A covered wooden bridge over a river, surrounded by rocky terrain and greenery.

Holiday Homes in Chester

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

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 AU$577
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 AU$899
includes taxes & fees
8 Sept - 9 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 AU$1,379
includes taxes & fees
13 Sept - 14 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 AU$356
includes taxes & fees
10 Sept - 11 Sept
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
A wooden deck with a white railing overlooking a lake, surrounded by trees and a small house.

5. 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 AU$570
includes taxes & fees
28 Sept - 29 Sept
Lakefront Family Fun Retreat
A garden with purple flowers and a river in the background.

6. 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 AU$383
includes taxes & fees
8 Sept - 9 Sept
Family Friendly Hilltop House In Putney Vermont
A cozy living room with a fireplace, comfortable seating, and a television.

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

Bear`s Den in Ludlow, Okemo Views + Epic Game Room
Ludlow
The price is AU$555
includes taxes & fees
8 Sept - 9 Sept
Bear`s Den in Ludlow, Okemo Views + Epic Game Room
A cozy cabin interior with a stone fireplace, leather sofas, and large windows offering a view of the forest.

8. 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 AU$678
includes taxes & fees
13 Sept - 14 Sept
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
A modern kitchen with a central island, built-in appliances, and a dining area with a wooden table and chairs.

9. 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 AU$831
includes taxes & fees
8 Sept - 9 Sept
New Ludlow Village Home with Stunning Okemo Mountain View
A red cabin with a green roof, a wooden deck, and a gravel driveway.

10. Secluded Spa Retreat | Hot Tub + Sauna | Okemo

Secluded Spa Retreat | Hot Tub + Sauna | Okemo
Ludlow
The price is AU$754
includes taxes & fees
8 Sept - 9 Sept
Secluded Spa Retreat | Hot Tub + Sauna | Okemo
A two-story house with a covered porch and a garage.

11. 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 AU$1,091
includes taxes & fees
8 Sept - 9 Sept
Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
A deck with outdoor furniture, a table, and a view of a forested hillside.

12. 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 AU$928
includes taxes & fees
17 Sept - 18 Sept
Modern Farm House…minutes to Okemo; 2 King beds!
A large house with a fire pit and outdoor seating.

13. 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 AU$650
includes taxes & fees
8 Sept - 9 Sept
Beautiful 3-bedroom house with AC in charming Bridgewater
A modern kitchen with granite countertops, stainless steel appliances, and a central island.

14. 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 AU$661
includes taxes & fees
8 Sept - 9 Sept
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
A hot tub surrounded by stone steps, wooden lounge chairs, and a wooden deck.

15. 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 AU$931
includes taxes & fees
8 Sept - 9 Sept
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
A four-poster bed with a grey bedspread, a wooden nightstand with a lamp, a wooden dresser, and a chair.

16. 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 AU$470
includes taxes & fees
8 Sept - 9 Sept
Cozy 3 bedroom Cottage on Farm with great outdoor space 10 min to Bellows Falls
A living room with a brick fireplace, a sofa, a chair, and a coffee table.

17. 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 AU$1,091
includes taxes & fees
21 Sept - 22 Sept
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
Two Adirondack chairs and a fire pit in a grassy field with a forested hill in the background.

18. Large Farmhouse with expansive views, firepit 15 min north of Keene

Large Farmhouse with expansive views, firepit 15 min north of Keene
Walpole
The price is AU$621
includes taxes & fees
8 Sept - 9 Sept
Large Farmhouse with expansive views, firepit 15 min north of Keene
A lodge with a large fireplace, a covered porch, and a staircase leading to the upper level.

19. 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 AU$841
includes taxes & fees
8 Sept - 9 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 cozy living room with a brick fireplace, comfortable seating, and large windows offering a view of the outdoors.

20. Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.

Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
Bridgewater
8.8 out of 10, Excellent, (3 reviews)
"Great place for a ski weekend"
United States
Kathryn F.
The price is AU$996
includes taxes & fees
8 Sept - 9 Sept
Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
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

The Jackson

The Jackson

10/10 Excellent
"The inn and the grounds are beautifully maintained. The room was comfortable, and the restaurant on the premises was convenient but also had a great breakfast, well worth purchasing. The location was also great relative to downtown."
Vicki 1-night trip
Posted 14 hours ago
The Jackson

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