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Check prices for these dates

In two weeks
26 Jun - 28 Jun
In two months
7 Aug - 9 Aug
In three months
4 Sept - 6 Sept
In four months
2 Oct - 4 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 £244
includes taxes & fees
24 Jun - 25 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.
The price is £245
includes taxes & fees
14 Jun - 15 Jun
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 £155
includes taxes & fees
30 Jun - 1 Jul
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
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 £121
includes taxes & fees
14 Jun - 15 Jun
Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102
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 £133
includes taxes & fees
24 Jun - 25 Jun
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 £297
includes taxes & fees
15 Jun - 16 Jun
Historic Home with Colonial Charm in Manchester
Private kitchen

Modern Mountain Retreat w/ Chef’s Kitchen

Modern Mountain Retreat w/ Chef’s Kitchen
Manchester
The price is £334
includes taxes & fees
16 Jun - 17 Jun
Modern Mountain Retreat w/ Chef’s Kitchen
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 £200
includes taxes & fees
17 Jun - 18 Jun
Okemo | Studio Condo + Loft | Near Slopes + Pool
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 £164
includes taxes & fees
15 Jun - 16 Jun
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 £531
includes taxes & fees
24 Jun - 25 Jun
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 £297
includes taxes & fees
14 Jun - 15 Jun
Long Trail House South Wing 2B2B Condo
Terrace/patio

Deluxe Studio | Murphy Bed + Sofa

Deluxe Studio | Murphy Bed + Sofa
West Dover
The price is £172
includes taxes & fees
15 Jun - 16 Jun
Deluxe Studio | Murphy Bed + Sofa
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 £121
includes taxes & fees
22 Jun - 23 Jun
103 Deluxe One bedroom Queen Suite w/ outdoor heated pool
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 £569
includes taxes & fees
13 Jun - 14 Jun
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 £174
includes taxes & fees
22 Jun - 23 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 £181
includes taxes & fees
22 Jun - 23 Jun
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 £160
includes taxes & fees
22 Jun - 23 Jun
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 £163
includes taxes & fees
15 Jun - 16 Jun
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

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

10/10 Excellent
"I can’t say enough about the Frontenac. The staff was sincerely friendly and went out of their way to help us with whatever we needed. We left the Fairmont Frontenac to head back to Connecticut. When we got back, my sister realized she left her Kindle in her room. We called to see if it had been found. They put us on hold got right back to us and said they had it and would send it to her address. The location is ideal. The rooms are immaculate. The people that came to our rooms for the turndown service. We’re very sweet with big smiles on their face as they brought us freshwater/free every evening. This is the third time I’ve been to the Frantenac. I’m sure it won’t be our last."
Richard 1-night trip
Posted 12 hours ago
Kimpton Taconic Hotel by IHG

Find out more about Chester

Chester Apartments information

Number of reviews
9,207
Accommodation
155 Apartments
Lowest Price
£71
Highest Price
£196

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 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 relaxing 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 . 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 a Smart TV . Access to on-site laundry facilities is available on site .
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.