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Check prices for these dates

In two weeks
13 Feb - 15 Feb
In two months
27 Mar - 29 Mar
In three months
24 Apr - 26 Apr
In four months
22 May - 24 May

Our top choices for Chester apartments

Outdoor pool, a heated pool

Apartment in Dover

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
9.2 out of 10, Wonderful, (20 reviews)
"So cute and in such a great area! It was a perfect stay"
United States
Jaden F.
The price is HK$438
HK$2,327 total
includes taxes & fees
4 Feb - 5 Feb
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Property grounds

Apartment in Bridgewater

Vermont Suite | 10 Min to Woodstock & Killington
10.0 out of 10, Exceptional, (5 reviews)
"We had a lovely time in Woodstock Vermont. The Bridgewater Inn was cozy and perfect for our weekend get away"
United States
Rosie L.
The price is HK$811
HK$1,748 total
includes taxes & fees
28 Jan - 29 Jan
Vermont Suite | 10 Min to Woodstock & Killington
Children’s area

Apartment in Bromley Mountain

Cozy Bromley Retreat
9.4 out of 10, Exceptional, (10 reviews)
"As always, an excellent stay. Wonderful unit, very nicely stocked in a perfect location. Communication was quick and easy. Easily my favorite place to stay!"
United States
Vanessa P.
The price is HK$707
HK$2,535 total
includes taxes & fees
28 Jan - 29 Jan
Cozy Bromley Retreat
Golf

Apartment in Ludlow

Well-appointed studio right downtown - less than a mile to Okemo Mountain
8.6 out of 10, Excellent, (12 reviews)
"Clean with everything we needed for a few nights stay."
United States
Sandra S.
The price is HK$990
HK$2,868 total
includes taxes & fees
2 Feb - 3 Feb
Well-appointed studio right downtown - less than a mile to Okemo Mountain
Golf

Apartment in Ludlow

Efficient condo near slopes with kitchenette & great location
8.6 out of 10, Excellent, (32 reviews)
"Nice place close to mountain easy in easy out"
United States
Aaron B.
The price is HK$819
HK$1,861 total
includes taxes & fees
2 Feb - 3 Feb
Efficient condo near slopes with kitchenette & great location
Indoor pool

Apartment in Dover

Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn
9.6 out of 10, Exceptional, (5 reviews)
"Amazing experience at Mount Snow! Leah is the best owner! Attentive and accessible. "
United States
Jayanne S.
The price is HK$1,544
HK$3,754 total
includes taxes & fees
28 Jan - 29 Jan
Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn
Indoor pool, a heated pool

Apartment in Manchester Village Historic District

Equinox Haven | King Room + Culinary Delights
8.0 out of 10, Very good, (1 review)
"Clean room. There was a trip hazard from bedroom to bathroom. Servers in restaurant were very attentive, courteous and professional. Food adequate but over priced."
United States
Anne Marie
The price is HK$1,369
HK$1,717 total
includes taxes & fees
29 Jan - 30 Jan
Equinox Haven | King Room + Culinary Delights
Smart TV, fireplace

Apartment in Dover

6BR 3BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
The price is HK$1,743
HK$5,873 total
includes taxes & fees
25 Feb - 26 Feb
6BR 3BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Property grounds

Apartment in Bridgewater

Vermont Double Queen Suite | 10 Mins to Killington
8.8 out of 10, Excellent, (5 reviews)
"This was perfect for our girls weekend! Great location, spacious & clean. Our host was so responsive & kind- highly recommend staying here when you visit Salem! "
United States
Brianna L.
The price is HK$764
HK$1,689 total
includes taxes & fees
28 Jan - 29 Jan
Vermont Double Queen Suite | 10 Mins to Killington
Exterior

Apartment in Ludlow

Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK
9.8 out of 10, Exceptional, (172 reviews)
"Great spot to stay in with a group for skiing. Easy check in and check out process."
United States
Aidan O.
The price is HK$2,339
HK$3,674 total
includes taxes & fees
18 Feb - 19 Feb
Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK
Terrace/patio

Apartment in West Dover

Deluxe Studio | Murphy Bed + Sofa
The price is HK$2,830
HK$3,556 total
includes taxes & fees
2 Feb - 3 Feb
Deluxe Studio | Murphy Bed + Sofa
Interior

Apartment in Killington

103 Deluxe One bedroom Queen Suite w/ outdoor heated pool
9.6 out of 10, Exceptional, (17 reviews)
"Would stay again!"
United States
Hannah M.
The price is HK$1,844
HK$2,605 total
includes taxes & fees
29 Jan - 30 Jan
103 Deluxe One bedroom Queen Suite w/ outdoor heated pool
Property grounds

Apartment in Bridgewater

Vermont Suite | Minutes to Killington | Skiing
8.0 out of 10, Very good, (2 reviews)
"clean, easy to check in and out, convenient location to the GMHA grounds - we stay here every summer! "
United States
Amanda K.
The price is HK$1,037
HK$2,030 total
includes taxes & fees
28 Jan - 29 Jan
Vermont Suite | Minutes to Killington | Skiing
Outdoor dining

Apartment in Jackson Gore Base Area

Okemo | Studio Condo + Loft | Near Slopes + Pool
10.0 out of 10, Exceptional, (2 reviews)
"Very conveinent check in, nice property."
United States
michael
The price is HK$4,293
HK$5,409 total
includes taxes & fees
3 Feb - 4 Feb
Okemo | Studio Condo + Loft | Near Slopes + Pool
Terrace/patio

