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Apartments in Chester for Rent

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Check prices for these dates

In two weeks
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Chester apartments

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 27 - Jul 28
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 27 - Jul 28
Total with taxes and fees
Cozy Studio Condo with Great Location, WiFi & Kitchenette
Children's area

Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.4 out of 10, Exceptional, (15 reviews)
"Nice place "
United States
Janja L.
$288 nightly
The price is $325
Jul 26 - Jul 27
Total with taxes and fees
Cozy Bromley Retreat
Exterior

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
$280 nightly
The price is $316
Aug 2 - Aug 3
Total with taxes and fees
Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.
Outdoor dining

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.
$193 nightly
The price is $213
Jul 26 - Jul 27
Total with taxes and fees
Okemo | Spacious Executive Room w Amenities Nearby
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
$209 nightly
The price is $236
Aug 5 - Aug 6
Total with taxes and fees
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
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 27 - Jul 28
Total with taxes and fees
Well-appointed studio right downtown - less than a mile to Okemo Mountain
Coffee/tea maker, fridge, microwave, oven

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.
$156 nightly
The price is $174
Jul 27 - Jul 28
Total with taxes and fees
Quiet Apt. close to Okemo and Killington. Off Rt. 7 with private driveway.
Smart TV

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.
$433 nightly
The price is $489
Jul 31 - Aug 1
Total with taxes and fees
Long Trail House South Wing 2B2B Condo
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.
$656 nightly
The price is $761
Jul 25 - Jul 26
Total with taxes and fees
The Treehouse at 11 Gables Ludlow – Dining, Shopping & Okemo Shuttle
Outdoor dining

Okemo | Studio Condo + Close to All Amenities

Okemo | Studio Condo + Close to All Amenities
Jackson Gore Base Area
$203 nightly
The price is $224
Jul 26 - Jul 27
Total with taxes and fees
Okemo | Studio Condo + Close to All Amenities
Outdoor dining

Okemo | Charming Room & Amenities Nearby | Pools

Okemo | Charming Room & Amenities Nearby | Pools
Jackson Gore Base Area
$212 nightly
The price is $234
Jul 26 - Jul 27
Total with taxes and fees
Okemo | Charming Room & Amenities Nearby | Pools
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
$241 nightly
The price is $266
Jul 26 - Jul 27
Total with taxes and fees
Okemo | Studio Condo + Loft | Near Slopes + Pool
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 26 - Jul 27
Total with taxes and fees
Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102
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.
$444 nightly
The price is $502
Jul 31 - Aug 1
Total with taxes and fees
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
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 27 - Jul 28
Total with taxes and fees
Cozy Studio | Ski-In Access + Kitchenette
Private kitchen

Modern Mountain Retreat w/ Chef’s Kitchen

Modern Mountain Retreat w/ Chef’s Kitchen
Manchester
$458 nightly
The price is $517
Aug 18 - Aug 19
Total with taxes and fees
Modern Mountain Retreat w/ Chef’s Kitchen
Exterior

Deluxe Studio | Murphy Bed + Sofa

Deluxe Studio | Murphy Bed + Sofa
West Dover
$209 nightly
The price is $230
Jul 27 - Jul 28
Total with taxes and fees
Deluxe Studio | Murphy Bed + Sofa
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, (19 reviews)
"Would stay again!"
United States
Hannah M.
$145 nightly
The price is $157
Aug 9 - Aug 10
Total with taxes and fees
103 Deluxe One bedroom Queen Suite w/ outdoor heated pool
Pool

Equinox Haven | King Room w/ Pool & Spa Access

Equinox Haven | King Room w/ Pool & Spa Access
Manchester Village Historic District
$326 nightly
The price is $360
Jul 29 - Jul 30
Total with taxes and fees
Equinox Haven | King Room w/ 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.
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Top Chester Hotel Reviews

Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"I loved everything about this hotel! They recently underwent a remodel so everything is brand new and beautiful. The breakfast was amazing. It is the first time that I see plant based patties in the breakfast for those of us that can’t have meat. the front desk personnel were always very informative and unhurried. I would absolutely love to come back here. The surroundings are amazing as well. Downtown Brattleboro is cute."
Mildred 1-night trip
Posted less than an hour ago
Hampton Inn Brattleboro

Find out more about Chester

Chester Apartments information

Number of reviews
6,577
Accommodation
151 Apartments
Lowest Price
$93
Highest Price
$277

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 64 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 quaint 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?
Here 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. 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. Cozy Bromley Retreat: It's situated in Peru, 17.8 mi/28.6 km away. Includes free WiFi, private balconies, and fireplaces. Lake-View Spofford Apartment w/ Shared Dock!: 26 mi/41.8 km away in Spofford. Carriage House Studio Apt- secluded, mountain views, babbling brook, countryside: Located in Dorset, 22.8 mi/36.8 km from Chester. Includes free WiFi, private balconies, and fireplaces. 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.

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