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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Chester vacation homes

Dining

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 CA $297
CA $602 total
includes taxes & fees
Oct 26 - Oct 27
Charming Chester Farmhouse near Near VT Slopes
A two-story house with a deck, surrounded by dense forest.

2. 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, (5 reviews)
"Clean, spacous house, good location and great scenes of the mountains."
United States
pauline
The price is CA $766
CA $1,429 total
includes taxes & fees
Oct 13 - Oct 14
4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
Exterior

3. 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 CA $398
CA $1,006 total
includes taxes & fees
Oct 20 - Oct 21
Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
A kitchen with wooden ceiling, a stove, a microwave, and a refrigerator.

4. Peaceful Stay w/ Pond & Massage Chair | Near Okemo

Peaceful Stay w/ Pond & Massage Chair | Near Okemo
Ludlow
The price is CA $190
CA $665 total
includes taxes & fees
Oct 8 - Oct 9
Peaceful Stay w/ Pond & Massage Chair | Near Okemo
A compact kitchen with a red bench, a microwave, a sink, and a window with a view of a snowy landscape.

5. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
The price is CA $102
CA $148 total
includes taxes & fees
Nov 3 - Nov 4
Cozy Vermont Tiny Home Get Away
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 CA $171
CA $593 total
includes taxes & fees
Nov 3 - Nov 4
Lakefront Family Fun Retreat
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

7. 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 CA $106
CA $368 total
includes taxes & fees
Oct 7 - Oct 8
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.

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 CA $237
CA $747 total
includes taxes & fees
Oct 7 - Oct 8
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, (21 reviews)
"This was a lovely, well-kept home in a great location to Okemo Mountain."
United States
Nancy F.
The price is CA $381
CA $850 total
includes taxes & fees
Oct 13 - Oct 14
New Ludlow Village Home with Stunning Okemo Mountain View
A two-story house with a covered porch and a garage.

10. 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 CA $306
CA $1,180 total
includes taxes & fees
Oct 7 - Oct 8
Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
A garden with a wooden pergola, purple flowers, and a river view.

11. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (64 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 CA $189
CA $378 total
includes taxes & fees
Oct 20 - Oct 21
Family Friendly Hilltop House In Putney Vermont
A compact kitchen with a refrigerator, stove, microwave, and sink.

12. The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6

The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
Plymouth
The price is CA $254
CA $809 total
includes taxes & fees
Oct 7 - Oct 8
The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
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, (41 reviews)
"Our family had a wonderful vacation. The house and location were great. We will come back."
United States
Victoria L.
The price is CA $281
CA $934 total
includes taxes & fees
Oct 21 - Oct 22
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
A spacious living area with a fireplace, a dining area, and a kitchen.

14. Luxe Mountain Home w/ Chef’s Kitchen & Okemo Views

Luxe Mountain Home w/ Chef’s Kitchen & Okemo Views
Ludlow
10.0 out of 10, Exceptional, (1 review)
"My family and I stayed at this property last weekend and it was amazing!!! We were the first to rent as this is a brand new construction home. Everything inside is brand new from the bedding, furniture and amazing cookware. This house has a few great features that make it top notch: 1: Every bedroom has an en-suite bathroom, so we all had our own space and privacy. The bedrooms were big and beds were so comfortable. The master bedroom has this huge shower and tub that was so nicely designed. 2:...
United States
Michael
The price is CA $1,711
CA $3,208 total
includes taxes & fees
Oct 13 - Oct 14
Luxe Mountain Home w/ Chef’s Kitchen & Okemo Views
A lodge with a large fireplace, a covered porch, and a staircase leading to the upper level.

15. 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 CA $523
CA $772 total
includes taxes & fees
Oct 7 - Oct 8
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 wooden cabin with a balcony, surrounded by trees.

16. Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River

Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
Newport
9.6 out of 10, Exceptional, (27 reviews)
"Amazing weekend stay with our pup! Looking forward to staying here in the summer! "
United States
Naydene G.
The price is CA $321
CA $616 total
includes taxes & fees
Oct 12 - Oct 13
Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
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, (15 reviews)
"Clean, lots of room, easy access to Stratton, responsive host."
United States
Mark H.
The price is CA $549
CA $1,291 total
includes taxes & fees
Oct 25 - Oct 26
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
A large house with a fire pit and outdoor seating.

18. Pet Friendly | Game Room | Minutes to Woodstock and Killington

Pet Friendly | Game Room | Minutes to Woodstock and Killington
Bridgewater
10.0 out of 10, Exceptional, (3 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 CA $285
CA $746 total
includes taxes & fees
Nov 3 - Nov 4
Pet Friendly | Game Room | Minutes to Woodstock and Killington
A modern two-story house with a front porch, a staircase, and a driveway.

19. 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 CA $376
CA $1,356 total
includes taxes & fees
Oct 14 - Oct 15
Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
A bedroom with a large bed, a window with blinds, a bookshelf, and a wall-mounted ship's wheel.

20. The Eagles Wing at The CHM - Private Apartment

The Eagles Wing at The CHM - Private Apartment
Dover
9.6 out of 10, Exceptional, (5 reviews)
"I loved the super comfy bed and fully stocked coffee cart!"
United States
Ava M.
The price is CA $219
CA $283 total
includes taxes & fees
Oct 20 - Oct 21
The Eagles Wing at The CHM - Private Apartment
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

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

8/10 Good
"Or stay here was unique and that we checked ourselves in for the code, the same for checking out. Very strange to have no other humans there. All in all, it was clean and comfortable. We wish they had breakfast like in the old days"
Denise 2-night trip
Posted 1 hour ago
Hideaway Inn Mt. Snow

Find out more about Chester

Chester Vacation Homes information

Number of reviews
123
Accommodation
979 Vacation Homes
Lowest Price
CA $148
Highest Price
CA $3,208

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