Search Apartments in Chester

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Apartments in Chester

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

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 AED 143
AED 933 total
includes taxes & fees
1 Dec - 2 Dec
2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

Woodstock Suite | 10 Min to Mountains |A/C| Hiking

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 AED 290
AED 707 total
includes taxes & fees
20 Nov - 21 Nov
Woodstock Suite | 10 Min to Mountains |A/C| Hiking

Cozy Bromley Retreat

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 AED 333
AED 1,194 total
includes taxes & fees
20 Nov - 21 Nov
Cozy Bromley Retreat

Cozy apt in beautiful secluded spot 15 mins from Mt Snow

Dover
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
30 Nov - 1 Dec
Cozy apt in beautiful secluded spot 15 mins from Mt Snow

Efficient condo near slopes with kitchenette & great location

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 AED 290
AED 751 total
includes taxes & fees
1 Dec - 2 Dec
Efficient condo near slopes with kitchenette & great location

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

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 AED 290
AED 926 total
includes taxes & fees
1 Dec - 2 Dec
Well-appointed studio right downtown - less than a mile to Okemo Mountain

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

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 AED 545
AED 1,538 total
includes taxes & fees
20 Nov - 21 Nov
Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn

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

Ludlow
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!"
United States
Alessia
The price is AED 713
AED 1,643 total
includes taxes & fees
30 Nov - 1 Dec
Remodeled condo with free WiFi & shared W/D - ski bus pickup across street

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

Dover
The price is AED 746
AED 2,636 total
includes taxes & fees
15 Dec - 16 Dec
6BR 3BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

Entire private apartment suite in home with own entrance, views and private gym.

Keene
The price is AED 1,010
AED 1,463 total
includes taxes & fees
19 Dec - 20 Dec
Entire private apartment suite in home with own entrance, views and private gym.

Equinox Haven | King Room + Culinary Delights

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 AED 653
AED 813 total
includes taxes & fees
20 Nov - 21 Nov
Equinox Haven | King Room + Culinary Delights

2 Queens | 10 Mins to the Mountains | Foliage

Bridgewater
8.8 out of 10, Excellent, (5)
"As advertised"
United States
mark r.
The price is AED 294
AED 711 total
includes taxes & fees
20 Nov - 21 Nov
2 Queens | 10 Mins to the Mountains | Foliage

Cozy Studio | Ski-In Access + Kitchenette

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 AED 1,014
AED 1,278 total
includes taxes & fees
20 Nov - 21 Nov
Cozy Studio | Ski-In Access + Kitchenette

Okemo | Spacious Executive Room w Amenities Nearby

Jackson Gore Base Area
8.0 out of 10, Very Good, (1)
The price is AED 859
AED 1,087 total
includes taxes & fees
23 Nov - 24 Nov
Okemo | Spacious Executive Room w Amenities Nearby

Deluxe Studio | Murphy Bed + Sofa

West Dover
The price is AED 1,084
AED 1,376 total
includes taxes & fees
20 Nov - 21 Nov
Deluxe Studio | Murphy Bed + Sofa

Long Trail Suite | 10 Mins to Mountains | Skiing

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 AED 272
AED 683 total
includes taxes & fees
1 Dec - 2 Dec
Long Trail Suite | 10 Mins to Mountains | Skiing

Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102

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 AED 667
AED 958 total
includes taxes & fees
3 Dec - 4 Dec
Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102

Ben & Jerry Suite | Skiing | Hiking | Biking

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 AED 294
AED 711 total
includes taxes & fees
1 Dec - 2 Dec
Ben & Jerry Suite | Skiing | Hiking | Biking

Cozy Studio Condo with Great Location, WiFi & Kitchenette

Ludlow
8.8 out of 10, Excellent, (29)
"Great location and great place!"
United States
Linda G.
The price is AED 290
AED 786 total
includes taxes & fees
1 Dec - 2 Dec
Cozy Studio Condo with Great Location, WiFi & Kitchenette

Equinox Getaway | Queen Room + Culinary Delights

Manchester
The price is AED 618
AED 763 total
includes taxes & fees
20 Nov - 21 Nov
Equinox Getaway | Queen Room + Culinary Delights
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chester Hotel Reviews

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 68 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: Long Trail House Studio at Stratton Mountain Resort: Located in Stratton, 18.7 mi/30 km from the heart of Chester. Includes fireplaces and sofa beds. Onsite laundry facilities and a hot tub are on site. Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn: Located 25 mi/40.3 km away in West Dover. Private balconies, fireplaces, and separate dining areas are included. Onsite laundry facilities and an indoor 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 private balconies, fireplaces, and sofa beds. Onsite laundry facilities and an outdoor pool are on site. Nana's House: 22.2 mi/35.7 km away in Bridgewater. Free WiFi and Smart TVs are included. Deluxe Studio | Murphy Bed + Sofa: Located in West Dover, 25.4 mi/40.9 km from Chester. Includes free WiFi. 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. Stratton Mountain Resort 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.