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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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, (34 reviews)
"the home was clean and very nice. "
United States
Frank R.
The price is CA $140
CA $321 total
includes taxes & fees
Oct 22 - Oct 23
Efficient condo near slopes with kitchenette & great location
A golf course with a winding path, trees, and a hilly landscape.

2. 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, (14 reviews)
"This place was so close to Okemo, and walking distance to the local pub and restaurants."
United States
Brian
The price is CA $140
CA $434 total
includes taxes & fees
Oct 22 - Oct 23
Well-appointed studio right downtown - less than a mile to Okemo Mountain
Living area

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

Modern 3BR/2BA | 3 Min to Okemo Mountain
Ludlow
The price is CA $267
CA $836 total
includes taxes & fees
Nov 3 - Nov 4
Modern 3BR/2BA | 3 Min to Okemo Mountain
A two-story house with a porch, a staircase, and a front door.

4. 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 $140
CA $329 total
includes taxes & fees
Oct 22 - Oct 23
Cozy Studio Condo with Great Location, WiFi & Kitchenette
A multi-story building with a red and yellow facade, surrounded by lush greenery and flowering plants.

5. Okemo | Studio Condo + Close to All Amenities

Okemo | Studio Condo + Close to All Amenities
Jackson Gore Base Area
The price is CA $319
CA $414 total
includes taxes & fees
Oct 26 - Oct 27
Okemo | Studio Condo + Close to All Amenities
A wooden deck with a white railing, a bench, and a door with glass panels.

6. 11 Gables Treehouse- Shuttle Bus, Short Walk to Shops, Bars, Dining

11 Gables Treehouse- Shuttle Bus, Short Walk to Shops, Bars, Dining
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 $381
CA $889 total
includes taxes & fees
Oct 22 - Oct 23
11 Gables Treehouse- Shuttle Bus, Short Walk to Shops, Bars, Dining
A playground with slides and climbing structures surrounded by trees.

7. Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.4 out of 10, Exceptional, (21 reviews)
"The place was clean and had all the essentials. Right across from pool and great stay."
United States
Andrew P.
The price is CA $181
CA $529 total
includes taxes & fees
Oct 26 - Oct 27
Cozy Bromley Retreat
A building with a sign reading 'Fire Tower Restaurant & Tavern.'

8. 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 $314 total
includes taxes & fees
Oct 22 - Oct 23
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
A two-story house with a porch, surrounded by a well-maintained lawn and dense trees.

9. Bridgewater Living - Ben&Jerry Suite

Bridgewater Living - Ben&Jerry Suite
Bridgewater
10.0 out of 10, Exceptional, (1 review)
"Swati, my host, helped me when I had difficulties with tech issues and my stay was as smooth as silk. Thanks!"
United States
Sylvia F.
The price is CA $141
CA $285 total
includes taxes & fees
Nov 17 - Nov 18
Bridgewater Living - Ben&Jerry Suite
A dormitory room with bunk beds, a television mounted on the wall, and a chair in the center.

10. Two Ski-On Condos at Winterplace

Two Ski-On Condos at Winterplace
Okemo Village
The price is CA $495
CA $1,284 total
includes taxes & fees
Nov 3 - Nov 4
Two Ski-On Condos at Winterplace
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 CA $172
CA $585 total
includes taxes & fees
Oct 27 - Oct 28
Historic Home with Colonial Charm in Manchester
A rectangular pool with a brick deck, surrounded by lounge chairs and umbrellas.

12. 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 $87
CA $449 total
includes taxes & fees
Oct 26 - Oct 27
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
A living room with a television, sofa, and coffee table.

13. Long Trail House South Wing 2B2B Condo

Long Trail House South Wing 2B2B Condo
Stratton
10.0 out of 10, Exceptional, (6 reviews)
"Very clean 2br 2ba condo in excellent location. Host provided detailed important information that helped us find property and how to access unit. I would definitely recommend staying here."
United States
Eileen R.
The price is CA $263
CA $644 total
includes taxes & fees
Oct 27 - Oct 28
Long Trail House South Wing 2B2B Condo
A multi-story building with a red and yellow facade, surrounded by lush greenery and flowering plants.

14. Okemo | Charming Room & Amenities Nearby | Pools

Okemo | Charming Room & Amenities Nearby | Pools
Jackson Gore Base Area
10.0 out of 10, Exceptional, (1 review)
"Very nice."
United States
James H.
The price is CA $307
CA $393 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.

15. 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 $305
CA $395 total
includes taxes & fees
Oct 26 - Oct 27
Okemo | Spacious Executive Room w Amenities Nearby
A modern kitchen with a central island, stainless steel appliances, pendant lighting, and a view to the dining area.

16. 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 $192
CA $611 total
includes taxes & fees
Oct 27 - Oct 28
Modern Mountain Retreat w/ Chef’s Kitchen
A multi-story building with a red and yellow facade, surrounded by lush greenery and flowering plants.

17. 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 $345
CA $446 total
includes taxes & fees
Oct 26 - Oct 27
Okemo | Studio Condo + Loft | Near Slopes + Pool
A signboard for The Bridgewater Inn with a simple design, located beside a road with a white fence and greenery.

18. Bridgewater Living - Woodstock Suite

Bridgewater Living - Woodstock Suite
Bridgewater
The price is CA $141
CA $288 total
includes taxes & fees
Nov 3 - Nov 4
Bridgewater Living - Woodstock Suite
A bedroom with two beds, a door, and a small table with a lamp.

19. Bridgewater Living - Ski VT Suite

Bridgewater Living - Ski VT Suite
Bridgewater
The price is CA $141
CA $288 total
includes taxes & fees
Nov 9 - Nov 10
Bridgewater Living - Ski VT 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
9.6 out of 10, Exceptional, (9 reviews)
"Friendly hosts and excellent location to walk to downtown."
United States
Joshua
The price is CA $246
CA $306 total
includes taxes & fees
Oct 31 - Nov 1
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

The Jackson

The Jackson

10/10 Excellent
"Quaint and elegant property. Thebinsite restaurant was great. Enjoyed our 1 night stay here at The Jackson."
Clarissa 1-night trip
Posted 8 hours ago
The Jackson

Find out more about Chester

Chester Apartments information

Number of reviews
115
Accommodation
172 Apartments
Lowest Price
CA $285
Highest Price
CA $1,284

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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