Hot Chester Chalet Rates

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Chalets in Chester

Okemo 6 Bedroom Chalet.

Okemo 6 Bedroom Chalet.

Ludlow
With a stay at this chalet in Ludlow, you'll be in the mountains, within a 10-minute drive of Okemo Mountain Resort and Dorsey Park.
Okemo 6 Bedroom Chalet.
Cozy Creekside Chalet centrally located near 4 ski resorts

Cozy Creekside Chalet centrally located near 4 ski resorts

Weston
The price is AU$1,178 per night from 27 Dec to 28 Dec
AU$1,178
includes taxes & fees
27 Dec - 28 Dec
Located in Weston, this chalet is in the mountains, within a 5-minute drive of West River and Mill Museum.
Cozy Creekside Chalet centrally located near 4 ski resorts
 WE ARE BACK! COME AND ENJOY YOUR STAY AT OUR TREE HOUSE LIKE! CHECK LOW RATES.

WE ARE BACK! COME AND ENJOY YOUR STAY AT OUR TREE HOUSE LIKE! CHECK LOW RATES.

West Dover
With a stay at this chalet in West Dover, you'll be within a 5-minute drive of Mount Snow and North Branch Deerfield River.
WE ARE BACK! COME AND ENJOY YOUR STAY AT OUR TREE HOUSE LIKE! CHECK LOW RATES.
Save an average of 15% on thousands of hotels when you're signed in
Amazing 3-Level Chalet; 2 Kitchens, 2 Decks, HOT TUB, 5 Ski Mountains, Pets OK

Amazing 3-Level Chalet; 2 Kitchens, 2 Decks, HOT TUB, 5 Ski Mountains, Pets OK

Londonderry
Located in Londonderry, this chalet is within a 5-minute drive of West River and Magic Mountain Ski Resort.
Amazing 3-Level Chalet; 2 Kitchens, 2 Decks, HOT TUB, 5 Ski Mountains, Pets OK
Modern Lux Cabin w/ Mtn Views | Fire Pit

Modern Lux Cabin w/ Mtn Views | Fire Pit

Stratton
With a stay at this chalet in Wardsboro, you'll be in the mountains, within a 15-minute drive of Mount Snow and Green Mountain National Forest.
Modern Lux Cabin w/ Mtn Views | Fire Pit
Brand new hot tub, spacious Chalet 1 min from Okemo base and Ludlow Downtown!

Brand new hot tub, spacious Chalet 1 min from Okemo base and Ludlow Downtown!

2 out of 5
Ludlow
With a stay at this chalet in Ludlow, you'll be next to a golf course, within a 5-minute drive of Okemo Mountain Resort and Blue Lot.
Brand new hot tub, spacious Chalet 1 min from Okemo base and Ludlow Downtown!
Summer Adventures Await -- Book now for the Horse Show & Explore Manchester

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

Winhall
With a stay at this chalet in Winhall, you'll be on the waterfront, just steps from Green Mountain National Forest and a 3-minute drive from Battenkill ...
Summer Adventures Await -- Book now for the Horse Show & Explore Manchester
Beautiful Manchester VT Mountain Retreat w/Hot Tub

Beautiful Manchester VT Mountain Retreat w/Hot Tub

Winhall
Located in Winhall, this chalet is in the mountains, a 1-minute drive from Green Mountain National Forest and 6 minutes from Bromley Mountain Ski Resort.
Beautiful Manchester VT Mountain Retreat w/Hot Tub
Expansive 7-BR Chalet 5-min from Mt. Snow

Expansive 7-BR Chalet 5-min from Mt. Snow

West Dover
Located in West Dover, this chalet is in a rural location, within a 15-minute walk of North Branch Deerfield River and Green Mountain National Forest.
Expansive 7-BR Chalet 5-min from Mt. Snow
Don't see what you're looking for?
See all available properties in Chester
View all properties
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.

