Search Apartments in Chester

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
20 Feb - 22 Feb
In two months
3 Apr - 5 Apr
In three months
1 May - 3 May
In four months
29 May - 31 May

Our top choices for Chester apartments

Property grounds

Unique and charming guesthouse in Brattleboro, Vermont

Unique and charming guesthouse in Brattleboro, Vermont
Brattleboro
Unique and charming guesthouse in Brattleboro, Vermont
Interior

Cozy apt in beautiful secluded spot 15 mins from Mt Snow

Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Dover
10.0 out of 10, Exceptional, (4 reviews)
"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!"
United States
Erica H.
The price is SAR 319
SAR 776 total
includes taxes & fees
28 Feb - 1 Mar
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Property grounds

Vermont Double Queen Suite | 10 Mins to Killington

Vermont Double Queen Suite | 10 Mins to Killington
Bridgewater
8.8 out of 10, Excellent, (5 reviews)
"This was perfect for our girls weekend! Great location, spacious & clean. Our host was so responsive & kind- highly recommend staying here when you visit Salem! "
United States
Brianna L.
The price is SAR 368
SAR 812 total
includes taxes & fees
4 Feb - 5 Feb
Vermont Double Queen Suite | 10 Mins to Killington
Property grounds

Vermont Suite | 10 Min to Woodstock & Killington

Vermont Suite | 10 Min to Woodstock & Killington
Bridgewater
10.0 out of 10, Exceptional, (5 reviews)
"We had a lovely time in Woodstock Vermont. The Bridgewater Inn was cozy and perfect for our weekend get away"
United States
Rosie L.
The price is SAR 443
SAR 907 total
includes taxes & fees
4 Feb - 5 Feb
Vermont Suite | 10 Min to Woodstock & Killington
Property grounds

Vermont Suite | 10 Min to Killington & Woodstock

Vermont Suite | 10 Min to Killington & Woodstock
Bridgewater
9.2 out of 10, Wonderful, (7 reviews)
"Overall, a great stay. "
United States
Meghan J.
The price is SAR 304
SAR 734 total
includes taxes & fees
4 Feb - 5 Feb
Vermont Suite | 10 Min to Killington & Woodstock
Property grounds

Vermont Suite | Minutes to Killington | Skiing

Vermont Suite | Minutes to Killington | Skiing
Bridgewater
8.0 out of 10, Very Good, (2 reviews)
"clean, easy to check in and out, convenient location to the GMHA grounds - we stay here every summer! "
United States
Amanda K.
The price is SAR 559
SAR 1,050 total
includes taxes & fees
4 Feb - 5 Feb
Vermont Suite | Minutes to Killington | Skiing
Exterior

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
Ludlow
9.8 out of 10, Exceptional, (173 reviews)
"Great spot to stay in with a group for skiing. Easy check in and check out process."
United States
Aidan O.
Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK
Terrace/patio

Downtown Remodel: Restaurants & Mountain Shuttle

Downtown Remodel: Restaurants & Mountain Shuttle
Ludlow
The price is SAR 1,215
SAR 2,392 total
includes taxes & fees
4 Feb - 5 Feb
Downtown Remodel: Restaurants & Mountain Shuttle
Golf

Efficient condo near slopes with kitchenette & great location

Efficient condo near slopes with kitchenette & great location
Ludlow
8.6 out of 10, Excellent, (32 reviews)
"Nice place close to mountain easy in easy out"
United States
Aaron B.
The price is SAR 473
SAR 1,005 total
includes taxes & fees
4 Feb - 5 Feb
Efficient condo near slopes with kitchenette & great location
Golf

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

Well-appointed studio right downtown - less than a mile to Okemo Mountain
Ludlow
8.6 out of 10, Excellent, (12 reviews)
"Clean with everything we needed for a few nights stay."
United States
Sandra S.
The price is SAR 499
SAR 1,411 total
includes taxes & fees
9 Feb - 10 Feb
Well-appointed studio right downtown - less than a mile to Okemo Mountain
Exterior

Cozy Studio Condo with Great Location, WiFi & Kitchenette

Cozy Studio Condo with Great Location, WiFi & Kitchenette
Ludlow
8.8 out of 10, Excellent, (29 reviews)
"Great location and great place!"
United States
Linda G.
The price is SAR 503
SAR 1,083 total
includes taxes & fees
11 Feb - 12 Feb
Cozy Studio Condo with Great Location, WiFi & Kitchenette
Outdoor dining

