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

  • 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
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Weston holiday homes

Exterior

1. Secluded Spa Retreat | Hot Tub + Sauna | Okemo

Secluded Spa Retreat | Hot Tub + Sauna | Okemo
Ludlow
The price is €491
includes taxes & fees
13 Sept - 14 Sept
Secluded Spa Retreat | Hot Tub + Sauna | Okemo
Exterior

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, (1 review)
"Very nice stay. Owners were very gracious. House was clean & comfortable."
United States
Lorraine C.
The price is €552
includes taxes & fees
6 Sept - 7 Sept
Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
Interior

3. 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 €228
includes taxes & fees
8 Sept - 9 Sept
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Living area

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 €448
includes taxes & fees
7 Sept - 8 Sept
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Living area

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

Bear`s Den in Ludlow, Okemo Views + Epic Game Room
Ludlow
The price is €343
includes taxes & fees
7 Sept - 8 Sept
Bear`s Den in Ludlow, Okemo Views + Epic Game Room
Outdoor spa tub

6. 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, (40 reviews)
"Our family had a wonderful vacation. The house and location were great. We will come back."
United States
Victoria L.
The price is €574
includes taxes & fees
7 Sept - 8 Sept
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Exterior

7. 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 €733
includes taxes & fees
9 Sept - 10 Sept
Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
Dining

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, (18 reviews)
"This was a lovely, well-kept home in a great location to Okemo Mountain."
United States
Nancy F.
The price is €514
includes taxes & fees
7 Sept - 8 Sept
New Ludlow Village Home with Stunning Okemo Mountain View
Dining

9. 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 €359
includes taxes & fees
8 Sept - 9 Sept
Charming Chester Farmhouse near Near VT Slopes
Property grounds

10. Modern Farm House…minutes to Okemo; 2 King beds!

Modern Farm House…minutes to Okemo; 2 King beds!
Mount Holly
9.6 out of 10, Exceptional, (20 reviews)
"Fantastic house! Christine was easy to communicate with and made us and our dogs feel incredibly welcome. Looking forward to staying there again."
United States
Rachel L.
The price is €586
includes taxes & fees
17 Sept - 18 Sept
Modern Farm House…minutes to Okemo; 2 King beds!
Living area

11. 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, (14 reviews)
"Clean, lots of room, easy access to Stratton, responsive host."
United States
Mark H.
The price is €710
includes taxes & fees
15 Sept - 16 Sept
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
Private kitchen

12. 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 €205
includes taxes & fees
7 Sept - 8 Sept
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Room

13. 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 €163
includes taxes & fees
9 Sept - 10 Sept
Cozy Rutland Retreat
Living area

14. Killington Retreat | Deck-Fire Pit-Mountain Views!

Killington Retreat | Deck-Fire Pit-Mountain Views!
Clarendon
9.2 out of 10, Wonderful, (5 reviews)
"The living area is bigger than we expected, and we loved watching the horses next door. It's a short drive to downtown Rutland, and it's quiet. "
United States
Ahmad H.
The price is €325
includes taxes & fees
20 Sept - 21 Sept
Killington Retreat | Deck-Fire Pit-Mountain Views!
Exterior

15. 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 €534
includes taxes & fees
9 Sept - 10 Sept
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.
Exterior

16. 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, (4 reviews)
"Clean, spacous house, good location and great scenes of the mountains."
United States
pauline
The price is €862
includes taxes & fees
12 Sept - 13 Sept
4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
Exterior

17. Cozy farmhouse in Manchester - short drive to multiple ski mountains!

Cozy farmhouse in Manchester - short drive to multiple ski mountains!
Manchester
9.4 out of 10, Exceptional, (3 reviews)
"The hosts were very friendly and responsive during our stay. Loved that the house is close to the main town as well as close to the ski slopes (Bromley). "
United States
Marissa H.
The price is €640
includes taxes & fees
15 Sept - 16 Sept
Cozy farmhouse in Manchester - short drive to multiple ski mountains!
Private kitchen

18. 1812 House, 2 Stays, 1 home

1812 House, 2 Stays, 1 home
Manchester
The price is €670
includes taxes & fees
13 Sept - 14 Sept
1812 House, 2 Stays, 1 home
Living area

19. 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 €1,909
includes taxes & fees
6 Sept - 7 Sept
Luxe Mountain Home w/ Chef’s Kitchen & Okemo Views
Living area

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

Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
Bridgewater
8.8 out of 10, Excellent, (3 reviews)
"Great place for a ski weekend"
United States
Kathryn F.
The price is €608
includes taxes & fees
6 Sept - 7 Sept
Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
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

Bromley View Inn

Bromley View Inn

10/10 Excellent
"Exceptional stay. Many amenities here. Separate areas for pool table and community TV’s or games. Views were great. Breakfast was good and even had gluten free bread. 24/7 hot coffee and tea with Keurig. Front desk lady was wonderful- so helpful and kind. 10/10 stay."
Brandie 1-night trip
Posted 16 hours ago
Bromley View Inn

Find out more about Weston

Weston Holiday Homes information

Number of reviews
189
Accommodation
840 Holiday Homes
Lowest Price
€163
Highest Price
€1,909