Chester Chalet Accommodation

We see you over there, so lost in your own thoughts, you might miss your next meeting. You know it’s time to up your holiday game, and we know you’ve been googling things like “ski holidays” and “mountain retreats”. Don’t worry—we won’t tell your boss. We just have a tip for you: If you really want to slay, you need a chalet. Specifically, cheap chalet accommodation in Chester.

A budget chalet hotel in Chester is the perfect new topic for your office chit-chat, but unlike that office retreat, there will be no trust falls. You will find all sorts of adventurous activities on offer in Chester, but none of them will involve your coworkers having to catch you (at least we hope not). Outside, nature awaits, with endless trails and endless fun. Inside, you’ll find all the right amenities for recharging after an active day, from luxurious linens to fully equipped kitchens.

Speaking of kitchens, chalet hotels in Chester have everything you need for a romantic getaway. Cook up a candlelit dinner and open that perfectly chilled bottle of red. A crackling fireplace and the amazing views of Chester out your picture window will do the rest.

Our deals practically move mountains, bringing cheap ski chalets and more to you right where you sit. Yes, you’ll have to pack eventually, but for now, browse our sweet selection of Chester chalets and start dreaming. After all, didn’t your mum always tell you that you can be anything you want to be? Well, you want to be on holiday in Chester, and it’s time to make it happen.

Chester Chalets essential information

Accommodation
87 Chalets
Lowest Price
AU$238
Highest Price
AU$1,178
Popular accommodation
Okemo 6 Bedroom Chalet., Cozy Creekside Chalet centrally located near 4 ski resorts, WE ARE BACK! COME AND ENJOY YOUR STAY AT OUR TREE HOUSE LIKE! CHECK LOW RATES., Amazing 3-Level Chalet; 2 Kitchens, 2 Decks, HOT TUB, 5 Ski Mountains, Pets OK, Modern Lux Cabin w/ Mtn Views | Fire Pit, Brand new hot tub, spacious Chalet 1 min from Okemo base and Ludlow Downtown!, Summer Adventures Await -- Book now for the Horse Show & Explore Manchester, Beautiful Manchester VT Mountain Retreat w/Hot Tub, Expansive 7-BR Chalet 5-min from Mt. Snow

Top trending hotels in Chester

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3 out of 5
698 VT-11, Chester, VT
Fully refundableReserve now, pay when you stay
The price is AU$390 per night from 30 Dec to 31 Dec
AU$390
includes taxes & fees
30 Dec - 31 Dec
With a stay at Stone Hearth Inn and Eatery in Chester, you'll be 8.5 mi (13.7 km) from Vermont Country Store and 11 mi (17.6 km) from Magic Mountain Ski ...
Stone Hearth Inn and Eatery
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is AU$597 per night from 20 Jan to 21 Jan
AU$597
includes taxes & fees
20 Jan - 21 Jan 2025
A stay at Woodstock Inn & Resort places you in the heart of Woodstock, a 1-minute drive from Billings Farm and Museum and 7 minutes from Saskadena Six Ski ...
Woodstock Inn & Resort
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

2.5 out of 5
4519 Main St, Manchester Center, VT
Fully refundableReserve now, pay when you stay
The price is AU$238 per night from 5 Jan to 6 Jan
AU$238
includes taxes & fees
5 Jan - 6 Jan 2025
A stay at Hampton Inn and Suites Manchester places you in the heart of Manchester Center, steps from Green Mountain National Forest and 8 minutes by foot from ...
Hampton Inn and Suites Manchester
Save an average of 15% on thousands of hotels when you're signed in
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103, Cavendish, VT
The price is AU$308 per night from 5 Jan to 6 Jan
AU$308
includes taxes & fees
5 Jan - 6 Jan 2025
With a stay at Pointe at Castle Hill Resort in Cavendish, you'll be near ski lifts, within a 10-minute drive of Okemo Mountain Resort and Fletcher Farm School ...
Pointe at Castle Hill Resort
Don't see what you're looking for?
See all available properties in Chester
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.