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Check prices for these dates

In two weeks
26 Sep - 28 Sep
In two months
7 Nov - 9 Nov
In three months
5 Dec - 7 Dec
In four months
2 Jan - 4 Jan

Apartments in Chester

Our top choices for Chester apartments

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

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

9.4 out of 10, Exceptional, (16)
"Highly recommend clean beautiful stay!"
The price is SAR 203
SAR 992 total
includes taxes & fees
6 Oct - 7 Oct
2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Property grounds

Cozy apt in beautiful secluded spot 15 mins from Mt Snow

10.0 out of 10, Exceptional, (3)
"There was a little problem with the lockbox, but Catherine was available to help solve it. We were staying in the house instead of the “cozy apartment.” Except for a somewhat difficult staircase and a couple of doors to the deck that did not have screens, we have no complaints. They location was beautiful, but a bit of a distance from places we wanted to go to. The price was very fair, and I would recommend this location to others."
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Riverfront studio with river view, full kitchen, & free WiFi
Fridge, microwave, oven, stovetop

Riverfront studio with river view, full kitchen, & free WiFi

7.4 out of 10, Good, (13)
"Easy to find, somewhat dated but clean and tidy, comfortable bed; perfect for a short stay."
Riverfront studio with river view, full kitchen, & free WiFi
Green Mountain Tiny House: a mountainside retreat
Interior

Green Mountain Tiny House: a mountainside retreat

9.4 out of 10, Exceptional, (3)
"Such a fun little house! Really cozy and comfortable and communication with the hosts was excellent. Highly recommended!"
The price is SAR 390
SAR 1,141 total
includes taxes & fees
17 Sep - 18 Sep
Green Mountain Tiny House: a mountainside retreat
Foxglove Tiny House - a modern tiny getaway
Outdoor dining

Foxglove Tiny House - a modern tiny getaway

The price is SAR 453
SAR 1,291 total
includes taxes & fees
15 Sep - 16 Sep
Foxglove Tiny House - a modern tiny getaway
2 Queens | 10 Mins to the Mountains | Foliage
Iron/ironing board, WiFi, bed sheets

2 Queens | 10 Mins to the Mountains | Foliage

8.6 out of 10, Excellent, (4)
"As advertised"
The price is SAR 386
SAR 833 total
includes taxes & fees
15 Sep - 16 Sep
2 Queens | 10 Mins to the Mountains | Foliage
Well-appointed studio right downtown - less than a mile to Okemo Mountain
Golf

Well-appointed studio right downtown - less than a mile to Okemo Mountain

9.2 out of 10, Wonderful, (11)
"Clean with everything we needed for a few nights stay."
The price is SAR 199
SAR 914 total
includes taxes & fees
23 Sep - 24 Sep
Well-appointed studio right downtown - less than a mile to Okemo Mountain
Efficient condo near slopes with kitchenette & great location
Property grounds

Efficient condo near slopes with kitchenette & great location

8.6 out of 10, Excellent, (32)
"great location, close walkto store, restaurants. Okemoabout a minute drive toparking lots. "
The price is SAR 184
SAR 609 total
includes taxes & fees
14 Sep - 15 Sep
Efficient condo near slopes with kitchenette & great location
6BR 3BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Terrace/patio

6BR 3BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

The price is SAR 1,276
SAR 3,210 total
includes taxes & fees
30 Sep - 1 Oct
6BR 3BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Grand Equinox | 2 Queen Room + Adventure Delights
Indoor pool, a heated pool

Grand Equinox | 2 Queen Room + Adventure Delights

The price is SAR 713
SAR 899 total
includes taxes & fees
17 Sep - 18 Sep
Grand Equinox | 2 Queen Room + Adventure Delights
Cozy Studio | Ski-In Access + Kitchenette
Property grounds

Cozy Studio | Ski-In Access + Kitchenette

10.0 out of 10, Exceptional, (1)
"Lovely "
The price is SAR 975
SAR 1,221 total
includes taxes & fees
26 Sep - 27 Sep
Cozy Studio | Ski-In Access + Kitchenette
Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn
Fridge, microwave, stovetop, dishwasher

Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn

9.6 out of 10, Exceptional, (4)
"Property was clean, well presented and very comfortable. We had a great time, checking out nearby waterfalls and history of such places as Bennington. We would stay again and recommend to friends and family.."
Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn
Okemo | Studio Condo + Close to All Amenities
Exterior

Okemo | Studio Condo + Close to All Amenities

The price is SAR 754
SAR 948 total
includes taxes & fees
18 Sep - 19 Sep
Okemo | Studio Condo + Close to All Amenities
Perfect Getaway! Cozy, Modern condo & Convenient to Everything you will need.
Fridge, microwave, oven, stovetop

Perfect Getaway! Cozy, Modern condo & Convenient to Everything you will need.

