Search Apartments in Chester

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 164 Apartments in Chester with updated reviews, rates, and availability.

Long Trail House Studio at Stratton Mountain Resort
Exterior

Long Trail House Studio at Stratton Mountain Resort

10.0 out of 10, Exceptional, (62)
"Great location, the studio feels bigger than it seems on pictures. "
Long Trail House Studio at Stratton Mountain Resort
Cozy Studio Condo with Great Location, WiFi & Kitchenette
Internet, bed sheets

Cozy Studio Condo with Great Location, WiFi & Kitchenette

8.6 out of 10, Excellent, (27)
"Perfect spot to stay for a ski weekend at Okemo. Itā€™s literally down the block. Canā€™t say enough great things about the room. Clean, comfortable, safe. It had everything I needed. "
Cozy Studio Condo with Great Location, WiFi & Kitchenette
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly
Fridge, microwave, oven, stovetop

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

9.2 out of 10, Wonderful, (26)
"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
Unexpected Style in a Cosy, Convenient In-Town Apartment
Dining

Unexpected Style in a Cosy, Convenient In-Town Apartment

9.8 out of 10, Exceptional, (70)
"We enjoyed our stay. Did not bring our pet but would do so in the future."
Unexpected Style in a Cosy, Convenient In-Town Apartment
Hawks Mountain Farm, full apartment on a working farm.
Property grounds

Hawks Mountain Farm, full apartment on a working farm.

9.8 out of 10, Exceptional, (38)
"Very nice place "
Hawks Mountain Farm, full apartment on a working farm.
Peaceful farm stay with mountain views, sunny patio, & firepit - near skiing
Interior

Peaceful farm stay with mountain views, sunny patio, & firepit - near skiing

8.0 out of 10, Very Good, (3)
"Everything was very clean for my family. It was a bit musty and because the space is over a garage they were woken up every morning between 5:30-6am when the owners would leave. Otherwise everything was great"
Peaceful farm stay with mountain views, sunny patio, & firepit - near skiing
Efficient condo near slopes with kitchenette & great location
Property grounds

Efficient condo near slopes with kitchenette & great location

8.8 out of 10, Excellent, (30)
"Very clean, thankful for NO smoke smell. Very close to Okeemo summit. Would stay again. "
The price is AEDĀ 180
AEDĀ 685 total
includes taxes & fees
17 May - 18 May
Efficient condo near slopes with kitchenette & great location
Riverfront studio with river view, full kitchen, & free WiFi
Fridge, microwave, oven, stovetop

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

6.8 out of 10, (11)
"Easy to find, somewhat dated but clean and tidy, comfortable bed; perfect for a short stay."
The price is AEDĀ 202
AEDĀ 809 total
includes taxes & fees
12 May - 13 May
Riverfront studio with river view, full kitchen, & free WiFi
Stratton South Long Trail Studio Adjacent to the Village and Lifts
Terrace/patio

Stratton South Long Trail Studio Adjacent to the Village and Lifts

9.4 out of 10, Exceptional, (67)
"Clean place, great location. We enjoyed the stay "
Stratton South Long Trail Studio Adjacent to the Village and Lifts
Carriage House Studio Apt- secluded, mountain views, babbling brook, countryside
Interior

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

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

9.8 out of 10, Exceptional, (170)
"It was a described. Well maintained, great communication."
Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK
Vermont Retreat
Fridge, microwave, oven, stovetop

Vermont Retreat

9.8 out of 10, Exceptional, (20)
"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
Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn
Fridge, microwave, stovetop, dishwasher

Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn

9.6 out of 10, Exceptional, (4)
"Property is very clean, beautiful condo and scenery, owner was great and communication was incredible! Highly recommend, great stay!"
The price is AEDĀ 463
AEDĀ 1,432 total
includes taxes & fees
12 May - 13 May
Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn
Cozy private apartment with winter views of Mt Equinox
Fridge, microwave, oven, stovetop

Cozy private apartment with winter views of Mt Equinox

10.0 out of 10, Exceptional, (20)
"I stayed with my daughter for a local horse show and the house was perfect! Clean, roomy and perfect location. "
Cozy private apartment with winter views of Mt Equinox
Gorgeous ski retreat apartment with fireplace and Mountain View.
Miscellaneous

Gorgeous ski retreat apartment with fireplace and Mountain View.

