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

Weston Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Weston vacation rentals

A view through a window with a wooden frame, revealing a forested area with snow on the ground.

1. Cozy cabin in charming Londonderry

Cozy cabin in charming Londonderry
Londonderry
8.4 out of 10, Very good, (5 reviews)
"Very cozy and quiet. "
United States
Eric H.
The price is ￥22,044
￥43,483 total
includes taxes & fees
Oct 22 - Oct 23
Cozy cabin in charming Londonderry
A modern living room with a fireplace, a dining area, and a kitchen in the background.

2. Ground Floor ski-in/out condo, full kitchen & high-speed WiFi

Ground Floor ski-in/out condo, full kitchen & high-speed WiFi
Clock Tower Base Area
9.4 out of 10, Exceptional, (27 reviews)
"No interaction with host but all amenities were excellent "
United States
Dan M.
The price is ￥24,888
￥64,956 total
includes taxes & fees
Oct 22 - Oct 23
Ground Floor ski-in/out condo, full kitchen & high-speed WiFi
A cozy cabin interior with a sofa, dining table, chairs, wooden cabinets, and a kitchen area.

3. Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Ludlow
The price is ￥8,794
￥46,637 total
includes taxes & fees
Oct 25 - Oct 26
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
A two-story house with a porch, a staircase, and a front door.

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

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Ludlow
8.8 out of 10, Excellent, (27 reviews)
"You better ask for one of the rear units because the front one is practically in the middle of the road. It’s noisy. It’s dingy, the owner refused to let us check in an hour early, which actually worked out in our favor since we didn’t want to stay there after we saw the place. We asked to move to a rear unit. The answer was no. We didn’t ask for a refund. We just went and booked another room and left this place empty for the night. There are so many other nice places to stay in this area. I...
United States
William
The price is ￥16,592
￥42,888 total
includes taxes & fees
Oct 22 - Oct 23
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
A view of a grassy area with a ski lift and a building in the background.

5. 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)
"It was a perfect location and had everything we needed for a great stay."
United States
Danna K.
The price is ￥11,780
￥42,072 total
includes taxes & fees
Oct 22 - Oct 23
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
A picnic table and a fire pit by a lake with a forest in the background.

6. Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
3.0 star property
Ludlow
The price is ￥29,392
￥53,594 total
includes taxes & fees
Oct 21 - Oct 22
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
A two-story house with a porch, a staircase, and a front door.

7. Cozy Studio Condo with Great Location, WiFi & Kitchenette

Cozy Studio Condo with Great Location, WiFi & Kitchenette
Ludlow
8.6 out of 10, Excellent, (32 reviews)
"Small but well organized and super convenient!"
United States
Mikhail R.
The price is ￥15,762
￥37,714 total
includes taxes & fees
Oct 22 - Oct 23
Cozy Studio Condo with Great Location, WiFi & Kitchenette
A golf course with a winding path, trees, and a distant mountain range.

8. Efficient condo near slopes with kitchenette & great location

Efficient condo near slopes with kitchenette & great location
Ludlow
8.6 out of 10, Excellent, (34 reviews)
"the home was clean and very nice. "
United States
Frank R.
The price is ￥15,762
￥36,643 total
includes taxes & fees
Oct 18 - Oct 19
Efficient condo near slopes with kitchenette & great location
A modern living room with a fireplace, a television, and a ceiling fan.

9. 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 ￥29,036
￥80,095 total
includes taxes & fees
Oct 22 - Oct 23
Ski-In/Out Condo with Mountain Views, and Washer/Dryer
A playground with slides and climbing structures surrounded by trees.

10. Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.4 out of 10, Exceptional, (21 reviews)
"Nice place "
United States
Janja L.
The price is ￥20,345
￥59,449 total
includes taxes & fees
Oct 28 - Oct 29
Cozy Bromley Retreat
A red house with a covered porch and a chimney.

11. 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, (173 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 ￥26,863
￥58,758 total
includes taxes & fees
Oct 22 - Oct 23
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
An outdoor dining area with a wooden deck, a table set with plates, glasses, and a vase of flowers.

12. Tranquil Brookside Retreat with Hot Tub & Firepit

Tranquil Brookside Retreat with Hot Tub & Firepit
Peru
10.0 out of 10, Exceptional, (9 reviews)
"Beautiful place. Comfortable and well furnished. "
United States
Michael B.
The price is ￥38,494
￥109,959 total
includes taxes & fees
Nov 16 - Nov 17
Tranquil Brookside Retreat with Hot Tub & Firepit
A modern kitchen with a central island, built-in appliances, and a dining area with a wooden table and chairs.

13. 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, (22 reviews)
"The perfect stop on the way to UVM. Super clean! Walkable eateries & a beautiful view. Thank you!"
United States
Tara
The price is ￥42,381
￥94,496 total
includes taxes & fees
Oct 22 - Oct 23
New Ludlow Village Home with Stunning Okemo Mountain View
A cozy cabin interior with a wooden ceiling, a round table with chairs, a fireplace, and a large window overlooking a snowy landscape.

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

Beautiful country cabin with hot tub and outdoor shower in Londonderry
Londonderry
10.0 out of 10, Exceptional, (3 reviews)
"Stay is very cozy and rustic. Be prepared for house to be cold when you show up. Host is very responsive and accommodating."
United States
Michael D.
The price is ￥23,478
￥57,975 total
includes taxes & fees
Oct 28 - Oct 29
Beautiful country cabin with hot tub and outdoor shower in Londonderry
A cozy living room with a fireplace, comfortable seating, and a television.

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

Bear`s Den in Ludlow, Okemo Views + Epic Game Room
Ludlow
The price is ￥28,581
￥64,051 total
includes taxes & fees
Oct 19 - Oct 20
Bear`s Den in Ludlow, Okemo Views + Epic Game Room
A wooden deck with a white lattice base, a metal roof, and a house with a garage door in the background.

16. 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, (3 reviews)
"Beautiful location with Mountain views. Property owners were wonderful hosts."
United States
Jane
The price is ￥17,777
￥23,451 total
includes taxes & fees
Oct 29 - Oct 30
Beautiful 1-bedroom cabin with AC in wonderful Wells
A living room with a sofa, a bench, a fireplace, a TV, and a large window.

17. 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)
"Great property, clean and close to the slope"
United States
tiliger01
The price is ￥8,130
￥36,676 total
includes taxes & fees
Oct 22 - Oct 23
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
A spacious living room with a stone fireplace, wooden beams, and a large sofa.

18. 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, (25 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 ￥47,615
￥112,552 total
includes taxes & fees
Nov 17 - Nov 18
Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester
A modern kitchen with a black stove, a red microwave, and a stainless steel sink. There are two black chairs and a black table.

19. 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 ￥14,087
￥36,642 total
includes taxes & fees
Nov 1 - Nov 2
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
A cozy cabin interior with a stone fireplace, leather sofas, and large windows offering a view of the forest.

20. 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 ￥25,612
￥82,869 total
includes taxes & fees
Oct 20 - Oct 21
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
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

Turn of River Lodge

Turn of River Lodge

10/10 Excellent
"We stayed here last minute on our way through. The owner was delightful to talk to about the area. Rooms were clean and the breakfast was just right for us including homemade donuts and muffins. The only downfall was the stairs as we are both in our sixties."
Deb 1-night trip
Posted 2 hours ago
Turn of River Lodge

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:

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

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.