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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Chester apartments

Outdoor pool, a heated pool

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dover
9.4 out of 10, Exceptional, (23 reviews)
"Location was excellent, hosts were responsive, cozy little place with the fireplace, great stay!"
United States
Tania J.
The price is €396
includes taxes & fees
31 Jul - 1 Aug
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Exterior

Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna

Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
Stratton
The price is €210
includes taxes & fees
19 Jul - 20 Jul
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
Coffee/tea maker, fridge, microwave, oven

Quiet Apt. close to Okemo and Killington. Off Rt. 7 with private driveway.

Quiet Apt. close to Okemo and Killington. Off Rt. 7 with private driveway.
Wallingford
10.0 out of 10, Exceptional, (2 reviews)
"Great stay as always. "
United States
debbie r.
The price is €156
includes taxes & fees
29 Jul - 30 Jul
Quiet Apt. close to Okemo and Killington. Off Rt. 7 with private driveway.
Golf

Efficient condo near slopes with kitchenette & great location

Efficient condo near slopes with kitchenette & great location
Ludlow
8.6 out of 10, Excellent, (33 reviews)
"the home was clean and very nice. "
United States
Frank R.
The price is €207
includes taxes & fees
20 Jul - 21 Jul
Efficient condo near slopes with kitchenette & great location
Exterior

Cozy Studio Condo with Great Location, WiFi & Kitchenette

Cozy Studio Condo with Great Location, WiFi & Kitchenette
Ludlow
8.6 out of 10, Excellent, (32 reviews)
"Small but well organized and super convenient!"
United States
Mikhail R.
The price is €213
includes taxes & fees
23 Jul - 24 Jul
Cozy Studio Condo with Great Location, WiFi & Kitchenette
Children’s area

Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.4 out of 10, Exceptional, (14 reviews)
"Nice place "
United States
Janja L.
The price is €291
includes taxes & fees
19 Jul - 20 Jul
Cozy Bromley Retreat
Exterior

Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.

Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.
Ludlow
9.8 out of 10, Exceptional, (16 reviews)
"Great stay, house is clean and has everything you’de ever need. Perfect location to explore the ludlow area. Thanks Bob, we enjoyed ourselves "
United States
Tyler
The price is €224
includes taxes & fees
30 Jul - 31 Jul
Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.
Interior

103 Deluxe One bedroom Queen Suite w/ outdoor heated pool

103 Deluxe One bedroom Queen Suite w/ outdoor heated pool
Killington
9.6 out of 10, Exceptional, (18 reviews)
"Would stay again!"
United States
Hannah M.
The price is €142
includes taxes & fees
23 Jul - 24 Jul
103 Deluxe One bedroom Queen Suite w/ outdoor heated pool
Smart TV

Long Trail House South Wing 2B2B Condo

Long Trail House South Wing 2B2B Condo
Stratton
10.0 out of 10, Exceptional, (2 reviews)
"Very clean 2br 2ba condo in excellent location. Host provided detailed important information that helped us find property and how to access unit. I would definitely recommend staying here."
United States
Eileen R.
The price is €371
includes taxes & fees
26 Jul - 27 Jul
Long Trail House South Wing 2B2B Condo
Outdoor dining

Okemo | Studio Condo + Close to All Amenities

Okemo | Studio Condo + Close to All Amenities
Jackson Gore Base Area
The price is €197
includes taxes & fees
19 Jul - 20 Jul
Okemo | Studio Condo + Close to All Amenities
Golf

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

Well-appointed studio right downtown - less than a mile to Okemo Mountain
Ludlow
8.8 out of 10, Excellent, (13 reviews)
"This place was so close to Okemo, and walking distance to the local pub and restaurants."
United States
Brian
The price is €276
includes taxes & fees
19 Jul - 20 Jul
Well-appointed studio right downtown - less than a mile to Okemo Mountain
Private kitchen

Modern Mountain Retreat w/ Chef’s Kitchen

Modern Mountain Retreat w/ Chef’s Kitchen
Manchester
The price is €440
includes taxes & fees
18 Aug - 19 Aug
Modern Mountain Retreat w/ Chef’s Kitchen
Terrace/patio

Ski-In/Ski-Out ADA Studio w/ Kitchenette!

