Holiday Homes in Weston

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Check prices for these dates

Our top choices for Weston holiday homes

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 AU$965
includes taxes & fees
5 Nov - 6 Nov
Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover

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

Peaceful Stay w/ Pond & Massage Chair | Near Okemo
Ludlow
The price is AU$619
includes taxes & fees
16 Nov - 17 Nov
Peaceful Stay w/ Pond & Massage Chair | Near Okemo

3. 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 AU$673
includes taxes & fees
16 Nov - 17 Nov
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

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

Bear`s Den in Ludlow, Okemo Views + Epic Game Room
Ludlow
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our weekend stay off peak season. Walkable to town. Clean. Everything you may need is provided. It’s an older house with character. The game room is a bonus for sure!"
United States
Elaine H.
The price is AU$544
includes taxes & fees
5 Nov - 6 Nov
Bear`s Den in Ludlow, Okemo Views + Epic Game Room

5. 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 AU$375
includes taxes & fees
11 Nov - 12 Nov
Long Trail House 368 condo in Stratton Village, walk to the lifts

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 AU$660
includes taxes & fees
16 Nov - 17 Nov
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

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 AU$668
includes taxes & fees
9 Nov - 10 Nov
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

8. Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.8 out of 10, Exceptional, (18 reviews)
"WE ENJOYED OUR STAY"
United States
Susan E.
The price is AU$241
includes taxes & fees
10 Nov - 11 Nov
Cozy Rutland Retreat

9. 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 AU$797
includes taxes & fees
16 Nov - 17 Nov
New Ludlow Village Home with Stunning Okemo Mountain View

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 AU$1,101
includes taxes & fees
8 Nov - 9 Nov
Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!

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
9.4 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 AU$301
includes taxes & fees
12 Nov - 13 Nov
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

12. 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 AU$534
includes taxes & fees
8 Nov - 9 Nov
Charming Chester Farmhouse near Near VT Slopes

13. 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 AU$1,543
includes taxes & fees
5 Nov - 6 Nov
Gorgeous couples barn with WiFi & hot tub in lovely Londonderry

14. 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 AU$1,013
includes taxes & fees
17 Nov - 18 Nov
Your Vermont Mountain Haven Pet Friendly home with Hot tub!

15. 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 AU$2,946
includes taxes & fees
5 Nov - 6 Nov
Luxe Mountain Home w/ Chef’s Kitchen & Okemo Views

16. Wonderful hilltop house with breathtaking views

Wonderful hilltop house with breathtaking views
Dorset
The price is AU$751
includes taxes & fees
29 Nov - 30 Nov
Wonderful hilltop house with breathtaking views

17. 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, (6 reviews)
"Clean, spacous house, good location and great scenes of the mountains."
United States
pauline
The price is AU$1,339
includes taxes & fees
5 Nov - 6 Nov
4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo

18. 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 AU$581
includes taxes & fees
16 Nov - 17 Nov
large ski ranch hot tub close to killington pets ok

19. 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 AU$1,077
includes taxes & fees
9 Nov - 10 Nov
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

20. 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.
The price is AU$381
includes taxes & fees
9 Nov - 10 Nov
CozyDen- Fireplace, Ski Off/ Shuttle On
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.

Learn more about Weston

The Vermont Country Store in this charming village offers three floors of nostalgic treasures and local foods to sample. Catch a performance at the historic Weston Playhouse or visit the Weston Village Christmas Shop, open year-round for holiday magic.

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

Top reviews in Weston