Search Apartments in Chester

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Compare 116 Apartments in Chester with updated reviews, rates, and availability.

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
2 block walk to Manchester shops! Short drive to slopes! Pet friendly.
2 block walk to Manchester shops! Short drive to slopes! Pet friendly.
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly
9.8 out of 10, Exceptional, (16)
"Great location to restaurant and ski mountain"
The price is AED 342
AED 1,051 total
includes taxes & fees
27 Jun - 28 Jun
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly
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Efficient condo near slopes with kitchenette & great location
9.0 out of 10, Wonderful, (22)
"Beautiful area, very close to the mountain. Property is clean and easily accessible."
Efficient condo near slopes with kitchenette & great location
Long Trail House Studio at Stratton Mountain Resort
10.0 out of 10, Exceptional, (54)
"Our stay was incredible. The location was perfect, room and facility was clean. Thank you for being a great host, 10/10!"
Long Trail House Studio at Stratton Mountain Resort
Hawks Mountain Farm, full apartment on a working farm.
9.6 out of 10, Exceptional, (22)
"Hosts were lovely and helpful, the property is unique, the apartment was private and comfortable with great light, and the location was convenient to Okemo. Very happy with our stay! Thank you!"
Hawks Mountain Farm, full apartment on a working farm.
Carriage House Studio Apt- secluded, mountain views, babbling brook, countryside
10.0 out of 10, Exceptional, (2)
"Near the end of the road (and well off of it) and at the base of Dorset Peak, this studio was an excellent spot for a quiet getaway. The main house is within view, but only as much as an average neighbor would be. It's one room, but it's above a three+ stall garage and PLENTY big enough for a full kitchen, dining table, two large beds, a wood burning fireplace and sitting area. The last three miles to the house have breathtaking views of the surrounding mountains and valleys. It's 10 minutes to...
Carriage House Studio Apt- secluded, mountain views, babbling brook, countryside
Okemo | Spacious Executive Room w Amenities Nearby
Okemo | Spacious Executive Room w Amenities Nearby
Skyeship House Condo with Hot Tub! - 1 Minute from Gondola - Sleeps 12 Easily
10.0 out of 10, Exceptional, (9)
"This location is so very close to the skyship gondola, which is the bottom most lift. It’s actually a great spot because you can do the peak to creek run (the great eastern) as a day ender and basically end up walking distance from the home! Overall, the place was big enough to fit all 6 of us very comfortably with plenty of space to get ready and move about. The kitchen was well equipped with all the cookware you can imagine and some. Also, not to mention the HOT TUB!! There were 2, but we only...
Skyeship House Condo with Hot Tub! - 1 Minute from Gondola - Sleeps 12 Easily
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)
Unexpected Style in a Cosy, Convenient In-Town Apartment
9.6 out of 10, Exceptional, (58)
"This place was a gem. The location was great. We were 2-3 blocks from the Main Street and it was an easy walk to great restaurants. The space was on the second floor of a house. The house was clean, neat and well stocked with everything you need for cooking. (Even some condiments, cooking oils and sugar, and then some.) It is a dog friendly place, however, we decided not to bring our pet because we wanted to celebrate some anniversary dinners out. I was a little nervous that the place may have...
Unexpected Style in a Cosy, Convenient In-Town Apartment
2 Bedroom with Hot Tub - 1 Minute from Gondola - Skyeship House
9.0 out of 10, Wonderful, (4)
"My husband and I had a very comfortable stay. This was a place like home and I was very comfortable. The hot tub was amazing And a plus to the apartment. Having the space outside on the deck To relax was very nice, relaxing in the apartment was all worth my stay. The bathroom floors which were heated were remarkable. One of my favorite parts of staying here was driving up the long Mountainous driveway On the edge. The hot tub was a pleasure however it needs more privacy around it to block...
2 Bedroom with Hot Tub - 1 Minute from Gondola - Skyeship House
Comfortable Dover Apartment: Walk to Mt Snow!
3.5 star property
9.0 out of 10, Wonderful, (2)
Comfortable Dover Apartment: Walk to Mt Snow!
Charming Ludlow Studio - 8 Mi to Okemo Mtn!
3.5 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!
Perfect Getaway minutes to Killington & Woodstock
Perfect Getaway minutes to Killington & Woodstock
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!
Cozy Dover Condo < 1 Mi to Mt Snow Resort!
3.0 star property
10.0 out of 10, Exceptional, (1)
"Very comfortable "
Cozy Dover Condo < 1 Mi to Mt Snow Resort!
Sunny Stratton Townhome ~ 1 Mi to Skiing!
3.0 star property
Sunny Stratton Townhome ~ 1 Mi to Skiing!
Riverfront studio with river view, full kitchen, & free WiFi
7.2 out of 10, Good, (9)
"Sufficient space and easy distance to center of Ludlow and Okemo Mt"
The price is AED 213
AED 855 total
includes taxes & fees
27 Jun - 28 Jun
Riverfront studio with river view, full kitchen, & free WiFi
Well-appointed studio right downtown - less than a mile to Okemo Mountain
9.2 out of 10, Wonderful, (7)
"The room was exactly as advertised, small but nicely done, updated and the kitchen was well stocked. Great accommodations and super close to Okemo."
The price is AED 202
AED 1,098 total
includes taxes & fees
2 Jul - 3 Jul
Well-appointed studio right downtown - less than a mile to Okemo Mountain
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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.

Other property types in Chester

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
9.6 out of 10, Exceptional, (32)
"Lovely property and great location to outdoor activities."
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Long Trail House at Stratton Mountain Resort
3.0 star property
8.4 out of 10, Very Good, (70)
"The unit was perfect for our ski race weekend. Very accessible, underground parking included (ski boxes on top of SUVs will not fit - thankfully we left ours at home), really nice place with everything we needed!"
The price is AED 1,240
AED 1,475 total
includes taxes & fees
4 Jul - 5 Jul
Long Trail House at Stratton Mountain Resort
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
9.8 out of 10, Exceptional, (178)
"There was an issue at our check in that was quickly resolved and we enjoyed our stay a lot. Quiet, relaxing, and the area has some great restaurants. We stayed for our anniversary and will definitely will return."
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
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 70 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 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 Baltimore Covered Bridge 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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