Weston Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Browse Select Weston Vacation Homes

NEW Charming ski retreat w/heated plunge pool & endless views in peaceful Weston

9.6 out of 10, Exceptional, (4)
"Absolutely gorgeous home with a lovely host! The endless views and cozy but elegant atmosphere of the property were exactly what we wanted for our Vermont stay. Highly recommend!"
The price is CA $955
CA $1,576 total
includes taxes & fees
Sep 2 - Sep 3
NEW Charming ski retreat w/heated plunge pool & endless views in peaceful Weston

104 Two Queen Bed Standard Hotel Room outdoor heated pool

8.6 out of 10, Excellent, (27)
"Excellent customer service and beautiful, well-maintained property."
The price is CA $144
CA $218 total
includes taxes & fees
Aug 18 - Aug 19
104 Two Queen Bed Standard Hotel Room outdoor heated pool

Whimsical Room & Private Bathroom in Historic Inn

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!"
The price is CA $123
CA $215 total
includes taxes & fees
Sep 1 - Sep 2
Whimsical Room & Private Bathroom in Historic Inn

Two Double bed Standard Hotel room 218

7.0 out of 10, Good, (2)
"The room was nice, clean and comfortable, but there was no coffee maker, no refrigerator, no microwave... we couldn't even make hot water in our room, let alone coffee. There wasn't even any coffee available in the lobby/office area in the morning! We had a restful stay, but if you're a morning coffee drinker, make sure you plan ahead for no coffee availability at all!!"
The price is CA $144
CA $218 total
includes taxes & fees
Aug 18 - Aug 19
Two Double bed Standard Hotel room 218

Queen Studio on the 2nd floor with outdoor heated pool 210

9.0 out of 10, Wonderful, (2)
"My wife and I found the property to be clean, comfortable, and just what was advertised. We very much enjoyed our stay. The location is nothing special, but not bad either – a little down the highway from Killington. Our only complaint was that information about the check-in process was not clearly presented beforehand and was difficult to come by. When we called the property management, we received misinformation about where to check-in. It was a bit of a mess, but when we finally got in the...
The price is CA $144
CA $217 total
includes taxes & fees
Aug 18 - Aug 19
Queen Studio on the 2nd floor with outdoor heated pool 210

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

7.8 out of 10, Good, (50)
"Great condo in great location. Easy walk to restaurants and lifts."
The price is CA $98
CA $343 total
includes taxes & fees
Aug 24 - Aug 25
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Two Double bed Standard Hotel room 219

7.6 out of 10, Good, (4)
"Very clean and easy access."
The price is CA $144
CA $217 total
includes taxes & fees
Aug 18 - Aug 19
Two Double bed Standard Hotel room 219

The Carol - 10 minutes to Okemo & Newly Renovated- NEW SAUNA SEPT 2025!

10.0 out of 10, Exceptional, (6)
"Check in and check out were incredibly easy, house decor was eclectic upscale, beds were super comfortable. Thank you Chris! Would definitely stay here again"
The price is CA $261
CA $453 total
includes taxes & fees
Sep 7 - Sep 8
The Carol - 10 minutes to Okemo & Newly Renovated- NEW SAUNA SEPT 2025!

The Mountain Escape!

9.8 out of 10, Exceptional, (17)
"Easy booking, clean home, great location and the owner very easy to get in touch with."
The price is CA $169
CA $787 total
includes taxes & fees
Sep 1 - Sep 2
The Mountain Escape!

Charming Cavendish Guesthouse NEW SAUNA SEPT 2025!

9.8 out of 10, Exceptional, (6)
"Very cozy and had all the essentials we needed for our trip! Check in and check out were easy, and it was perfect for our winter trip. It's a short drive to Okemo, which is super convenient - would definitely stay here again!"
The price is CA $260
CA $440 total
includes taxes & fees
Sep 1 - Sep 2
Charming Cavendish Guesthouse NEW SAUNA SEPT 2025!

117 Two Double bed Standard Hotel room

8.4 out of 10, Very good, (6)
"Staff were great made us feel welcomed"
117 Two Double bed Standard Hotel room

116 Two Double bed Standard Hotel room

8.6 out of 10, Excellent, (10)
"The place is good. It was our first time here and enjoyed our stay. The brook overlooking our window made the day"
The price is CA $144
CA $217 total
includes taxes & fees
Aug 24 - Aug 25
116 Two Double bed Standard Hotel room

Mtn View & Hot Tub-Peaceful Property w/ stream-mins to Hiking, Biking, Swimming

9.0 out of 10, Wonderful, (2)
"Our family had the best time staying here. The home was spacious and gave our two young children plenty of room to roam and explore. It was also close enough to the main road where everything was accessible but also isolated enough where you feel like you're getting away. Erin was great about answering any questions and making sure our stay was comfortable. We'd definitely return here!"
The price is CA $218
CA $613 total
includes taxes & fees
Aug 18 - Aug 19
Mtn View & Hot Tub-Peaceful Property w/ stream-mins to Hiking, Biking, Swimming

Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

9.4 out of 10, Exceptional, (16)
"We celebrated my sister's 80th birthday at Blueberry Hill. It was very quiet, pleasant and perfect for our family."
The price is CA $221
CA $720 total
includes taxes & fees
Sep 3 - Sep 4
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

WhiSki Cabin - 12 Acres With a Mountain View!

10.0 out of 10, Exceptional, (3)
"We really enjoyed our stay at this home. It had everything we needed and was very comfortable. The countryside around this part of Vermont is beautiful. We found lots of great museums and restaurants. "
The price is CA $745
CA $1,378 total
includes taxes & fees
Aug 19 - Aug 20
WhiSki Cabin - 12 Acres With a Mountain View!

Ski in Ski out Condo! Pool access

9.0 out of 10, Wonderful, (2)
"Great location with plenty of space for the whole family. Highly recommend!"
The price is CA $262
CA $721 total
includes taxes & fees
Sep 9 - Sep 10
Ski in Ski out Condo! Pool access

The Grizz- AC, Pool, Sauna, Gym, Near Resort

10.0 out of 10, Exceptional, (4)
"Place was overall great and just as advertised. Beds were awesome including the Murphy bed. Thanks for a wonderful weekend! I would definitely stay again. "
The price is CA $142
CA $590 total
includes taxes & fees
Aug 19 - Aug 20
The Grizz- AC, Pool, Sauna, Gym, Near Resort

Mountain Oasis - Hot Tub, Sauna, Fire Pit, & MORE!

9.8 out of 10, Exceptional, (26)
"Amazing stay. Perfect weekend friend getaway"
The price is CA $169
CA $787 total
includes taxes & fees
Aug 24 - Aug 25
Mountain Oasis - Hot Tub, Sauna, Fire Pit, & MORE!

Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.

8.0 out of 10, Very good, (2)
"Great place for a ski weekend"
The price is CA $303
CA $695 total
includes taxes & fees
Aug 18 - Aug 19
Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.

Charming Chester Farmhouse – peaceful and close to everything!

9.6 out of 10, Exceptional, (12)
"Great location. Beautiful house. All the amenties. We came up for a ski trip and it was perfect. "
The price is CA $289
CA $587 total
includes taxes & fees
Aug 18 - Aug 19
Charming Chester Farmhouse – peaceful and close to everything!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Weston Hotel Reviews