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

Chester Vacation Rentals

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Chester vacation 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 CA $290
CA $582 total
includes taxes & fees
Sep 28 - Sep 29
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 CA $389
CA $890 total
includes taxes & fees
Oct 5 - Oct 6
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 CA $749
CA $1,398 total
includes taxes & fees
Sep 22 - Sep 23
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 CA $104
CA $357 total
includes taxes & fees
Sep 22 - Sep 23
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.

5. 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 CA $373
CA $831 total
includes taxes & fees
Sep 22 - Sep 23
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.

6. 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 $188
CA $679 total
includes taxes & fees
Sep 22 - Sep 23
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
A person relaxing in a hot tub outdoors with string lights in a forested area.

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

Secluded Spa Retreat | Hot Tub + Sauna | Okemo
Ludlow
The price is CA $362
CA $621 total
includes taxes & fees
Sep 17 - Sep 18
Secluded Spa Retreat | Hot Tub + Sauna | Okemo
A wooden deck with a white railing overlooking a lake, surrounded by trees and a small house.

8. 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 $167
CA $575 total
includes taxes & fees
Sep 20 - Sep 21
Lakefront Family Fun Retreat
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, (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 $219
CA $410 total
includes taxes & fees
Sep 22 - Sep 23
Family Friendly Hilltop House In Putney Vermont
A cozy living room with a fireplace, comfortable seating, and a television.

10. 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 $251
CA $566 total
includes taxes & fees
Sep 21 - Sep 22
Bear`s Den in Ludlow, Okemo Views + Epic Game Room
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 CA $322
CA $1,179 total
includes taxes & fees
Sep 17 - Sep 18
Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
A hot tub surrounded by stone steps, wooden lounge chairs, and a wooden deck.

12. 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 $274
CA $921 total
includes taxes & fees
Sep 22 - Sep 23
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
A deck with outdoor furniture, a table, and a view of a forested hillside.

13. 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 CA $430
CA $938 total
includes taxes & fees
Sep 17 - Sep 18
Modern Farm House…minutes to Okemo; 2 King beds!
A living room with a brick fireplace, a sofa, a chair, and a coffee table.

14. 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 CA $445
CA $1,087 total
includes taxes & fees
Sep 21 - Sep 22
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.

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 $491
CA $730 total
includes taxes & fees
Sep 17 - Sep 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.
A large house with a fire pit and outdoor seating.

16. 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 CA $362
CA $829 total
includes taxes & fees
Sep 27 - Sep 28
Beautiful 3-bedroom house with AC in charming Bridgewater
A snow-covered wooden cabin with a balcony, surrounded by snow-covered trees.

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

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
The price is CA $288
CA $913 total
includes taxes & fees
Sep 22 - Sep 23
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
A cabin with a deck and a stone chimney.

18. The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.

The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.
Killington
10.0 out of 10, Exceptional, (63 reviews)
"Great stay, everything was clean and location was amazing."
United States
John D.
The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.
A modern kitchen with granite countertops, stainless steel appliances, and a central island.

19. 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 CA $267
CA $674 total
includes taxes & fees
Sep 22 - Sep 23
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

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"I loved that they have 2 room suites with a full kitchen. Everyone who worked there was beyond efficient and friendly. The fact that its dog friendly was great as I had been on the road almost 3 weeks and was missing my pups ."
Linda 3-night trip
Posted 11 hours ago
Pointe at Castle Hill Resort

Find out more about Chester

Chester Vacation Homes information

Number of reviews
185
Accommodation
979 Vacation Homes
Lowest Price
CA $357
Highest Price
CA $1,398

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