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Our top choices for Chester apartments

1. Cozy Village Condo-Okemo Shuttle

Cozy Village Condo-Okemo Shuttle
Ludlow
9.8 out of 10, Exceptional, (89 reviews)
"simple, sweet, CLEAN and easy"
United States
walter s.
The price is AED 309
AED 917 total
includes taxes & fees
13 Nov - 14 Nov
Cozy Village Condo-Okemo Shuttle

2. Compact downtown studio condo with kitchenette near the Okemo slopes

Compact downtown studio condo with kitchenette near the Okemo slopes
Ludlow
8.6 out of 10, Excellent, (34 reviews)
"the home was clean and very nice. "
United States
Frank R.
The price is AED 412
AED 848 total
includes taxes & fees
15 Nov - 16 Nov
Compact downtown studio condo with kitchenette near the Okemo slopes

3. First-floor downtown studio near dining and gear shops, under a mile to Okemo

First-floor downtown studio near dining and gear shops, under a mile to Okemo
Ludlow
8.8 out of 10, Excellent, (14 reviews)
"This place was so close to Okemo, and walking distance to the local pub and restaurants."
United States
Brian
The price is AED 412
AED 1,109 total
includes taxes & fees
15 Nov - 16 Nov
First-floor downtown studio near dining and gear shops, under a mile to Okemo

4. 3BR/2BA Near Okemo | Vermont Mountain Getaway

3BR/2BA Near Okemo | Vermont Mountain Getaway
Ludlow
The price is AED 688
AED 2,175 total
includes taxes & fees
17 Nov - 18 Nov
3BR/2BA Near Okemo | Vermont Mountain Getaway

5. Downtown studio with kitchenette, shuttle stop right across the street

Downtown studio with kitchenette, shuttle stop right across the street
Ludlow
8.6 out of 10, Excellent, (32 reviews)
"Small but well organized and super convenient!"
United States
Mikhail R.
The price is AED 412
AED 914 total
includes taxes & fees
16 Nov - 17 Nov
Downtown studio with kitchenette, shuttle stop right across the street

6. Fourth-floor Stratton Village studio with valley-view balcony

Fourth-floor Stratton Village studio with valley-view balcony
Stratton
The price is AED 342
AED 900 total
includes taxes & fees
15 Nov - 16 Nov
Fourth-floor Stratton Village studio with valley-view balcony

7. Bridgewater Living - Ben&Jerry Suite

Bridgewater Living - Ben&Jerry Suite
Bridgewater
10.0 out of 10, Exceptional, (1 review)
"Swati, my host, helped me when I had difficulties with tech issues and my stay was as smooth as silk. Thanks!"
United States
Sylvia F.
The price is AED 397
AED 757 total
includes taxes & fees
15 Nov - 16 Nov
Bridgewater Living - Ben&Jerry Suite

8. Okemo | Studio Condo + Close to All Amenities

Okemo | Studio Condo + Close to All Amenities
Jackson Gore Base Area
The price is AED 915
AED 1,097 total
includes taxes & fees
16 Nov - 17 Nov
Okemo | Studio Condo + Close to All Amenities

9. Cozy Bromley Retreat — Ski-In, Ski-Out

Cozy Bromley Retreat — Ski-In, Ski-Out
Bromley Mountain
9.4 out of 10, Exceptional, (21 reviews)
"The place was clean and had all the essentials. Right across from pool and great stay."
United States
Andrew P.
The price is AED 528
AED 1,594 total
includes taxes & fees
15 Nov - 16 Nov
Cozy Bromley Retreat — Ski-In, Ski-Out

10. 11 Gables Treehouse- Shuttle Bus, Short Walk to Shops, Bars, Dining

11 Gables Treehouse- Shuttle Bus, Short Walk to Shops, Bars, Dining
Ludlow
10.0 out of 10, Exceptional, (1 review)
"Cute place right in town, super convenient to the mountain (although if you’re relying on the shuttle it’s only once an hour so can be annoying if you don’t time it well). Rooms comfortably slept 4 plus one on the sofa bed, annd everything was in good shape, Andrew and Jillian were great hosts!"
United States
Max R.
The price is AED 1,201
AED 2,354 total
includes taxes & fees
30 Nov - 1 Dec
11 Gables Treehouse- Shuttle Bus, Short Walk to Shops, Bars, Dining

11. Modern 3BR/2BA | 3 Min to Okemo Mountain

Modern 3BR/2BA | 3 Min to Okemo Mountain
Ludlow
The price is AED 716
AED 2,216 total
includes taxes & fees
16 Nov - 17 Nov
Modern 3BR/2BA | 3 Min to Okemo Mountain

