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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

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, (2 reviews)
"Very nice stay. Owners were very gracious. House was clean & comfortable."
United States
Lorraine C.
The price is AED 1,028
AED 2,583 total
includes taxes & fees
22 Oct - 23 Oct
Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
A kitchen with wooden ceiling, a stove, a microwave, and a refrigerator.

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

Peaceful Stay w/ Pond & Massage Chair | Near Okemo
Ludlow
The price is AED 423
AED 1,610 total
includes taxes & fees
2 Nov - 3 Nov
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 AED 664
AED 1,480 total
includes taxes & fees
22 Oct - 23 Oct
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 AED 496
AED 1,810 total
includes taxes & fees
22 Oct - 23 Oct
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
A rustic kitchen with wooden beams, a large island, and a hanging light fixture.

5. Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
Londonderry
7.0 out of 10, Good, (2 reviews)
"I was "sold" & excited when I saw the pictures online bc the barn looked really neat. Although the barn was a neat concept, the pictures ARE NOT accurate, it is not as updated as pictured & it was VERY DISAPPOINTING. I now understand the non-refundable policy bc what you see online is definitely NOT what you walked into when you opened the door & they don't want to have to give people their back. Although we had fun, the accommodations were VERY misleading & disappointing. "
United States
Christine M.
The price is AED 932
AED 1,838 total
includes taxes & fees
12 Nov - 13 Nov
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

6. 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 Shuttle
Ludlow
9.8 out of 10, Exceptional, (114 reviews)
"Wendi was very responsive when I had questions. We enjoyed our weekend getaway. Great location we walked into town to the Farmers Market Sunday."
United States
Tina l.
The price is AED 801
AED 1,838 total
includes taxes & fees
18 Nov - 19 Nov
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
A room with two wooden beds with floral bedding, a small wooden table with a lamp, and a window with blinds.

7. View of okemo south side and okemo valley

View of okemo south side and okemo valley
Ludlow
View of okemo south side and okemo valley
A modern kitchen with a central island, built-in appliances, and a dining area with a wooden table and chairs.

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, (22 reviews)
"The perfect stop on the way to UVM. Super clean! Walkable eateries & a beautiful view. Thank you!"
United States
Tara
The price is AED 985
AED 2,196 total
includes taxes & fees
22 Oct - 23 Oct
New Ludlow Village Home with Stunning Okemo Mountain View
A spacious room with wooden beams, large windows, and a cozy seating area with white furniture.

9. Gorgeous couples barn with WiFi & hot tub in lovely Londonderry

Gorgeous couples barn with WiFi & hot tub in lovely Londonderry
Londonderry
10.0 out of 10, Exceptional, (2 reviews)
"The converted barn was absolutely stunning. Kitchen was well appointed and the family room spacious and comfortible."
United States
Tim M.
The price is AED 2,965
AED 4,538 total
includes taxes & fees
1 Nov - 2 Nov
Gorgeous couples barn with WiFi & hot tub in lovely Londonderry
A two-story house with a covered porch and a garage.

10. 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 AED 774
AED 3,059 total
includes taxes & fees
22 Oct - 23 Oct
Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
A hot tub surrounded by stone steps, wooden lounge chairs, and a wooden deck.

11. Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Winhall
9.2 out of 10, Wonderful, (44 reviews)
"Our family had a wonderful vacation. The house and location were great. We will come back."
United States
Victoria L.
The price is AED 725
AED 2,435 total
includes taxes & fees
22 Oct - 23 Oct
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

12. 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 AED 274
AED 941 total
includes taxes & fees
26 Oct - 27 Oct
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
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 AED 327
AED 851 total
includes taxes & fees
25 Oct - 26 Oct
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.

14. 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 AED 364
AED 719 total
includes taxes & fees
2 Nov - 3 Nov
Cozy Rutland Retreat
Dining

15. 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 AED 768
AED 1,551 total
includes taxes & fees
1 Nov - 2 Nov
Charming Chester Farmhouse near Near VT Slopes
A compact kitchen with a refrigerator, stove, microwave, and sink.

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

The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
Plymouth
The price is AED 655
AED 2,093 total
includes taxes & fees
22 Oct - 23 Oct
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.

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 AED 1,194
AED 3,084 total
includes taxes & fees
1 Nov - 2 Nov
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
A two-story house with a deck, surrounded by dense forest.

18. 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 AED 1,980
AED 3,674 total
includes taxes & fees
22 Oct - 23 Oct
4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
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 AED 575
AED 1,659 total
includes taxes & fees
3 Nov - 4 Nov
large ski ranch hot tub close to killington pets ok
A bedroom with a bed, a framed collage, a window with floral curtains, and a striped rug.

20. Cozy 2 Bedroom close distance to downtown.

Cozy 2 Bedroom close distance to downtown.
Rutland
The price is AED 453
AED 535 total
includes taxes & fees
22 Oct - 23 Oct
Cozy 2 Bedroom close distance to downtown.
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

The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa

8/10 Good
"The property is a beautiful old hotel, but you can tell they are having a hard time keeping it up. The rooms are big and cozy at the same time, the beds comfortable but the bathroom had some ventilation issues and therefore was a little moldy. While the pool was great, it was a shame the sauna was not working. All in all a nice stay though."
Sylvie 3-night trip
Posted 2 hours ago
The Equinox Golf Resort And Spa