Search Apartments in Chester

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
10 Oct - 12 Oct
In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov

Apartments in Chester

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

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

9.4 out of 10, Exceptional, (16)
"So cute and in such a great area! It was a perfect stay"
The price is AED 143
AED 908 total
includes taxes & fees
6 Oct - 7 Oct
2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
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, (4)
"There was a little problem with the lockbox, but Catherine was available to help solve it. We were staying in the house instead of the “cozy apartment.” Except for a somewhat difficult staircase and a couple of doors to the deck that did not have screens, we have no complaints. They location was beautiful, but a bit of a distance from places we wanted to go to. The price was very fair, and I would recommend this location to others."
The price is AED 312
AED 751 total
includes taxes & fees
31 Oct - 1 Nov
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Cozy Bromley Retreat
Fridge, microwave, oven, stovetop

Cozy Bromley Retreat

10.0 out of 10, Exceptional, (5)
"There is no place I’d rather stay in VT. It’s a perfect condo and the recent renovations are really nice. It’s got all the comforts of home and great touches throughout. Bromley is a great community to be in, it’s close to town, obviously the slopes, and just a overall stay!"
The price is AED 333
AED 1,196 total
includes taxes & fees
28 Oct - 29 Oct
Cozy Bromley Retreat
Ben & Jerry Suite | Minutes to Woodstock | Hiking
Interior

Ben & Jerry Suite | Minutes to Woodstock | Hiking

9.6 out of 10, Exceptional, (5)
"Pleasant and convenient. "
The price is AED 378
AED 815 total
includes taxes & fees
3 Nov - 4 Nov
Ben & Jerry Suite | Minutes to Woodstock | Hiking
Well-appointed studio right downtown - less than a mile to Okemo Mountain
Golf

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

9.2 out of 10, Wonderful, (11)
"Clean with everything we needed for a few nights stay."
The price is AED 298
AED 911 total
includes taxes & fees
5 Oct - 6 Oct
Well-appointed studio right downtown - less than a mile to Okemo Mountain
6BR 3BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Terrace/patio

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

The price is AED 1,142
AED 3,022 total
includes taxes & fees
6 Oct - 7 Oct
6BR 3BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
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 was clean, well presented and very comfortable. We had a great time, checking out nearby waterfalls and history of such places as Bennington. We would stay again and recommend to friends and family.."
The price is AED 514
AED 1,498 total
includes taxes & fees
5 Oct - 6 Oct
Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn
SunBear- AC, Pool, Game Room, Fireplace, Hiking!
Smart TV, fireplace, video games, books

SunBear- AC, Pool, Game Room, Fireplace, Hiking!

10.0 out of 10, Exceptional, (28)
"Stayed 3 nights in early summer. Location was quiet and away from most killington activity.Condo was comfortable and clean. A/C was portable unit type and adequate but a little noisy."
The price is AED 869
AED 2,492 total
includes taxes & fees
8 Oct - 9 Oct
SunBear- AC, Pool, Game Room, Fireplace, Hiking!
Cozy Studio | Ski-In Access + Kitchenette
Property grounds

Cozy Studio | Ski-In Access + Kitchenette

10.0 out of 10, Exceptional, (1)
"Lovely "
The price is AED 584
AED 734 total
includes taxes & fees
2 Nov - 3 Nov
Cozy Studio | Ski-In Access + Kitchenette
Equinox Haven | King Room + Culinary Delights
Indoor pool, a heated pool

Equinox Haven | King Room + Culinary Delights

The price is AED 700
AED 882 total
includes taxes & fees
3 Nov - 4 Nov
Equinox Haven | King Room + Culinary Delights
Okemo | Studio Condo + Close to All Amenities
Exterior

Okemo | Studio Condo + Close to All Amenities

The price is AED 793
AED 1,001 total
includes taxes & fees
9 Oct - 10 Oct
Okemo | Studio Condo + Close to All Amenities
Perfect Getaway minutes to Killington & Woodstock
Exterior

Perfect Getaway minutes to Killington & Woodstock

10.0 out of 10, Exceptional, (1)
"Stayed with my trainer for show at GMHA. Place is lovely and clean, rooms are large, great Wi-Fi so I could do work in evenings. I don’t sleep well away from my own bed normally but the beds are really comfortable and linens and towels soft. I slept great- to my surprise. Also lots of nice places to eat nearby and close to showgrounds. Manager incredibly fast at communicating. Hope it’s available next year- we will be back!"
The price is AED 1,369
AED 2,619 total
includes taxes & fees
13 Oct - 14 Oct
Perfect Getaway minutes to Killington & Woodstock
Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102
Dining

Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102

9.0 out of 10, Wonderful, (7)
"We have stayed here numerous times and it is always a nice experience. This suite is spacious and clean and it felt homey. Love the pool :) and it is so close to Killington making it a really convenient spot. "
The price is AED 525
AED 764 total
includes taxes & fees
5 Oct - 6 Oct
Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102
Remodeled condo with free WiFi & shared W/D - ski bus pickup across street
Fridge, microwave, oven, stovetop

Remodeled condo with free WiFi & shared W/D - ski bus pickup across street

8.6 out of 10, Excellent, (10)
"This property was perfectly located across the street from a local shuttle (or a 5 min drive) to the ski resort and within walking distance to restaurants in town. The unit was clean and spacious. The guest services were easily available. The only minor downside was that the smart TV wouldn’t connect to WiFi - would recommend bringing a firestick or tablet. Would stay here again!"
The price is AED 735
AED 1,631 total
includes taxes & fees
5 Oct - 6 Oct
Remodeled condo with free WiFi & shared W/D - ski bus pickup across street
Efficient condo near slopes with kitchenette & great location
Property grounds

Efficient condo near slopes with kitchenette & great location

8.6 out of 10, Excellent, (32)
"great location, close walkto store, restaurants. Okemoabout a minute drive toparking lots. "
The price is AED 345
AED 805 total
includes taxes & fees
3 Nov - 4 Nov
Efficient condo near slopes with kitchenette & great location
Perfect Getaway! Cozy, Modern condo & Convenient to Everything you will need.
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (72)
"Wonderful, cozy, and comfy (bed is amazing) place to stay. Also very convenient location. Hosts clearly place directions and helpful tips around. Everything was a breeze! "
The price is AED 367
AED 942 total
includes taxes & fees
3 Nov - 4 Nov
Perfect Getaway! Cozy, Modern condo & Convenient to Everything you will need.
Breathtaking Riverfront Farmhouse w/Mountain Views
Fridge, microwave, oven, stovetop

Breathtaking Riverfront Farmhouse w/Mountain Views

9.8 out of 10, Exceptional, (8)
"We loved our stay at this property. Cool, unique layout, lots of space, impressive master bedroom, amazing scenery with the river flowing literally behind the property. Great location in between Woodstock and Killington. Very helpful hosts and easy check in. Would definitely recommend"
Breathtaking Riverfront Farmhouse w/Mountain Views
Deluxe Studio | Murphy Bed + Sofa
Property grounds

Deluxe Studio | Murphy Bed + Sofa

The price is AED 635
AED 799 total
includes taxes & fees
2 Nov - 3 Nov
Deluxe Studio | Murphy Bed + Sofa
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, (28)
"Great location and great place!"
The price is AED 294
AED 771 total
includes taxes & fees
5 Oct - 6 Oct
Cozy Studio Condo with Great Location, WiFi & Kitchenette
Long Trail Suite | 10 Mins to Mountains | A/C
Exterior

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

8.0 out of 10, Very Good, (2)
"clean, easy to check in and out, convenient location to the GMHA grounds - we stay here every summer! "
The price is AED 485
AED 948 total
includes taxes & fees
28 Oct - 29 Oct
Long Trail Suite | 10 Mins to Mountains | A/C
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

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

10/10 Excellent
"Would definitely stay again. Very convenient location "
Stephanie 2-night trip
Posted 2 days ago
Best Western Plus Keene Hotel

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 67 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 top apartments in the area to choose from: Peaceful getaway at Stratton View Lodge: Located in Winhall, 17.4 mi/28 km from the heart of Chester. Includes free WiFi, private patios, and fireplaces. Onsite laundry facilities and a game room are on site. Nana's House: Located 22.2 mi/35.7 km away in Bridgewater. Free WiFi and Smart TVs are included. 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 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den: Located 26.5 mi/42.7 km away in West Dover. Free WiFi, fireplaces, and Smart TVs are included. A fitness center and an outdoor pool are on site. Ben & Jerry Suite | Minutes to Woodstock | Hiking: It's located in Bridgewater, 22.5 mi/36.3 km from Chester. Includes private balconies.
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 Museum of Mining and Minerals and Vermont Country Store 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.