10.0 out of 10, Exceptional, (13)
"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.
Cozy studio with WiFi and fitness room in Springfield. Close to Okemo and Magic.
Game room

Cozy studio with WiFi and fitness room in Springfield. Close to Okemo and Magic.

10.0 out of 10, Exceptional, (1)
"Close to Okemo, property is fun, and owner is respectful/great communication. "
The price is AEDĀ 702
AEDĀ 991 total
includes taxes & fees
20 May - 21 May
Cozy studio with WiFi and fitness room in Springfield. Close to Okemo and Magic.
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Property grounds

Cozy apt in beautiful secluded spot 15 mins from Mt Snow

10.0 out of 10, Exceptional, (1)
"We stayed here for couple of days. We loved it all! The place is lovely, very clean, spacious, big, and very convenient. The price is very reasonable. The property is beautiful overall! It has orchard trees and a lake. It reminded us the Vermont house in the movie Baby Boom. The location is very convenient too. 10 mins of driving to the MT Snow Ski Resort with lots of winter activities , and also 10 mins of driving to town center of West Dover. We walked in town and shopped in the small...
The price is AEDĀ 257
AEDĀ 685 total
includes taxes & fees
13 May - 14 May
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Updated Vintage Apartment < 1/2 Mi to Main St
Fridge, microwave, stovetop, dishwasher

Updated Vintage Apartment < 1/2 Mi to Main St

10.0 out of 10, Exceptional, (15)
"This is my second stay and once again it was great. The home is very clean and in a wonderful location! Will definitely stay again"
Updated Vintage Apartment < 1/2 Mi to Main St
Long Trail Suite | 10 Mins to Mountains | A/C
Aerial view

Long Trail Suite | 10 Mins to Mountains | A/C

6.0 out of 10, (1)
Long Trail Suite | 10 Mins to Mountains | A/C
Cozy In Town Manchester Studio w/ Loft Bedroom.
Outdoor dining

Cozy In Town Manchester Studio w/ Loft Bedroom.

Cozy In Town Manchester Studio w/ Loft Bedroom.
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.
Don't see what you're looking for?
See all available properties in Chester
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Chester

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Miscellaneous

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

10.0 out of 10, Exceptional, (23)
"Loved being tucked away in the wilderness. Owners were very responsive. "
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Exterior

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

9.6 out of 10, Exceptional, (209)
"We absolutely loved our stay in the Honeymoon Cottage! Place was well stocked and clean. We loved the location, very private and close to the Appalachian Long Trail, which we enjoyed hiking. Location is close to Manchester for shopping, groceries and dining. Would happily return. Thank you for a lovely few romantic days."
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Fridge, microwave, oven, stovetop

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (42)
"Very nice place only negative was the sauna did not work"
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?
Youā€™ll find a lot of options for your stay in Chester with 68 accommodations. Though there arenā€™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 areaā€™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 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 hot tub is available on site. Cozy apt in beautiful secluded spot 15 mins from Mt Snow: Itā€™s located in East Dover, 24.9 mi/40.1 km away. Riverfront studio with river view, full kitchen, & free WiFi: Itā€™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 65Ā°F, while the coldest months are January and February with an average of 25Ā°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 Bonnieā€™s Bundles Dolls are a couple of family-friendly sights. Vermont Country Store and Lowell Lake State Park are a couple of places youā€™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 youā€™d like to venture out around the area, consider renting a car to take in more sights.