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Compare 164 Apartments in Chester with updated reviews, rates, and availability.

Unexpected Style in a Cosy, Convenient In-Town Apartment

9.8 out of 10, Exceptional, (70)
"Property was in a great location communication with owners was spot on. Great place to stay for a weekend or week."
Unexpected Style in a Cosy, Convenient In-Town Apartment

Cozy Studio Condo with Great Location, WiFi & Kitchenette

8.6 out of 10, Excellent, (25)
"Great location and great place!"
The price is AED 198
AED 766 total
includes taxes & fees
25 Mar - 26 Mar
Cozy Studio Condo with Great Location, WiFi & Kitchenette

Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly

9.0 out of 10, Wonderful, (26)
"The tiny houses were cute and well equipped. They were ideal for 2 friends traveling together having their own space. I would definitely rent this property again. Only negative was having 3 empty propane tanks when we wanted to use the fire table(something to be added to the maintenance checklust) however once i text them they dropped a fresh tank off that same evening."
The price is AED 400
AED 979 total
includes taxes & fees
7 Apr - 8 Apr
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly

Long Trail House Studio at Stratton Mountain Resort

10.0 out of 10, Exceptional, (60)
"The studio condo we reserved had a last minute appliance issue so the owner upgraded us to a one bedroom and even accommodated an early check in. Everything worked out fine. The condo is next to village and to get to the lifts it’s a quick walk through the village and you’re there. Very clean unit with excellent water pressure and hot water. Plan to come back soon. "
Long Trail House Studio at Stratton Mountain Resort

Efficient condo near slopes with kitchenette & great location

8.8 out of 10, Excellent, (30)
"great location, close walkto store, restaurants. Okemoabout a minute drive toparking lots. "
The price is AED 195
AED 718 total
includes taxes & fees
7 Apr - 8 Apr
Efficient condo near slopes with kitchenette & great location

Hawks Mountain Farm, full apartment on a working farm.

9.8 out of 10, Exceptional, (38)
"My husband and I love visiting Dave and Carol‘s place this time we got to meet all of the fun animals and enjoy fresh chicken, eggs, and goose egg! They are so welcoming and have a sweet little place to stay while we are skiing. We look forward to staying again."
Hawks Mountain Farm, full apartment on a working farm.

Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK

9.8 out of 10, Exceptional, (170)
"It was a described. Well maintained, great communication."
Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK

Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn

9.6 out of 10, Exceptional, (4)
"We had a mixed experience during our stay at Leah's property. On the positive side, Leah was an incredibly friendly and communicative host. She was quick to respond to any questions, and the location was absolutely fantastic—very convenient and close to everything.However, upon arrival, we noticed the unit wasn’t as clean as we expected. There were stains on the rug, dust on the furniture, crumbs on the coffee table, and a dirty stovetop. The dishes appeared to have been used but weren’t...
The price is AED 386
AED 1,324 total
includes taxes & fees
14 Apr - 15 Apr
Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn

MT SNOW | SKI BACK TRAIL | FREE SHUTTLE - Green Mountain Den

9.4 out of 10, Exceptional, (14)
"Everything about this place was perfect for a quick ski weekend. The house was clean, warm and had everything needed. The information presented in the description is accurate. You do hear the people in the house above, but it was not an issue for us.It is a two minute drive to Corinthia base lodge. "
The price is AED 213
AED 867 total
includes taxes & fees
1 Apr - 2 Apr
MT SNOW | SKI BACK TRAIL | FREE SHUTTLE - Green Mountain Den

Well-appointed studio right downtown - less than a mile to Okemo Mountain

9.2 out of 10, Wonderful, (11)
"Easy check in clean place "
The price is AED 195
AED 887 total
includes taxes & fees
7 Apr - 8 Apr
Well-appointed studio right downtown - less than a mile to Okemo Mountain

Stratton South Long Trail Studio Adjacent to the Village and Lifts

9.4 out of 10, Exceptional, (63)
"Walk to village and lifts. Covered parking. "
Stratton South Long Trail Studio Adjacent to the Village and Lifts

Riverfront studio with river view, full kitchen, & free WiFi

6.8 out of 10, (11)
"Sufficient space and easy distance to center of Ludlow and Okemo Mt"
The price is AED 220
AED 874 total
includes taxes & fees
25 Mar - 26 Mar
Riverfront studio with river view, full kitchen, & free WiFi

Carriage House Studio Apt- secluded, mountain views, babbling brook, countryside

10.0 out of 10, Exceptional, (11)
"We had a very nice stay, the place is cozy and charming, exceptionally clean, easy to access, and had all the amenities we could've expected for a weekend away. It's comfortable and clearly cared for, and the kitchen is stocked with tools. Neighborhood is lovely and within easy commute to several ski areas. The property is very beautiful as well, though based on the photos and description we were expecting a more secluded siting. The unit is the second floor of a detached garage, located 20-30...
Carriage House Studio Apt- secluded, mountain views, babbling brook, countryside

Cozy studio with WiFi and fitness room in Springfield. Close to Okemo and Magic.

