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

Search Vacation Homes in Weston

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

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 ￥44,038
￥94,770 total
includes taxes & fees
Sep 30 - Oct 1
Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
A cozy cabin interior with a stone fireplace, leather sofas, and large windows offering a view of the forest.

2. 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 ￥22,648
￥75,041 total
includes taxes & fees
Sep 30 - Oct 1
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

3. 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 ￥11,725
￥39,210 total
includes taxes & fees
Oct 1 - Oct 2
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
A bunk bed room with a small table and a door labeled 'Ranger House'.

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

Peaceful Stay w/ Pond & Massage Chair | Near Okemo
Ludlow
The price is ￥20,082
￥67,991 total
includes taxes & fees
Sep 30 - Oct 1
Peaceful Stay w/ Pond & Massage Chair | Near Okemo
A two-story house with a covered porch and a garage.

5. 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 ￥33,972
￥125,814 total
includes taxes & fees
Oct 7 - Oct 8
Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
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 ￥28,433
￥59,809 total
includes taxes & fees
Oct 1 - Oct 2
Bear`s Den in Ludlow, Okemo Views + Epic Game Room
A modern kitchen with a central island, built-in appliances, and a dining area with a wooden table and chairs.

7. 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 ￥42,182
￥88,543 total
includes taxes & fees
Oct 4 - Oct 5
New Ludlow Village Home with Stunning Okemo Mountain View
Dining

8. 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 ￥32,872
￥62,711 total
includes taxes & fees
Oct 20 - Oct 21
Charming Chester Farmhouse near Near VT Slopes
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 ￥31,039
￥98,948 total
includes taxes & fees
Oct 19 - Oct 20
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
A two-story house with a deck, surrounded by dense forest.

10. 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 ￥84,790
￥148,163 total
includes taxes & fees
Sep 30 - Oct 1
4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
A compact kitchen with a refrigerator, stove, microwave, and sink.

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

The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
Plymouth
The price is ￥28,049
￥85,027 total
includes taxes & fees
Sep 30 - Oct 1
The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
A living room with a brick fireplace, a sofa, a chair, and a coffee table.

12. 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 ￥54,306
￥128,602 total
includes taxes & fees
Sep 30 - Oct 1
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
A modern kitchen with a black stove, a red microwave, and a stainless steel sink. There are two black chairs and a black table.

13. 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 ￥14,580
￥36,025 total
includes taxes & fees
Sep 30 - Oct 1
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
A spacious kitchen with a large island, a stone fireplace, and wooden beams.

14. 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 ￥36,882
￥97,661 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 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 ￥65,271
￥90,659 total
includes taxes & fees
Sep 30 - Oct 1
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 spacious kitchen with a central island, stainless steel appliances, and pendant lighting.

16. 1812 House, 2 Stays, 1 home

1812 House, 2 Stays, 1 home
Manchester
The price is ￥46,802
￥114,557 total
includes taxes & fees
Oct 21 - Oct 22
1812 House, 2 Stays, 1 home
A wooden cabin interior with a wooden dresser, a floral chair, a teal refrigerator, and a shelf with mugs and a coffee maker.

17. Peaceful 1-bedroom bungalow with AC in charming Wells

Peaceful 1-bedroom bungalow with AC in charming Wells
Wells
10.0 out of 10, Exceptional, (1 review)
"Clean comfy quiet spot."
United States
Dillon B.
The price is ￥29,018
￥36,025 total
includes taxes & fees
Oct 6 - Oct 7
Peaceful 1-bedroom bungalow with AC in charming Wells
A two-story white house with a front porch, a door with a wreath, and a chimney.

18. Cozy farmhouse in Manchester - short drive to multiple ski mountains!

Cozy farmhouse in Manchester - short drive to multiple ski mountains!
Manchester
9.4 out of 10, Exceptional, (3 reviews)
"The hosts were very friendly and responsive during our stay. Loved that the house is close to the main town as well as close to the ski slopes (Bromley). "
United States
Marissa H.
The price is ￥59,452
￥111,257 total
includes taxes & fees
Oct 5 - Oct 6
Cozy farmhouse in Manchester - short drive to multiple ski mountains!
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 ￥27,767
￥70,686 total
includes taxes & fees
Oct 5 - Oct 6
large ski ranch hot tub close to killington pets ok
A modern kitchen with stainless steel appliances, a dining table, and a wooden floor.

20. 4BR Home | Walk Downtown Rutland + Trails

4BR Home | Walk Downtown Rutland + Trails
Rutland
10.0 out of 10, Exceptional, (7 reviews)
"House was clean, organized and spacious. Great location as well, close to grocery, gas and restaurants. Host answered questions quickly. "
United States
Dominic C.
The price is ￥31,141
￥58,961 total
includes taxes & fees
Oct 26 - Oct 27
4BR Home | Walk Downtown Rutland + 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Weston Hotel Reviews

Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

10/10 Excellent
"Everything good"
Evelyn 2-night trip
Posted 2 hours ago
Hampton Inn and Suites Manchester

Find out more about Weston

Weston Vacation Homes information

Number of reviews
127
Accommodation
832 Vacation Homes
Lowest Price
￥36,025
Highest Price
￥148,163

Explore a world of travel with Expedia