Holiday Homes in Weston

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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Weston holiday homes

Interior

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (85 reviews)
"Great proximity to mountain and Ludlow downtown area."
United States
Yasmine O.
The price is €291
includes taxes & fees
8 Jun - 9 Jun
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Smart TV, fireplace, video games, books

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 €459
includes taxes & fees
8 Jun - 9 Jun
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Private kitchen

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 €243
includes taxes & fees
14 Jun - 15 Jun
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Property grounds

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, (109 reviews)
"Couldn’t have picked a better place! Warm and comfy and sooo close to okemo "
United States
Erica B.
The price is €285
includes taxes & fees
10 Jun - 11 Jun
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Exterior detail

Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!

Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
Jamaica
9.6 out of 10, Exceptional, (29 reviews)
"EXCELLENT location managed by an amazing host who was very communicative and helpful!Hottub was perfect, plenty of sleeping and activities available at the house and in the immediate area (local food was AWESOME)."
United States
s w.
The price is €737
includes taxes & fees
9 Jun - 10 Jun
Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
Exterior

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 €692
includes taxes & fees
8 Jun - 9 Jun
Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
Interior

CozyDen - AC, Grill, Bike to Mountain, Porch!

CozyDen - AC, Grill, Bike to Mountain, Porch!
Killington
9.0 out of 10, Wonderful, (2 reviews)
"Place was clean and location was great"
United States
Berni H.
The price is €236
includes taxes & fees
7 Jun - 8 Jun
CozyDen - AC, Grill, Bike to Mountain, Porch!
Exterior

Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft

Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
Jamaica
9.6 out of 10, Exceptional, (26 reviews)
"Easy booking, clean home, great location and the owner very easy to get in touch with."
United States
Chris M.
The price is €708
includes taxes & fees
8 Jun - 9 Jun
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
Exterior

Tranquil 3 bedroom Home with Hot Tub and Standby Generator in Andover

Tranquil 3 bedroom Home with Hot Tub and Standby Generator in Andover
Andover
The price is €483
includes taxes & fees
14 Jun - 15 Jun
Tranquil 3 bedroom Home with Hot Tub and Standby Generator in Andover
Shower, soap, shampoo, toilet paper

Okemo's Back Room - in the heart of the village on the shuttle route!

Okemo's Back Room - in the heart of the village on the shuttle route!
Ludlow
9.6 out of 10, Exceptional, (15 reviews)
"Perfect location. Neat place. Very clean!"
United States
Frank F.
Okemo's Back Room - in the heart of the village on the shuttle route!
Dining

Charming Chester Farmhouse near Near VT Slopes

Charming Chester Farmhouse near Near VT Slopes
Chester Depot
9.6 out of 10, Exceptional, (20 reviews)
"We had a great stay! The house was clean, comfortable, and exactly as described. The location was perfect and the host was very responsive. We’d definitely stay here again and highly recommend it."
United States
Stephanie F.
The price is €345
includes taxes & fees
14 Jun - 15 Jun
Charming Chester Farmhouse near Near VT Slopes
Smart TV, books

Cozy Moonship Yurt in the woods

Cozy Moonship Yurt in the woods
West Rutland
10.0 out of 10, Exceptional, (1 review)
"Clean and cozy with a working hot tub. Would highly recommend"
United States
Justin E.
The price is €323
includes taxes & fees
8 Jun - 9 Jun
Cozy Moonship Yurt in the woods
TV, fireplace, table football, stereo

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

Bear`s Den in Ludlow, Okemo Views + Epic Game Room
Ludlow
Bear`s Den in Ludlow, Okemo Views + Epic Game Room
Terrace/patio

The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.

The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.
Killington
10.0 out of 10, Exceptional, (63 reviews)
"Great stay, everything was clean and location was amazing."
United States
John D.
The price is €913
includes taxes & fees
8 Jun - 9 Jun
The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.
Interior

Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown

Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown
Rutland
10.0 out of 10, Exceptional, (5 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 €368
includes taxes & fees
7 Jun - 8 Jun
Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown
Outdoor spa tub

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, (38 reviews)
"Our family had a wonderful time staying in this home."
United States
Meghan C.
The price is €572
includes taxes & fees
9 Jun - 10 Jun
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Exterior

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 €618
includes taxes & fees
10 Jun - 11 Jun
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.
TV, fireplace, books, music library

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, (12 reviews)
"Clean, lots of room, easy access to Stratton, responsive host."
United States
Mark H.
The price is €779
includes taxes & fees
14 Jun - 15 Jun
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
Interior

RoundTop Chalet | Hot Tub, Fire Pit & Mountain Views near Killington & Okemo

RoundTop Chalet | Hot Tub, Fire Pit & Mountain Views near Killington & Okemo
Plymouth
9.0 out of 10, Wonderful, (2 reviews)
"Everything about the property was beautiful and relaxing. We loved our stay .... We did however run into one issue, while we were enjoying the property, someone claiming to be there to service the hot tub decided to let themselves in with the lock code unannounced while we were undressed and stood there listening to us and only when the dog ran down there did he announce himself. Not sure if simple sent them or if they showed up on their own accord but boy did we get quite the scare and hope...
United States
Adam S.
The price is €487
includes taxes & fees
7 Jun - 8 Jun
RoundTop Chalet | Hot Tub, Fire Pit & Mountain Views near Killington & Okemo
Exterior

Cozy Vermont Cabin · Mountain Views · Near Okemo

Cozy Vermont Cabin · Mountain Views · Near Okemo
Chester
10.0 out of 10, Exceptional, (4 reviews)
"Clean, spacous house, good location and great scenes of the mountains."
United States
pauline
The price is €862
includes taxes & fees
13 Jun - 14 Jun
Cozy Vermont Cabin · Mountain Views · Near Okemo
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

The Mountain Inn at Killington

The Mountain Inn at Killington

6/10 Okay
"They definitely have a moisture problem which is why they have dehumidifiers every 30 ft. The rooms are musty which is why they machines in the rooms. Breakfast was not great. The location was good."
Mark 1-night trip
Posted 8 hours ago
The Mountain Inn at Killington

Find out more about Weston

Weston Holiday Homes information

Number of reviews
Accommodation
812 Holiday Homes
Lowest Price
€938
Highest Price
€938