Search Chalets in Ascutney

    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

Chalets in Ascutney

Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults

10.0 out of 10, Exceptional, (24)
"A terrific place. Highly recommended. We had a great family ski vacation."
The price is SAR 3,748
SAR 7,495 total
includes taxes & fees
10 Aug - 11 Aug
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults

Spacious 5-bedroom chalet with AC and WiFi in charming Chester

10.0 out of 10, Exceptional, (4)
"Girls family weekend, relaxing, visiting and enjoying the hot tub."
Spacious 5-bedroom chalet with AC and WiFi in charming Chester

Cozy Creekside Chalet centrally located near 4 ski resorts

10.0 out of 10, Exceptional, (10)
"We spent a great week in Weston. Great location to ski Stratton. Hosts were very responsive. Would def go back."
The price is SAR 579
SAR 1,699 total
includes taxes & fees
28 Jul - 29 Jul
Cozy Creekside Chalet centrally located near 4 ski resorts

Pet-friendly escape to Vermont for fall foliage and fun

2.0 star property
10.0 out of 10, Exceptional, (12)
"Excellent week at a cozy property, convenient to Killington and Okemo. Easy check in and check out; highly responsive and helpful host. Would recommend to those looking for a great VT escape."
The price is SAR 807
SAR 1,871 total
includes taxes & fees
30 Jul - 31 Jul
Pet-friendly escape to Vermont for fall foliage and fun

Modern 4-Bedroom Mountain Retreat Minutes to Lake Rescue & Echo and Hiking

9.6 out of 10, Exceptional, (5)
"Roshanak was an excellent host and the place is beautiful. We love the location and its proximity to Okemo and the town. The property is gorgeous, we would book again."
Modern 4-Bedroom Mountain Retreat Minutes to Lake Rescue & Echo and Hiking

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

9.8 out of 10, Exceptional, (35)
"We very much enjoyed our stay and the property is in excellent proximity to Killington/Pico."
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo

Gorgeous Ski Chalet with Game Room & Hot Tub on Okemo Mt. under 1 mile to base!

9.8 out of 10, Exceptional, (125)
"We found the hosts to be super helpful and friendly. Location was fantastic. We loved the hot tub and wood burning stove. It was a perfect stay for my extended family and I. The beds were also super comfortable-we slept great! We would definitely recommend this spot!"
Gorgeous Ski Chalet with Game Room & Hot Tub on Okemo Mt. under 1 mile to base!

Falcon House: VT Modern Chalet w/Sauna on 25 Acres - Hike - Bike to Village

10.0 out of 10, Exceptional, (69)
"We had a wonderful relaxing time at Falcon house. The house was clean, just as listed, and had everything we needed to make for an enjoyable relaxing time. Really enjoyed the scenery and walking around Woodstock."
Falcon House: VT Modern Chalet w/Sauna on 25 Acres - Hike - Bike to Village

Okemo 6 Bedroom Chalet.

9.4 out of 10, Exceptional, (23)
"We were up for a weekend in February. Perfect place. Plenty of beds. The hot tub was a bonus. Excellent communication by the hosts. "
Okemo 6 Bedroom Chalet.

Ski On, Ski off Okemo Trailside Appartment, Sleeps 6/ $550per night,

9.6 out of 10, Exceptional, (33)
"We had a fabulous stay here. Owner was v communicative and accommodating."
Ski On, Ski off Okemo Trailside Appartment, Sleeps 6/ $550per night,

Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails

10.0 out of 10, Exceptional, (39)
"This is our second year staying at this beautiful home. We love the space and amenities, not to mention the location to the mountain. The owners have been very accommodating and communicative. Overall, a wonderful stay for our group of families and hope to return again when we come back to Ludlow."
Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails

Okemo Mountain Chalet W/ Hot Tub and Game Room

9.8 out of 10, Exceptional, (160)
"This was our second time staying at the Bear Chalet and we absolutely loved it. So much space for multiple families and very kid friendly!"
Okemo Mountain Chalet W/ Hot Tub and Game Room

Modern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from Okemo

10.0 out of 10, Exceptional, (10)
"Great house, made our ski weekend easy and fun. House is better than the pictures."
Modern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from Okemo

Cozy Family Chalet with Mountain Views – 15 Mins to Okemo & Ludlow

10.0 out of 10, Exceptional, (14)
"The house was wonderful. House was clean. Our family had a wonderful time playing in the backyard. Close to numerous ski towns. The bunkbed downstairs was a nice surprise."
Cozy Family Chalet with Mountain Views – 15 Mins to Okemo & Ludlow

Black Dog Lodge - Ski Chalet centered between Okemo and Killington Mt.

9.8 out of 10, Exceptional, (22)
"Victoria and Erica were wonderful hosts, everything was as expected and they were very responsive. Graciously arranged for extra snow plowing due to some pretty significant snowfall. Had room for three couples and kids, 10 in all, very comfortably. Would stay again!"
Black Dog Lodge - Ski Chalet centered between Okemo and Killington Mt.

The Whimsical Chalet is a lovely cape on acres. Private setting less than 10 minutes to skiing.

9.0 out of 10, Wonderful, (2)
"Stayed for a ski weekend and it was a nice quiet house on a quiet street but still situated close to the resorts."
The Whimsical Chalet is a lovely cape on acres. Private setting less than 10 minutes to skiing.

Relaxing retreat in the mountains 20 min to Killington

8.0 out of 10, Very Good, (2)
"Our biggest issue is that the listing says 3 bedrooms, 1 with a queen, 1 with twin bunks, and 1 with a queen and 2 twins. But it’s actually a full with 2 twins—a bouncy, mushy full. The twins in that room are paper thin mattresses on boards and they felt a bit like 2x4’s, so I’d only recommend them for kids, even though they were roomy twins. This presented a major issue in our vacation. We surprised my older parents by inviting them for part of it and were happy to give them the queen. This...
Relaxing retreat in the mountains 20 min to Killington

Modern Chalet w/ Serene Views and Jacuzzi Hot Tub- 15 Minutes to Okemo Mountain

9.0 out of 10, Wonderful, (4)
"We had a blast and had fund using the hot tub and firepit."
Modern Chalet w/ Serene Views and Jacuzzi Hot Tub- 15 Minutes to Okemo Mountain

Cozy 4bd - Ski Okemo, Killington, Magic & Bromley

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!"
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley

The Whimsical Chalet 3 Bedroom Chalet by RedAwning

3.0 star property
The Whimsical Chalet 3 Bedroom Chalet by RedAwning
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 Ascutney Hotel Reviews