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Compare 134 Apartments in Chester with updated reviews, rates, and availability.

Unexpected Style in a Cosy, Convenient In-Town Apartment

9.8 out of 10, Exceptional, (69)
"Beautiful place love the decor close to everything."
Unexpected Style in a Cosy, Convenient In-Town Apartment

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 SAR 203
SAR 641 total
includes taxes & fees
19 Mar - 20 Mar
Efficient condo near slopes with kitchenette & great location

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

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

9.8 out of 10, Exceptional, (169)
"It was a described. Well maintained, great communication."
Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK

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 SAR 203
SAR 902 total
includes taxes & fees
16 Mar - 17 Mar
Well-appointed studio right downtown - less than a mile to Okemo Mountain

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

Perfect Getaway! Cozy, Modern condo & Convenient to Everything you will need.

9.8 out of 10, Exceptional, (65)
"Perfect for a quick ski trip for 2 of us. Clean and comfortable and walkable to the spots in town. We will be back! "
The price is SAR 338
SAR 907 total
includes taxes & fees
8 Apr - 9 Apr
Perfect Getaway! Cozy, Modern condo & Convenient to Everything you will need.

Cozy Studio Condo with Great Location, WiFi & Kitchenette

8.6 out of 10, Excellent, (25)
"Great location and great place!"
The price is SAR 203
SAR 672 total
includes taxes & fees
16 Mar - 17 Mar
Cozy Studio Condo with Great Location, WiFi & Kitchenette

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!

Comfortable Dover Apartment: Walk to Mt Snow!

3.0 star property
9.0 out of 10, Wonderful, (2)
Comfortable Dover Apartment: Walk to Mt Snow!

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 SAR 825
SAR 1,565 total
includes taxes & fees
17 Mar - 18 Mar
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly

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 SAR 218
SAR 886 total
includes taxes & fees
1 Apr - 2 Apr
MT SNOW | SKI BACK TRAIL | FREE SHUTTLE - Green Mountain Den

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 SAR 225
SAR 885 total
includes taxes & fees
16 Mar - 17 Mar
Riverfront studio with river view, full kitchen, & free WiFi

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.

First-floor condo with shared laundry - steps to ski bus pickup, walk to dining

7.4 out of 10, Good, (6)
"Quick but relaxing stay in Ludlow. Perfect 3"
The price is SAR 926
SAR 2,096 total
includes taxes & fees
16 Mar - 17 Mar
First-floor condo with shared laundry - steps to ski bus pickup, walk to dining

Cozy 2-BR Winterplace Condo Steps from Okemo Mtn.

2.0 star property
10.0 out of 10, Exceptional, (1)
"From the moment we arrived, we were impressed! The condo was impeccably clean, very well decorated and just steps from the slopes. The wood burning fireplace was an added bonus. We couldn't have been happier with our stay and would 100% return next season."
Cozy 2-BR Winterplace Condo Steps from Okemo Mtn.

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

Okemo Mountain, Family Affordable 2 fl village location walk to town, Dogs OK.

9.6 out of 10, Exceptional, (15)
"We enjoyed staying upstairs and all the room that the apartment has. We remembered to bring our own sheets & towels and everything else we needed was in the apartment. Robert is very friendly and helpful. "
Okemo Mountain, Family Affordable 2 fl village location walk to town, Dogs OK.

Sunny Stratton Townhome ~ 1 Mi to Skiing!

3.0 star property
Sunny Stratton Townhome ~ 1 Mi to Skiing!

Renovated Ski-in/ski-out Peru Condo at Bromley Mtn

3.0 star property
10.0 out of 10, Exceptional, (1)
"Location right next to Bromley Ski Area- easy access to the mountain and short drive to Manchester. Comfortable for our family of 6. Communication with the owner was very easy. "
Renovated Ski-in/ski-out Peru Condo at Bromley Mtn
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
8.4 out of 10, Very Good, (73)
"Condo was great, cozy, and clean. Has access to the pool and hot tubs from back porch and has great Mountain View’s. The village had plenty of food, little expensive, but pretty good. Overall great place to stay and enjoy the mountain. "
The price is SAR 1,294
SAR 1,608 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 top apartments in the area to choose from: Efficient condo near slopes with kitchenette & great location: Situated in Ludlow, 10.9 mi/17.5 km from the heart of Chester. Includes sofa beds. Unexpected Style in a Cosy, Convenient In-Town Apartment: Located 23.7 mi/38.1 km away in Manchester Center. Free WiFi, private balconies, and Smart TVs are included. Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly: Located in Ludlow, 10.4 mi/16.7 km away. Includes private patios and sofa beds. Access to a hot tub is available on site. Carriage House Studio Apt- secluded, mountain views, babbling brook, countryside: 22.8 mi/36.8 km away in Dorset. Free WiFi, private balconies, and Smart TVs are included. Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK: Located in Ludlow, 10.4 mi/16.7 km from Chester. Includes laundry facilities, free WiFi, and private patios. A fitness center and an outdoor pool are 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. 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.