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

Holiday Homes in Weston

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Weston holiday homes

A golf course with sand bunkers and a forested area.

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

Peaceful Stay w/ Pond & Massage Chair | Near Okemo
Ludlow
The price is NZ$759
includes taxes & fees
2 Nov - 3 Nov
Peaceful Stay w/ Pond & Massage Chair | Near Okemo
A cozy living room with a stone fireplace, large windows, and a wooden ceiling.

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, (2 reviews)
"Very nice stay. Owners were very gracious. House was clean & comfortable."
United States
Lorraine C.
The price is NZ$1,165
includes taxes & fees
2 Nov - 3 Nov
Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
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 NZ$667
includes taxes & fees
2 Nov - 3 Nov
Bear`s Den in Ludlow, Okemo Views + Epic Game Room
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

4. 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 NZ$849
includes taxes & fees
18 Nov - 19 Nov
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
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, (23 reviews)
"The perfect stop on the way to UVM. Super clean! Walkable eateries & a beautiful view. Thank you!"
United States
Tara
The price is NZ$998
includes taxes & fees
3 Nov - 4 Nov
New Ludlow Village Home with Stunning Okemo Mountain View
A cozy cabin interior with a stone fireplace, leather sofas, and large windows offering a view of the forest.

6. 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 NZ$809
includes taxes & fees
2 Nov - 3 Nov
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.

7. 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 NZ$808
includes taxes & fees
9 Nov - 10 Nov
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
A bedroom with a bed, bedside lamps, a desk, a TV, and a window with a view.

8. Long Trail House 368 condo in Stratton Village, walk to the lifts

Long Trail House 368 condo in Stratton Village, walk to the lifts
Stratton
The price is NZ$454
includes taxes & fees
2 Nov - 3 Nov
Long Trail House 368 condo in Stratton Village, walk to the lifts
A modern kitchen with a dishwasher, a coffee maker, and a dining area with a wooden table set for two.

9. Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.8 out of 10, Exceptional, (18 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 NZ$292
includes taxes & fees
2 Nov - 3 Nov
Cozy Rutland Retreat
A modern kitchen with a black stove, a red microwave, and a stainless steel sink. There are two black chairs and a black table.

10. 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
9.4 out of 10, Exceptional, (8 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 NZ$387
includes taxes & fees
2 Nov - 3 Nov
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
A spacious room with wooden beams, large windows, and a cozy seating area with white furniture.

11. 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 NZ$1,823
includes taxes & fees
3 Nov - 4 Nov
Gorgeous couples barn with WiFi & hot tub in lovely Londonderry
A hot tub surrounded by stone steps, wooden lounge chairs, and a wooden deck.

12. 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 NZ$1,253
includes taxes & fees
2 Nov - 3 Nov
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Dining

13. 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 NZ$672
includes taxes & fees
15 Nov - 16 Nov
Charming Chester Farmhouse near Near VT Slopes
A red house with a gravel driveway and lush greenery.

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

The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
Plymouth
The price is NZ$1,057
includes taxes & fees
2 Nov - 3 Nov
The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
A house with a wooden deck, solar panels, and a well-maintained garden.

15. Kingsley Homestead - 2 Bedroom retreat

Kingsley Homestead - 2 Bedroom retreat
Rutland
The price is NZ$284
includes taxes & fees
3 Nov - 4 Nov
Kingsley Homestead - 2 Bedroom retreat
A living room with a brick fireplace, a sofa, a chair, and a coffee table.

16. 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 NZ$1,361
includes taxes & fees
2 Nov - 3 Nov
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
A wooden cabin with a green door, a small porch, and a set of stairs leading to the entrance.

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

Peaceful 1-bedroom bungalow with AC in charming Wells
Wells
9.6 out of 10, Exceptional, (4 reviews)
"This is the most amazing spot. Our second time staying here after the horse races and we will definitely be back next summer. You guys are awesome!"
United States
Donna A.
The price is NZ$393
includes taxes & fees
7 Nov - 8 Nov
Peaceful 1-bedroom bungalow with AC in charming Wells
A modern living room with a flat-screen TV, grey sofas, a dining table with chairs, and a large window with a view of greenery.

18. CozyDen- Fireplace, Ski Off/ Shuttle On

CozyDen- Fireplace, Ski Off/ Shuttle On
Killington
9.6 out of 10, Exceptional, (4 reviews)
"Place was clean and location was great"
United States
Berni H.
CozyDen- Fireplace, Ski Off/ Shuttle On
A rustic interior with a wooden ceiling, a bar area with stools, a sofa, and a dining table.

19. Wonderful hilltop house with breathtaking views

Wonderful hilltop house with breathtaking views
Dorset
The price is NZ$945
includes taxes & fees
29 Nov - 30 Nov
Wonderful hilltop house with breathtaking views
A house with a covered deck, a barbecue grill, and a wooden pergola.

20. 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, (10 reviews)
"The hot tub was great after a day of skiing."
United States
Callison A.
The price is NZ$752
includes taxes & fees
4 Nov - 5 Nov
large ski ranch hot tub close to killington pets ok
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
"This is our third visit. Always a great pleasure to stay here. -PM"
Paul 2-night trip
Posted 23 hours ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Find out more about Weston

Weston Holiday Homes information

Number of reviews
184
Accommodation
840 Holiday Homes
Lowest Price
NZ$284
Highest Price
NZ$1,823