Okemo | Studio Condo + Loft | Near Slopes + Pool

Okemo | Studio Condo + Loft | Near Slopes + Pool
Jackson Gore Base Area
10.0 out of 10, Exceptional, (2 reviews)
"Very conveinent check in, nice property."
United States
michael
The price is SAR 2,348
SAR 2,926 total
includes taxes & fees
2 Mar - 3 Mar
Okemo | Studio Condo + Loft | Near Slopes + Pool
Outdoor dining

Okemo | Spacious Executive Room w Amenities Nearby

Okemo | Spacious Executive Room w Amenities Nearby
Jackson Gore Base Area
8.0 out of 10, Very Good, (1 review)
The price is SAR 2,085
SAR 2,610 total
includes taxes & fees
2 Mar - 3 Mar
Okemo | Spacious Executive Room w Amenities Nearby
Outdoor dining

Okemo | Studio Condo + Close to All Amenities

Okemo | Studio Condo + Close to All Amenities
Jackson Gore Base Area
The price is SAR 2,171
SAR 2,740 total
includes taxes & fees
2 Mar - 3 Mar
Okemo | Studio Condo + Close to All Amenities
Outdoor dining

Okemo | Charming Room & Amenities Nearby | Pools

Okemo | Charming Room & Amenities Nearby | Pools
Jackson Gore Base Area
The price is SAR 2,085
SAR 2,599 total
includes taxes & fees
2 Mar - 3 Mar
Okemo | Charming Room & Amenities Nearby | Pools
Smart TV, fireplace

6BR 3BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

6BR 3BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Dover
The price is SAR 761
SAR 2,725 total
includes taxes & fees
2 Mar - 3 Mar
6BR 3BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Outdoor pool, a heated pool

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dover
9.2 out of 10, Wonderful, (20 reviews)
"So cute and in such a great area! It was a perfect stay"
United States
Jaden F.
The price is SAR 135
SAR 1,068 total
includes taxes & fees
4 Feb - 5 Feb
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Indoor pool, a heated pool

Spacious cozy bedroom with pvt. full bath. Walking distance to Mt Snow ski lifts

Spacious cozy bedroom with pvt. full bath. Walking distance to Mt Snow ski lifts
Dover
2.0 out of 10, (1 review)
"Vrbo screwed up booking Had to find alternate accommodations"
United States
T H.
The price is SAR 844
SAR 1,326 total
includes taxes & fees
14 Feb - 15 Feb
Spacious cozy bedroom with pvt. full bath. Walking distance to Mt Snow ski lifts
Terrace/patio

Deluxe Studio | Murphy Bed + Sofa

Deluxe Studio | Murphy Bed + Sofa
West Dover
The price is SAR 1,361
SAR 1,697 total
includes taxes & fees
4 Feb - 5 Feb
Deluxe Studio | Murphy Bed + Sofa
Terrace/patio

Cozy Studio | Ski-In Access + Kitchenette

Cozy Studio | Ski-In Access + Kitchenette
West Dover
10.0 out of 10, Exceptional, (2 reviews)
"Room was spacious & kitchen was equipped with essentials needed for a weekend stay. The extra sink area outside the Bathroom was an added bonus."
United States
Jean Marie L.
The price is SAR 1,271
SAR 1,592 total
includes taxes & fees
4 Feb - 5 Feb
Cozy Studio | Ski-In Access + Kitchenette
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chester Hotel Reviews

The Shire Woodstock

The Shire Woodstock

10/10 Excellent
"Woodstock is a magical place! We love staying at the Shire! They really make it feel like home! So cozy! The staff is very friendly and accommodating! We will always stay at the Shire!"
Stephanie 3-night trip
Posted 5 days ago
The Shire Woodstock

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 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 top apartments in the area to choose from: Efficient condo near slopes with kitchenette & great location: Situated in Ludlow, 10.9 mi/17.5 km from the heart of Chester. Includes 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. Onsite laundry facilities and a hot tub 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. Onsite laundry facilities and an outdoor pool are on site. 2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den: Located in West Dover, 26.5 mi/42.7 km from Chester. Includes free WiFi, fireplaces, and Smart TVs. A fitness center and an outdoor 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. Bonnie's Bundles Dolls and DaVallia Art & Accents 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.