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Apartments in Chester for Rent

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Chester apartments

A bunk bed with patterned bedding, a single mattress against the wall, and a carpeted floor.

1. Charming 2-bedroom apartment in Springfield

Charming 2-bedroom apartment in Springfield
Springfield
Charming 2-bedroom apartment in Springfield
A golf course with a winding path, trees, and a distant mountain range.

2. 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 ￥15,791
￥36,710 total
includes taxes & fees
Oct 14 - Oct 15
Efficient condo near slopes with kitchenette & great location
A two-story house with a porch, a staircase, and a front door.

3. 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 ￥15,791
￥37,783 total
includes taxes & fees
Oct 14 - Oct 15
Cozy Studio Condo with Great Location, WiFi & Kitchenette
A hotel room with a bed, a bathroom with a mirror, and a window with curtains.

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

Modern 3BR/2BA | 3 Min to Okemo Mountain
Ludlow
The price is ￥30,092
￥95,184 total
includes taxes & fees
Oct 19 - Oct 20
Modern 3BR/2BA | 3 Min to Okemo Mountain
A golf course with a winding path, trees, and a hilly landscape.

5. 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 ￥15,791
￥48,875 total
includes taxes & fees
Oct 21 - Oct 22
Well-appointed studio right downtown - less than a mile to Okemo Mountain
A two-story house with a porch, surrounded by a well-maintained lawn and dense trees.

6. 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 ￥18,997
￥36,702 total
includes taxes & fees
Nov 2 - Nov 3
Bridgewater Living - Ben&Jerry Suite
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)
"Nice place "
United States
Janja L.
The price is ￥20,382
￥59,557 total
includes taxes & fees
Oct 26 - Oct 27
Cozy Bromley Retreat
A multi-story building with a red and yellow facade, surrounded by lush greenery and flowering plants.

8. Okemo | Studio Condo + Close to All Amenities

Okemo | Studio Condo + Close to All Amenities
Jackson Gore Base Area
The price is ￥35,949
￥45,448 total
includes taxes & fees
Oct 26 - Oct 27
Okemo | Studio Condo + Close to All Amenities
A building with a sign reading 'Fire Tower Restaurant & Tavern.'

9. 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 ￥11,802
￥35,531 total
includes taxes & fees
Oct 13 - Oct 14
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
A wooden deck with a white railing, a bench, and a door with glass panels.

10. 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 ￥47,453
￥105,521 total
includes taxes & fees
Oct 22 - Oct 23
11 Gables Treehouse- Shuttle Bus, Short Walk to Shops, Bars, Dining
A dormitory room with bunk beds, a television mounted on the wall, and a chair in the center.

11. Two Ski-On Condos at Winterplace

Two Ski-On Condos at Winterplace
Okemo Village
The price is ￥55,725
￥146,468 total
includes taxes & fees
Nov 1 - Nov 2
Two Ski-On Condos at Winterplace
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 ￥9,746
￥49,833 total
includes taxes & fees
Oct 26 - Oct 27
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
A dining room with a wooden table, four chairs, a vase with flowers, and a view of greenery outside.

13. 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 ￥18,809
￥64,367 total
includes taxes & fees
Nov 3 - Nov 4
Historic Home with Colonial Charm in Manchester
A living room with a television, sofa, and coffee table.

14. 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 ￥32,770
￥77,280 total
includes taxes & fees
Oct 19 - Oct 20
Long Trail House South Wing 2B2B Condo
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
10.0 out of 10, Exceptional, (1 review)
"Very nice."
United States
James H.
The price is ￥34,518
￥43,515 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 | 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 ￥34,353
￥43,334 total
includes taxes & fees
Oct 26 - Oct 27
Okemo | Spacious Executive Room w Amenities Nearby
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 ￥38,813
￥48,956 total
includes taxes & fees
Oct 26 - Oct 27
Okemo | Studio Condo + Loft | Near Slopes + Pool
A bedroom with two beds, a door, and a small table with a lamp.

18. Bridgewater Living - Ski VT Suite

Bridgewater Living - Ski VT Suite
Bridgewater
The price is ￥18,997
￥36,525 total
includes taxes & fees
Nov 1 - Nov 2
Bridgewater Living - Ski VT Suite
A modern kitchen with a central island, stainless steel appliances, pendant lighting, and a view to the dining area.

19. 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 ￥24,158
￥71,664 total
includes taxes & fees
Oct 28 - Oct 29
Modern Mountain Retreat w/ Chef’s Kitchen
A signboard for The Bridgewater Inn with a simple design, located beside a road with a white fence and greenery.

20. Bridgewater Living - Woodstock Suite

Bridgewater Living - Woodstock Suite
Bridgewater
The price is ￥18,997
￥36,525 total
includes taxes & fees
Nov 1 - Nov 2
Bridgewater Living - Woodstock Suite
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

Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

8/10 Good
""Great location, and the staff made it right!" The room was on the smaller side, and we had an issue with the AC. The staff quickly gave us a new room and handled our luggage, so we didn't have to move it ourselves. We slept peacefully after that. The location is great, and there are plenty of options nearby for kids to play. We will definitely book again!"
Bharath Reddy 1-night trip
Posted less than an hour ago
Jackson Gore Village, A Vail Resorts Property

Find out more about Chester

Chester Apartments information

Number of reviews
105
Accommodation
176 Apartments
Lowest Price
￥35,531
Highest Price
￥146,468

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.