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Check prices for these dates

Next weekend
16 Jan - 18 Jan
In two weeks
23 Jan - 25 Jan
In one month
6 Feb - 8 Feb
In two months
6 Mar - 8 Mar

Our top choices for Chester apartments

Children's area
Cozy Bromley Retreat

Apartment in Bromley Mountain

Cozy Bromley Retreat
9.4 out of 10, Exceptional, (10)
"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 AED 363
AED 1,234 total
includes taxes & fees
13 Jan - 14 Jan
Cozy Bromley Retreat
Property grounds
Woodstock Studio | 10 Min to Killington

Apartment in Bridgewater

Woodstock Studio | 10 Min to Killington
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 AED 441
AED 896 total
includes taxes & fees
12 Jan - 13 Jan
Woodstock Studio | 10 Min to Killington
Interior
Cozy apt in beautiful secluded spot 15 mins from Mt Snow

Apartment in Dover

Cozy apt in beautiful secluded spot 15 mins from Mt Snow
10.0 out of 10, Exceptional, (4)
"Cozy little spot that had everything we needed. Peaceful, quiet, and once the rain let up on our stay we walked out to the gorgeous little pond on the property. So serene. Catherine was great!"
United States
Erica H.
The price is AED 312
AED 755 total
includes taxes & fees
31 Jan - 1 Feb
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Outdoor pool, a heated pool
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

Apartment in Dover

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
9.2 out of 10, Wonderful, (18)
"So cute and in such a great area! It was a perfect stay"
United States
Jaden F.
The price is AED 179
AED 1,102 total
includes taxes & fees
27 Jan - 28 Jan
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Golf
Well-appointed studio right downtown - less than a mile to Okemo Mountain

Apartment in Ludlow

Well-appointed studio right downtown - less than a mile to Okemo Mountain
8.6 out of 10, Excellent, (12)
"Clean with everything we needed for a few nights stay."
United States
Sandra S.
The price is AED 437
AED 1,311 total
includes taxes & fees
12 Jan - 13 Jan
Well-appointed studio right downtown - less than a mile to Okemo Mountain
Golf
Efficient condo near slopes with kitchenette & great location

Apartment in Ludlow

Efficient condo near slopes with kitchenette & great location
8.6 out of 10, Excellent, (32)
"Nice place close to mountain easy in easy out"
United States
Aaron B.
The price is AED 433
AED 980 total
includes taxes & fees
12 Jan - 13 Jan
Efficient condo near slopes with kitchenette & great location
Interior
Perfect Getaway! Cozy, Modern & Convenience to Everything!

Apartment in Ludlow

Perfect Getaway! Cozy, Modern & Convenience to Everything!
9.8 out of 10, Exceptional, (76)
"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! "
United States
Vanessa
The price is AED 507
AED 1,146 total
includes taxes & fees
19 Jan - 20 Jan
Perfect Getaway! Cozy, Modern & Convenience to Everything!
Indoor pool, a heated pool
Equinox Haven | King Room + Culinary Delights

Apartment in Manchester Village Historic District

Equinox Haven | King Room + Culinary Delights
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 AED 771
AED 961 total
includes taxes & fees
4 Feb - 5 Feb
Equinox Haven | King Room + Culinary Delights
Indoor pool
Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn

Apartment in Dover

Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn
9.6 out of 10, Exceptional, (5)
"Amazing experience at Mount Snow! Leah is the best owner! Attentive and accessible. "
United States
Jayanne S.
The price is AED 1,212
AED 2,403 total
includes taxes & fees
1 Feb - 2 Feb
Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn
Exterior
Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102

Apartment in Killington

Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102
9.0 out of 10, Wonderful, (7)
"Great room, plenty of amenities, close to restaurants and mountains"
United States
Daniel T.
The price is AED 586
AED 850 total
includes taxes & fees
11 Jan - 12 Jan
Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102
Property grounds
Long Trail Studio | 10 Min to Killington

Apartment in Bridgewater

Long Trail Studio | 10 Min to Killington
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 AED 404
AED 848 total
includes taxes & fees
8 Jan - 9 Jan
Long Trail Studio | 10 Min to Killington
Outdoor dining
Okemo | Spacious Executive Room w Amenities Nearby

