Chester Chalets

    price find illustration

    Upfront pricing

    Our total price for your stay includes taxes and fees
    deals illustration

    Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Chalets in Chester

Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults
Stunning hallway with carpeted floor, wooden staircase, and panelled walls.

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."
$1,768 nightly
The price is $1,998
Aug 10 - Aug 11
Total includes taxes and fees
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults
Spacious 5-bedroom chalet with AC and WiFi in charming Chester
Enjoy cooking in this warm kitchen with a large island and dishwasher, surrounded by natural light and a view of the landscape.

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
Relax in this serene living space with a view of the surrounding trees, featuring a large window, two sofas, a coffee table, and a mounted television.

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
Summer Adventures Await -- Book now for the Horse Show & Explore Manchester
Escape to a serene cabin surrounded by lush greenery, perfect for relaxation and nature.

Summer Adventures Await -- Book now for the Horse Show & Explore Manchester

10.0 out of 10, Exceptional, (51)
"All around great stay. Had some slight heat issues day 1 that were fixed imemdiately!"
Summer Adventures Await -- Book now for the Horse Show & Explore Manchester
New! Mt Snow Chalet w/land, privacy, relaxation
Situated over a small stream, this gazebo offers a serene outdoor space surrounded by trees and grass.

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

9.2 out of 10, Wonderful, (5)
"Excellent location to skiing Spacious rooms Plenty of towels Kitchen stocked with appliances Close to market "
New! Mt Snow Chalet w/land, privacy, relaxation
Cozy Creekside Chalet centrally located near 4 ski resorts
Escape to a serene forest retreat with a cozy cabin featuring a charming front porch and balcony overlooking the surrounding trees.

Cozy Creekside Chalet centrally located near 4 ski resorts

10.0 out of 10, Exceptional, (11)
"We spent a great week in Weston. Great location to ski Stratton. Hosts were very responsive. Would def go back."
$411 nightly
The price is $460
Sep 5 - Sep 6
Total includes taxes and fees
Cozy Creekside Chalet centrally located near 4 ski resorts
Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski
Exterior

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

10.0 out of 10, Exceptional, (23)
"House was great, we loved our stay. Definitely walk down the road and get pizza! It was our favorite dinner of our trip and absolutely delicious! "
Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski
Wine Moose Hot tub Fireplace Sauna 9min to Mt Snow
Welcome to 50 Colonial Ridge, a charming home in a wooded setting.

Wine Moose Hot tub Fireplace Sauna 9min to Mt Snow

10.0 out of 10, Exceptional, (6)
"We had a great time at the Wine Moose! The sauna kept us super warm in the super cold temps. Very very close to Mt. Snow and we also hit up Berkshire East and Magic an hour south and north respectively, easily. I'd recommend staying here!"
Wine Moose Hot tub Fireplace Sauna 9min to Mt Snow
Charming Chalet w. Hot Tub - 1 mile to Mt. Snow
Relax in a hot tub surrounded by lush foliage on a secluded deck with a seating area.

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

10.0 out of 10, Exceptional, (12)
"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!"
$524 nightly
The price is $592
Aug 12 - Aug 13
Total includes taxes and fees
Charming Chalet w. Hot Tub - 1 mile to Mt. Snow
Log Home# w/ Incomparable Peace, Serenity, Privacy And The First Class Amenities
Cozy cabin with a rustic charm, featuring a dining table, bar area, and kitchen with a view of the surrounding landscape.

Log Home# w/ Incomparable Peace, Serenity, Privacy And The First Class Amenities

10.0 out of 10, Exceptional, (107)
"The house was equipped with everything we needed! Cant wait to come back! "
Log Home# w/ Incomparable Peace, Serenity, Privacy And The First Class Amenities
Fall into Cozy at Bigfoot Chalet
Beach

Fall into Cozy at Bigfoot Chalet

2.0 star property
10.0 out of 10, Exceptional, (13)
"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."
$435 nightly
The price is $487
Sep 1 - Sep 2
Total includes taxes and fees
Fall into Cozy at Bigfoot Chalet
The MountainTop
Enjoy cooking in this well-equipped kitchen with a central island and bar seating, featuring a refrigerator, dishwasher, and granite countertop.

The MountainTop

10.0 out of 10, Exceptional, (1)
"Nick’s cabin was perfect. Beautifully built and decorated, the cabin was amazing. Nick’s place had everything we needed and more. The location was tucked away with beautiful surroundings and close to Stratton mountain. Nick was always quick to reply with any questions and made sure our stay was perfect. Only regret is we didn’t stay here longer! "
The MountainTop
Stylish Mountain Getaway close to Stratton w/ Spa
Relax in this spacious living area with a high ceiling, featuring a flat-screen TV, comfortable sofa, and dining table.

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
Modern 4-Bedroom Mountain Retreat Minutes to Lake Rescue & Echo and Hiking
Enjoy cooking in this kitchen with a central island, bar stools, stainless steel appliances, and a large window offering a view of the outdoors.

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
Stratton Ski Chalet: Spacious Modern Oasis w/Hot Tub, Fireplace, Pond & BBQ Deck
Fridge, microwave, oven, stovetop

Stratton Ski Chalet: Spacious Modern Oasis w/Hot Tub, Fireplace, Pond & BBQ Deck

8.6 out of 10, Excellent, (11)
"When we first arrived we couldn’t find extra trash bags. We sent a message to the host, Jason, and he replied immediately to assist us. I appreciate the attentiveness and genuine hospitality. This place is cozy and clean. Made for the perfect weekend getaway!"
$673 nightly
The price is $760
Aug 19 - Aug 20
Total includes taxes and fees
Stratton Ski Chalet: Spacious Modern Oasis w/Hot Tub, Fireplace, Pond & BBQ Deck
Beautiful Manchester VT Mountain Retreat w/Hot Tub
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, and oven, complemented by a dining area with a wooden table and chairs.

Beautiful Manchester VT Mountain Retreat w/Hot Tub

10.0 out of 10, Exceptional, (35)
"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
Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!
Enjoy cooking in this well-equipped kitchen with a large island, stainless steel range hood, and oven.

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. "
$331 nightly
The price is $374
Aug 21 - Aug 22
Total includes taxes and fees
Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!
Gorgeous Ski Chalet with Game Room & Hot Tub on Okemo Mt. under 1 mile to base!
Relax in a serene forest setting with a fire pit and Adirondack chair.

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!
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Relax on the deck with a seating area featuring two chairs and a table, surrounded by a railing and lush greenery.

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

9.6 out of 10, Exceptional, (19)
"We had an amazing trip, and the host was very responsive and helpful with everything. The house was great, had everything we needed, and the private ski run back to the property was really fun. Highly recommend this property and the best host we have ever had!! Favoriting this place for a future stay!"
$324 nightly
The price is $366
Sep 2 - Sep 3
Total includes taxes and fees
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Two Bedroom Chalet, Charming, Quiet, River Front
Relax in this inviting living room with a comfortable sofa and large glass doors leading to an outdoor area.

Two Bedroom Chalet, Charming, Quiet, River Front

9.4 out of 10, Exceptional, (74)
"Loved the location and the house was great. All amenities were as described. Great host. Highly recommend. "
Two Bedroom Chalet, Charming, Quiet, River Front
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
Sign in
Sign up, it's free

Top Chester Hotel Reviews

Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

10/10 Excellent
"We really enjoyed our stay at this property. It's nicely kept.. and EV charging is included in stay. Great breakfast, too. "
Deberah L 2-night trip
Posted 2 days ago
Hampton Inn and Suites Manchester