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

Weston Holiday Rentals

  • 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
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Weston holiday rentals

A living room with a sofa, a bench, a fireplace, a TV, and a large window.

1. Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Clock Tower Base Area
9.2 out of 10, Wonderful, (30 reviews)
"The slope side condo was wonderful, warm and had everything we needed. Thank you, Amy"
United States
AMY K.
The price is HK$403
HK$1,820 total
includes taxes & fees
9 Sept - 10 Sept
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
A view of a grassy area with a ski lift and a building in the background.

2. Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Clock Tower Base Area
8.8 out of 10, Excellent, (81 reviews)
"Lots of steps but great space. Blankets were dirty, which was the only downside. "
United States
serena m.
The price is HK$584
HK$2,087 total
includes taxes & fees
9 Sept - 10 Sept
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
A playground with slides and climbing structures surrounded by trees.

3. Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.4 out of 10, Exceptional, (19 reviews)
"Nice place "
United States
Janja L.
The price is HK$1,009
HK$2,940 total
includes taxes & fees
13 Sept - 14 Sept
Cozy Bromley Retreat
A modern living room with a fireplace, a television, and a ceiling fan.

4. Ski-In/Out Condo with Mountain Views, and Washer/Dryer

Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Ludlow
9.6 out of 10, Exceptional, (18 reviews)
"Very clean and comfortable for our family of 4. Great ski-in/ski-out location - easily accessible to all lifts. Highly recommend. "
United States
Carey S.
The price is HK$1,029
HK$3,348 total
includes taxes & fees
9 Sept - 10 Sept
Ski-In/Out Condo with Mountain Views, and Washer/Dryer
A two-story house with a porch, a staircase, and a front door.

5. Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Ludlow
9.0 out of 10, Wonderful, (26 reviews)
"Great location - walkable to small town. Very close drive to slopes"
United States
Keath
The price is HK$823
HK$2,128 total
includes taxes & fees
9 Sept - 10 Sept
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
A golf course with a winding path, trees, and a distant mountain range.

6. Efficient condo near slopes with kitchenette & great location

Efficient condo near slopes with kitchenette & great location
Ludlow
8.6 out of 10, Excellent, (33 reviews)
"the home was clean and very nice. "
United States
Frank R.
The price is HK$782
HK$1,818 total
includes taxes & fees
9 Sept - 10 Sept
Efficient condo near slopes with kitchenette & great location
A golf course with a winding path, trees, and a hilly landscape.

7. Well-appointed studio right downtown - less than a mile to Okemo Mountain

Well-appointed studio right downtown - less than a mile to Okemo Mountain
Ludlow
8.8 out of 10, Excellent, (13 reviews)
"This place was so close to Okemo, and walking distance to the local pub and restaurants."
United States
Brian
The price is HK$782
HK$2,420 total
includes taxes & fees
9 Sept - 10 Sept
Well-appointed studio right downtown - less than a mile to Okemo Mountain
A red house with a covered porch and a chimney.

8. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
9.6 out of 10, Exceptional, (172 reviews)
"We had a very lovely stay. The kitchen was well-equipped and the whole home was very cozy. There was wood for the wood stove and lots of games and puzzles to do. Check-in and check-out was simple. Just what we were looking for! "
United States
Eleanor D.
The price is HK$1,333
HK$2,836 total
includes taxes & fees
9 Sept - 10 Sept
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
A wooden deck with a white lattice base, a metal roof, and a house with a garage door in the background.

9. Beautiful 1-bedroom cabin with AC in wonderful Wells

Beautiful 1-bedroom cabin with AC in wonderful Wells
Wells
10.0 out of 10, Exceptional, (1 review)
"We last minute booked this place just for a place to sleep that night. What we found was much more beauty. A place you could just sit outside watching the mountains and sky. The owners are as sweet as can be! We definitely want to come back soon for a quiet beautiful view!"
United States
Melissa
The price is HK$882
HK$1,163 total
includes taxes & fees
9 Sept - 10 Sept
Beautiful 1-bedroom cabin with AC in wonderful Wells
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

10. 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 HK$584
HK$1,999 total
includes taxes & fees
13 Sept - 14 Sept
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

11. 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 HK$2,195
HK$5,014 total
includes taxes & fees
12 Sept - 13 Sept
Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
A cabin with a large, curved roof and a smaller adjacent structure, surrounded by dense forest and mountains in the background.

12. Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.

Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.
Ludlow
9.8 out of 10, Exceptional, (16 reviews)
"Great stay, house is clean and has everything you’de ever need. Perfect location to explore the ludlow area. Thanks Bob, we enjoyed ourselves "
United States
Tyler
The price is HK$1,411
HK$2,480 total
includes taxes & fees
9 Sept - 10 Sept
Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.
A spacious living room with a stone fireplace, wooden beams, and a large sofa.

13. Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester

Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester
Londonderry
9.6 out of 10, Exceptional, (24 reviews)
"Super attentive and accommodating host! It was a perfect cozy getaway on a frigid weekend, and the fireplace and hot tub were just the ticket. "
United States
Meghan R.
The price is HK$2,040
HK$5,167 total
includes taxes & fees
9 Sept - 10 Sept
Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester
A building with a sign reading 'Fire Tower Restaurant & Tavern.'

14. Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna

Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
Stratton
The price is HK$584
HK$1,760 total
includes taxes & fees
9 Sept - 10 Sept
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
A cozy cabin interior with a stone fireplace, leather sofas, and large windows offering a view of the forest.

15. 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 HK$1,058
HK$3,863 total
includes taxes & fees
9 Sept - 10 Sept
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
A living room with a sofa, a television, a fireplace, and a dining area with chairs and a table.

16. Lovely ski-in/out condo steps from ski lift with trails and amazing views

Lovely ski-in/out condo steps from ski lift with trails and amazing views
Stratton
8.4 out of 10, Very good, (36 reviews)
"I have stayed in this condo a few times now, and for my needs it is a great value; affordable, comfortable and ideal location. "
United States
eric m.
The price is HK$584
HK$2,459 total
includes taxes & fees
9 Sept - 10 Sept
Lovely ski-in/out condo steps from ski lift with trails and amazing views
A cozy cabin interior with a TV displaying 'NETFLIX', a fireplace, wooden walls, a window with a forest view, and a comfortable seating area.

17. Luxury Adventure Cabin #2—Kayaks, Trails, Lakes & 24/7 Hot Tub Access

Luxury Adventure Cabin #2—Kayaks, Trails, Lakes & 24/7 Hot Tub Access
Cavendish
10.0 out of 10, Exceptional, (27 reviews)
"We had a great stay. The hot tub was perfect after a long day of skiing."
United States
Michael L.
The price is HK$1,372
HK$2,913 total
includes taxes & fees
9 Sept - 10 Sept
Luxury Adventure Cabin #2—Kayaks, Trails, Lakes & 24/7 Hot Tub Access
A hot tub surrounded by stone steps, wooden lounge chairs, and a wooden deck.

18. 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 HK$1,547
HK$5,198 total
includes taxes & fees
9 Sept - 10 Sept
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
A swimming pool with a stone border, surrounded by a snow-covered landscape and a wooden fence.

19. Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort
3.0 star property
Stratton
8.6 out of 10, Excellent, (83 reviews)
"Nice place and great location!!!"
United States
William
The price is HK$2,736
HK$3,401 total
includes taxes & fees
9 Sept - 10 Sept
Long Trail House at Stratton Mountain Resort
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 Manchester View

The Manchester View

10/10 Excellent
"Breathtaking views, beautiful property. Very relaxing and had everything needed in the room. Would certainly stay here again. Loved whet everything about this inn."
Kimberly 2-night trip
Posted 11 hours ago
The Manchester View

Find out more about Weston

Search for holiday rentals in Weston on Expedia! You can easily find your home rentals, villas, holiday apartments in Weston using one of the methods below:

  • View our selection of featured holiday rentals in Weston
  • Use the map to find apartments and other holiday homes in the Weston neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Weston while they last

Look no further and take a look at our great range of rental properties in Weston!

Frequently asked questions

Are there holiday rentals in Weston?

Yes, there are holiday rentals close to the most popular sights in Weston, or you can select a more secluded option if you're looking for a relaxing stay. Weston is known for its ski areas and entertainment choices. Make sure you have time to check out the theatres and shopping during your trip.

What are some of the best holiday rentals that Weston has to offer?

Mountainside 5-BR Ski-In/Out Okemo Villa: This holiday home rental outside of Weston is located in the mountains, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and 1 hot tub.

How many holiday rentals are there in Weston?

Choose from 11 Expedia holiday rentals in Weston for a memorable holiday.

What can I see and do in Weston?

Enjoy the outdoors at Green Mountain National Forest and West River, or simply take in cultural attractions like Weston Playhouse and Mill Museum. In the wider area, you’ll find Weston Priory and Viking Nordic Center.

What are holiday rentals like in Weston?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Weston. Holiday rentals feature amenities such as hot tubs, fire pits and patios to help you enjoy your stay. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from shared hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for a family trip or a small group gathering.