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

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Chester holiday 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)
"We had a great stay! The house was clean, comfortable, and exactly as described. The location was perfect and the host was very responsive. We’d definitely stay here again and highly recommend it."
United States
Stephanie F.
The price is £302
includes taxes & fees
25 Aug - 26 Aug
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 £479
includes taxes & fees
23 Aug - 24 Aug
Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
Exterior

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 £730
includes taxes & fees
28 Aug - 29 Aug
4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
Terrace/patio

4. Okemo's Back Room - in the heart of the village on the shuttle route!

Okemo's Back Room - in the heart of the village on the shuttle route!
Ludlow
9.6 out of 10, Exceptional, (16 reviews)
"Perfect location. Neat place. Very clean!"
United States
Frank F.
The price is £294
includes taxes & fees
26 Aug - 27 Aug
Okemo's Back Room - in the heart of the village on the shuttle route!
TV, fireplace, table football, stereo

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 £288
includes taxes & fees
23 Aug - 24 Aug
Bear`s Den in Ludlow, Okemo Views + Epic Game Room
Interior

6. 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 £194
includes taxes & fees
23 Aug - 24 Aug
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Smart TV, fireplace, video games, books

7. 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 £365
includes taxes & fees
23 Aug - 24 Aug
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Dining

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, (18 reviews)
"This was a lovely, well-kept home in a great location to Okemo Mountain."
United States
Nancy F.
The price is £436
includes taxes & fees
23 Aug - 24 Aug
New Ludlow Village Home with Stunning Okemo Mountain View
Property grounds

9. 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 £324
includes taxes & fees
1 Sept - 2 Sept
Lakefront Family Fun Retreat
Exterior detail

10. 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 £651
includes taxes & fees
26 Aug - 27 Aug
Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
Exterior

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 £623
includes taxes & fees
27 Aug - 28 Aug
Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
Property grounds

12. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (63 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is £228
includes taxes & fees
1 Sept - 2 Sept
Family Friendly Hilltop House In Putney Vermont
Exterior

13. Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft

Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
Jamaica
9.2 out of 10, Wonderful, (27 reviews)
"We enjoyed our stay at a great ski house that was in a good location to the mountain. Accommodations were comfortable for 6 adults and 4 kids and the shuffleboard, foosball and pool tables were a hit. "
United States
Jonathan H.
The price is £631
includes taxes & fees
26 Aug - 27 Aug
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
Outdoor spa tub

14. 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)
"House was clean and pet-friendly! Great location between Bromley and Stratton!"
United States
Michael I.
The price is £491
includes taxes & fees
25 Aug - 26 Aug
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Microwave, oven, stovetop, dishwasher

15. Large Farmhouse Steps from Downtown Ludlow & Okemo Shuttle

Large Farmhouse Steps from Downtown Ludlow & Okemo Shuttle
Ludlow
10.0 out of 10, Exceptional, (2 reviews)
"Host was very attentive and house was charming. Easy drive to slopes. Well maintained and super comfy beds!"
United States
Leina L.
The price is £696
includes taxes & fees
23 Aug - 24 Aug
Large Farmhouse Steps from Downtown Ludlow & Okemo Shuttle
Property grounds

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, (1 review)
"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 £407
includes taxes & fees
9 Sept - 10 Sept
Beautiful 3-bedroom house with AC in charming Bridgewater
Terrace/patio

17. 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, (52 reviews)
"We had a very lovely stay. "
United States
mary c.
The price is £549
includes taxes & fees
4 Sept - 5 Sept
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
TV, fireplace, books, music library

18. 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, (13 reviews)
"Clean, lots of room, easy access to Stratton, responsive host."
United States
Mark H.
The price is £582
includes taxes & fees
24 Aug - 25 Aug
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
3 bedrooms

19. 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 £282
includes taxes & fees
10 Sept - 11 Sept
Cozy 3 bedroom Cottage on Farm with great outdoor space 10 min to Bellows Falls
Exterior

20. 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 £446
includes taxes & fees
26 Aug - 27 Aug
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.
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

On The River Inn

On The River Inn

8/10 Good
"Staff was friendly and the room was clean. Nice social atmosphere, game rooms."
Neriman 1-night trip
Posted 19 hours ago
On The River Inn

Find out more about Chester

Chester Holiday Homes information

Number of reviews
350
Accommodation
1022 Holiday Homes
Lowest Price
£194
Highest Price
£730