Lodging Image

Search Apartments in Chester

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

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 HK$1,059
HK$2,029 total
includes taxes & fees
3 Aug - 4 Aug
Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.
Outdoor pool, a heated pool

2. 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 HK$534
HK$2,561 total
includes taxes & fees
30 Aug - 31 Aug
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Children’s area

3. Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.4 out of 10, Exceptional, (16 reviews)
"Nice place "
United States
Janja L.
The price is HK$711
HK$2,550 total
includes taxes & fees
23 Aug - 24 Aug
Cozy Bromley Retreat
Smart TV

4. Long Trail House South Wing 2B2B Condo

Long Trail House South Wing 2B2B Condo
Stratton
10.0 out of 10, Exceptional, (2 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 HK$1,461
HK$3,609 total
includes taxes & fees
9 Aug - 10 Aug
Long Trail House South Wing 2B2B Condo
Exterior

5. Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102

Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102
Killington
8.8 out of 10, Excellent, (8 reviews)
"Great room, plenty of amenities, close to restaurants and mountains"
United States
Daniel T.
The price is HK$815
HK$1,234 total
includes taxes & fees
16 Aug - 17 Aug
Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102
Interior

6. 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 HK$815
HK$1,234 total
includes taxes & fees
9 Aug - 10 Aug
103 Deluxe One bedroom Queen Suite w/ outdoor heated pool
Outdoor dining

7. 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 HK$1,654
HK$2,116 total
includes taxes & fees
3 Aug - 4 Aug
Okemo | Studio Condo + Loft | Near Slopes + Pool
Golf

8. 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 HK$782
HK$1,819 total
includes taxes & fees
10 Aug - 11 Aug
Efficient condo near slopes with kitchenette & great location
Exterior

9. 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 HK$782
HK$1,872 total
includes taxes & fees
3 Aug - 4 Aug
Cozy Studio Condo with Great Location, WiFi & Kitchenette
Exterior

10. 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 HK$585
HK$1,778 total
includes taxes & fees
4 Aug - 5 Aug
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
Golf

11. 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 HK$782
HK$2,421 total
includes taxes & fees
3 Aug - 4 Aug
Well-appointed studio right downtown - less than a mile to Okemo Mountain
Coffee/tea maker, fridge, microwave, oven

12. Quiet Apt. close to Okemo and Killington. Off Rt. 7 with private driveway.

Quiet Apt. close to Okemo and Killington. Off Rt. 7 with private driveway.
Wallingford
10.0 out of 10, Exceptional, (2 reviews)
"Great stay as always. "
United States
debbie r.
The price is HK$671
HK$1,366 total
includes taxes & fees
3 Aug - 4 Aug
Quiet Apt. close to Okemo and Killington. Off Rt. 7 with private driveway.
Private kitchen

13. Modern Mountain Retreat w/ Chef’s Kitchen

Modern Mountain Retreat w/ Chef’s Kitchen
Manchester
The price is HK$1,564
HK$4,027 total
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 HK$1,416
HK$1,788 total
includes taxes & fees
3 Aug - 4 Aug
Okemo | Studio Condo + Close to All Amenities
Interior

15. 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 HK$2,659
HK$6,020 total
includes taxes & fees
3 Aug - 4 Aug
The Treehouse at 11 Gables Ludlow – Dining, Shopping & Okemo Shuttle
Outdoor dining

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 HK$1,349
HK$1,705 total
includes taxes & fees
3 Aug - 4 Aug
Okemo | Spacious Executive Room w Amenities Nearby
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 HK$1,365
HK$1,723 total
includes taxes & fees
4 Aug - 5 Aug
Cozy Studio | Ski-In Access + Kitchenette
Outdoor dining

18. Okemo | Charming Room & Amenities Nearby | Pools

Okemo | Charming Room & Amenities Nearby | Pools
Jackson Gore Base Area
The price is HK$1,464
HK$1,864 total
includes taxes & fees
11 Aug - 12 Aug
Okemo | Charming Room & Amenities Nearby | Pools
Exterior

19. Deluxe Studio | Murphy Bed + Sofa

Deluxe Studio | Murphy Bed + Sofa
West Dover
The price is HK$1,466
HK$1,869 total
includes taxes & fees
3 Aug - 4 Aug
Deluxe Studio | Murphy Bed + Sofa
Pool

20. Grand Equinox | 2 Queen Room + Pool & Spa Access

Grand Equinox | 2 Queen Room + Pool & Spa Access
Manchester Village Historic District
The price is HK$2,792
HK$3,523 total
includes taxes & fees
12 Aug - 13 Aug
Grand Equinox | 2 Queen Room + Pool & Spa Access
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chester Hotel Reviews

Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"Nice pool and jacuzzi! Co venison to restaurants and shops"
Mary 1-night trip
Posted 9 hours ago
Hampton Inn Brattleboro

Find out more about Chester

Chester Apartments information

Number of reviews
162
Accommodation
146 Apartments
Lowest Price
HK$1,234
Highest Price
HK$6,020

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 . Charming King Loft in Downtown Woodstock: Located 25.4 mi/40.8 km away in Woodstock . Free WiFi and a Smart TV are included . Access to on-site laundry facilities is available on site . Cozy Bromley Retreat: It's situated in Peru , 17.8 mi/28.6 km away. Includes free WiFi, a balcony and a fireplace . Lake-View Spofford Apartment w/ Shared Dock!: 26 mi/41.8 km away in Spofford . Lakeside Spofford Retreat Near Hiking & Boating!: 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.

Explore a world of travel with Expedia