The price is AED 551
AED 798 total
includes taxes & fees
25 Mar - 26 Mar
Cozy studio with WiFi and fitness room in Springfield. Close to Okemo and Magic.

Gorgeous ski retreat apartment with fireplace and Mountain View.

10.0 out of 10, Exceptional, (12)
"Super clean and updated condo close to mountain. Perfect for my family with two kids. Well stocked. Owner very communicative and easy to check in and out."
Gorgeous ski retreat apartment with fireplace and Mountain View.

Peaceful farm stay with mountain views, sunny patio, & firepit - near skiing

9.0 out of 10, Wonderful, (2)
"Everything was very clean for my family. It was a bit musty and because the space is over a garage they were woken up every morning between 5:30-6am when the owners would leave. Otherwise everything was great"
Peaceful farm stay with mountain views, sunny patio, & firepit - near skiing

Cozy private apartment with winter views of Mt Equinox

10.0 out of 10, Exceptional, (20)
"This home is located perfectly very near all the shops and restaurants in Manchester. The unit is very quiet and there are no shared walls with others. The unit is extremely clean and well stocked with amenities like shampoo and body wash as well as kitchen supplies such as tea, coffee and condiments. Would definitely book again if in the area."
Cozy private apartment with winter views of Mt Equinox

103 Deluxe One bedroom Queen Suite w/ outdoor heated pool

9.6 out of 10, Exceptional, (17)
"Clean, spacious, everything you want out of a cabin style inn in Vermont. Close to Burlington, very informative. "
The price is AED 636
AED 914 total
includes taxes & fees
6 Apr - 7 Apr
103 Deluxe One bedroom Queen Suite w/ outdoor heated pool

Comfortable Dover Apartment: Walk to Mt Snow!

9.2 out of 10, Wonderful, (5)
"Great condo located on the Mount Snow property. Great view of the slopes!! My kids and I enjoyed our stay very much. Would recommend this place to all skiers and snowboarders."
Comfortable Dover Apartment: Walk to Mt Snow!

Superb apartment in prime location - Ludlow centre just minutes from ski slopes

9.8 out of 10, Exceptional, (50)
"Hard to beat the location with okemo shuttle stopping right out front and 1 block from downtown Ludlow for food and drink after a great day on the slopes!"
Superb apartment in prime location - Ludlow centre just minutes from ski slopes
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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Other property types in Chester

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

10.0 out of 10, Exceptional, (23)
"This lovingly built off-grid glamping cabin is drenched with sun! It’s absolutely gorgeous! The kids enjoyed pumping their own water and sledding down the front hill. Paris is an excellent hostess- she answered all our questions very promptly & thoroughly. We cant wait to come back! Thank you!!!"
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

Long Trail House at Stratton Mountain Resort

3.0 star property
8.6 out of 10, Excellent, (74)
"Nice, clean room in prime location"
The price is AED 1,267
AED 1,575 total
includes taxes & fees
13 Apr - 14 Apr
Long Trail House at Stratton Mountain Resort

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (41)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
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.

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 68 accommodations. Though there aren’t many apartments, we can help you locate similar accommodations. When you search for a place to stay on Expedia, you can use the filters to search for conveniences you might find in an apartment like a kitchen. You can also filter by similar property types like vacation homes, condos, or guest houses. During your trip, you can check out this quaint area’s ski slopes and shops. Discover the region’s top sights such as Stratton Mountain Resort.
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. Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly: Located 10.4 mi/16.7 km away in Ludlow. Private patios and sofa beds are included. Access to a hot tub is available on site. Unexpected Style in a Cosy, Convenient In-Town Apartment: It’s situated in Manchester Center, 23.7 mi/38.1 km away. Includes free WiFi, private balconies, and Smart TVs. Long Trail House Studio at Stratton Mountain Resort: Located 18.7 mi/30 km away in Stratton. Fireplaces and sofa beds are included. A hot tub and a sauna are on site. Cozy Studio Condo with Great Location, WiFi & Kitchenette: It’s located in Ludlow, 10.9 mi/17.5 km from Chester. Includes private patios and sofa beds.
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. Bonnie’s Bundles Dolls and DaVallia Art & Accents are a couple of family-friendly sights. Stratton Mountain Resort and Vermont Country Store 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.