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Compare 114 Apartments in Chester with updated reviews, rates, and availability.

Long Trail House Studio at Stratton Mountain Resort
Living room with view of bar seating and kitchen

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
Hawks Mountain Farm, full apartment on a working farm.
Hawk Mountain Farm

Hawks Mountain Farm, full apartment on a working farm.

9.8 out of 10, Exceptional, (30)
"Beautiful spot in a natural setting. Property owner was very informative about the areas around us as well as the area we were in. A tour of his rescue animals was very enjoyable and informative. It was the perfect getaway. The apartment supplied everything we needed. I would highly recommend a stay there."
Hawks Mountain Farm, full apartment on a working farm.
Efficient condo near slopes with kitchenette & great location

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 SAR 195
SAR 639 total
includes taxes & fees
26 Nov - 27 Nov
Efficient condo near slopes with kitchenette & great location
Stratton South Long Trail Studio Adjacent to the Village and Lifts
Bar seating area adjacent to living room

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
Cozy Studio Condo with Great Location, WiFi & Kitchenette

Cozy Studio Condo with Great Location, WiFi & Kitchenette

8.6 out of 10, Excellent, (24)
"Conveniently located within a 5 min. drive to Okemo Mountain Resort and within walking distance of a number of restaurant/bars. Has all the necessities for a weekend in Ludlow."
The price is SAR 195
SAR 671 total
includes taxes & fees
1 Dec - 2 Dec
Cozy Studio Condo with Great Location, WiFi & Kitchenette
Carriage House Studio Apt- secluded, mountain views, babbling brook, countryside
Exterior

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

10.0 out of 10, Exceptional, (6)
"This is the perfect cabin in Dorset VT! The views on the way in are spectacular. Hiking right out the back door and cozy natural wood experience on the inside. I will definitely be returning to the same location every October! "
Carriage House Studio Apt- secluded, mountain views, babbling brook, countryside
Cozy 1 king bed Apt Minutes to Okemo (Pet Friendly)
Living area

Cozy 1 king bed Apt Minutes to Okemo (Pet Friendly)

10.0 out of 10, Exceptional, (2)
"We had a great weekend staying in this wonderful little vrbo. A great surprise was a general store that had everything we needed right across the street, and beautiful hiking and places to eat within a half hour. I also appreciated the updated and very comfortable king size mattress and bed! Hosts were very accommodating and had great communication. We would definitely stay here again."
Cozy 1 king bed Apt Minutes to Okemo (Pet Friendly)
Well-appointed studio right downtown - less than a mile to Okemo Mountain

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

9.2 out of 10, Wonderful, (9)
"great"
The price is SAR 195
SAR 913 total
includes taxes & fees
26 Nov - 27 Nov
Well-appointed studio right downtown - less than a mile to Okemo Mountain
Minutes to Woodstock | Hiking | Ben & Jerry Suite
Queen sized bed, extra blankets, Roku TV and plenty of locally inspired charm.

Minutes to Woodstock | Hiking | Ben & Jerry Suite

9.6 out of 10, Exceptional, (4)
"Older building on the outside and yard. But rooms were remodeled and very nice. No contact with any staff except by text and emails. They give you a code for the doors. A little different."
The price is SAR 297
SAR 713 total
includes taxes & fees
26 Nov - 27 Nov
Minutes to Woodstock | Hiking | Ben & Jerry Suite
Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK
#68 Pleasant Street Ludlow ,Vt.

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!
Manchester Center Vacation Rental | 1BR | 1BA | 2,000 Sq Ft | Stairs Required

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

10.0 out of 10, Exceptional, (33)
"This place exceeded our expectations so dreamy and beautiful the location was perfect"
Luxe 'Green Barn' Near Skiing w/ Mt Equinox Views!
Cozy private apartment with winter views of Mt Equinox
Living area

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
Unexpected Style in a Cosy, Convenient In-Town Apartment
The bar is open. Help yourself and just replenish what you use. Honor system.

Unexpected Style in a Cosy, Convenient In-Town Apartment

9.6 out of 10, Exceptional, (64)
"Quaint cute apartment. Beds were comfortable. Cute tiny, but well-appointed kitchen. There was a Breville coffee maker but no instructions on how to use it, or where we could get the Breville pods. (Did not see them at the local grocery store.) Shower is understandably small, and we noticed some mold. All in all we were very happy with our stay!"
Unexpected Style in a Cosy, Convenient In-Town Apartment
Okemo Mountain, Family Affordable 2 fl village location walk to town, Dogs OK.
Exterior

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
Living area

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

9.0 out of 10, Wonderful, (6)
"We had a great stay here. Thank you!"
2 Bedroom with Hot Tub - 1 Minute from Gondola - Skyeship House
Charming Ludlow Studio - 8 Mi to Okemo Mtn!
Living area

Charming Ludlow Studio - 8 Mi to Okemo Mtn!

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,...
Charming Ludlow Studio - 8 Mi to Okemo Mtn!
Updated Vintage Apartment < 1/2 Mi to Main St
Living area

Updated Vintage Apartment < 1/2 Mi to Main St

3.0 star property
Updated Vintage Apartment < 1/2 Mi to Main St
Renovated Ski-in/ski-out Peru Condo at Bromley Mtn
Terrace/patio

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

3.0 star property
Renovated Ski-in/ski-out Peru Condo at Bromley Mtn
Perfect Getaway minutes to Killington & Woodstock

Perfect Getaway minutes to Killington & Woodstock

10.0 out of 10, Exceptional, (1)
"Stayed with my trainer for show at GMHA. Place is lovely and clean, rooms are large, great Wi-Fi so I could do work in evenings. I don’t sleep well away from my own bed normally but the beds are really comfortable and linens and towels soft. I slept great- to my surprise. Also lots of nice places to eat nearby and close to showgrounds. Manager incredibly fast at communicating. Hope it’s available next year- we will be back!"
Perfect Getaway minutes to Killington & Woodstock
Charming Ludlow Studio - 8 Mi to Okemo Mtn!
Ludlow Vacation Rental | Studio | 1BA | Step-Free Entry | 1,100 Sq Ft

Charming Ludlow Studio - 8 Mi to Okemo Mtn!

10.0 out of 10, Exceptional, (3)
"Place was much bigger than expected, perfect set up for what we needed. Tons of privacy and great communication by the owner."
Charming Ludlow Studio - 8 Mi to Okemo 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

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Front of property

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (39)
"Everything was wonderful. Easy in and out. Near to almost everything. Beautiful area. I left my keys by mistake and they were wonderful in getting them back to me. I would stay there again. "
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Outdoor spa tub

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (196)
"It was a wonderful little cabin that was clean and decorated comfortably. It had everything we needed. The hot tub was delightful! "
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree! 45% Off! Free Pool
Located in the Okemo Mt. Community, a mile to the base lodge

Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree! 45% Off! Free Pool

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 "
Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree! 45% Off! Free Pool
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 relaxing 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. Long Trail House Studio at Stratton Mountain Resort: Located 18.7 mi/30 km away in Stratton. Fireplaces and sofa beds are included. A spa tub and a sauna are on site. Stratton South Long Trail Studio Adjacent to the Village and Lifts: Located in Stratton, 18.7 mi/30 km away. Includes private balconies, fireplaces, and sofa beds. An outdoor pool and a spa tub are on site. 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. 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. 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.