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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

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 $263
CA $527 total
includes taxes & fees
Nov 12 - Nov 13
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, (6 reviews)
"Clean, spacous house, good location and great scenes of the mountains."
United States
pauline
The price is CA $753
CA $1,330 total
includes taxes & fees
Nov 3 - Nov 4
4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
A cozy living room with a stone fireplace, large windows, and a wooden ceiling.

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, (2 reviews)
"Very nice stay. Owners were very gracious. House was clean & comfortable."
United States
Lorraine C.
The price is CA $391
CA $900 total
includes taxes & fees
Nov 3 - Nov 4
Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
A room with a stone fireplace, wooden ceiling, and a window with curtains.

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

Peaceful Stay w/ Pond & Massage Chair | Near Okemo
Ludlow
The price is CA $167
CA $608 total
includes taxes & fees
Nov 3 - Nov 4
Peaceful Stay w/ Pond & Massage Chair | Near Okemo
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

5. Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Ludlow
9.8 out of 10, Exceptional, (114 reviews)
"Wendi was very responsive when I had questions. We enjoyed our weekend getaway. Great location we walked into town to the Farmers Market Sunday."
United States
Tina l.
The price is CA $279
CA $667 total
includes taxes & fees
Nov 18 - Nov 19
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
A cozy living room with a fireplace, comfortable seating, and a television.

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

Bear`s Den in Ludlow, Okemo Views + Epic Game Room
Ludlow
The price is CA $253
CA $536 total
includes taxes & fees
Nov 3 - Nov 4
Bear`s Den in Ludlow, Okemo Views + Epic Game Room
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

7. Long Trail House 368 condo in Stratton Village, walk to the lifts

Long Trail House 368 condo in Stratton Village, walk to the lifts
Stratton
The price is CA $117
CA $362 total
includes taxes & fees
Nov 3 - Nov 4
Long Trail House 368 condo in Stratton Village, walk to the lifts
A modern kitchen with a central island, built-in appliances, and a dining area with a wooden table and chairs.

8. 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, (23 reviews)
"The perfect stop on the way to UVM. Super clean! Walkable eateries & a beautiful view. Thank you!"
United States
Tara
The price is CA $375
CA $795 total
includes taxes & fees
Nov 3 - Nov 4
New Ludlow Village Home with Stunning Okemo Mountain View
A cozy cabin interior with a stone fireplace, leather sofas, and large windows offering a view of the forest.

9. 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 $189
CA $650 total
includes taxes & fees
Nov 3 - Nov 4
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
A rustic kitchen with wooden beams, a large island, and a hanging light fixture.

10. Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
Londonderry
7.0 out of 10, Good, (2 reviews)
"I was "sold" & excited when I saw the pictures online bc the barn looked really neat. Although the barn was a neat concept, the pictures ARE NOT accurate, it is not as updated as pictured & it was VERY DISAPPOINTING. I now understand the non-refundable policy bc what you see online is definitely NOT what you walked into when you opened the door & they don't want to have to give people their back. Although we had fun, the accommodations were VERY misleading & disappointing. "
United States
Christine M.
The price is CA $355
CA $636 total
includes taxes & fees
Nov 9 - Nov 10
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
A wooden deck with a white railing overlooking a lake, surrounded by trees and a small house.

11. Lakefront Family Fun Retreat

Lakefront Family Fun Retreat
Newport
10.0 out of 10, Exceptional, (5 reviews)
"Had a lot here to use and The place was very cute. It’s good if you have small kids they have a lot for that sort of thing. Very clean as well"
United States
sean c.
The price is CA $181
CA $568 total
includes taxes & fees
Nov 3 - Nov 4
Lakefront Family Fun Retreat
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 CA $321
CA $1,091 total
includes taxes & fees
Nov 4 - Nov 5
Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
A compact kitchen with wooden cabinets, a built-in microwave, and a refrigerator.

13. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
10.0 out of 10, Exceptional, (1 review)
"Cozy, clean and peaceful spot! Host was responsive and helpful."
United States
Maggie G.
The price is CA $101
CA $133 total
includes taxes & fees
Nov 30 - Dec 1
Cozy Vermont Tiny Home Get Away
A spacious room with wooden beams, large windows, and a cozy seating area with white furniture.

14. Gorgeous couples barn with WiFi & hot tub in lovely Londonderry

Gorgeous couples barn with WiFi & hot tub in lovely Londonderry
Londonderry
10.0 out of 10, Exceptional, (2 reviews)
"The converted barn was absolutely stunning. Kitchen was well appointed and the family room spacious and comfortible."
United States
Tim M.
The price is CA $1,029
CA $1,519 total
includes taxes & fees
Nov 3 - Nov 4
Gorgeous couples barn with WiFi & hot tub in lovely Londonderry
A spacious living area with a fireplace, a dining area, and a kitchen.

15. 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 $1,682
CA $2,994 total
includes taxes & fees
Nov 3 - Nov 4
Luxe Mountain Home w/ Chef’s Kitchen & Okemo Views
A red house with a gravel driveway and lush greenery.

16. 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 $295
CA $835 total
includes taxes & fees
Nov 3 - Nov 4
The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
A garden with a wooden pergola, purple flowers, and a river view.

17. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (65 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 $204
CA $375 total
includes taxes & fees
Nov 3 - Nov 4
Family Friendly Hilltop House In Putney Vermont
A deck with two wicker chairs and a string of lights against a backdrop of trees and a sunset.

18. The Eagles Wing at The CHM - Private Apartment

The Eagles Wing at The CHM - Private Apartment
Dover
9.8 out of 10, Exceptional, (6 reviews)
"I loved the super comfy bed and fully stocked coffee cart!"
United States
Ava M.
The price is CA $140
CA $177 total
includes taxes & fees
Nov 4 - Nov 5
The Eagles Wing at The CHM - Private Apartment
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 CA $579
CA $802 total
includes taxes & fees
Nov 3 - Nov 4
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.

20. 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 $447
CA $1,097 total
includes taxes & fees
Nov 3 - Nov 4
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
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

Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

10/10 Excellent
"**Wonderful stay — best hotel in Manchester!** We stayed here for a family birthday weekend and everything was excellent. The pool is great — clean, warm, and perfect for our little one. The breakfast was genuinely great too, plenty of fresh options and coffee available around the clock. Rooms were spotless and comfortable, staff were friendly and helpful, and the location is right in the middle of everything in Manchester Center. All-round the best stay we've had in Vermont — we'll definitely be back.."
rakeshreddy 1-night trip
Posted 8 hours ago
Hampton Inn and Suites Manchester

Find out more about Chester

Chester Vacation Homes information

Number of reviews
198
Accommodation
983 Vacation Homes
Lowest Price
CA $133
Highest Price
CA $2,994

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