fees
Dec 3 - Dec 4
3-bedroom house in marvelous Goshen. Luxury cabin vibes for your getaway.

6. Amazing Home Near West Point, Shopping, Skiing and Legoland

Amazing Home Near West Point, Shopping, Skiing and Legoland
Monroe
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. "
United States
Kimberly R.
The price is CA $494
CA $996 total
includes taxes & fees
Nov 9 - Nov 10
Amazing Home Near West Point, Shopping, Skiing and Legoland

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 Town
Warwick
8.8 out of 10, Excellent, (28 reviews)
"Great value and beautiful room and In ."
United States
Paul E.
The price is CA $123
CA $210 total
includes taxes & fees
Nov 16 - Nov 17
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

8. Lakefront Paradise Pool + Paddle Boats Sleeps 12

Lakefront Paradise Pool + Paddle Boats Sleeps 12
Monroe
10.0 out of 10, Exceptional, (5 reviews)
"We had a wonderful week long stay. The house is beautiful and right on the lake, with beautiful views and sunsetsWe were there for a West Point Graduation and was about a 30 minute drive to the school, even on the busy days of the parade and graduation dayThe house had plenty of room for our group and the host was easy to get ahold of. There are 4 official bedroom and 4 bathrooms and a basement and 2 office/den, 2 washer and dryers - one in the top floor and another in the basement which has...
United States
Courtney D.
The price is CA $665
CA $1,938 total
includes taxes & fees
Nov 16 - Nov 17
Lakefront Paradise Pool + Paddle Boats Sleeps 12

9. Lakefront • 7BR Retreat • Sleeps 12 • Massage Chair

Lakefront • 7BR Retreat • Sleeps 12 • Massage Chair
Monroe
10.0 out of 10, Exceptional, (5 reviews)
"The combination of an antique, old-style house with a modernized interior featuring all the amenities you could dream of made for an enjoyable and cozy experience. The house is located right at the back of the lake in a quiet neighborhood and comes fully equipped with:- A spacious layout- High-speed Wi-Fi- Useful massage chair - Fun recreational areas- Lovely decorThis house will truly become a staple in the area."
United States
Moshe F.
The price is CA $834
CA $1,632 total
includes taxes & fees
Nov 9 - Nov 10
Lakefront • 7BR Retreat • Sleeps 12 • Massage Chair

10. Spectacular Historic Mansion w/Pool&Tennis

Spectacular Historic Mansion w/Pool&Tennis
Goshen
10.0 out of 10, Exceptional, (20 reviews)
"Truly amazing house, incredible pool, easy renting experience. Would definitely be back. "
United States
Aditya U.
The price is CA $2,258
CA $3,606 total
includes taxes & fees
Nov 9 - Nov 10
Spectacular Historic Mansion w/Pool&Tennis

11. Waterfront Home with Hot Tub, Firepit, and Kayaks

Waterfront Home with Hot Tub, Firepit, and Kayaks
Greenwood Lake
10.0 out of 10, Exceptional, (47 reviews)
"We have stayed here a few times and the house is always perfect. Will stay here again in the future! "
United States
Lex S.
The price is CA $319
CA $738 total
includes taxes & fees
Dec 1 - Dec 2
Waterfront Home with Hot Tub, Firepit, and Kayaks

12. A Cozy Private Suite in a Country Home near New Paltz

A Cozy Private Suite in a Country Home near New Paltz
Wallkill
9.2 out of 10, Wonderful, (20 reviews)
"The room was super cute and clean. It had everything that I needed."
United States
Carrie
The price is CA $102
CA $188 total
includes taxes & fees
Nov 9 - Nov 10
A Cozy Private Suite in a Country Home near New Paltz

13. Latitude Lake House | Lake Access • Fire Pit

Latitude Lake House | Lake Access • Fire Pit
Greenwood Lake
10.0 out of 10, Exceptional, (8 reviews)
"Great property and loved the lake access!"
United States
Dan and Kristen L.
The price is CA $222
CA $672 total
includes taxes & fees
Nov 9 - Nov 10
Latitude Lake House | Lake Access • Fire Pit

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 NYC
Warwick
9.6 out of 10, Exceptional, (7 reviews)
"Excellent location to explore Warwick and launch for a trip to NYC!"
United States
David K.
The price is CA $431
CA $772 total
includes taxes & fees
Nov 16 - Nov 17
La Victoria 5-bedroom estate in the heart of Warwick, an Hour away from NYC

15. 3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point

3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point
Cornwall
10.0 out of 10, Exceptional, (16 reviews)
"Everything you could ask for!!"
United States
Elisabeth
The price is CA $321
CA $619 total
includes taxes & fees
Nov 9 - Nov 10
3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point

16. Panoramic Fall Foliage Escape, Fire Pit, Wood Stove

Panoramic Fall Foliage Escape, Fire Pit, Wood Stove
Greenwood Lake
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful home...it is clear that much thought and time went into the decor and functionality....complete with welcomed amenities."
United States
andrea e.
The price is CA $324
CA $572 total
includes taxes & fees
Dec 1 - Dec 2
Panoramic Fall Foliage Escape, Fire Pit, Wood Stove

17. Lakefront Couples Escape | Dock • Kayaks • Firepit

Lakefront Couples Escape | Dock • Kayaks • Firepit
Hewitt
9.8 out of 10, Exceptional, (6 reviews)
"Absolutely amazing place"
United States
Mehdy K.
The price is CA $258
CA $632 total
includes taxes & fees
Nov 9 - Nov 10
Lakefront Couples Escape | Dock • Kayaks • Firepit

18. Entire Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ 2 Decks

Entire Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ 2 Decks
Greenwood Lake
10.0 out of 10, Exceptional, (12 reviews)
"We had lovely and relaxing stay at this property! The surrounding area is beautiful and the crowd are amazing!"
United States
Susan R.
The price is CA $631
CA $1,192 total
includes taxes & fees
Nov 9 - Nov 10
Entire Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ 2 Decks

19. Dock Holiday | Lakefront • Boathouse Bar • Kayaks

Dock Holiday | Lakefront • Boathouse Bar • Kayaks
Greenwood Lake
10.0 out of 10, Exceptional, (2 reviews)
"Property was right on Greenwood lake with excellent views. Kayak available to use was a nice convenience. We enjoyed sitting off the deck and admiring views. We can see ourselves going back to this property. Thank you !"
United States
PETER E.
The price is CA $464
CA $1,186 total
includes taxes & fees
Nov 20 - Nov 21
Dock Holiday | Lakefront • Boathouse Bar • Kayaks

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
Perfect 2BR with Free Parking! Walk to West Point!
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.

A bridge with a plaque reading "City of Chester Queens Park Bridge 1923".

Top reviews in Chester

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