Search Apartments in Chester

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Compare 126 Apartments in Chester with updated reviews, rates, and availability.

Efficient condo near slopes with kitchenette & great location

9.0 out of 10, Wonderful, (24)
"Stay was good. Couldn’t figure out the TV - Not sure if there was actually cable or not. Close to the main road so traffic was a bit loud. Other than that great stay. "
The price is AED 301
AED 774 total
includes taxes & fees
24 Dec - 25 Dec
Efficient condo near slopes with kitchenette & great location

Stratton South Long Trail Studio Adjacent to the Village and Lifts

9.4 out of 10, Exceptional, (56)
"Right across the road from Stratton Mountain. Check in was easy. Place was clean and comfortable. Much nicer and roomier than a typical hotel room. Highly recommended"
Stratton South Long Trail Studio Adjacent to the Village and Lifts

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

7.2 out of 10, Good, (10)
"Sufficient space and easy distance to center of Ludlow and Okemo Mt"
The price is AED 342
AED 1,055 total
includes taxes & fees
5 Jan - 6 January 2025
Riverfront studio with river view, full kitchen, & free WiFi

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 929
AED 1,812 total
includes taxes & fees
24 Dec - 25 Dec
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, (58)
"This property is located in the center of action at Stratton. The apartment is even more attractive than pictures present. The bed is very comfortable and it's spacious, clean and bright. I would stay there again. Thank you. "
Long Trail House Studio at Stratton Mountain Resort

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

9.2 out of 10, Wonderful, (10)
"Great stay. Close to okemo"
The price is AED 529
AED 1,357 total
includes taxes & fees
25 Dec - 26 Dec
Well-appointed studio right downtown - less than a mile to Okemo Mountain

Vermont Retreat

9.8 out of 10, Exceptional, (17)
"Cozy and everything you could need. Really nice kitchen set up and excellent appliances. After a week on the road, the washer & dryer were a welcome refresh of clothing. It's a few minutes west of Woodstock down a country road, so secluded. Takes dogs - wish we had one!"
Vermont Retreat

Hawks Mountain Farm, full apartment on a working farm.

9.8 out of 10, Exceptional, (32)
"Place was quiet, quaint and comfortable. Host was very friendly making it a great stay. "
Hawks Mountain Farm, full apartment on a working farm.

Skyeship House Condo with Hot Tub! - 1 Minute from Gondola - Sleeps 12 Easily

9.2 out of 10, Wonderful, (15)
"Great price, location, and property owner. "
Skyeship House Condo with Hot Tub! - 1 Minute from Gondola - Sleeps 12 Easily

Gorgeous ski retreat apartment with fireplace and Mountain View.

10.0 out of 10, Exceptional, (3)
"We have stayed in dozens of Mt. Snow rentals and this was by far the best. Close to the mountain, clean and spacious, it was the perfect place to stay."
Gorgeous ski retreat apartment with fireplace and Mountain View.

Remodeled condo with free WiFi & shared W/D - ski bus pickup across street

8.6 out of 10, Excellent, (9)
"Property was cozy and comfortable! Definitely would not be able to fit more than 4 as when the sofa bed is expanded, the "living room" floor space is basically full. Showers and amenities were great, but they did not have a pan in case you were planning on cooking. Also price was pretty high for 1 night, but presumably cleaning fees would be cheaper when split over more nights."
The price is AED 837
AED 1,763 total
includes taxes & fees
26 Dec - 27 Dec
Remodeled condo with free WiFi & shared W/D - ski bus pickup across street

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

9.8 out of 10, Exceptional, (163)
"Bob has always been easy to communicate with and we love the cozy yes spacious stay. Highly recommend!"
Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK

Luxe 'Green Barn' Near Skiing w/ Mt Equinox Views!

10.0 out of 10, Exceptional, (34)
"Pros: Great setting in Equinox valley. Property owners super friendly with great communication. Beds were super comfortable and the unit was clean & spacious. Parking for one car in garage was much appreciated. 5 minute drive into Manchester Center with tons of nice shoos& restaurants Con: For those with mobility issues: about 14 stairs into the unit to navigate & haul up luggage so may not work for everybody. "
Luxe 'Green Barn' Near Skiing w/ Mt Equinox Views!

Cozy private apartment with winter views of Mt Equinox

10.0 out of 10, Exceptional, (17)
"We loved this little apartment, it was spotless and cozy! It was very close to town and easy to get in and out of with a code. My only suggestion to the owners would be to put some soap in the shower and maybe a little side table at one of the sofas to make it easier to put a drink or cup of coffee on. But other than that, it was wonderful!"
Cozy private apartment with winter views of Mt Equinox

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.

2 Bedroom with Hot Tub - 1 Minute from Gondola - Skyeship House

9.0 out of 10, Wonderful, (7)
"We enjoyed our stay! Stephen was very nice just a message away if we needed anything. "
2 Bedroom with Hot Tub - 1 Minute from Gondola - Skyeship House

Private 2 Bdr Apartment minutes from Mt Snow and Stratton!

9.4 out of 10, Exceptional, (6)
"Very charming private retreat where all you can hear is the river. The house has wonderful charm and all the modern comforts. We had a lovely stay "
Private 2 Bdr Apartment minutes from Mt Snow and Stratton!

8 Mi to Okemo Mtn: Charming Ludlow Studio!

3.0 star property
10.0 out of 10, Exceptional, (1)
"I decided to stay a bit out of town for a ski trip....and it was perfect. Just a 10 min ride down the hill to OKEMO and LUDLOW. It is absolutely beautiful and quiet...the sunsets and sunrises are amazing from the top of that hill. It is secluded and you really get a slice of VT. The unit is very large and spacious. It has everything you need for a short stay...for some, not having a microwave is an issue, but not for me. Toaster over, full stove, fridge, electric water kettle, coffee maker,...
8 Mi to Okemo Mtn: Charming Ludlow Studio!

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

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

Sunny Stratton Townhome ~ 1 Mi to Skiing!

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

Long Trail House at Stratton Mountain Resort

3.0 star property
8.4 out of 10, Very Good, (72)
"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 AED 1,392
AED 1,731 total
includes taxes & fees
6 Jan - 7 January 2025
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, (40)
"Like property— sad the lift that made it ski and in out was closed due weather conditions "
The price is AED 1,939
AED 2,618 total
includes taxes & fees
10 Jan - 11 January 2025
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

9.8 out of 10, Exceptional, (164)
"The property is exactly like the pictures indicate. The house is in a friendly neighborhood outside of town. The house is very comfortable and spacious. The host responds to your messages in timely manner, and, she is very workable. Would definitely stay there again "
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
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 73 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 some favorite sights in the larger region like Okemo Mountain Resort and 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 spa tub is available on site. Efficient condo near slopes with kitchenette & great location: It’s situated in Ludlow, 10.9 mi/17.5 km away. Includes sofa beds. Stratton South Long Trail Studio Adjacent to the Village and Lifts: Located 18.7 mi/30 km away in Stratton. Private balconies, fireplaces, and sofa beds are included. An outdoor pool and a spa tub are on site. Riverfront studio with river view, full kitchen, & free WiFi: It’s situated in Cavendish, 8.4 mi/13.5 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. You’ll find favorite places to visit like Okemo Mountain Resort and Stratton Mountain Resort 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.