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Check prices for these dates

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5 Dec - 7 Dec
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12 Dec - 14 Dec
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26 Dec - 28 Dec
In two months
23 Jan - 25 Jan

Apartments in Chester

Exterior
2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

Apartment in Dover

9.4 out of 10, Exceptional, (16)
"So cute and in such a great area! It was a perfect stay"
United States
Jaden F.
The price is SAR 146
SAR 958 total
includes taxes & fees
9 Dec - 10 Dec
2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Fridge, microwave, oven, stovetop
Cozy Bromley Retreat

Apartment in Bromley Mountain

9.8 out of 10, Exceptional, (7)
"There is no place I’d rather stay in VT. It’s a perfect condo and the recent renovations are really nice. It’s got all the comforts of home and great touches throughout. Bromley is a great community to be in, it’s close to town, obviously the slopes, and just a overall stay!"
United States
Vanessa P.
The price is SAR 379
SAR 1,265 total
includes taxes & fees
14 Dec - 15 Dec
Cozy Bromley Retreat
Iron/ironing board, WiFi, bed sheets
Woodstock Suite | 10 Min to Mountains |A/C| Hiking

Apartment in Bridgewater

10.0 out of 10, Exceptional, (5)
"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 SAR 296
SAR 722 total
includes taxes & fees
2 Dec - 3 Dec
Woodstock Suite | 10 Min to Mountains |A/C| Hiking
Golf
Efficient condo near slopes with kitchenette & great location

Apartment in Ludlow

8.6 out of 10, Excellent, (32)
"great location, close walkto store, restaurants. Okemoabout a minute drive toparking lots. "
United States
C A.
The price is SAR 356
SAR 852 total
includes taxes & fees
2 Dec - 3 Dec
Efficient condo near slopes with kitchenette & great location
Golf
Well-appointed studio right downtown - less than a mile to Okemo Mountain

Apartment in Ludlow

8.6 out of 10, Excellent, (12)
"Clean with everything we needed for a few nights stay."
United States
Sandra S.
The price is SAR 356
SAR 1,030 total
includes taxes & fees
2 Dec - 3 Dec
Well-appointed studio right downtown - less than a mile to Okemo Mountain
Terrace/patio
6BR 3BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

Apartment in Dover

The price is SAR 762
SAR 2,692 total
includes taxes & fees
15 Dec - 16 Dec
6BR 3BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Interior
Entire private apartment suite in home with own entrance, views and private gym.

Apartment in Keene

The price is SAR 1,032
SAR 1,490 total
includes taxes & fees
15 Dec - 16 Dec
Entire private apartment suite in home with own entrance, views and private gym.
Fridge, microwave, stovetop, dishwasher
Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn

Apartment in Dover

9.6 out of 10, Exceptional, (5)
"Property is very clean, beautiful condo and scenery, owner was great and communication was incredible! Highly recommend, great stay!"
United States
Douglas D.
The price is SAR 825
SAR 1,925 total
includes taxes & fees
2 Dec - 3 Dec
Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn
Exterior
Okemo | Spacious Executive Room w Amenities Nearby

Apartment in Jackson Gore Base Area

8.0 out of 10, Very Good, (1)
The price is SAR 878
SAR 1,101 total
includes taxes & fees
2 Dec - 3 Dec
Okemo | Spacious Executive Room w Amenities Nearby
Iron/ironing board, WiFi, bed sheets
2 Queens | 10 Mins to the Mountains | Foliage

Apartment in Bridgewater

8.8 out of 10, Excellent, (5)
"As advertised"
United States
mark r.
The price is SAR 300
SAR 726 total
includes taxes & fees
2 Dec - 3 Dec
2 Queens | 10 Mins to the Mountains | Foliage
Property grounds
Cozy Studio | Ski-In Access + Kitchenette

Apartment in West Dover

10.0 out of 10, Exceptional, (2)
"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 SAR 634
SAR 803 total
includes taxes & fees
3 Dec - 4 Dec
Cozy Studio | Ski-In Access + Kitchenette
Exterior detail
Long Trail Suite | 10 Mins to Mountains | Skiing

Apartment in Bridgewater

8.0 out of 10, Very Good, (2)
"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 SAR 428
SAR 882 total
includes taxes & fees
8 Dec - 9 Dec
Long Trail Suite | 10 Mins to Mountains | Skiing
Property grounds
Deluxe Studio | Murphy Bed + Sofa

Apartment in West Dover

The price is SAR 679
SAR 867 total
includes taxes & fees
2 Dec - 3 Dec
Deluxe Studio | Murphy Bed + Sofa
Fridge, microwave, oven, stovetop
103 Deluxe One bedroom Queen Suite w/ outdoor heated pool