12. Two Ski-On Condos at Winterplace

Two Ski-On Condos at Winterplace
Okemo Village
The price is AED 1,653
AED 3,750 total
includes taxes & fees
22 Nov - 23 Nov
Two Ski-On Condos at Winterplace

13. Historic Home with Colonial Charm in Manchester

Historic Home with Colonial Charm in Manchester
Manchester
10.0 out of 10, Exceptional, (3 reviews)
"Wonderful old historic house, a pleasure and treasure to get to stay there!"
United States
Mary Ann E.
The price is AED 432
AED 1,431 total
includes taxes & fees
1 Dec - 2 Dec
Historic Home with Colonial Charm in Manchester

14. 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
9.4 out of 10, Exceptional, (23 reviews)
"Location was excellent, hosts were responsive, cozy little place with the fireplace, great stay!"
United States
Tania J.
The price is AED 280
AED 1,154 total
includes taxes & fees
16 Nov - 17 Nov
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

15. Long Trail House South Wing 2B2B Condo

Long Trail House South Wing 2B2B Condo
Stratton
10.0 out of 10, Exceptional, (8 reviews)
"Very clean 2br 2ba condo in excellent location. Host provided detailed important information that helped us find property and how to access unit. I would definitely recommend staying here."
United States
Eileen R.
Long Trail House South Wing 2B2B Condo

16. Modern Mountain Retreat w/ Chef’s Kitchen

Modern Mountain Retreat w/ Chef’s Kitchen
Manchester
10.0 out of 10, Exceptional, (1 review)
"Communication with Caroline was top notch and speedy! Very clear instructions for accessing the property and check out. Even though this place is connected with two other rooms/units ( I think that is what it is) we never heard them and hopefully we didn't bother them either!The house was amazing inside and out. The location was exceptional!Thank you for a beautiful stay!"
United States
Eva G.
The price is AED 552
AED 1,566 total
includes taxes & fees
15 Nov - 16 Nov
Modern Mountain Retreat w/ Chef’s Kitchen

17. Bridgewater Living - Ski VT Suite

Bridgewater Living - Ski VT Suite
Bridgewater
The price is AED 397
AED 753 total
includes taxes & fees
15 Nov - 16 Nov
Bridgewater Living - Ski VT Suite

18. Okemo | Spacious Executive Room w Amenities Nearby

Okemo | Spacious Executive Room w Amenities Nearby
Jackson Gore Base Area
9.0 out of 10, Wonderful, (2 reviews)
"We waited outside the room for 30 minutes to check in at exactly 5 PM when it was obvious that the room was ready earlier. The lack of early check in was a hassle."
United States
David K.
The price is AED 832
AED 999 total
includes taxes & fees
16 Nov - 17 Nov
Okemo | Spacious Executive Room w Amenities Nearby

19. Okemo | Charming Room & Amenities Nearby | Pools

Okemo | Charming Room & Amenities Nearby | Pools
Jackson Gore Base Area
10.0 out of 10, Exceptional, (1 review)
"Very nice."
United States
James H.
The price is AED 878
AED 1,053 total
includes taxes & fees
16 Nov - 17 Nov
Okemo | Charming Room & Amenities Nearby | Pools

20. Okemo | Studio Condo + Loft | Near Slopes + Pool

Okemo | Studio Condo + Loft | Near Slopes + Pool
Jackson Gore Base Area
10.0 out of 10, Exceptional, (3 reviews)
"Very conveinent check in, nice property."
United States
michael
The price is AED 987
AED 1,173 total
includes taxes & fees
16 Nov - 17 Nov
Okemo | Studio Condo + Loft | Near Slopes + Pool
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.

Learn more about Chester

Nestled in a relaxing small-town setting, Chester invites visitors to explore DaVallia Art & Accents and browse handcrafted treasures at Bonnie's Bundles Dolls. Outdoor enthusiasts can enjoy nearby Stoughton Pond Recreation Area or take a scenic drive to Lowell Lake State Park and the charming Vermont Country Store.

A nighttime view of a large, illuminated bridge with intricate metalwork and a prominent arch.

Top reviews in Chester

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?

Below are some of the favorite apartments in the area: Hawks Mountain Farm, full upstairs apartment on a working farm.: Includes free WiFi, private patios, and sofa beds. Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna: Located in Stratton, 18.7 mi/30 km away. Includes free WiFi, private balconies, and fireplaces. A fitness center and a hot tub are on site. Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.: Located 10.4 mi/16.7 km away in Ludlow. Free WiFi, private patios, and fireplaces are included. A fitness center and onsite laundry facilities are on site. Charming King Loft in Downtown Woodstock: Located in Woodstock, 25.4 mi/40.8 km from Chester. Includes free WiFi and Smart TVs. Access to onsite laundry facilities is available 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.