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Compare 167 Apartments in Chester with updated reviews, rates, and availability.

Cozy apt in beautiful secluded spot 15 mins from Mt Snow

10.0 out of 10, Exceptional, (2)
"Cozy little spot that had everything we needed. Peaceful, quiet, and once the rain let up on our stay we walked out to the gorgeous little pond on the property. So serene. Catherine was great!"
The price is AED 312
AED 755 total
includes taxes & fees
9 Jun - 10 Jun
Cozy apt in beautiful secluded spot 15 mins from Mt Snow

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

9.8 out of 10, Exceptional, (170)
"Great spot to stay in with a group for skiing. Easy check in and check out process."
Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK

Ambient Manchester Village Apt w/ Deck & Pond!

10.0 out of 10, Exceptional, (2)
"The carriage house apartment was cozy. The location is within walking distance to good restaurants. The hosts were friendly and welcoming. "
Ambient Manchester Village Apt w/ Deck & Pond!

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 180
AED 649 total
includes taxes & fees
9 Jun - 10 Jun
Efficient condo near slopes with kitchenette & great location

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

9.0 out of 10, Wonderful, (28)
"We had a great time here and would definitely stay again!"
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly

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

10.0 out of 10, Exceptional, (11)
"Amazing property and place to stay. So warm and cozy. Definitely off the grid feeling but not far from great Vermont towns. Will stay again. Place was perfect "
Carriage House Studio Apt- secluded, mountain views, babbling brook, countryside

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

9.8 out of 10, Exceptional, (67)
"This was a perfect spot for two to stay. Close walk to town and quick drive to Okemo. Had everything you would need to cook simple meals also."
The price is AED 275
AED 819 total
includes taxes & fees
16 Jun - 17 Jun
Perfect Getaway! Cozy, Modern condo & Convenient to Everything you will need.

Unexpected Style in a Cosy, Convenient In-Town Apartment

9.8 out of 10, Exceptional, (71)
"Beautiful place love the decor close to everything."
Unexpected Style in a Cosy, Convenient In-Town Apartment

Long Trail House Studio at Stratton Mountain Resort

10.0 out of 10, Exceptional, (63)
"Great location, the studio feels bigger than it seems on pictures. "
Long Trail House Studio at Stratton Mountain Resort

Hawks Mountain Farm, full apartment on a working farm.

9.8 out of 10, Exceptional, (39)
"Very nice place "
Hawks Mountain Farm, full apartment on a working farm.

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

9.6 out of 10, Exceptional, (15)
"Bob was an incredible host and very responsive! This was a perfect getaway for me and the property was great. I'd stay again in a heartbeat. Thanks Bob for the great stay!"
Okemo Mountain, Family Affordable 2 fl village location walk to town, Dogs OK.

Vermont Retreat

10.0 out of 10, Exceptional, (21)
"We thoroughly enjoyed our stay. It was the perfect location between events that we were attending. Beautiful location, wonderful house and attentive/ helpful hosts."
Vermont Retreat

Updated Vintage Apartment < 1/2 Mi to Main St

10.0 out of 10, Exceptional, (16)
"Great experience. "
Updated Vintage Apartment < 1/2 Mi to Main St

Comfortable Dover Apartment: Walk to Mt Snow!

3.0 star property
9.4 out of 10, Exceptional, (3)
"As a small family of 3 with one 6 year old child we don't mind sharing a hotel room, but when staying longer than 2 days we would prefer a more comfortable environment, especially when weather conditions are not favorable for skiing. We loved the comfort of the apartment, the flexibility of mobility throughout the floor plan, the ability to grocery shop and prepare food, the access to the amenities such as pool, sauna, jacuzzi, laundry and then of course the Mountain View! The outdoor patio was...
Comfortable Dover Apartment: Walk to Mt Snow!

Woodstock Suite | 10 Min to Mountains |A/C| Hiking

10.0 out of 10, Exceptional, (5)
"We had a lovely time in Woodstock Vermont. The Bridgewater Inn was cozy and perfect for our weekend get away"
The price is AED 334
AED 755 total
includes taxes & fees
9 Jun - 10 Jun
Woodstock Suite | 10 Min to Mountains |A/C| Hiking

Manchester Center Retreat w/ Mtn View, Near Skiing

3.0 star property
Manchester Center Retreat w/ Mtn View, Near 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

Cozy private apartment with winter views of Mt Equinox

10.0 out of 10, Exceptional, (22)
"A great apartment close to the heart of town. We enjoyed walking to town for coffee. The apartment had everything we needed to make breakfast and a light dinner. Clean and cozy...perfect for a weekend getaway."
Cozy private apartment with winter views of Mt Equinox

Cozy In Town Manchester Studio w/ Loft Bedroom.

Cozy In Town Manchester Studio w/ Loft Bedroom.

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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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 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'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: Cozy apt in beautiful secluded spot 15 mins from Mt Snow: Situated in East Dover, 24.9 mi/40.1 km from the heart of Chester. 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. Onsite laundry facilities and a hot tub are on site. Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK: Located in Ludlow, 10.4 mi/16.7 km away. Includes laundry facilities, free WiFi, and private patios. A fitness center and onsite laundry facilities are on site. Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn: Located in West Dover, 25 mi/40.3 km from Chester. Includes private balconies, fireplaces, and separate dining areas. Onsite laundry facilities and an indoor 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. Vermont Country Store and Lowell Lake State Park 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.