Apartment in Jackson Gore Base Area

Okemo | Spacious Executive Room w Amenities Nearby
8.0 out of 10, Very Good, (1)
The price is AED 1,587
AED 1,990 total
includes taxes & fees
13 Jan - 14 Jan
Okemo | Spacious Executive Room w Amenities Nearby
Property grounds
Ben & Jerry’s Studio | 10 Min to Killington

Apartment in Bridgewater

Ben & Jerry’s Studio | 10 Min to Killington
9.2 out of 10, Wonderful, (7)
"Overall, a great stay. "
United States
Meghan J.
The price is AED 356
AED 791 total
includes taxes & fees
12 Jan - 13 Jan
Ben & Jerry’s Studio | 10 Min to Killington
Property grounds
2 Queen Studio | 10 Min to Killington | Ski Base

Apartment in Bridgewater

2 Queen Studio | 10 Min to Killington | Ski Base
8.8 out of 10, Excellent, (5)
"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 AED 466
AED 920 total
includes taxes & fees
8 Jan - 9 Jan
2 Queen Studio | 10 Min to Killington | Ski Base
Terrace/patio
Deluxe Studio | Murphy Bed + Sofa

Apartment in West Dover

Deluxe Studio | Murphy Bed + Sofa
The price is AED 1,333
AED 1,681 total
includes taxes & fees
13 Jan - 14 Jan
Deluxe Studio | Murphy Bed + Sofa
Terrace/patio
Cozy Studio | Ski-In Access + Kitchenette

Apartment in West Dover

Cozy Studio | Ski-In Access + Kitchenette
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 AED 1,245
AED 1,555 total
includes taxes & fees
13 Jan - 14 Jan
Cozy Studio | Ski-In Access + Kitchenette
Exterior
Cozy Studio Condo with Great Location, WiFi & Kitchenette

Apartment in Ludlow

Cozy Studio Condo with Great Location, WiFi & Kitchenette
8.8 out of 10, Excellent, (29)
"Great location and great place!"
United States
Linda G.
The price is AED 433
AED 1,015 total
includes taxes & fees
12 Jan - 13 Jan
Cozy Studio Condo with Great Location, WiFi & Kitchenette
Indoor pool, a heated pool
Grand Equinox | 2 Queen Room + Adventure Delights

Apartment in Manchester Village Historic District

Grand Equinox | 2 Queen Room + Adventure Delights
8.0 out of 10, Very Good, (1)
"Yes, but you have to drive to town "
United States
Cathy W.
The price is AED 901
AED 1,133 total
includes taxes & fees
4 Feb - 5 Feb
Grand Equinox | 2 Queen Room + Adventure Delights
Pool
Equinox Getaway | Queen Room + Culinary Delights

Apartment in Manchester Village Historic District

Equinox Getaway | Queen Room + Culinary Delights
The price is AED 740
AED 910 total
includes taxes & fees
4 Feb - 5 Feb
Equinox Getaway | Queen Room + Culinary Delights
Indoor pool
Accessible Retreat | King Room + Mountain View

Apartment in Manchester Village Historic District

Accessible Retreat | King Room + Mountain View
The price is AED 771
AED 973 total
includes taxes & fees
4 Feb - 5 Feb
Accessible Retreat | 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

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

10/10 Excellent
"Staff, cleanliness, ambience, restaurant, all perfect! We can’t wait to return! "
Heather 1-night trip
Posted 2 days ago
Kimpton Taconic Hotel 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 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 some favorite sights in the larger region like Okemo Mountain Resort and 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: The Owl's Nest A Cozy 1-bed studio apartment in Bridgewater: Situated in Bridgewater, 22.1 mi/35.6 km from the heart of Chester. Stratton South Long Trail Studio Adjacent to the Village and Lifts: Located 18.7 mi/30 km away in Stratton. Private balconies, fireplaces, and sofa beds are included. Onsite laundry facilities and an outdoor pool are on site. 2BR 1BA - 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. Efficient condo near slopes with kitchenette & great location: 10.9 mi/17.5 km away in Ludlow. Amenities include sofa beds. Long Trail House Studio at Stratton Mountain Resort: Located in Stratton, 18.7 mi/30 km from Chester. Includes fireplaces and sofa beds. Onsite laundry facilities and a hot tub 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. Bonnie's Bundles Dolls and DaVallia Art & Accents are a couple of family-friendly sights. You'll find favorite places to visit like Okemo Mountain Resort and Stratton Mountain Resort 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.