Search Chalets in Chester

Start date: Check-in selected.
End date: Check-out
    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

In two weeks
In one month
In two months
In three months

Chalets in Chester

Cozy Creekside Chalet centrally located near 4 ski resorts

10.0 out of 10, Exceptional, (13)
"We had the best time at this cozy spot with some friends for a weekend - highly recommend!"
The price is SAR 673
SAR 1,809 total
includes taxes & fees
24 Sep - 25 Sep
Cozy Creekside Chalet centrally located near 4 ski resorts

Beautiful Manchester VT Mountain Retreat w/Hot Tub

10.0 out of 10, Exceptional, (38)
"Really enjoyed this home. Was a weekend getaway with friends and there was lots of room for us. Especially enjoyed the sauna. Kitchen is well stocked. All was great. "
Beautiful Manchester VT Mountain Retreat w/Hot Tub

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

Mid-Century Arty Chalet - 2 Min to Stratton Slopes

8.8 out of 10, Excellent, (3)
"The house is in a great location for skiing at Stratton! 5 mins drive to the base or shuttle service running every 30 mins. Perfect for a cozy ski weekend with the fireplace. We enjoyed it very much! "
Mid-Century Arty Chalet - 2 Min to Stratton Slopes

Mountain chalet

10.0 out of 10, Exceptional, (42)
"Owner is very nice, easy communications. "
Mountain chalet

Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski

10.0 out of 10, Exceptional, (24)
"We had a great stay at the Woodbridge Inn. Definitely would recommend to others"
Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski

Stratton Mountain Getaway: Ski Oasis w/Hot Tub, Fireplace, BBQ & Pond Views

8.6 out of 10, Excellent, (11)
"We enjoyed ourselves arriving after a week of Vermont rain so the outside of the house and property were a bit messy from the weather, the deck, grill and hot tub area affected. It was fine as rain continued. The house was pretty organized with enough room for 8 adults to cook/ serve and socialize. We enjoyed nice neighborhood walks and a trip to Manchester and Hildene. There’s some maintenance needed as would be expected after the busy winter season. New pillows and towels would be a plus....
The price is SAR 1,069
SAR 2,790 total
includes taxes & fees
15 Sep - 16 Sep
Stratton Mountain Getaway: Ski Oasis w/Hot Tub, Fireplace, BBQ & Pond Views

Where crisp air meets cozy nights—your Vermont fall escape awaits.

10.0 out of 10, Exceptional, (52)
"We enjoyed skylight lodge. We get together with family and friends each year to do an annual fundraising event. The house was perfect for our group. The big fireplace was a great way to relax after a day of skiing or snowshoeing. "
Where crisp air meets cozy nights—your Vermont fall escape awaits.

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

9.8 out of 10, Exceptional, (126)
"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!

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

9.6 out of 10, Exceptional, (33)
"Great stay"
Ski On, Ski off Okemo Trailside Appartment, Sleeps 6/ $550per night,

COZY TREE LIKE HOUSE. WALK TO MARKET & REST. LOW RATES. 1 MILE TO MT SNOW.

9.8 out of 10, Exceptional, (35)
"We enjoyed our time skiing and relaxing! "
COZY TREE LIKE HOUSE. WALK TO MARKET & REST. LOW RATES. 1 MILE TO MT SNOW.

Charming Chalet w. Hot Tub - 1 mile to Mt. Snow

10.0 out of 10, Exceptional, (13)
"This spot was perfect for a weekend at mount snow! It was so quick to get to the mountain and good area for food and shops. I would definitely stay here again!"
The price is SAR 747
SAR 2,209 total
includes taxes & fees
15 Sep - 16 Sep
Charming Chalet w. Hot Tub - 1 mile to Mt. Snow

"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

Stylish Mountain Getaway close to Stratton w/ Spa

9.8 out of 10, Exceptional, (7)
"Amazing! Host was readily available to handle any questions and the house was very comfortable and relaxing. "
Stylish Mountain Getaway close to Stratton w/ Spa

Green Mountain Manor - Ski and Summer Chalet

9.8 out of 10, Exceptional, (7)
"Beautiful property less than 5 minutes from Stratton!! Very private and secluded"
Green Mountain Manor - Ski and Summer Chalet

Private Chalet: walk to hiking/biking trails and golf course

2.0 star property
9.6 out of 10, Exceptional, (5)
"We spent the week, excellent location and the home was exactly as described in listing."
The price is SAR 657
SAR 2,103 total
includes taxes & fees
11 Sep - 12 Sep
Private Chalet: walk to hiking/biking trails and golf course

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

10.0 out of 10, Exceptional, (26)
"A terrific place. Highly recommended. We had a great family ski vacation."
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults

Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!

10.0 out of 10, Exceptional, (4)
"We had a great time at the Chalet. Great accommodations Jennifer made sure we had everything we needed She went above and beyond to accommodate our group. "
The price is SAR 2,063
SAR 3,744 total
includes taxes & fees
11 Sep - 12 Sep
Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!

8 minutes to Mount Snow, Dog Friendly, Fire Pit, Hot Tub, Game Room, Private

10.0 out of 10, Exceptional, (20)
"Wonderful time..the home was very spacious and comfortable..great location!"
The price is SAR 638
SAR 2,247 total
includes taxes & fees
11 Sep - 12 Sep
8 minutes to Mount Snow, Dog Friendly, Fire Pit, Hot Tub, Game Room, Private

New! Mt Snow Chalet w/land, privacy, relaxation

8.8 out of 10, Excellent, (6)
"Fun place"
New! Mt Snow Chalet w/land, privacy, relaxation
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 Chester Hotel Reviews