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Apartments in Chester for Rent

Check prices for these dates

In two weeks
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

Our top choices for Chester apartments

Fridge, microwave, oven, stovetop

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, (1 review)
"Great stay as always. "
United States
debbie r.
$156 nightly
The price is $174
Jul 6 - Jul 7
Total with taxes and fees
Quiet Apt. close to Okemo and Killington. Off Rt. 7 with private driveway.
Outdoor pool, a heated pool

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.
$289 nightly
The price is $327
Jul 5 - Jul 6
Total with taxes and fees
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Interior

Cozy apt in beautiful secluded spot 15 mins from Mt Snow

Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Dover
10.0 out of 10, Exceptional, (4 reviews)
"Cozy little spot that had everything we needed. Peaceful, quiet, and once the rain let up on our stay we walked out to the gorgeous little pond on the property. So serene. Catherine was great!"
United States
Erica H.
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Exterior

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
$231 nightly
The price is $261
Jul 1 - Jul 2
Total with taxes and fees
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
Golf

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.
$205 nightly
The price is $232
Jul 1 - Jul 2
Total with taxes and fees
Efficient condo near slopes with kitchenette & great location
Exterior

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.
$211 nightly
The price is $239
Jul 1 - Jul 2
Total with taxes and fees
Cozy Studio Condo with Great Location, WiFi & Kitchenette
Interior

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, (18 reviews)
"Would stay again!"
United States
Hannah M.
$145 nightly
The price is $157
Jul 1 - Jul 2
Total with taxes and fees
103 Deluxe One bedroom Queen Suite w/ outdoor heated pool
Smart TV

Long Trail House South Wing 2B2B Condo

Long Trail House South Wing 2B2B Condo
Stratton
10.0 out of 10, Exceptional, (1 review)
"Host was very accommodating and understanding. Really smooth communication with the host. And the location couldn’t have been much better."
United States
Ernesto M.
$357 nightly
The price is $403
Jul 1 - Jul 2
Total with taxes and fees
Long Trail House South Wing 2B2B Condo
Outdoor dining

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
$242 nightly
The price is $268
Jul 2 - Jul 3
Total with taxes and fees
Okemo | Studio Condo + Loft | Near Slopes + Pool
Terrace/patio

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.
$193 nightly
The price is $213
Jul 1 - Jul 2
Total with taxes and fees
Cozy Studio | Ski-In Access + Kitchenette
Smart TV, fireplace

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.
$614 nightly
The price is $693
Jul 13 - Jul 14
Total with taxes and fees
6BR 3BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Dining

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.
$466 nightly
The price is $527
Jul 5 - Jul 6
Total with taxes and fees
Historic Home with Colonial Charm in Manchester
Exterior

Deluxe Studio | Murphy Bed + Sofa

Deluxe Studio | Murphy Bed + Sofa
West Dover
$204 nightly
The price is $225
Jul 1 - Jul 2
Total with taxes and fees
Deluxe Studio | Murphy Bed + Sofa
Private kitchen

Modern Mountain Retreat w/ Chef’s Kitchen

Modern Mountain Retreat w/ Chef’s Kitchen
Manchester
$505 nightly
The price is $571
Jul 5 - Jul 6
Total with taxes and fees
Modern Mountain Retreat w/ Chef’s Kitchen
Golf

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
$273 nightly
The price is $309
Jul 1 - Jul 2
Total with taxes and fees
Well-appointed studio right downtown - less than a mile to Okemo Mountain
Interior

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.
$655 nightly
The price is $760
Jul 1 - Jul 2
Total with taxes and fees
The Treehouse at 11 Gables Ludlow – Dining, Shopping & Okemo Shuttle
Exterior

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.
$145 nightly
The price is $157
Jul 5 - Jul 6
Total with taxes and fees
Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102
Outdoor dining

Okemo | Charming Room & Amenities Nearby | Pools

Okemo | Charming Room & Amenities Nearby | Pools
Jackson Gore Base Area
$210 nightly
The price is $232
Jul 2 - Jul 3
Total with taxes and fees
Okemo | Charming Room & Amenities Nearby | Pools
Outdoor dining

Okemo | Studio Condo + Close to All Amenities

Okemo | Studio Condo + Close to All Amenities
Jackson Gore Base Area
$219 nightly
The price is $242
Jul 2 - Jul 3
Total with taxes and fees
Okemo | Studio Condo + Close to All Amenities
Terrace/patio

Ski-In/Ski-Out ADA Studio w/ Kitchenette!

Ski-In/Ski-Out ADA Studio w/ Kitchenette!
West Dover
$191 nightly
The price is $211
Jul 1 - Jul 2
Total with taxes and fees
Ski-In/Ski-Out ADA Studio w/ Kitchenette!
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

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"It was clean staff was nice friendly and dressed in uniforms breakfast nice breakfast area was clean i would stay at ascend collection hotel again.. i wish would have done so near bar harbor area but didnt"
karen 1-night trip
Posted 19 hours ago
Keene Elm City Hotel, an Ascend Collection Hotel

Find out more about Chester

Chester Apartments information

Number of reviews
10,398
Accommodation
151 Apartments
Lowest Price
$95
Highest Price
$238

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 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 apartment on a working farm.: Includes free WiFi, private patios, and sofa beds. Carriage House Studio Apt- secluded, mountain views, babbling brook, countryside: Located in Dorset, 22.8 mi/36.8 km away. Includes free WiFi, private balconies, and fireplaces. Access to onsite laundry facilities is available on site. Charming King Loft in Downtown Woodstock: Located 25.4 mi/40.8 km away in Woodstock. Free WiFi and Smart TVs are included. Access to onsite 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 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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