Weston Holiday Rentals

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Holiday Rentals in Weston

Cozy Creekside Chalet centrally located near 4 ski resorts

10.0 out of 10, Exceptional, (7)
"We had the best time at this cozy spot with some friends for a weekend - highly recommend!"
The price is AU$874
includes taxes & fees
25 Nov - 26 Nov
Cozy Creekside Chalet centrally located near 4 ski resorts

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (39)
"Amazing house great price but note that there are only two split units cooling down the house which means one bed room only gets ac if the other bedrooms split unit is on and both doors are open"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (196)
"It was a wonderful little cabin that was clean and decorated comfortably. It had everything we needed. The hot tub was delightful! "
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree! 45% Off! Free Pool

9.8 out of 10, Exceptional, (164)
"The property is exactly like the pictures indicate. The house is in a friendly neighborhood outside of town. The house is very comfortable and spacious. The host responds to your messages in timely manner, and, she is very workable. Would definitely stay there again "
Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree! 45% Off! Free Pool

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

9.6 out of 10, Exceptional, (148)
"The area was amazing and the views were incredible. "
The price is AU$573
includes taxes & fees
25 Nov - 26 Nov
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

9.6 out of 10, Exceptional, (34)
"Great weekend! Beautiful location !!"
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.

10.0 out of 10, Exceptional, (159)
"Quiet getaway for the weekend just the two of us. It was the perfect spot. Out of the busy but a quick drive to get something to eat when you get hungry. The drive wasn’t bad either. Deb and Angelo were amazing to communicate with also. "
Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.

Long Trail House at Stratton Mountain Resort

3.0 star property
8.4 out of 10, Very good, (72)
"Condo was great, cozy, and clean. Has access to the pool and hot tubs from back porch and has great Mountain View’s. The village had plenty of food, little expensive, but pretty good. Overall great place to stay and enjoy the mountain. "
The price is AU$613
includes taxes & fees
25 Nov - 26 Nov
Long Trail House at Stratton Mountain Resort

Ski-in/ski-out condo with W/D, indoor pool, & hot tub

9.0 out of 10, Wonderful, (18)
"We loved the condo and the easy walking avvess to all of what Killington offers! We would definitely stay here again! "
Ski-in/ski-out condo with W/D, indoor pool, & hot tub

VT Cabin overlooking the West River and Village

10.0 out of 10, Exceptional, (27)
"We loved our stay! Such lovely cabin! We loved it so much that we were bummed we didn’t book a longer stay. It had everything we needed to make our stay comfortable."
The price is AU$509
includes taxes & fees
1 Dec - 2 Dec
VT Cabin overlooking the West River and Village

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

9.6 out of 10, Exceptional, (200)
"A true joy, and a home away from home. This was our second time here and we loved it so much all over again. Would recommend to anyone looking for a romantic getaway with all the comforts of home. Minutes away from Manchester, a cute lil town for all those tourist tendencies. "
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio

9.6 out of 10, Exceptional, (8)
"Great place. Super close to everything. Host was super helpful. Everything you need for an amazing ski weekend."
5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio

Trail Creek 33 | Condo in Killington

9.8 out of 10, Exceptional, (20)
"The location of the property was great.. Centrally located to everything we wanted to see. I would have liked to have a vacuum or even a broom available. The place had a few areas that could have been cleaner. "
Trail Creek 33 | Condo in Killington

Ski & Ride VT! Private indoor pool to enjoy after a day on the slopes!

9.6 out of 10, Exceptional, (40)
"The owner had the place ready to go when we arrived. It was a late arrival, but there were outside lights that were warm and inviting. Plenty of space for our party of 12 (6 adults and 6 kids). Kitchen was welled stocked with cooking necessities, great hangout spaces in the basement and first floor, and a convenient space for ski boots and outer gear in the basement near parking. Kids absolutely loved the pool - and have the pruned hands to prove it. The location couldn't have been better, ~25...
Ski & Ride VT! Private indoor pool to enjoy after a day on the slopes!

"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo

9.8 out of 10, Exceptional, (30)
"We had a lovely time at the Arched Chalet for my family's annual vacation in Vermont. It was very comfortable, well-appointed, and in a great location. Even in the summer heat we did not need the AC - it was so comfortable with the fans and the lower level is naturally cool. Great location near Camp Plymouth (we went to the lake twice), and restaurants/shops in Ludlow and Woodstock."
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo

Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

9.8 out of 10, Exceptional, (18)
"Gorgeous property with everything that we needed! It was relaxing and comfortable for everyone. The kids had a blast! The property management team was great with communication and offered early check in and late check out. Would absolutely stay here again!"
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly

9.0 out of 10, Wonderful, (26)
"The tiny houses were cute and well equipped. They were ideal for 2 friends traveling together having their own space. I would definitely rent this property again. Only negative was having 3 empty propane tanks when we wanted to use the fire table(something to be added to the maintenance checklust) however once i text them they dropped a fresh tank off that same evening."
The price is AU$693
includes taxes & fees
25 Nov - 26 Nov
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

8.2 out of 10, Very good, (33)
"All in all it was a great trip. The place was very cute and as described. The upstairs bedrooms are not for light sleepers as the walls only go so far up so they are not really divided. I had read this in other reveiws but honestly for us it wasn't a problem. We went as a family group and it was kind of nice to be able to lay in bed and talk to the others in the room next to you. When we got there the hot tub was so hot that we were not able to get in. Maybe a problem with the thermostat but...
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

9.4 out of 10, Exceptional, (19)
"My husband and I decided to rent out this property for our reception and could not have been more pleased. The property was perfect for our intimate wedding. It was rustic, quiet, and had a ton of fun activities. The entire home was full of character and each room was unique. The two houses on the property were clean and taken care of, just older so do not expect modern and new. I personally love older rustic locations, especially ones that you know have been lived in and loved. I gave the...
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

9.8 out of 10, Exceptional, (113)
"Terrific and comfortable place to stay! Amazing firepit!"
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
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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Other types of properties in Weston you may be interested in

The Weston

5.0 star property
10.0 out of 10, Exceptional, (7)
"The inn is beautiful and the service was exemplary. We asked for early check in and the staff was very accommodating. The room was very comfortable. We would love to visit again."
The price is AU$754
includes taxes & fees
1 Dec - 2 Dec
The Weston

Cozy Creekside Chalet centrally located near 4 ski resorts

10.0 out of 10, Exceptional, (7)
"We had the best time at this cozy spot with some friends for a weekend - highly recommend!"
The price is AU$874
includes taxes & fees
25 Nov - 26 Nov
Cozy Creekside Chalet centrally located near 4 ski resorts

Comfort Inn Rutland - Killington

2.5 star property
8.0 out of 10, Very good, (1002)
"Staff helpful and friendly. Rooms small, but space is used efficiently. Rooms were clean and welcoming. There is occasional noise from the mechanics of the building (e.g. HVAC). A bit outside of town, probably a 20 minute walk to city center. I was comfortable, felt safe, and would stay there again if in the area."
The price is AU$175
includes taxes & fees
8 Dec - 9 Dec
Comfort Inn Rutland - Killington
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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?

Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree! 45% Off!: This holiday home rental outside of Weston is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a private garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Weston?

Choose from 14 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 popular places such as Okemo Mountain Resort and Stratton Mountain Resort.

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.