9.8 out of 10, Exceptional, (71)
"Wonderful, cozy, and comfy (bed is amazing) place to stay. Also very convenient location. Hosts clearly place directions and helpful tips around. Everything was a breeze! "
The price is SAR 281
SAR 844 total
includes taxes & fees
15 Sep - 16 Sep
Perfect Getaway! Cozy, Modern condo & Convenient to Everything you will need.
Remodeled condo with free WiFi & shared W/D - ski bus pickup across street
Fridge, microwave, oven, stovetop

Remodeled condo with free WiFi & shared W/D - ski bus pickup across street

8.6 out of 10, Excellent, (10)
"This property was perfectly located across the street from a local shuttle (or a 5 min drive) to the ski resort and within walking distance to restaurants in town. The unit was clean and spacious. The guest services were easily available. The only minor downside was that the smart TV wouldn’t connect to WiFi - would recommend bringing a firestick or tablet. Would stay here again!"
The price is SAR 713
SAR 1,614 total
includes taxes & fees
14 Sep - 15 Sep
Remodeled condo with free WiFi & shared W/D - ski bus pickup across street
Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102
Dining

Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102

8.8 out of 10, Excellent, (6)
"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. "
Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102
Deluxe Studio | Murphy Bed + Sofa
Property grounds

Deluxe Studio | Murphy Bed + Sofa

The price is SAR 1,058
SAR 1,325 total
includes taxes & fees
26 Sep - 27 Sep
Deluxe Studio | Murphy Bed + Sofa
Cozy Studio Condo with Great Location, WiFi & Kitchenette
Internet, bed sheets

Cozy Studio Condo with Great Location, WiFi & Kitchenette

8.6 out of 10, Excellent, (28)
"Great location and great place!"
The price is SAR 882
SAR 1,549 total
includes taxes & fees
13 Oct - 14 Oct
Cozy Studio Condo with Great Location, WiFi & Kitchenette
Ben & Jerry Suite | Minutes to Woodstock | Hiking
Interior

Ben & Jerry Suite | Minutes to Woodstock | Hiking

9.6 out of 10, Exceptional, (5)
"Pleasant and convenient. "
The price is SAR 536
SAR 1,022 total
includes taxes & fees
21 Sep - 22 Sep
Ben & Jerry Suite | Minutes to Woodstock | Hiking
Long Trail Suite | 10 Mins to Mountains | A/C
Exterior

Long Trail Suite | 10 Mins to Mountains | A/C

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! "
The price is SAR 341
SAR 780 total
includes taxes & fees
14 Sep - 15 Sep
Long Trail Suite | 10 Mins to Mountains | A/C
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

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent
"Strongly recommend and will go back again!"
Craig 2-night trip
Posted 2 days ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

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 find similar accommodations. When you search for a place to stay on Expedia, you can filter by amenities you might find in an apartment like a kitchen. You can even filter by similar properties such as vacation homes, condos, or cabins. During your trip, you can check out this quaint area's ski slopes and shops.
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 favorite apartments in the area: Hawks Mountain Farm, full apartment on a working farm.: Includes free WiFi, private patios, and sofa beds. Nana's House: Located 22.2 mi/35.7 km away in Bridgewater. Free WiFi and Smart TVs are included. 2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den: Located in West Dover, 26.5 mi/42.7 km away. Includes free WiFi, fireplaces, and Smart TVs. A fitness center and an outdoor pool are on site. Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly: Located 10.4 mi/16.7 km away in Ludlow. Private patios and sofa beds are included. Onsite laundry facilities and a hot tub are on site. Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK: Located in Ludlow, 10.4 mi/16.7 km from Chester. Includes laundry facilities, free WiFi, and private patios. A fitness center and onsite laundry facilities 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. Vermont Museum of Mining and Minerals and Vermont Country Store 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.