Apartment in West Dover

Cozy Studio | Ski-In Access + Kitchenette
10.0 out of 10, Exceptional, (2 reviews)
"Room was spacious & kitchen was equipped with essentials needed for a weekend stay. The extra sink area outside the Bathroom was an added bonus."
United States
Jean Marie L.
The price is HK$2,405
HK$3,012 total
includes taxes & fees
2 Feb - 3 Feb
Cozy Studio | Ski-In Access + Kitchenette
Property grounds

Apartment in Bridgewater

Vermont Suite | 10 Min to Killington & Woodstock
9.2 out of 10, Wonderful, (7 reviews)
"Overall, a great stay. "
United States
Meghan J.
The price is HK$702
HK$1,612 total
includes taxes & fees
28 Jan - 29 Jan
Vermont Suite | 10 Min to Killington & Woodstock
Indoor pool, a heated pool

Apartment in Manchester Village Historic District

Grand Equinox | 2 Queen Room + Adventure Delights
8.0 out of 10, Very good, (1 review)
"Yes, but you have to drive to town "
United States
Cathy W.
The price is HK$1,637
HK$2,064 total
includes taxes & fees
4 Feb - 5 Feb
Grand Equinox | 2 Queen Room + Adventure Delights
Exterior

Apartment in Ludlow

Cozy Studio Condo with Great Location, WiFi & Kitchenette
8.8 out of 10, Excellent, (29 reviews)
"Great location and great place!"
United States
Linda G.
The price is HK$1,014
HK$2,212 total
includes taxes & fees
4 Feb - 5 Feb
Cozy Studio Condo with Great Location, WiFi & Kitchenette
Indoor pool

Apartment in Manchester Village Historic District

Accessible Retreat | King Room + Mountain View
The price is HK$1,434
HK$1,807 total
includes taxes & fees
1 Feb - 2 Feb
Accessible Retreat | King Room + Mountain View
Indoor pool

Apartment in Manchester Village Historic District

Adaptable Escape | King Room + Mountain View
The price is HK$1,434
HK$1,798 total
includes taxes & fees
1 Feb - 2 Feb
Adaptable Escape | King Room + Mountain View
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.
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Top Chester Hotel Reviews

Chalet 239

Chalet 239

10/10 Excellent
"I stayed at Chalet 239 near Mount Snow and had a pleasant experience. The room was clean, cozy, and well maintained, with easy self check-in via door code, which was convenient. As a boutique hotel, it’s simple and quiet, though not fully ski-oriented (no ski closet). The bathroom is on the smaller side, and breakfast is light (oatmeal and yogurt), but sufficient for a quick start. Overall, a nice, clean boutique stay and a good option if you’re looking for something simple and peaceful near the mountain."
Boban 1-night trip
Posted 21 hours ago
Chalet 239

Find out more about Chester

Chester Apartments information

Number of reviews
265
Accommodation
174 Apartments
Lowest Price
HK$1,612
Highest Price
HK$5,873

Frequently asked questions

What's it like to stay at an apartment in Chester?
You'll find a lot of options for your stay in Chester with 66 accommodation options. Though there aren't many apartments, we can help you find similar accommodation. When you search for a place to stay on Expedia, you can use the filters to search for a kitchen— just one of the conveniences you might find in an apartment. You can even filter by similar property types like condos, holiday homes or cottages. During your trip, you can explore this relaxing area's ski slopes and shops. Discover some favourite sights in the wider region such as Okemo Mountain Resort and Stratton Mountain Resort.
Are you considering an apartment instead of a traditional hotel?
Often offering more space than a traditional hotel room, an apartment comes equipped with a kitchen, so you can cook some of your meals. Apartments are ideal for families who want the conveniences of home, and also for couples looking for something with a more local feel.
What's a favourite apartment for my stay in Chester?
Here are some of the top apartments in the area to choose from: Efficient condo near slopes with kitchenette & great location: Situated in Ludlow , 10.9 mi/17.5 km from the heart of Chester. Includes a sofa bed . 2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den: Located 26.5 mi/42.7 km away in West Dover . Free WiFi, a fireplace and a Smart TV are included . A fitness centre and an outdoor pool are on site . Stratton South Long Trail Studio Adjacent to the Village and Lifts: Located in Stratton , 18.7 mi/30 km away. Includes a balcony, a fireplace and a sofa bed . On-site laundry facilities and an outdoor pool are on site . Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK: Located 10.4 mi/16.7 km away in Ludlow . A washer/dryer, free WiFi and a patio are included . A fitness centre and on-site laundry facilities are on site . Long Trail House Studio at Stratton Mountain Resort: Located in Stratton , 18.7 mi/30 km from Chester. Includes a fireplace and a sofa bed . On-site laundry facilities and 1 hot tub are on site .
What will the weather be like when I travel to Chester?
Although weather is just one factor, it can really affect your travel plans, especially if you are planning a longer stay in Chester. The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Chester are January, March, November and February, with each month seeing an average of 35 cm of snowfall.
What should I see and do in Chester?
Chester is known for its ski slopes and shops. DaVallia Art & Accents and Bonnie's Bundles Dolls are a couple of the family-friendly sights. You'll find favourite places to visit such as Okemo Mountain Resort and Stratton Mountain Resort in the wider area.
What's the best way to get to and around Chester?
Knowing a bit about the transportation options can you save you a headache when you get to your destination. Fly into Springfield, VT (VSF-Hartness State), which is located 6.6 mi (10.7 km) away from the city centre. Otherwise, look for flights into Rutland, VT (RUT-Rutland Southern Vermont Regional), which is 25.4 mi (40.8 km) away. If you'd like to venture out around the area, consider renting a car to explore more sights.

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