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Apartments in Chester for Rent

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Chester apartments

A golf course with a winding path, trees, and a hilly landscape.

1. 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
$273 nightly
The price is $309
Oct 24 - Oct 25
Total with taxes and fees
First-floor downtown studio near dining and gear shops, under a mile to Okemo
A golf course with a winding path, trees, and a distant mountain range.

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.
$205 nightly
The price is $232
Oct 24 - Oct 25
Total with taxes and fees
Compact downtown studio condo with kitchenette near the Okemo slopes
A two-story house with a porch, a staircase, and a front door.

3. 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.
$211 nightly
The price is $239
Oct 24 - Oct 25
Total with taxes and fees
Downtown studio with kitchenette, shuttle stop right across the street
Living area

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

Modern 3BR/2BA | 3 Min to Okemo Mountain
Ludlow
$532 nightly
The price is $601
Nov 1 - Nov 2
Total with taxes and fees
Modern 3BR/2BA | 3 Min to Okemo Mountain
A building with a sign reading 'Fire Tower Restaurant & Tavern.'

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

Fourth-floor Stratton Village studio with valley-view balcony
Stratton
$199 nightly
The price is $224
Oct 25 - Oct 26
Total with taxes and fees
Fourth-floor Stratton Village studio with valley-view balcony
A bathroom with a large mirror, a sink, a vanity, a window with a view of greenery, and a shower curtain.

6. 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.
$184 nightly
The price is $206
Nov 8 - Nov 9
Total with taxes and fees
Bridgewater Living - Ben&Jerry Suite
A multi-story building with a red and yellow facade, surrounded by lush greenery and flowering plants.

7. Okemo | Studio Condo + Close to All Amenities

Okemo | Studio Condo + Close to All Amenities
Jackson Gore Base Area
$267 nightly
The price is $295
Oct 26 - Oct 27
Total with taxes and fees
Okemo | Studio Condo + Close to All Amenities
A playground with slides and climbing structures surrounded by trees.

8. Cozy Bromley Retreat

Cozy Bromley Retreat
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.
$333 nightly
The price is $376
Oct 26 - Oct 27
Total with taxes and fees
Cozy Bromley Retreat
A wooden deck with a white railing, a bench, and a door with glass panels.

9. 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.
$530 nightly
The price is $622
Oct 25 - Oct 26
Total with taxes and fees
11 Gables Treehouse- Shuttle Bus, Short Walk to Shops, Bars, Dining
A dining room with a wooden table, four chairs, a vase with flowers, and a view of greenery outside.

10. Historic Home with Colonial Charm in Manchester

Historic Home with Colonial Charm in Manchester
Manchester
10.0 out of 10, Exceptional, (2 reviews)
"The accommodations were absolutely amazing. We had a wonderful time. The home is beautiful. The host is very communicative."
United States
Victor G.
$350 nightly
The price is $395
Oct 27 - Oct 28
Total with taxes and fees
Historic Home with Colonial Charm in Manchester
A rectangular pool with a brick deck, surrounded by lounge chairs and umbrellas.

11. 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.
$264 nightly
The price is $299
Oct 25 - Oct 26
Total with taxes and fees
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
A hot tub in a room with large windows, a sink, and a sign on the wall.

12. Two Ski-On Condos at Winterplace

Two Ski-On Condos at Winterplace
Okemo Village
$907 nightly
The price is $974
Nov 1 - Nov 2
Total with taxes and fees
Two Ski-On Condos at Winterplace
A living room with a television, sofa, and coffee table.

13. Long Trail House South Wing 2B2B Condo

Long Trail House South Wing 2B2B Condo
Stratton
10.0 out of 10, Exceptional, (6 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.
$431 nightly
The price is $487
Oct 30 - Oct 31
Total with taxes and fees
Long Trail House South Wing 2B2B Condo
A large house with a fire pit and outdoor seating.

14. Bridgewater Living - Ski VT Suite

Bridgewater Living - Ski VT Suite
Bridgewater
$182 nightly
The price is $204
Nov 4 - Nov 5
Total with taxes and fees
Bridgewater Living - Ski VT Suite
A modern kitchen with a central island, stainless steel appliances, pendant lighting, and a view to the dining area.

15. 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.
$389 nightly
The price is $439
Oct 27 - Oct 28
Total with taxes and fees
Modern Mountain Retreat w/ Chef’s Kitchen
A multi-story building with a red and yellow facade, surrounded by lush greenery and flowering plants.

16. 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.
$243 nightly
The price is $268
Oct 26 - Oct 27
Total with taxes and fees
Okemo | Charming Room & Amenities Nearby | Pools
A multi-story building with a red and yellow facade, surrounded by lush greenery and flowering plants.

17. 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.
$254 nightly
The price is $281
Oct 26 - Oct 27
Total with taxes and fees
Okemo | Spacious Executive Room w Amenities Nearby
A multi-story building with a red and yellow facade, surrounded by lush greenery and flowering plants.

18. 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
$279 nightly
The price is $308
Oct 26 - Oct 27
Total with taxes and fees
Okemo | Studio Condo + Loft | Near Slopes + Pool
A small building with a porch labeled 'GUEST ROOMS,' two chairs, a green door, and a wooden bench.

19. Bridgewater Living - Woodstock Suite

Bridgewater Living - Woodstock Suite
Bridgewater
$182 nightly
The price is $204
Nov 4 - Nov 5
Total with taxes and fees
Bridgewater Living - Woodstock Suite
A small building with a porch labeled 'GUEST ROOMS,' two chairs, a green door, and a wooden bench.

20. Bridgewater Living - Long Trail Suite

Bridgewater Living - Long Trail Suite
Bridgewater
8.0 out of 10, Very good, (1 review)
"The studio was clean with rustic feel. On the main road so easy to find. Short drive to restaurant and brewery. About 1/2 to Woodstock."
United States
Ann
$182 nightly
The price is $204
Nov 4 - Nov 5
Total with taxes and fees
Bridgewater Living - Long Trail Suite
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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Top Chester Hotel Reviews

Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

10/10 Excellent
"the only fly in the ointment was an insect found in our bedding on the first night. removed it and there were no further issues. All in all a great stay from a repeat customer. Thanks !"
ed manjuck 2-night trip
Posted 3 hours ago
Hampton Inn and Suites Manchester

Find out more about Chester

Chester Apartments information

Number of reviews
107
Accommodation
176 Apartments
Lowest Price
$204
Highest Price
$974

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.

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