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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Chester holiday homes

1. Charming Chester Farmhouse near Near VT Slopes

Charming Chester Farmhouse near Near VT Slopes
Chester Depot
9.4 out of 10, Exceptional, (22 reviews)
"Beautiful classic farmhouse in lovely neighbourhood."
United States
Kimberly B.
The price is HK$1,639
HK$3,310 total
includes taxes & fees
8 Sept - 9 Sept
Charming Chester Farmhouse near Near VT Slopes

2. Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover

Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
Andover
10.0 out of 10, Exceptional, (1 review)
"Very nice stay. Owners were very gracious. House was clean & comfortable."
United States
Lorraine C.
The price is HK$2,195
HK$5,014 total
includes taxes & fees
5 Sept - 6 Sept
Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
A two-story house with a deck, surrounded by dense forest.

3. 4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo

4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
Chester
10.0 out of 10, Exceptional, (4 reviews)
"Clean, spacous house, good location and great scenes of the mountains."
United States
pauline
The price is HK$4,226
HK$7,895 total
includes taxes & fees
11 Sept - 12 Sept
4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

4. Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Stratton
The price is HK$584
HK$2,008 total
includes taxes & fees
8 Sept - 9 Sept
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
A cozy cabin interior with a stone fireplace, leather sofas, and large windows offering a view of the forest.

5. Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Mt Holly
9.8 out of 10, Exceptional, (42 reviews)
"This house has great hang out space and plenty of space for a big family!"
United States
Cheri V.
The price is HK$1,305
HK$4,184 total
includes taxes & fees
7 Sept - 8 Sept
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
A wooden deck with a white railing overlooking a lake, surrounded by trees and a small house.

6. Lakefront Family Fun Retreat

Lakefront Family Fun Retreat
Newport
10.0 out of 10, Exceptional, (5 reviews)
"Great visit! The house is perfectly outfitted for a relaxing vacation. Super clean and updated. Really enjoyed the warm waters of Crescent Lake!"
United States
Ann R.
The price is HK$941
HK$3,232 total
includes taxes & fees
28 Sept - 29 Sept
Lakefront Family Fun Retreat
A modern kitchen with a central island, built-in appliances, and a dining area with a wooden table and chairs.

7. New Ludlow Village Home with Stunning Okemo Mountain View

New Ludlow Village Home with Stunning Okemo Mountain View
Ludlow
10.0 out of 10, Exceptional, (18 reviews)
"This was a lovely, well-kept home in a great location to Okemo Mountain."
United States
Nancy F.
The price is HK$2,103
HK$4,679 total
includes taxes & fees
6 Sept - 7 Sept
New Ludlow Village Home with Stunning Okemo Mountain View
A modern two-story house with a front porch, a staircase, and a driveway.

8. Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!

Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
Jamaica
9.6 out of 10, Exceptional, (30 reviews)
"House was perfect for a guys trip for skiing. Just as expected. Would stay again. "
United States
Michael A.
The price is HK$1,430
HK$6,427 total
includes taxes & fees
9 Sept - 10 Sept
Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
A garden with purple flowers and a river in the background.

9. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (63 reviews)
"The house was all we expected. Very comfortable and ready for us when we arrived. It’s a bit out of the way, at the end of a private road, but quiet and secluded. Our host was attentive without being intrusive. She clearly wanted to make sure our stay met our expectations and was pleasant. All in all, a delightful way to visit Vermont!"
United States
Susan G.
The price is HK$1,122
HK$2,161 total
includes taxes & fees
8 Sept - 9 Sept
Family Friendly Hilltop House In Putney Vermont
A deck with outdoor furniture, a table, and a view of a forested hillside.

10. Modern Farm House…minutes to Okemo; 2 King beds!

Modern Farm House…minutes to Okemo; 2 King beds!
Mount Holly
9.6 out of 10, Exceptional, (20 reviews)
"Fantastic house! Christine was easy to communicate with and made us and our dogs feel incredibly welcome. Looking forward to staying there again."
United States
Rachel L.
The price is HK$2,421
HK$5,320 total
includes taxes & fees
17 Sept - 18 Sept
Modern Farm House…minutes to Okemo; 2 King beds!
A cozy living room with a fireplace, comfortable seating, and a television.

11. Bear`s Den in Ludlow, Okemo Views + Epic Game Room

Bear`s Den in Ludlow, Okemo Views + Epic Game Room
Ludlow
The price is HK$1,417
HK$3,185 total
includes taxes & fees
7 Sept - 8 Sept
Bear`s Den in Ludlow, Okemo Views + Epic Game Room
A two-story house with a covered porch and a garage.

12. Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!

Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
Mount Holly
10.0 out of 10, Exceptional, (11 reviews)
"We had a great time in this beautiful house for a family ski trip. It is located right off the main highway and 8min drive away from Okemo. It has all the amenities we wanted- including hot tub, cozy underground family entertainment room and parking garage. Heidi, the host was super prompt and all instructions about the house were very thorough. "
United States
Chi L.
The price is HK$1,888
HK$6,842 total
includes taxes & fees
10 Sept - 11 Sept
Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
A hot tub surrounded by stone steps, wooden lounge chairs, and a wooden deck.

13. Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Winhall
9.4 out of 10, Exceptional, (40 reviews)
"Our family had a wonderful vacation. The house and location were great. We will come back."
United States
Victoria L.
The price is HK$1,547
HK$5,198 total
includes taxes & fees
7 Sept - 8 Sept
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
A patio area with outdoor furniture, a small garden with purple flowers, and a white building in the background.

14. Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Walpole
10.0 out of 10, Exceptional, (52 reviews)
"We had a very lovely stay. "
United States
mary c.
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
A living room with a brick fireplace, a sofa, a chair, and a coffee table.

15. Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
Winhall
10.0 out of 10, Exceptional, (14 reviews)
"Clean, lots of room, easy access to Stratton, responsive host."
United States
Mark H.
The price is HK$2,353
HK$6,327 total
includes taxes & fees
15 Sept - 16 Sept
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
A lodge with a large fireplace, a covered porch, and a staircase leading to the upper level.

16. Cozy Vermont A-frame on a quiet private road, minutes from Stratton. Enjoy year-round adventure, then unwind in the hot tub under the stars. Spacious, stylish, and perfect for groups seeking both relaxation and outdoor fun.

Cozy Vermont A-frame on a quiet private road, minutes from Stratton. Enjoy year-round adventure, then unwind in the hot tub under the stars. Spacious, stylish, and perfect for groups seeking both relaxation and outdoor fun.
Jamaica
8.8 out of 10, Excellent, (8 reviews)
"Beautiful home, we enjoyed our stay!"
United States
Luke B.
The price is HK$3,254
HK$4,785 total
includes taxes & fees
14 Sept - 15 Sept
Cozy Vermont A-frame on a quiet private road, minutes from Stratton. Enjoy year-round adventure, then unwind in the hot tub under the stars. Spacious, stylish, and perfect for groups seeking both relaxation and outdoor fun.
A large house with a fire pit and outdoor seating.

17. Beautiful 3-bedroom house with AC in charming Bridgewater

Beautiful 3-bedroom house with AC in charming Bridgewater
Bridgewater
10.0 out of 10, Exceptional, (2 reviews)
"Great house with fun decorations. Comfortable with lots of room; full kitchen with ample dining area. Loved the coffee available and the sound machine in the bedroom- great conveniences! Communication around booking were great with easy check in and check out."
United States
Susan S.
The price is HK$1,192
HK$3,618 total
includes taxes & fees
5 Sept - 6 Sept
Beautiful 3-bedroom house with AC in charming Bridgewater
A four-poster bed with a grey bedspread, a wooden nightstand with a lamp, a wooden dresser, and a chair.

18. Cozy 3 bedroom Cottage on Farm with great outdoor space 10 min to Bellows Falls

Cozy 3 bedroom Cottage on Farm with great outdoor space 10 min to Bellows Falls
Walpole
10.0 out of 10, Exceptional, (6 reviews)
"A cozy little cottage on a beautiful property. Great for 4 adults or a small family "
United States
Sheilah Z.
The price is HK$2,304
HK$2,823 total
includes taxes & fees
7 Sept - 8 Sept
Cozy 3 bedroom Cottage on Farm with great outdoor space 10 min to Bellows Falls
A bunk bed room with wooden walls, a red door, and a small table.

19. MtSnow* HotTub* Pool * AirHockey*PingPong * Darts

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
The price is HK$1,785
HK$5,416 total
includes taxes & fees
9 Sept - 10 Sept
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
A modern kitchen with granite countertops, stainless steel appliances, and a central island.

20. Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Keene
10.0 out of 10, Exceptional, (4 reviews)
"Communication with the host was easy and the house was great. I would definitely book this home again if/when I come back to Keene."
United States
Jeremy S.
The price is HK$1,505
HK$3,760 total
includes taxes & fees
7 Sept - 8 Sept
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
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

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

8/10 Good
"The property was very nice. Clean rooms. Plenty of towels. Comfortable bed and pillows."
Katrina 2-night trip
Posted 4 hours ago
Keene Elm City Hotel, an Ascend Collection Hotel

Find out more about Chester

Chester Vacation Homes information

Number of reviews
317
Accommodation
979 Vacation Homes
Lowest Price
HK$2,008
Highest Price
HK$7,895

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