Apartment in Killington

9.6 out of 10, Exceptional, (17)
"Would stay again!"
United States
Hannah M.
The price is SAR 681
SAR 979 total
includes taxes & fees
2 Dec - 3 Dec
103 Deluxe One bedroom Queen Suite w/ outdoor heated pool
Iron/ironing board, WiFi, bed sheets
Ben & Jerry Suite | Skiing | Hiking | Biking

Apartment in Bridgewater

9.2 out of 10, Wonderful, (7)
"Close to Woodstock and market. Easy check in. Very quiet. Kurig, no cups for coffee."
United States
Nancy
The price is SAR 278
SAR 698 total
includes taxes & fees
2 Dec - 3 Dec
Ben & Jerry Suite | Skiing | Hiking | Biking
Indoor pool, a heated pool
Equinox Haven | King Room + Culinary Delights

Apartment in Manchester

8.0 out of 10, Very Good, (1)
"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 SAR 823
SAR 1,045 total
includes taxes & fees
7 Dec - 8 Dec
Equinox Haven | King Room + Culinary Delights
Internet, bed sheets
Cozy Studio Condo with Great Location, WiFi & Kitchenette

Apartment in Ludlow

8.8 out of 10, Excellent, (29)
"Great location and great place!"
United States
Linda G.
The price is SAR 356
SAR 888 total
includes taxes & fees
2 Dec - 3 Dec
Cozy Studio Condo with Great Location, WiFi & Kitchenette
Exterior
Okemo | Studio Condo + Loft | Near Slopes + Pool

Apartment in Jackson Gore Base Area

10.0 out of 10, Exceptional, (2)
"Very conveinent check in, nice property."
United States
michael
The price is SAR 987
SAR 1,255 total
includes taxes & fees
2 Dec - 3 Dec
Okemo | Studio Condo + Loft | Near Slopes + Pool
Dining
Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102

Apartment in Killington

9.0 out of 10, Wonderful, (7)
"We have stayed here numerous times and it is always a nice experience. This suite is spacious and clean and it felt homey. Love the pool :) and it is so close to Killington making it a really convenient spot. "
United States
patricia
The price is SAR 681
SAR 979 total
includes taxes & fees
2 Dec - 3 Dec
Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102
Exterior
Okemo | Charming Room & Amenities Nearby | Pools

Apartment in Jackson Gore Base Area

The price is SAR 878
SAR 1,114 total
includes taxes & fees
2 Dec - 3 Dec
Okemo | Charming Room & Amenities Nearby | Pools
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

Jackson Gore Village

Jackson Gore Village

10/10 Excellent
"Very clean, everyone was so nice. Food at restaurant is a little pricey but was very good. "
William 2-night trip
Posted 8 hours ago
Jackson Gore Village

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 67 accommodations. Though there aren't many apartments, we can help you locate similar accommodations. When you search for a place to stay on Expedia, you can use the filters to search for conveniences you might find in an apartment like a kitchen. You can also filter by similar property types like vacation homes, condos, or guest houses. During your trip, you can check out this quaint area's ski slopes and shops. Discover the region's top sights such as Stratton Mountain Resort.
Are you thinking about apartments over traditional hotel rooms?
Often more spacious than a traditional hotel room, an apartment includes a kitchen, so you can have some home-cooked meals. Apartments are ideal for families who want the conveniences of home but also for couples who want to stay in a quieter area.
What's a favorite apartment I should consider for a stay in Chester?
Here are some of the top apartments in the area to choose from: Stratton South Long Trail Studio Adjacent to the Village and Lifts: Located in Stratton, 18.7 mi/30 km from the heart of Chester. Includes private balconies, fireplaces, and sofa beds. Onsite laundry facilities and an outdoor pool are on site. Long Trail House Studio at Stratton Mountain Resort: Located 18.7 mi/30 km away in Stratton. Fireplaces and sofa beds are included. Onsite laundry facilities and a hot tub are on site. Efficient condo near slopes with kitchenette & great location: It's situated in Ludlow, 10.9 mi/17.5 km away. Includes sofa beds. 2BR 2BA - 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, fireplaces, and Smart TVs are included. A fitness center and an outdoor pool are on site. Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn: Located in West Dover, 25 mi/40.3 km from Chester. Includes private balconies, fireplaces, and separate dining areas. Onsite laundry facilities and an indoor pool are on site.
What will the weather be like during my trip to Chester?
Though 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 temp of 65°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Chester are January, March, November, and February, with each month seeing an average of 14 inches 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 family-friendly sights. Stratton Mountain Resort and Grafton Historical Society are a couple of places you'll find in the larger area.
What's the best way to get to and around Chester?
Knowing a bit about the transportation options can save you time when you get to your destination. Fly into Springfield, VT (VSF-Hartness State), which is located 6.6 mi (10.7 km) from the heart of the city. 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 take in more sights.