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

Weston Vacation Rentals

Dates

November 2026

December 2026

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Our top choices for Weston vacation rentals

A cozy cabin interior with a wooden ceiling, a sofa, a red armchair, a small table with magazines, and a window with curtains.

1. Cozy Vermont Cabin at Trail End Ranch! The Best of VT is all around you!

Andover

Betsy S.

AED 1,497 total

includes taxes & fees

10 Nov - 11 Nov

A cozy living room with a stone fireplace, large windows, and a wooden ceiling.

2. Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover

Andover

Lorraine C.

AED 2,365 total

includes taxes & fees

10 Nov - 11 Nov

A swimming pool with a stone border, surrounded by a snow-covered landscape and a wooden fence.

3. Long Trail House at Stratton Mountain Resort

Stratton

Michael

AED 1,621 total

includes taxes & fees

10 Nov - 11 Nov

A spacious living room with a high ceiling, wooden beams, a fireplace, and large windows.

4. Game Room, Fire Pit & Views! Spacious Ludlow Home

Ludlow

AED 2,954 total

includes taxes & fees

10 Nov - 11 Nov

A modern kitchen with stainless steel appliances, a wooden dining table set for four, and a seating area with a sofa and chairs.

5. Cozy Village Condo-Okemo Shuttle

Ludlow

Vanessa W.

AED 942 total

includes taxes & fees

10 Nov - 11 Nov

A cozy cabin interior with a wooden ceiling, a round table with chairs, a fireplace, and a large window overlooking a snowy landscape.

6. Beautiful country cabin with hot tub and outdoor shower in Londonderry

Londonderry

Michael D.

AED 1,280 total

includes taxes & fees

10 Nov - 11 Nov

A wooden cabin with a balcony and a staircase leading to a second level.

7. Romantic Riverbed Treehouse - hot tub & new sauna!

londonderry

Tracey V.

AED 2,163 total

includes taxes & fees

10 Nov - 11 Nov

A spacious living room with a stone fireplace, wooden beams, and a large sofa.

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

Londonderry

Meghan R.

AED 1,994 total

includes taxes & fees

16 Nov - 17 Nov

A spacious living area with a gray sofa, a coffee table, and a kitchen area with a bar counter and stools.

9. Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!

Londonderry

Marcel P.

AED 2,951 total

includes taxes & fees

16 Nov - 17 Nov

A playground with slides and climbing structures surrounded by trees.

10. Cozy Bromley Retreat — Ski-In, Ski-Out

Bromley Mountain

Andrew P.

AED 1,589 total

includes taxes & fees

10 Nov - 11 Nov

A fire pit with logs, surrounded by Adirondack chairs and a table with a mug.

11. Mountain Chalet, sleeps 8, with hot tub

Peru

Michael B.

AED 2,734 total

includes taxes & fees

16 Nov - 17 Nov

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

12. Ground-floor ski-in/ski-out condo facing the Clock Tower base lodge

Clock Tower Base Area

tiliger01

AED 837 total

includes taxes & fees

11 Nov - 12 Nov

A cozy living room with a fireplace, a black leather sofa, and a television mounted above it.

13. Village Fireplace Shuttle Boot Warmers

Ludlow

Justin P.

AED 1,544 total

includes taxes & fees

23 Nov - 24 Nov

A spacious living area with a fireplace, a dining area, and a kitchen.

14. Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

Ludlow

AED 7,899 total

includes taxes & fees

10 Nov - 11 Nov

A red house with a covered porch and a chimney.

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

Grafton

Neil S.

AED 1,366 total

includes taxes & fees

10 Nov - 11 Nov

A modern living room with a fireplace, a television, and a ceiling fan.

16. Ground-floor ski-in/ski-out condo near the Sachem trail, ski to Sunburst

Ludlow

Carey S.

AED 1,853 total

includes taxes & fees

11 Nov - 12 Nov

A view of a grassy area with a ski lift and a building in the background.

17. Okemo ski-in/ski-out condo a few feet from the A and B Quad lifts

Clock Tower Base Area

Danna K.

AED 967 total

includes taxes & fees

11 Nov - 12 Nov

A two-story house with a porch, a staircase, and a front door.

18. Downtown Ludlow condo with electric fireplace, shuttle stop across the street

Ludlow

Zach S.

AED 1,004 total

includes taxes & fees

11 Nov - 12 Nov

A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

19. Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Ludlow

Tina l.

AED 1,745 total

includes taxes & fees

18 Nov - 19 Nov

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Find vacation rentals that suit your style

Top Weston Hotel Reviews

A white two-story house with a front porch, a covered patio, and a well-maintained garden.

The Weston

Weston

10/10 Excellent

astrid

A large two-story house with a front porch and a well-maintained lawn.

The Landgrove

Londonderry

10/10 Excellent

The Inn is in a beautiful setting. The staff were very friendly and helpful. My room was spacious and a comfortable arm chair and good lamp provided a cozy place for R&R. The spacious common area & well kept grounds would be a very pleasant place to spend time with family and friends. I was advised in advance that the restaurant was not serving dinner, but the staff provided a list of eateries in the local area. I had a very good meal at the New American Grill. The breakfast menu at the...

