A red two-story building with a porch, labeled "The Vermont Country Store," featuring a sign for "The Orton Family Business."

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Check prices for these dates

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

Our top choices for Weston vacation homes

Exterior

1. 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 ￥44,064
￥101,347 total
includes taxes & fees
Oct 5 - Oct 6
Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
A bunk bed room with a small table and a door labeled 'Ranger House'.

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

Peaceful Stay w/ Pond & Massage Chair | Near Okemo
Ludlow
The price is ￥21,553
￥73,960 total
includes taxes & fees
Oct 1 - Oct 2
Peaceful Stay w/ Pond & Massage Chair | Near Okemo
A cozy living room with a fireplace, comfortable seating, and a television.

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

Bear`s Den in Ludlow, Okemo Views + Epic Game Room
Ludlow
The price is ￥28,449
￥63,755 total
includes taxes & fees
Oct 4 - Oct 5
Bear`s Den in Ludlow, Okemo Views + Epic Game Room
A cozy cabin interior with a stone fireplace, leather sofas, and large windows offering a view of the forest.

4. 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 ￥23,375
￥79,777 total
includes taxes & fees
Oct 1 - Oct 2
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
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, (19 reviews)
"This was a lovely, well-kept home in a great location to Okemo Mountain."
United States
Nancy F.
The price is ￥42,207
￥93,574 total
includes taxes & fees
Oct 1 - Oct 2
New Ludlow Village Home with Stunning Okemo Mountain View
Dining

6. 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 ￥32,890
￥65,919 total
includes taxes & fees
Oct 25 - Oct 26
Charming Chester Farmhouse near Near VT Slopes
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

7. 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 ￥11,732
￥40,299 total
includes taxes & fees
Oct 7 - Oct 8
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
A two-story house with a covered porch and a garage.

8. 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 ￥39,781
￥139,910 total
includes taxes & fees
Oct 4 - Oct 5
Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
A hot tub surrounded by stone steps, wooden lounge chairs, and a wooden deck.

9. 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 ￥31,057
￥104,339 total
includes taxes & fees
Oct 21 - Oct 22
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
A compact kitchen with a refrigerator, stove, microwave, and sink.

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

The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
Plymouth
The price is ￥28,072
￥89,328 total
includes taxes & fees
Oct 1 - Oct 2
The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
A modern kitchen with a black stove, a red microwave, and a stainless steel sink. There are two black chairs and a black table.

11. new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Mendon
9.8 out of 10, Exceptional, (6 reviews)
"Very pretty property, wish we could have spent more time there. Getting in and out was easy and there were plenty of options for food in town just a few minutes away. Great stay."
United States
Aurore H.
The price is ￥14,588
￥36,935 total
includes taxes & fees
Oct 5 - Oct 6
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
A dining table set with plates, glasses, and a vase with a plant.

12. Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.8 out of 10, Exceptional, (16 reviews)
"The location was perfect, the property is very well maintained and comfortable. I would highly recommend this place!"
United States
Valerie
The price is ￥14,635
￥29,881 total
includes taxes & fees
Oct 20 - Oct 21
Cozy Rutland Retreat
A spacious living room with wooden floors, a high ceiling with exposed beams, a dining area with a table and chairs, and large windows offering a view of the outdoors.

13. Killington Retreat | Deck-Fire Pit-Mountain Views!

Killington Retreat | Deck-Fire Pit-Mountain Views!
Clarendon
9.2 out of 10, Wonderful, (5 reviews)
"The living area is bigger than we expected, and we loved watching the horses next door. It's a short drive to downtown Rutland, and it's quiet. "
United States
Ahmad H.
The price is ￥26,611
￥71,889 total
includes taxes & fees
Oct 24 - Oct 25
Killington Retreat | Deck-Fire Pit-Mountain Views!
A two-story house with a deck, surrounded by dense forest.

14. 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 ￥84,838
￥158,999 total
includes taxes & fees
Oct 7 - Oct 8
4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
A hallway with a wooden beam ceiling, a door with a frosted glass panel, and a view of a living room with a sofa and a table.

15. Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace

Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
Killington
The price is ￥29,394
￥78,846 total
includes taxes & fees
Oct 1 - Oct 2
Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
A spacious kitchen with a large island, a stone fireplace, and wooden beams.

16. Views for Days | Hot Tub, Sauna, EV, A/C | 6 Min to Stratton, 15 to Bromley

Views for Days | Hot Tub, Sauna, EV, A/C | 6 Min to Stratton, 15 to Bromley
Winhall
10.0 out of 10, Exceptional, (13 reviews)
"House was great for our family ski trip! "
United States
Brooke S.
The price is ￥36,913
￥103,612 total
includes taxes & fees
Oct 1 - Oct 2
Views for Days | Hot Tub, Sauna, EV, A/C | 6 Min to Stratton, 15 to Bromley
A living room with a brick fireplace, a sofa, a chair, and a coffee table.

17. 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 ￥68,456
￥154,355 total
includes taxes & fees
Oct 18 - Oct 19
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
A spacious living area with a fireplace, a dining area, and a kitchen.

18. 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 ￥189,473
￥355,300 total
includes taxes & fees
Oct 4 - Oct 5
Luxe Mountain Home w/ Chef’s Kitchen & Okemo Views
A spacious kitchen with a large island, wooden dining table, and chairs. There are multiple windows providing natural light and views of the outdoors.

19. large ski ranch hot tub close to killington pets ok

large ski ranch hot tub close to killington pets ok
Mendon
9.2 out of 10, Wonderful, (9 reviews)
"The hot tub was great after a day of skiing."
United States
Callison A.
The price is ￥27,760
￥75,114 total
includes taxes & fees
Oct 5 - Oct 6
large ski ranch hot tub close to killington pets ok
A lodge with a large fireplace, a covered porch, and a staircase leading to the upper level.

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 ￥65,309
￥96,047 total
includes taxes & fees
Oct 20 - Oct 21
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 Weston Hotel Reviews

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent
"Beautiful location. Helpful staff"
Richard 1-night trip
Posted 19 hours ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Find out more about Weston

Weston Vacation Homes information

Number of reviews
138
Accommodation
832 Vacation Homes
Lowest Price
￥29,881
Highest Price
￥355,300

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