Holiday 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
3 July - 5 July
In two months
14 Aug - 16 Aug
In three months
11 Sept - 13 Sept
In four months
9 Oct - 11 Oct

Our top choices for Weston holiday homes

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 AU$400
includes taxes & fees
16 June - 17 June
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
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 AU$690
includes taxes & fees
16 June - 17 June
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
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, (111 reviews)
"Clean great cozy place!"
United States
Himanshu P.
The price is AU$478
includes taxes & fees
16 June - 17 June
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Microwave, oven, stovetop, dishwasher

3BR Family Home in Manchester, VT -Near Downtown, Outlets & Ski Resorts

3BR Family Home in Manchester, VT -Near Downtown, Outlets & Ski Resorts
Richville
The price is AU$607
includes taxes & fees
26 June - 27 June
3BR Family Home in Manchester, VT -Near Downtown, Outlets & Ski Resorts
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 AU$1,142
includes taxes & fees
16 June - 17 June
Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
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)
"We enjoyed our stay at a great ski house that was in a good location to the mountain. Accommodations were comfortable for 6 adults and 4 kids and the shuffleboard, foosball and pool tables were a hit. "
United States
Jonathan H.
The price is AU$1,124
includes taxes & fees
16 June - 17 June
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
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 AU$1,083
includes taxes & fees
16 June - 17 June
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 AU$389
includes taxes & fees
16 June - 17 June
CozyDen - AC, Grill, Bike to Mountain, Porch!
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 AU$495
includes taxes & fees
29 June - 30 June
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Dining

Charming Chester Farmhouse near Near VT Slopes

Charming Chester Farmhouse near Near VT Slopes
Chester Depot
9.4 out of 10, Exceptional, (22 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 AU$579
includes taxes & fees
16 June - 17 June
Charming Chester Farmhouse near Near VT Slopes
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 AU$819
includes taxes & fees
17 June - 18 June
Tranquil 3 bedroom Home with Hot Tub and Standby Generator in Andover
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 AU$1,485
includes taxes & fees
16 June - 17 June
The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.
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 AU$1,007
includes taxes & fees
16 June - 17 June
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.
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.
The price is AU$579
includes taxes & fees
9 July - 10 July
Okemo's Back Room - in the heart of the village on the shuttle route!
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 AU$606
includes taxes & fees
16 June - 17 June
Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown
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
The price is AU$658
includes taxes & fees
16 June - 17 June
Bear`s Den in Ludlow, Okemo Views + Epic Game Room
TV, fireplace

Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.

Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
Bridgewater
8.0 out of 10, Very good, (2 reviews)
"Great place for a ski weekend"
United States
Kathryn F.
The price is AU$1,010
includes taxes & fees
16 June - 17 June
Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
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 AU$1,129
includes taxes & fees
17 June - 18 June
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 AU$824
includes taxes & fees
16 June - 17 June
RoundTop Chalet | Hot Tub, Fire Pit & Mountain Views near Killington & Okemo
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 AU$527
includes taxes & fees
29 June - 30 June
Cozy Moonship Yurt in the woods
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 Mountain Inn at Killington

The Mountain Inn at Killington

8/10 Good
"The pool was dated and looks nothing like the photos. The breakfast, distillery and lobby look great. The rooms are new(ish) but the smell in the hallway……..like old mice and dates"
Khara 1-night trip
Posted 2 hours ago
The Mountain Inn at Killington

Find out more about Weston

Weston Holiday Homes information

Number of reviews
Accommodation
835 Holiday Homes
Lowest Price
Highest Price