A covered wooden bridge over a river, surrounded by rocky terrain and greenery.

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Chester apartments

A golf course with a winding path, trees, and a distant mountain range.

1. 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 £174
includes taxes & fees
15 Sept - 16 Sept
Efficient condo near slopes with kitchenette & great location
A two-story house with a porch, a staircase, and a front door.

2. 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 £179
includes taxes & fees
15 Sept - 16 Sept
Cozy Studio Condo with Great Location, WiFi & Kitchenette
A cabin with a large, curved roof and a smaller adjacent structure, surrounded by dense forest and mountains in the background.

3. 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 £234
includes taxes & fees
16 Sept - 17 Sept
Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.
A golf course with a winding path, trees, and a hilly landscape.

4. 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 £232
includes taxes & fees
15 Sept - 16 Sept
Well-appointed studio right downtown - less than a mile to Okemo Mountain
A building with a sign reading 'Fire Tower Restaurant & Tavern.'

5. 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 £170
includes taxes & fees
15 Sept - 16 Sept
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
A playground with slides and climbing structures surrounded by trees.

6. Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.4 out of 10, Exceptional, (19 reviews)
"Nice place "
United States
Janja L.
The price is £287
includes taxes & fees
15 Sept - 16 Sept
Cozy Bromley Retreat
A rectangular pool with a brick deck, surrounded by lounge chairs and umbrellas.

7. 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 £232
includes taxes & fees
21 Sept - 22 Sept
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
A multi-story building with a red and yellow facade, surrounded by lush greenery and flowering plants.

8. 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 £206
includes taxes & fees
15 Sept - 16 Sept
Okemo | Spacious Executive Room w Amenities Nearby
A two-story house with a green roof, a covered porch, and a driveway with a parked car.

9. Bridgewater Living - Ski VT Suite

Bridgewater Living - Ski VT Suite
Bridgewater
The price is £173
includes taxes & fees
15 Sept - 16 Sept
Bridgewater Living - Ski VT Suite
A red building with a bear logo, a stone pathway, and neatly trimmed bushes.

10. 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 £127
includes taxes & fees
15 Sept - 16 Sept
Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102
A dining room with a wooden table, four chairs, a vase with flowers, and a view of greenery outside.

11. 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 £329
includes taxes & fees
29 Sept - 30 Sept
Historic Home with Colonial Charm in Manchester
A living room with a television, sofa, and coffee table.

12. Long Trail House South Wing 2B2B Condo

Long Trail House South Wing 2B2B Condo
Stratton
10.0 out of 10, Exceptional, (4 reviews)
"Great location. Very clean accomodations with comfortable beds! Host was very communicative as well!"
United States
carlene p.
The price is £368
includes taxes & fees
22 Sept - 23 Sept
Long Trail House South Wing 2B2B Condo
A modern kitchen with a large island, stainless steel appliances, and pendant lighting.

13. Modern Mountain Retreat w/ Chef’s Kitchen

Modern Mountain Retreat w/ Chef’s Kitchen
Manchester
10.0 out of 10, Exceptional, (1 review)
"Communication with Caroline was top notch and speedy! Very clear instructions for accessing the property and check out. Even though this place is connected with two other rooms/units ( I think that is what it is) we never heard them and hopefully we didn't bother them either!The house was amazing inside and out. The location was exceptional!Thank you for a beautiful stay!"
United States
Eva G.
The price is £360
includes taxes & fees
20 Sept - 21 Sept
Modern Mountain Retreat w/ Chef’s Kitchen
A rustic interior with a wooden staircase, a kitchen area, and a seating area with a sofa and table.

14. 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 £789
includes taxes & fees
18 Sept - 19 Sept
The Treehouse at 11 Gables Ludlow – Dining, Shopping & Okemo Shuttle
A multi-story building with a red and yellow facade, surrounded by lush greenery and flowering plants.

15. Okemo | Charming Room & Amenities Nearby | Pools

Okemo | Charming Room & Amenities Nearby | Pools
Jackson Gore Base Area
The price is £208
includes taxes & fees
15 Sept - 16 Sept
Okemo | Charming Room & Amenities Nearby | Pools
An indoor swimming pool with a tiled floor, a pool table, and a bar area.

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

Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn
Dover
9.6 out of 10, Exceptional, (5 reviews)
"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 £322
includes taxes & fees
16 Sept - 17 Sept
Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn
A multi-story building with a red and yellow facade, surrounded by lush greenery and flowering plants.

17. Okemo | Studio Condo + Close to All Amenities

Okemo | Studio Condo + Close to All Amenities
Jackson Gore Base Area
The price is £214
includes taxes & fees
15 Sept - 16 Sept
Okemo | Studio Condo + Close to All Amenities
A multi-story building with a red and yellow facade, surrounded by lush greenery and flowering plants.

18. 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 £235
includes taxes & fees
21 Sept - 22 Sept
Okemo | Studio Condo + Loft | Near Slopes + Pool
A white building with a porch, a signboard, and a road with a white fence in the background.

19. Bridgewater Living - Ben&Jerry Suite

Bridgewater Living - Ben&Jerry Suite
Bridgewater
The price is £174
includes taxes & fees
15 Sept - 16 Sept
Bridgewater Living - Ben&Jerry Suite
A two-story house with a front porch, a staircase, and a small garden area.

20. Central Large 2-bedrooms with office in Keene

Central Large 2-bedrooms with office in Keene
Keene
9.8 out of 10, Exceptional, (6 reviews)
"Friendly hosts and excellent location to walk to downtown."
United States
Joshua
The price is £167
includes taxes & fees
21 Sept - 22 Sept
Central Large 2-bedrooms with office in Keene
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

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

10/10 Excellent
"Clean and quiet. Comfortable beds. Plenty of coffee."
Steve 1-night trip
Posted 8 hours ago
Days Inn by Wyndham Keene NH

Find out more about Chester

Chester Apartments information

Number of reviews
5,540
Accommodation
174 Apartments
Lowest Price
£70
Highest Price
£180

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 64 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?
Below are some of the more popular apartments in the area: Hawks Mountain Farm, full apartment on a working farm.: Includes free WiFi, a patio and a sofa bed . Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.: Located in Ludlow , 10.4 mi/16.7 km away. Includes free WiFi, a patio and a fireplace . A fitness centre and on-site laundry facilities are on site . 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 . Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna: Located in Stratton , 18.7 mi/30 km from Chester. Includes free WiFi, a balcony and a fireplace . A fitness centre and 1 hot tub are 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.