Holiday Rentals in Weston

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Our top choices for Weston holiday rentals

10.0 out of 10, Exceptional, (5)
"Great stay"
United States
Chelsea D.
The price is €196
includes taxes & fees
4 Jan - 5 Jan 2026
Cabin-7 minutes to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dog OK
10.0 out of 10, Exceptional, (2)
"On a farm in the country…..stars blazing at night for hot tub. Cozy loft had amazing mattress and pillows! Our dog enjoyed the surrounding field. Beautiful! "
United States
Laurel
The price is €314
includes taxes & fees
7 Jan - 8 Jan 2026
Beautiful country cabin with hot tub and outdoor shower in Londonderry

Apartment in Bromley Mountain

Cozy Bromley Retreat
9.8 out of 10, Exceptional, (7)
"There is no place I’d rather stay in VT. It’s a perfect condo and the recent renovations are really nice. It’s got all the comforts of home and great touches throughout. Bromley is a great community to be in, it’s close to town, obviously the slopes, and just a overall stay!"
United States
Vanessa P.
The price is €303
includes taxes & fees
13 Jan - 14 Jan 2026
Cozy Bromley Retreat
3.0 star property
8.4 out of 10, Very good, (78)
"The building and the units are old and tired. Early attic decorating. And the walls are paper thin. We could hear all neighbors. I would not go back. "
United States
Doug
The price is €427
includes taxes & fees
7 Jan - 8 Jan 2026
Long Trail House at Stratton Mountain Resort
10.0 out of 10, Exceptional, (11)
"Super easy check in, beautiful and peaceful. Will def be back "
United States
Tyler S.
The price is €340
includes taxes & fees
20 Jan - 21 Jan 2026
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
10.0 out of 10, Exceptional, (14)
"Really enjoyed the setup at the location and the owners were very responsive to any queries!"
United States
Ed N.
The price is €503
includes taxes & fees
5 Jan - 6 Jan 2026
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
9.6 out of 10, Exceptional, (166)
"Very nice and clean cabin, not too far from small towns, decently supplied for expected conveniences, charming area - a small stream nearby provides a pleasant background noise. "
United States
Philip
The price is €318
includes taxes & fees
6 Jan - 7 Jan 2026
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
9.2 out of 10, Wonderful, (5)
The price is €168
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland

Condo resort in Killington

Mountain Green
2.0 star property
6.8 out of 10, (16)
"Great communication from Jeff."
United States
Dennis
The price is €276
includes taxes & fees
30 Dec - 31 Dec
Mountain Green
10.0 out of 10, Exceptional, (5)
"We had a lovely time in Woodstock Vermont. The Bridgewater Inn was cozy and perfect for our weekend get away"
United States
Rosie L.
The price is €223
includes taxes & fees
12 Jan - 13 Jan 2026
Woodstock Studio | 10 Min to Killington
8.8 out of 10, Excellent, (9)
"After a long month of work I needed a weekend in VT to calm the nerves. This was a beautiful spot to be in, glad I was here!"
United States
Paul S.
The price is €176
includes taxes & fees
4 Jan - 5 Jan 2026
Whimsical Room & Private Bathroom in Historic Inn
9.6 out of 10, Exceptional, (17)
"Very nice home! Plenty of room for everyone and a short drive to the mountain! Perfect "
United States
Gerri B.
The price is €497
includes taxes & fees
13 Jan - 14 Jan 2026
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit
9.0 out of 10, Wonderful, (74)
"Perfect location for a quick ski trip. "
United States
Michael D.
The price is €291
includes taxes & fees
11 Jan - 12 Jan 2026
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
7.6 out of 10, Good, (53)
"Irish Bar nearby was a plus on St. Patrick’s Day !"
United States
Warren
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
9.4 out of 10, Exceptional, (9)
"Great property, as advertised."
United States
Chris A.
The price is €294
includes taxes & fees
7 Jan - 8 Jan 2026
5th-floor mountain-view condo, easy access to the slopes free shuttle or walk
8.6 out of 10, Excellent, (27)
"We loved staying at the townhome. It was a welcome place to stay while we traveled around, enjoying fall. It was very comfortable and the village amenities were great."
United States
John N.
The price is €462
includes taxes & fees
15 Jan - 16 Jan 2026
Lovely ski-in/out condo steps from ski lift with trails and amazing views

Holiday Home in Chester Depot

Chester Farmhouse Ski Retreat near Slopes
9.6 out of 10, Exceptional, (17)
"This was my second time staying at this property. Everything was great just like last year. I highly recommend it if you are staying in Chester, VT. "
United States
Lori N.
The price is €291
includes taxes & fees
7 Jan - 8 Jan 2026
Chester Farmhouse Ski Retreat near Slopes
10.0 out of 10, Exceptional, (10)
"We had a really sweet stay here. It was cozy and comfortable, and had everything as advertised. Plenty of towels and kitchen supplies when we needed them, and the beds were comfortable. We had a great trip to Okemo!"
United States
Carla C.
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
9.2 out of 10, Wonderful, (26)
"Loved the location"
United States
Steven W.
The price is €293
includes taxes & fees
4 Jan - 5 Jan 2026
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
10.0 out of 10, Exceptional, (14)
"Perfect weekend getaway "
United States
Seth G.
The price is €418
includes taxes & fees
20 Jan - 21 Jan 2026
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
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

Find out more about Weston

Everything you need to know about Weston holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Weston holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Weston holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Weston holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Weston. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Weston holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Weston holiday rentals we have selected for you start as low as €168 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Weston rentals

At Expedia, we put the best Weston holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Weston rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Weston holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Weston. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing: This holiday home rental outside of Weston is located on the waterfront, and has a balcony, a garden and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

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 Weston Priory 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.