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Check prices for these dates

In two weeks
Jun 26 - Jun 28
In two months
Aug 7 - Aug 9
In three months
Sep 4 - Sep 6
In four months
Oct 2 - Oct 4

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 CA $95
CA $412 total
includes taxes & fees
Jun 16 - Jun 17
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Children's area

Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.6 out of 10, Exceptional, (12 reviews)
"The best stay ever!!! Very clean, great location, super cozy, all the amenities you would need. 5/5 stars, we will be coming back :)"
United States
Carolina I.
The price is CA $126
CA $457 total
includes taxes & fees
Jun 11 - Jun 12
Cozy Bromley Retreat
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 CA $145
CA $220 total
includes taxes & fees
Jun 11 - Jun 12
103 Deluxe One bedroom Queen Suite w/ outdoor heated pool
Interior

Cozy apt in beautiful secluded spot 15 mins from Mt Snow

Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Dover
10.0 out of 10, Exceptional, (4 reviews)
"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 CA $119
CA $284 total
includes taxes & fees
Jun 30 - Jul 1
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Shower, hair dryer, towels, soap

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, (1 review)
"Great stay as always. "
United States
debbie r.
The price is CA $119
CA $243 total
includes taxes & fees
Jun 12 - Jun 13
Quiet Apt. close to Okemo and Killington. Off Rt. 7 with private driveway.
Dining

Historic Home with Colonial Charm in Manchester

Historic Home with Colonial Charm in Manchester
Manchester
10.0 out of 10, Exceptional, (2 reviews)
"The accommodations were absolutely amazing. We had a wonderful time. The home is beautiful. The host is very communicative."
United States
Victor G.
The price is CA $151
CA $555 total
includes taxes & fees
Jun 15 - Jun 16
Historic Home with Colonial Charm in Manchester
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 CA $292
CA $373 total
includes taxes & fees
Jun 14 - Jun 15
Okemo | Studio Condo + Loft | Near Slopes + Pool
Private kitchen

Modern Mountain Retreat w/ Chef’s Kitchen

Modern Mountain Retreat w/ Chef’s Kitchen
Manchester
The price is CA $205
CA $626 total
includes taxes & fees
Jun 16 - Jun 17
Modern Mountain Retreat w/ Chef’s Kitchen
Terrace/patio

Cozy Studio | Ski-In Access + Kitchenette

Cozy Studio | Ski-In Access + Kitchenette
West Dover
10.0 out of 10, Exceptional, (3 reviews)
"Fabulous! Clean, accommodating staff, great amenities, beautiful view, super easy access to skiing! Would def stay here again. "
United States
Kathy S.
The price is CA $236
CA $301 total
includes taxes & fees
Jun 17 - Jun 18
Cozy Studio | Ski-In Access + Kitchenette
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 CA $268
CA $995 total
includes taxes & fees
Jun 23 - Jun 24
6BR 3BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Smart TV

Long Trail House South Wing 2B2B Condo

Long Trail House South Wing 2B2B Condo
Stratton
The price is CA $226
CA $560 total
includes taxes & fees
Jun 11 - Jun 12
Long Trail House South Wing 2B2B Condo
Terrace/patio

Deluxe Studio | Murphy Bed + Sofa

Deluxe Studio | Murphy Bed + Sofa
West Dover
The price is CA $256
CA $325 total
includes taxes & fees
Jun 16 - Jun 17
Deluxe Studio | Murphy Bed + Sofa
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 CA $145
CA $220 total
includes taxes & fees
Jun 11 - Jun 12
Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102
Interior

The Treehouse at 11 Gables Ludlow – Dining, Shopping & Okemo Shuttle

The Treehouse at 11 Gables Ludlow – Dining, Shopping & Okemo Shuttle
Ludlow
10.0 out of 10, Exceptional, (1 review)
"Cute place right in town, super convenient to the mountain (although if you’re relying on the shuttle it’s only once an hour so can be annoying if you don’t time it well). Rooms comfortably slept 4 plus one on the sofa bed, annd everything was in good shape, Andrew and Jillian were great hosts!"
United States
Max R.
The price is CA $473
CA $1,071 total
includes taxes & fees
Jun 11 - Jun 12
The Treehouse at 11 Gables Ludlow – Dining, Shopping & Okemo Shuttle
Outdoor dining

Okemo | Charming Room & Amenities Nearby | Pools

Okemo | Charming Room & Amenities Nearby | Pools
Jackson Gore Base Area
The price is CA $256
CA $321 total
includes taxes & fees
Jun 18 - Jun 19
Okemo | Charming Room & Amenities Nearby | Pools
Outdoor dining

Okemo | Studio Condo + Close to All Amenities

Okemo | Studio Condo + Close to All Amenities
Jackson Gore Base Area
The price is CA $266
CA $334 total
includes taxes & fees
Jun 24 - Jun 25
Okemo | Studio Condo + Close to All Amenities
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 CA $235
CA $295 total
includes taxes & fees
Jun 24 - Jun 25
Okemo | Spacious Executive Room w Amenities Nearby
Terrace/patio

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

Ski-In/Ski-Out ADA Studio w/ Kitchenette!
West Dover
The price is CA $239
CA $303 total
includes taxes & fees
Jun 16 - Jun 17
Ski-In/Ski-Out ADA Studio w/ Kitchenette!
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

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

10/10 Excellent
"Very clean facility. The breakfast had a large selection. Comfortable beds. Friendly staff. Quiet area."
Dawn 1-night trip
Posted 20 hours ago
Best Western Plus Keene Hotel

Find out more about Chester

Chester Apartments information

Number of reviews
51
Accommodation
154 Apartments
Lowest Price
CA $220
Highest Price
CA $1,071

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 60 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 relaxing 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. Lake-View Spofford Apartment w/ Shared Dock!: Located 26 mi/41.8 km away in Spofford. Charming King Loft in Downtown Woodstock: Located in Woodstock, 25.4 mi/40.8 km away. Includes free WiFi and Smart TVs. Access to onsite laundry facilities is available 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 Country Store and Lowell Lake State Park 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.

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