Best Apartments in Chester, VT for Your Vacation from $224

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Our top choices for Chester apartments

A golf course with a winding path, trees, and a distant mountain range.

1. Efficient condo near slopes with kitchenette & great location

Ludlow

Frank R.

$205 nightly

Oct 14 - Oct 15

Total with taxes and fees

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

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

Ludlow

Brian

$273 nightly

Oct 21 - Oct 22

Total with taxes and fees

A hotel room with a bed, a bathroom with a mirror, and a window with curtains.

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

Ludlow

$532 nightly

Oct 19 - Oct 20

Total with taxes and fees

A two-story house with a porch, a staircase, and a front door.

4. Cozy Studio Condo with Great Location, WiFi & Kitchenette

Ludlow

Mikhail R.

$211 nightly

Oct 14 - Oct 15

Total with taxes and fees

A two-story house with a green roof, a covered porch, and a driveway with a parked car.

5. Bridgewater Living - Long Trail Suite

Bridgewater

Ann

$206 nightly

Nov 1 - Nov 2

Total with taxes and fees

A multi-story building with a red and yellow facade, surrounded by lush greenery and flowering plants.

6. Okemo | Studio Condo + Close to All Amenities

Jackson Gore Base Area

$260 nightly

Oct 26 - Oct 27

Total with taxes and fees

A playground with slides and climbing structures surrounded by trees.

7. Cozy Bromley Retreat

Bromley Mountain

Janja L.

$336 nightly

Oct 8 - Oct 9

Total with taxes and fees

A building with a sign reading 'Fire Tower Restaurant & Tavern.'

8. Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna

Stratton

$199 nightly

Oct 8 - Oct 9

Total with taxes and fees

A rectangular pool with a brick deck, surrounded by lounge chairs and umbrellas.

9. 2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

Dover

Tania J.

$271 nightly

Oct 26 - Oct 27

Total with taxes and fees

A dormitory room with bunk beds, a television mounted on the wall, and a chair in the center.

10. Two Ski-On Condos at Winterplace

Okemo Village

$865 nightly

Nov 1 - Nov 2

Total with taxes and fees

A living room with a television, sofa, and coffee table.

11. Long Trail House South Wing 2B2B Condo

Stratton

Eileen R.

$407 nightly

Oct 14 - Oct 15

Total with taxes and fees

A bedroom with two beds, a door, and a small table with a lamp.

12. Bridgewater Living - Ski VT Suite

Bridgewater

$206 nightly

Nov 2 - Nov 3

Total with taxes and fees

13. Okemo | Charming Room & Amenities Nearby | Pools

Jackson Gore Base Area

James H.

$249 nightly

Oct 26 - Oct 27

Total with taxes and fees

A two-story house with a porch, surrounded by a well-maintained lawn and dense trees.

14. Bridgewater Living - Ben&Jerry Suite

Bridgewater

Sylvia F.

$207 nightly

Nov 2 - Nov 3

Total with taxes and fees

15. Okemo | Spacious Executive Room w Amenities Nearby

Jackson Gore Base Area

David K.

$241 nightly

Nov 2 - Nov 3

Total with taxes and fees

A dining room with a wooden table, four chairs, a vase with flowers, and a view of greenery outside.

16. Historic Home with Colonial Charm in Manchester

Manchester

Victor G.

$392 nightly

Oct 27 - Oct 28

Total with taxes and fees

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

Jackson Gore Base Area

michael

$280 nightly

Oct 26 - Oct 27

Total with taxes and fees

18. Bridgewater Living - Woodstock Suite

Bridgewater

$206 nightly

Nov 2 - Nov 3

Total with taxes and fees

A modern kitchen with a central island, stainless steel appliances, pendant lighting, and a view to the dining area.

19. Modern Mountain Retreat w/ Chef’s Kitchen

Manchester

Eva G.

$412 nightly

Oct 27 - Oct 28

Total with taxes and fees

Wake up to breathtaking mountain views and slopeside convenience at this cozy retreat, where adventure and relaxation go hand in hand.

20. Deluxe Studio | Murphy Bed + Sofa

West Dover

$212 nightly

Oct 19 - Oct 20

Total with taxes and fees

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Top Chester Hotel Reviews

Hideaway Inn Mt. Snow

8/10 Good

"The room was VERY small, but it was clean and the bed was comfortable. There is not an attendant or any staff onsite. I had a bit of trouble getting the pet registration taken care of since I booked through a 3rd party. We asked for a 1st floor room since there's not an elevator. When we received our check-in information, we were given a room on the 2nd floor. If we only had to carry backpacks, it might have been fine. However, we had large cases, so it was difficult to drag them up the stairs. Also, if you are an above average size person, know that these rooms are small spaces. The bathroom is barely big enough to turn around in and the shower is tiny."

Jackson Gore Village, A Vail Resorts Property

8/10 Good

"Everything about this property was exceptional, EXCEPT the bed. We had an amazing time, enjoyed the lift to view fall colors & mountain coaster. But we had a miserable experience sleeping. The beds are like rock. I know it's the granite state, but get some toppers!"

On The River Inn

10/10 Excellent

"Karen at the front desk was absolutely delightful. She saw me struggling with my dog and bags, and helped me to my room. Dan on the housekeeping was so nice. We saw him almost every day. The hotel is incredibly pet friendly. It's so convenient to walk out of your room directly onto the rear lawn, and down toward the river. I had a nice chat with the lady who lives across the river. She also has a dog. The drive to downtown was just a few minutes. I highly recommend the farmer's market (you pass it on the way to downtown Woodstock). The room was very clean. The sink and bathroom door could use some updates, but other than that it was lovely. I would definitely return again with my pup."

Find out more about Chester

Chester Apartments information

Number of reviews	105
Accommodation	172 Apartments
Lowest Price	$224
Highest Price	$926

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.

Room 1

Check prices for these dates

Our top choices for Chester apartments

1. Efficient condo near slopes with kitchenette & great location

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

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