Rita

A large, snow-covered house with multiple windows and a well-lit porch.

The Inn at Manchester

Manchester Village Historic District

10/10 Excellent

Mary

A restaurant with tables set for dining, chairs, and a fireplace in the background.

The Reluctant Panther Inn and Restaurant

Manchester Village Historic District

10/10 Excellent

Anonymous traveler

A snow-covered cabin with a large window, surrounded by trees and a mountain in the background.

Blue Gentian Lodge at Magic Mountain

Londonderry

10/10 Excellent

Anonymous traveler

A two-story building with a bar and restaurant on the ground floor, a vintage car parked in front, and a sign indicating "Main Mountain".

Main and Mountain Bar & Motel

Ludlow

10/10 Excellent

Anonymous traveler

A red barn with a white door and shutters, surrounded by a garden with various plants and flowers.

Stone Hearth Inn and Eatery

Chester

10/10 Excellent

William

A shower area with a glass door, a showerhead, and a curtain with floral patterns.

Harvest Barn Inn

Bellows Falls

10/10 Excellent

Virginia

A traditional chalet with a sloped roof, flower boxes on the balcony, and a star-shaped emblem.

The Olympia Lodge

Manchester Center

10/10 Excellent

Brad

Snowed Inn

Killington

10/10 Excellent

Tammy

A white colonial-style building with a symmetrical facade, central entrance, and a small porch with chairs.

Four Columns Inn

Newfane

10/10 Excellent

Nettie

A hotel entrance with a wooden porch, a sign reading 'Ascend Collection Hotel,' and potted plants.

Sun Lodge near Manchester VT, Ascend Collection Hotel

Bromley Mountain

10/10 Excellent

Anonymous traveler

A cozy indoor space with a chalkboard sign advertising free fire entertainment from 7pm to 9pm.

Toll Road Inn

Manchester Center

10/10 Excellent

I had an incredible stay at this renovated 1960s motel! They've done an amazing job of preserving the vintage character while adding tasteful, modern updates. The retro decor instantly transports you back in time, with original furnishings that feel straight out of the ‘60s—quirky lamps, classic wood paneling, and a color palette that’s delightfully retro. Despite the vintage aesthetic, the amenities are modern and comfortable: fast Wi-Fi and cozy, plush beds that offer a great night’s sleep....

Abby

A two-story house with a snow-covered roof and yard, featuring multiple lit windows and a visible chimney.

The Inn at Ormsby Hill

Manchester Center

10/10 Excellent

The Inn at Ormsby Hill is a magnificent B&B in historic Manchester Vermont. We were in Vermont for a ski week vacation. We ended our trip staying at this Inn and skiing at Stratton Ski Area. When we arrived, the Innkeeper Maryanne greeted us then suggested we move our room to one more centrally located. Our room was beautiful with a 4 post king bed, gas fireplace and plush bathrobes. The daily breakfast was superb! The dining area was full of antiques, many from the Pullman Corporation. Edward...

Anonymous traveler

Frequently Asked Questions

Are there vacation rentals in Weston?

Yes, we offer vacation rentals close to popular attractions in Weston, or you can choose a more secluded option if you're looking for relaxation. Weston is known for its ski areas and entertainment choices. Make sure you have time to check out the theaters and shopping during your trip.

What are some of the best vacation home rentals in Weston?

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo: This vacation home rental near Weston is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Weston?

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

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 larger area, you’ll find Weston Priory and Viking Nordic Center.

What are vacation rentals like in Weston?

Vacation rentals are privately owned properties you can book for a few days or a quick weekend in Weston. Vacation rentals provide amenities such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, vacation rentals can offer a sense of security away from public hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for family gatherings.

Weston Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Weston vacation rentals

1. Cozy Vermont Cabin at Trail End Ranch! The Best of VT is all around you!

2. Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover

3. Long Trail House at Stratton Mountain Resort

4. Game Room, Fire Pit & Views! Spacious Ludlow Home

5. Cozy Village Condo-Okemo Shuttle

6. Beautiful country cabin with hot tub and outdoor shower in Londonderry

7. Romantic Riverbed Treehouse - hot tub & new sauna!

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

9. Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!

10. Cozy Bromley Retreat — Ski-In, Ski-Out

11. Mountain Chalet, sleeps 8, with hot tub

12. Ground-floor ski-in/ski-out condo facing the Clock Tower base lodge

13. Village Fireplace Shuttle Boot Warmers

14. Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

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

16. Ground-floor ski-in/ski-out condo near the Sachem trail, ski to Sunburst

17. Okemo ski-in/ski-out condo a few feet from the A and B Quad lifts

18. Downtown Ludlow condo with electric fireplace, shuttle stop across the street

19. Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Find vacation rentals that suit your style

Top Weston Hotel Reviews

The Weston

10/10 Excellent

Frequently Asked Questions

Are there vacation rentals in Weston?

What are some of the best vacation home rentals in Weston?

How many vacation rentals are there in Weston?

What can I see and do in Weston?

What are vacation rentals like in Weston?