Ski-In/Ski-Out ADA Studio w/ Kitchenette!
West Dover
The price is €176
includes taxes & fees
20 Jul - 21 Jul
Ski-In/Ski-Out ADA Studio w/ Kitchenette!
Exterior

Deluxe Studio | Murphy Bed + Sofa

Deluxe Studio | Murphy Bed + Sofa
West Dover
The price is €205
includes taxes & fees
20 Jul - 21 Jul
Deluxe Studio | Murphy Bed + Sofa
Smart TV, fireplace

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

6BR 3BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Dover
8.0 out of 10, Very good, (1 review)
"Location to Mount snow was great for skiing. Plenty of room for everyone to enjoy. The house has not been properly maintained though. Despite that, we did enjoy ourselves."
United States
Ian T.
The price is €695
includes taxes & fees
21 Jul - 22 Jul
6BR 3BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Outdoor dining

Okemo | Studio Condo + Loft | Near Slopes + Pool

Okemo | Studio Condo + Loft | Near Slopes + Pool
Jackson Gore Base Area
10.0 out of 10, Exceptional, (2 reviews)
"Very conveinent check in, nice property."
United States
michael
The price is €236
includes taxes & fees
26 Jul - 27 Jul
Okemo | Studio Condo + Loft | Near Slopes + Pool
Outdoor dining

Okemo | Charming Room & Amenities Nearby | Pools

Okemo | Charming Room & Amenities Nearby | Pools
Jackson Gore Base Area
The price is €209
includes taxes & fees
20 Jul - 21 Jul
Okemo | Charming Room & Amenities Nearby | Pools
Outdoor dining

Okemo | Spacious Executive Room w Amenities Nearby

Okemo | Spacious Executive Room w Amenities Nearby
Jackson Gore Base Area
9.0 out of 10, Wonderful, (2 reviews)
"We waited outside the room for 30 minutes to check in at exactly 5 PM when it was obvious that the room was ready earlier. The lack of early check in was a hassle."
United States
David K.
The price is €192
includes taxes & fees
23 Jul - 24 Jul
Okemo | Spacious Executive Room w Amenities Nearby
Pool

Equinox Getaway | Queen Guest Room w/ Sauna & Spa

Equinox Getaway | Queen Guest Room w/ Sauna & Spa
Manchester Village Historic District
The price is €272
includes taxes & fees
17 Aug - 18 Aug
Equinox Getaway | Queen Guest Room w/ Sauna & Spa
Exterior

Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102

Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102
Killington
8.8 out of 10, Excellent, (8 reviews)
"Great room, plenty of amenities, close to restaurants and mountains"
United States
Daniel T.
The price is €142
includes taxes & fees
26 Jul - 27 Jul
Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102
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

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"Thoughtful and attentive staff"
Charles 1-night trip
Posted 9 hours ago
Keene Elm City Hotel, an Ascend Collection Hotel

Find out more about Chester

Chester Apartments information

Number of reviews
138
Accommodation
154 Apartments
Lowest Price
€142
Highest Price
€695

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 61 accommodation options. Though there aren't many apartments, we can help you search for accommodation that is similar. When you search for a place to stay on Expedia, you can use the filters to search for a kitchen— one of the conveniences often found in an apartment. You can also filter by similar property types like condos, holiday homes or cottages. During your trip, you can explore this quaint area's ski slopes and shops.
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?
Listed below are some of the top apartments in the area: Hawks Mountain Farm, full apartment on a working farm.: Includes free WiFi, a patio and a sofa bed . Charming King Loft in Downtown Woodstock: Located 25.4 mi/40.8 km away in Woodstock . Free WiFi and a Smart TV are included . Access to on-site laundry facilities is available on site . Carriage House Studio Apt- secluded, mountain views, babbling brook, countryside: Located in Dorset , 22.8 mi/36.8 km away. Includes free WiFi, a balcony and a fireplace . Access to on-site laundry facilities is available on site . Lakeside Spofford Retreat Near Hiking & Boating!: It's situated in Spofford , 26 mi/41.8 km from Chester.
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. Vermont Country Store and Lowell Lake State Park are a couple of places you'll find 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.