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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

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 AED 768
AED 1,551 total
includes taxes & fees
25 Oct - 26 Oct
Charming Chester Farmhouse near Near VT Slopes
Exterior

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 AED 1,028
AED 2,600 total
includes taxes & fees
5 Oct - 6 Oct
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, (5 reviews)
"Clean, spacous house, good location and great scenes of the mountains."
United States
pauline
The price is AED 1,980
AED 3,711 total
includes taxes & fees
5 Oct - 6 Oct
4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
A room with a bunk bed, a dresser, a lamp, and a window with a view of greenery.

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

Peaceful Stay w/ Pond & Massage Chair | Near Okemo
Ludlow
The price is AED 447
AED 1,667 total
includes taxes & fees
5 Oct - 6 Oct
Peaceful Stay w/ Pond & Massage Chair | Near Okemo
A cozy living room with a fireplace, comfortable seating, and a television.

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

Bear`s Den in Ludlow, Okemo Views + Epic Game Room
Ludlow
The price is AED 664
AED 1,496 total
includes taxes & fees
5 Oct - 6 Oct
Bear`s Den in Ludlow, Okemo Views + Epic Game Room
A patio area with outdoor furniture, a small garden with purple flowers, and a white building in the background.

6. 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, (53 reviews)
"We had a very lovely stay. "
United States
mary c.
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
A child sliding down a water slide shaped like a frog, with a pool area in the background.

7. Mountain Lodge At Okemo-1br Fireplace & Updated Kitchen 1 Bedroom Condo by RedAwning

Mountain Lodge At Okemo-1br Fireplace & Updated Kitchen 1 Bedroom Condo by RedAwning
3.5 star property
Clock Tower Base Area
Mountain Lodge At Okemo-1br Fireplace & Updated Kitchen 1 Bedroom Condo by RedAwning
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 AED 624
AED 1,975 total
includes taxes & fees
25 Oct - 26 Oct
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
A bedroom with a skylight, a bed with floral bedding, a bedside table, and a nightstand.

9. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
The price is AED 264
AED 382 total
includes taxes & fees
30 Oct - 31 Oct
Cozy Vermont Tiny Home Get Away
A wooden deck with a white railing overlooking a lake, surrounded by trees and a small house.

10. 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 AED 441
AED 1,506 total
includes taxes & fees
3 Nov - 4 Nov
Lakefront Family Fun Retreat
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

11. 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 AED 274
AED 941 total
includes taxes & fees
5 Oct - 6 Oct
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
A modern kitchen with a central island, built-in appliances, and a dining area with a wooden table and chairs.

12. 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, (19 reviews)
"This was a lovely, well-kept home in a great location to Okemo Mountain."
United States
Nancy F.
The price is AED 985
AED 2,196 total
includes taxes & fees
6 Oct - 7 Oct
New Ludlow Village Home with Stunning Okemo Mountain View
A two-story house with a covered porch and a garage.

13. 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 AED 821
AED 3,123 total
includes taxes & fees
5 Oct - 6 Oct
Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
A garden with a wooden pergola, purple flowers, and a river view.

14. 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 AED 539
AED 1,031 total
includes taxes & fees
22 Oct - 23 Oct
Family Friendly Hilltop House In Putney Vermont
A compact kitchen with a refrigerator, stove, microwave, and sink.

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

The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
Plymouth
The price is AED 655
AED 2,093 total
includes taxes & fees
5 Oct - 6 Oct
The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
A hot tub surrounded by stone steps, wooden lounge chairs, and a wooden deck.

16. 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 AED 725
AED 2,419 total
includes taxes & fees
22 Oct - 23 Oct
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
A wooden cabin with a balcony, surrounded by trees.

17. 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 AED 826
AED 1,574 total
includes taxes & fees
12 Oct - 13 Oct
Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
A lodge with a large fireplace, a covered porch, and a staircase leading to the upper level.

18. 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 AED 1,928
AED 2,753 total
includes taxes & fees
15 Oct - 16 Oct
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 living room with a brick fireplace, a sofa, a chair, and a coffee table.

19. 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.
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
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 AED 566
AED 722 total
includes taxes & fees
26 Oct - 27 Oct
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

Colonial Motel

Colonial Motel

10/10 Excellent
"clean room"
Biplob 1-night trip
Posted 10 hours ago
Colonial Motel