
Holiday Homes in Chester
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Our top choices for Chester holiday homes

1. Charming Chester Farmhouse near Near VT Slopes
Charming Chester Farmhouse near Near VT SlopesChester Depot
9.4 out of 10, Exceptional, (22 reviews)
The price is NZ$659
includes taxes & fees
8 Nov - 9 Nov

2. 4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
4-Season Vermont Cabin · 12 Acres, Mountain Views · OkemoChester
10.0 out of 10, Exceptional, (6 reviews)
The price is NZ$1,677
includes taxes & fees
7 Nov - 8 Nov

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 AndoverAndover
10.0 out of 10, Exceptional, (2 reviews)
The price is NZ$1,173
includes taxes & fees
14 Nov - 15 Nov

4. Peaceful Stay w/ Pond & Massage Chair | Near Okemo
Peaceful Stay w/ Pond & Massage Chair | Near OkemoLudlow
The price is NZ$766
includes taxes & fees
9 Nov - 10 Nov

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 ShuttleLudlow
9.8 out of 10, Exceptional, (114 reviews)
The price is NZ$852
includes taxes & fees
16 Nov - 17 Nov

6. Long Trail House 368 condo in Stratton Village, walk to the lifts
Long Trail House 368 condo in Stratton Village, walk to the liftsStratton
The price is NZ$450
includes taxes & fees
10 Nov - 11 Nov

7. Bear`s Den in Ludlow, Okemo Views + Epic Game Room
Bear`s Den in Ludlow, Okemo Views + Epic Game RoomLudlow
10.0 out of 10, Exceptional, (1 review)
The price is NZ$813
includes taxes & fees
23 Nov - 24 Nov

8. New Ludlow Village Home with Stunning Okemo Mountain View
New Ludlow Village Home with Stunning Okemo Mountain ViewLudlow
10.0 out of 10, Exceptional, (23 reviews)
The price is NZ$1,001
includes taxes & fees
13 Nov - 14 Nov

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 GoreMt Holly
9.8 out of 10, Exceptional, (42 reviews)
The price is NZ$833
includes taxes & fees
15 Nov - 16 Nov

10. Cozy Vermont Tiny Home Get Away
Cozy Vermont Tiny Home Get AwayBrattleboro
10.0 out of 10, Exceptional, (2 reviews)
The price is NZ$172
includes taxes & fees
30 Nov - 1 Dec

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)
The price is NZ$1,384
includes taxes & fees
15 Nov - 16 Nov

12. Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
Enjoy this authentic and cozy VT Barn with Brand New Hot TubLondonderry
7.0 out of 10, Good, (2 reviews)
The price is NZ$827
includes taxes & fees
9 Nov - 10 Nov

13. Lakefront Family Fun Retreat
Lakefront Family Fun RetreatNewport
10.0 out of 10, Exceptional, (5 reviews)
The price is NZ$707
includes taxes & fees
10 Nov - 11 Nov

14. Gorgeous couples barn with WiFi & hot tub in lovely Londonderry
Gorgeous couples barn with WiFi & hot tub in lovely LondonderryLondonderry
10.0 out of 10, Exceptional, (2 reviews)
The price is NZ$1,907
includes taxes & fees
9 Nov - 10 Nov

15. The Eagles Wing at The CHM - Private Apartment
The Eagles Wing at The CHM - Private ApartmentDover
9.8 out of 10, Exceptional, (6 reviews)
The price is NZ$225
includes taxes & fees
9 Nov - 10 Nov

16. Family Friendly Hilltop House In Putney Vermont
Family Friendly Hilltop House In Putney VermontPutney
9.4 out of 10, Exceptional, (65 reviews)
The price is NZ$478
includes taxes & fees
9 Nov - 10 Nov

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

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)
The price is NZ$1,019
includes taxes & fees
8 Nov - 9 Nov

19. Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home GymWinhall
10.0 out of 10, Exceptional, (15 reviews)
The price is NZ$1,340
includes taxes & fees
9 Nov - 10 Nov

20. Luxe Mountain Home w/ Chef’s Kitchen & Okemo Views
Luxe Mountain Home w/ Chef’s Kitchen & Okemo ViewsLudlow
10.0 out of 10, Exceptional, (1 review)
The price is NZ$3,669
includes taxes & fees
15 Nov - 16 Nov
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
10/10 Excellent
Find out more about Chester
Chester Holiday Homes information
Number of reviews | 200 |
|---|---|
Accommodation | 978 Holiday Homes |
Lowest Price | NZ$172 |
Highest Price | NZ$3,669 |


































































