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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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 CA $141
CA $322 total
includes taxes & fees
Oct 20 - Oct 21
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 CA $141
CA $330 total
includes taxes & fees
Oct 20 - Oct 21
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 CA $255
CA $439 total
includes taxes & fees
Sep 30 - Oct 1
Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.
A building with a sign reading 'Fire Tower Restaurant & Tavern.'

4. 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 CA $105
CA $316 total
includes taxes & fees
Sep 30 - Oct 1
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
A playground with slides and climbing structures surrounded by trees.

5. Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.4 out of 10, Exceptional, (20 reviews)
"Nice place "
United States
Janja L.
The price is CA $182
CA $529 total
includes taxes & fees
Oct 18 - Oct 19
Cozy Bromley Retreat
A bedroom with a bed, bedside table, lamp, and curtains.

6. Modern 3BR/2BA | 3 Min to Okemo Mountain

Modern 3BR/2BA | 3 Min to Okemo Mountain
Ludlow
The price is CA $269
CA $850 total
includes taxes & fees
Oct 20 - Oct 21
Modern 3BR/2BA | 3 Min to Okemo Mountain
A golf course with a winding path, trees, and a hilly landscape.

7. 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 CA $141
CA $433 total
includes taxes & fees
Oct 21 - Oct 22
Well-appointed studio right downtown - less than a mile to Okemo Mountain
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 CA $308
CA $380 total
includes taxes & fees
Oct 26 - Oct 27
Okemo | Spacious Executive Room w Amenities Nearby
A rectangular pool with a brick deck, surrounded by lounge chairs and umbrellas.

9. 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 $69
CA $423 total
includes taxes & fees
Sep 30 - Oct 1
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
A living room with a television, sofa, and coffee table.

10. Long Trail House South Wing 2B2B Condo

Long Trail House South Wing 2B2B Condo
Stratton
10.0 out of 10, Exceptional, (5 reviews)
"Host was very accommodating and understanding. Really smooth communication with the host. And the location couldn’t have been much better."
United States
Ernesto M.
The price is CA $293
CA $678 total
includes taxes & fees
Oct 6 - Oct 7
Long Trail House South Wing 2B2B Condo
A bedroom with two beds, a door, and a small table with a lamp.

11. Bridgewater Living - Ski VT Suite

Bridgewater Living - Ski VT Suite
Bridgewater
The price is CA $232
CA $399 total
includes taxes & fees
Sep 30 - Oct 1
Bridgewater Living - Ski VT Suite
A modern kitchen with a central island, stainless steel appliances, pendant lighting, and a view to the dining area.

12. 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 CA $230
CA $661 total
includes taxes & fees
Sep 30 - Oct 1
Modern Mountain Retreat w/ Chef’s Kitchen
A multi-story building with a red and yellow facade, surrounded by lush greenery and flowering plants.

13. 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 $348
CA $435 total
includes taxes & fees
Oct 26 - Oct 27
Okemo | Studio Condo + Loft | Near Slopes + Pool
An indoor swimming pool with a tiled floor, a pool table, and a bar area.

14. 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 CA $174
CA $589 total
includes taxes & fees
Sep 30 - Oct 1
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.

15. Okemo | Charming Room & Amenities Nearby | Pools

Okemo | Charming Room & Amenities Nearby | Pools
Jackson Gore Base Area
The price is CA $308
CA $383 total
includes taxes & fees
Oct 26 - Oct 27
Okemo | Charming Room & Amenities Nearby | Pools
A multi-story building with a red and yellow facade, surrounded by lush greenery and flowering plants.

16. Okemo | Studio Condo + Close to All Amenities

Okemo | Studio Condo + Close to All Amenities
Jackson Gore Base Area
The price is CA $320
CA $396 total
includes taxes & fees
Oct 26 - Oct 27
Okemo | Studio Condo + Close to All Amenities
A dining room with a wooden table, four chairs, a vase with flowers, and a view of greenery outside.

17. 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 $198
CA $622 total
includes taxes & fees
Oct 21 - Oct 22
Historic Home with Colonial Charm in Manchester
Gather around the glowing fire pit and unwind under the open sky, the perfect way to end a day of adventure.

18. 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 $246
CA $309 total
includes taxes & fees
Sep 30 - Oct 1
Cozy Studio | Ski-In Access + Kitchenette
A spacious living room with a brown leather sofa, white armchairs, and a wooden coffee table. A staircase leads to an upper level with a balcony.

19. 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 $318
CA $1,069 total
includes taxes & fees
Sep 30 - Oct 1
6BR 3BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Wake up to breathtaking mountain views and slopeside convenience at this cozy retreat, where adventure and relaxation go hand in hand.

20. Deluxe Studio | Murphy Bed + Sofa

Deluxe Studio | Murphy Bed + Sofa
West Dover
The price is CA $264
CA $335 total
includes taxes & fees
Oct 19 - Oct 20
Deluxe Studio | Murphy Bed + Sofa
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

Find out more about Chester

Chester Apartments information

Number of reviews
138
Accommodation
172 Apartments
Lowest Price
CA $309
Highest Price
CA $1,069

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 67 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 upstairs apartment on a working farm.: Includes free WiFi, private patios, and sofa beds. Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna: Located in Stratton, 18.7 mi/30 km away. Includes free WiFi, private balconies, and fireplaces. A fitness center and a hot tub are on site. Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.: Located 10.4 mi/16.7 km away in Ludlow. Free WiFi, private patios, and fireplaces are included. A fitness center and onsite laundry facilities are on site. Charming King Loft in Downtown Woodstock: Located in Woodstock, 25.4 mi/40.8 km from Chester. 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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