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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

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 AED 225
AED 1,151 total
includes taxes & fees
28 Jun - 29 Jun
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.
Cozy Bromley Retreat
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 AED 312
AED 747 total
includes taxes & fees
30 Jun - 1 Jul
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
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 AED 274
AED 829 total
includes taxes & fees
28 Jun - 29 Jun
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
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 AED 382
AED 578 total
includes taxes & fees
28 Jun - 29 Jun
103 Deluxe One bedroom Queen Suite w/ outdoor heated pool
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 AED 366
AED 852 total
includes taxes & fees
28 Jun - 29 Jun
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 AED 366
AED 877 total
includes taxes & fees
28 Jun - 29 Jun
Cozy Studio Condo with Great Location, WiFi & Kitchenette
Fridge, microwave, oven, stovetop

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 AED 314
AED 640 total
includes taxes & fees
8 Jul - 9 Jul
Quiet Apt. close to Okemo and Killington. Off Rt. 7 with private driveway.
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 AED 769
AED 983 total
includes taxes & fees
29 Jun - 30 Jun
Okemo | Studio Condo + Loft | Near Slopes + Pool
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 AED 670
AED 2,513 total
includes taxes & fees
13 Jul - 14 Jul
6BR 3BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
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 AED 621
AED 791 total
includes taxes & fees
29 Jun - 30 Jun
Cozy Studio | Ski-In Access + Kitchenette
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 AED 577
AED 1,685 total
includes taxes & fees
30 Jun - 1 Jul
Historic Home with Colonial Charm in Manchester
Smart TV

Long Trail House South Wing 2B2B Condo

Long Trail House South Wing 2B2B Condo
Stratton
The price is AED 595
AED 1,473 total
includes taxes & fees
28 Jun - 29 Jun
Long Trail House South Wing 2B2B Condo
Exterior

Deluxe Studio | Murphy Bed + Sofa

Deluxe Studio | Murphy Bed + Sofa
West Dover
The price is AED 665
AED 835 total
includes taxes & fees
29 Jun - 30 Jun
Deluxe Studio | Murphy Bed + Sofa
Private kitchen

Modern Mountain Retreat w/ Chef’s Kitchen

Modern Mountain Retreat w/ Chef’s Kitchen
Manchester
The price is AED 713
AED 1,847 total
includes taxes & fees
28 Jun - 29 Jun
Modern Mountain Retreat w/ Chef’s Kitchen
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 AED 366
AED 1,134 total
includes taxes & fees
28 Jun - 29 Jun
Well-appointed studio right downtown - less than a mile to Okemo Mountain
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 AED 1,245
AED 2,820 total
includes taxes & fees
28 Jun - 29 Jun
The Treehouse at 11 Gables Ludlow – Dining, Shopping & Okemo Shuttle
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 AED 382
AED 578 total
includes taxes & fees
5 Jul - 6 Jul
Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102
Outdoor dining

Okemo | Charming Room & Amenities Nearby | Pools

Okemo | Charming Room & Amenities Nearby | Pools
Jackson Gore Base Area
The price is AED 673
AED 852 total
includes taxes & fees
28 Jun - 29 Jun
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 AED 701
AED 888 total
includes taxes & fees
28 Jun - 29 Jun
Okemo | Studio Condo + Close to All Amenities
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

Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"The staff were very professional. Hotel was clean and very nice"
Lauren 2-night trip
Posted 4 hours ago
Hampton Inn Brattleboro

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 62 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?
Below 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. Carriage House Studio Apt- secluded, mountain views, babbling brook, countryside: Located in Dorset, 22.8 mi/36.8 km away. Includes free WiFi, private balconies, and fireplaces. Access to onsite laundry facilities is available on site. Charming King Loft in Downtown Woodstock: Located 25.4 mi/40.8 km away in Woodstock. Free WiFi and Smart TVs are included. Access to onsite laundry facilities is available on site. Lake-View Spofford Apartment w/ Shared Dock!: It's situated in Spofford, 26 mi/41.8 km from Chester.
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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