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

Apartments in Chester

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Chester apartments

Exterior

1. 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 AU$359
includes taxes & fees
22 Aug - 23 Aug
Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.
Golf

2. 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 AU$326
includes taxes & fees
24 Aug - 25 Aug
Efficient condo near slopes with kitchenette & great location
Exterior

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 AU$334
includes taxes & fees
24 Aug - 25 Aug
Cozy Studio Condo with Great Location, WiFi & Kitchenette
Children’s area

4. Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.4 out of 10, Exceptional, (19 reviews)
"This is an amazing location. The home is exceptionally clean and well equipped. The pool was amazing and so was our experience. We were centrally located to everything we wanted to do. I would highly recommend this home and Management company to anyone visiting the Bromley area. Exceptional."
United States
Jaime
The price is AU$474
includes taxes & fees
23 Aug - 24 Aug
Cozy Bromley Retreat
Exterior

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 AU$319
includes taxes & fees
24 Aug - 25 Aug
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
Outdoor dining

6. 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 AU$351
includes taxes & fees
24 Aug - 25 Aug
Okemo | Spacious Executive Room w Amenities Nearby
Golf

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 AU$430
includes taxes & fees
24 Aug - 25 Aug
Well-appointed studio right downtown - less than a mile to Okemo Mountain
Pool

8. 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 AU$447
includes taxes & fees
23 Aug - 24 Aug
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dining

9. 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 AU$560
includes taxes & fees
8 Sept - 9 Sept
Historic Home with Colonial Charm in Manchester
Interior

10. 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 AU$1,059
includes taxes & fees
22 Aug - 23 Aug
The Treehouse at 11 Gables Ludlow – Dining, Shopping & Okemo Shuttle
Living area

11. Long Trail House South Wing 2B2B Condo

Long Trail House South Wing 2B2B Condo
Stratton
10.0 out of 10, Exceptional, (3 reviews)
"Great location. Very clean accomodations with comfortable beds! Host was very communicative as well!"
United States
carlene p.
The price is AU$664
includes taxes & fees
1 Sept - 2 Sept
Long Trail House South Wing 2B2B Condo
Interior

12. 103 Deluxe One bedroom Queen Suite w/ outdoor heated pool

103 Deluxe One bedroom Queen Suite w/ outdoor heated pool
Killington
9.6 out of 10, Exceptional, (19 reviews)
"Would stay again!"
United States
Hannah M.
The price is AU$224
includes taxes & fees
23 Aug - 24 Aug
103 Deluxe One bedroom Queen Suite w/ outdoor heated pool
Private kitchen

13. Modern Mountain Retreat w/ Chef’s Kitchen

Modern Mountain Retreat w/ Chef’s Kitchen
Manchester
The price is AU$619
includes taxes & fees
1 Sept - 2 Sept
Modern Mountain Retreat w/ Chef’s Kitchen
Outdoor dining

14. Okemo | Studio Condo + Close to All Amenities

Okemo | Studio Condo + Close to All Amenities
Jackson Gore Base Area
The price is AU$368
includes taxes & fees
24 Aug - 25 Aug
Okemo | Studio Condo + Close to All Amenities
Outdoor dining

15. Okemo | Charming Room & Amenities Nearby | Pools

Okemo | Charming Room & Amenities Nearby | Pools
Jackson Gore Base Area
The price is AU$383
includes taxes & fees
24 Aug - 25 Aug
Okemo | Charming Room & Amenities Nearby | Pools
Outdoor dining

16. 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 AU$437
includes taxes & fees
24 Aug - 25 Aug
Okemo | Studio Condo + Loft | Near Slopes + Pool
Terrace/patio

17. 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 AU$309
includes taxes & fees
31 Aug - 1 Sept
Cozy Studio | Ski-In Access + Kitchenette
Pool

18. 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)
"Amazing experience at Mount Snow! Leah is the best owner! Attentive and accessible. "
United States
Jayanne S.
The price is AU$619
includes taxes & fees
15 Sept - 16 Sept
Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn
Exterior

19. 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 AU$296
includes taxes & fees
31 Aug - 1 Sept
Central Large 2-bedrooms with office in Keene
Living area

20. 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 AU$1,180
includes taxes & fees
21 Sept - 22 Sept
6BR 3BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
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

Claremont Motor Lodge

Claremont Motor Lodge

10/10 Excellent
"Extremely clean room and staff was very helpful and accommodating. I would definitely stay here again!"
Michael 3-night trip
Posted 2 hours ago
Claremont Motor Lodge

Find out more about Chester

Chester Apartments information

Number of reviews
174
Accommodation
147 Apartments
Lowest Price
AU$224
Highest Price
AU$1,180

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 62 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 quaint 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?
Listed below are some of the top apartments in the area: Hawks Mountain Farm, full apartment on a working farm.: Includes free WiFi, a patio and a sofa bed . Cozy Bromley Retreat: Located 17.8 mi/28.6 km away in Peru . Free WiFi, a balcony and a fireplace are included . Charming King Loft in Downtown Woodstock: Located in Woodstock , 25.4 mi/40.8 km away. Includes free WiFi and a Smart TV . Access to on-site laundry facilities is available on site . Lake-View Spofford Apartment w/ Shared Dock!: It's situated in Spofford , 26 mi/41.8 km from Chester.
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.