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Check prices for these dates

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

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 €212
includes taxes & fees
18 Oct - 19 Oct
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 €217
includes taxes & fees
18 Oct - 19 Oct
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 €544
includes taxes & fees
2 Nov - 3 Nov
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 €278
includes taxes & fees
21 Oct - 22 Oct
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 €184
includes taxes & fees
16 Nov - 17 Nov
Bridgewater Living - Ben&Jerry Suite
A wooden deck with a white railing, a bench, and a door with glass panels.

7. 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 €553
includes taxes & fees
18 Oct - 19 Oct
11 Gables Treehouse- Shuttle Bus, Short Walk to Shops, Bars, Dining
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 €262
includes taxes & fees
17 Nov - 18 Nov
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 €202
includes taxes & fees
29 Oct - 30 Oct
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
A playground with slides and climbing structures surrounded by trees.

10. 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 €341
includes taxes & fees
26 Oct - 27 Oct
Cozy Bromley Retreat
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 €818
includes taxes & fees
17 Nov - 18 Nov
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 €284
includes taxes & fees
19 Oct - 20 Oct
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 €355
includes taxes & fees
3 Nov - 4 Nov
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 €442
includes taxes & fees
27 Oct - 28 Oct
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 €253
includes taxes & fees
26 Oct - 27 Oct
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 €254
includes taxes & fees
26 Oct - 27 Oct
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.

17. 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 €393
includes taxes & fees
3 Nov - 4 Nov
Modern Mountain Retreat w/ Chef’s Kitchen
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 €285
includes taxes & fees
26 Oct - 27 Oct
Okemo | Studio Condo + Loft | Near Slopes + Pool
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 €183
includes taxes & fees
17 Nov - 18 Nov
Bridgewater Living - Ski VT Suite
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 €183
includes taxes & fees
9 Nov - 10 Nov
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

Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

8/10 Good
"Breakfast could have been better, more healthly foods"
Angelena 2-night trip
Posted 7 hours ago
Hampton Inn and Suites Manchester

Find out more about Chester

Chester Apartments information

Number of reviews
105
Accommodation
176 Apartments
Lowest Price
€183
Highest Price
€818

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 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 upstairs apartment on a working farm.: Includes free WiFi, a patio and a sofa bed . Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna: Located in Stratton , 18.7 mi/30 km away. Includes free WiFi, a balcony and a fireplace . A fitness centre and 1 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, a patio and a fireplace are included . A fitness centre and on-site 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 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.