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Check prices for these dates

Next weekend
25 Apr - 27 Apr
In two weeks
2 May - 4 May
In one month
16 May - 18 May
In two months
13 Jun - 15 Jun

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, (63)
"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)
"Well appointed amenities "
The price is AED 180
AED 688 total
includes taxes & fees
16 Apr - 17 Apr
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, (27)
"Perfect location for a ski trip to Okemo! Very close to the mountain and shops in town. Hot tub was great!"
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, (71)
"Lovely apartment, perfect for me, my wife and teenage son. Everything you need. Close to town and shopping (walking distance). Very clean and well appointed. Host communication was great. "
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)
"My husband and I love visiting Dave and Carol‘s place this time we got to meet all of the fun animals and enjoy fresh chicken, eggs, and goose egg! They are so welcoming and have a sweet little place to stay while we are skiing. We look forward to staying again."
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)
"There were multiple issues with this unit mainly pertaining to our access. There were multiple issues with the vacasa key pad and the code not working. When we arrived, the code was improperly regenerated and we were not able to access the house for more than 30 minutes. We were then given a temporary code (although not told it was temporary) and able to get in. On the second night we were also unable to get in to the house. We called again and were told that the new code we had been given had...
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)
"great location, close walkto store, restaurants. Okemoabout a minute drive toparking lots. "
The price is AED 180
AED 649 total
includes taxes & fees
17 Apr - 18 Apr
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

6.4 out of 10, (12)
"I have always had great experiences renting. this is my very first negative review. I am sorry i had to do this but others should be aware.The owner never communicated with me and never sent me the code to enter the property. I had to call VRBO/ Vacasa to complain. They were able to send me the code. When i got to the property it was clear that there was no effort made for my arrival. A few inches of snow had piled up in front of the entrance. There was also a very musty smell that hit me a...
The price is AED 202
AED 853 total
includes taxes & fees
16 Apr - 17 Apr
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)
"Great, convenient studio with clear communications from owners. Perfect for my family ski weekend. We really enjoyed being able to walk across the street for apre ski, dinners, and morning coffee."
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)
"We had a very nice stay, the place is cozy and charming, exceptionally clean, easy to access, and had all the amenities we could've expected for a weekend away. It's comfortable and clearly cared for, and the kitchen is stocked with tools. Neighborhood is lovely and within easy commute to several ski areas. The property is very beautiful as well, though based on the photos and description we were expecting a more secluded siting. The unit is the second floor of a detached garage, located 20-30...
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)
"Everything was wonderful. There was excellent communication, the place was clean and had everything we needed for a weekend away. Ellen really personalizes the experience with special treats upon arrival and tips for places to eat. She even scraped off our jeep when we were heading out. Thank you Ellen! "
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)
"We had a mixed experience during our stay at Leah's property. On the positive side, Leah was an incredibly friendly and communicative host. She was quick to respond to any questions, and the location was absolutely fantastic—very convenient and close to everything.However, upon arrival, we noticed the unit wasn’t as clean as we expected. There were stains on the rug, dust on the furniture, crumbs on the coffee table, and a dirty stovetop. The dishes appeared to have been used but weren’t...
The price is AED 386
AED 1,324 total
includes taxes & fees
16 Apr - 17 Apr
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)
"This home is located perfectly very near all the shops and restaurants in Manchester. The unit is very quiet and there are no shared walls with others. The unit is extremely clean and well stocked with amenities like shampoo and body wash as well as kitchen supplies such as tea, coffee and condiments. Would definitely book again if in the area."
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)
"Super clean and updated condo close to mountain. Perfect for my family with two kids. Well stocked. Owner very communicative and easy to check in and out."
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 AED 727
AED 1,016 total
includes taxes & fees
16 Apr - 17 Apr
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 AED 257
AED 689 total
includes taxes & fees
1 May - 2 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)
"Great experience. "
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)
The price is AED 298
AED 715 total
includes taxes & fees
21 Apr - 22 Apr
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.
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Other property types in Chester

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)
"This property was perfectly situated for ski on ski off accessibility. It had plenty of room for four adults. We also enjoyed the Sauna after skiing. The host Ryan was very easy to deal with and the check in/out process was simple and efficient. "
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Outdoor spa tub

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

9.8 out of 10, Exceptional, (16)
"Family ski weekend. Our stay was very comfortable. Communication with host was phenomenal, always prompt and courteous Location is nice , very close to the ski resorts "
The price is AED 744
AED 2,332 total
includes taxes & fees
21 Apr - 22 Apr
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Outdoor dining

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (205)
"this cabin was absolutely adorable. The kitchen was great size living room, small but cozy. The only thing I think we would like to call out is that the stairs to the loft bedrooms are quite steep be very careful. Everything was impeccably, clean, very cozy and comfortable. Hot tub was perfect and all instructions for both of the hot tub and exit were clear and easy to read."
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 66 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 relaxing 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 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. Long Trail House Studio at Stratton Mountain Resort: Located in Stratton, 18.7 mi/30 km away. Includes fireplaces and sofa beds. A hot tub and a sauna are on site. Efficient condo near slopes with kitchenette & great location: It’s located in Ludlow, 10.9 mi/17.5 km from Chester. Includes 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. 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.