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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Chester condo rentals

A cozy cabin interior with a sofa, dining table, chairs, wooden cabinets, and a kitchen area.

1. Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Ludlow
$262 nightly
The price is $296
Oct 19 - Oct 20
Total with taxes and fees
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
A living room with a sofa, a bench, a fireplace, a TV, and a large window.

2. Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Clock Tower Base Area
9.2 out of 10, Wonderful, (30 reviews)
"Great property, clean and close to the slope"
United States
tiliger01
$205 nightly
The price is $232
Oct 20 - Oct 21
Total with taxes and fees
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
A view of a grassy area with a ski lift and a building in the background.

3. Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Clock Tower Base Area
8.8 out of 10, Excellent, (81 reviews)
"Property is on 4th floor almost at the end, so you have to walk the most with heavy bags..that was pain.. had problems with heating and cooling system. Also requested for 1 hour late check out at the time of booking, never received any response on top cleaning stuffs were sent to the property sharp at 10 am. Our friends rented another property on the same building and they could easily checked out late at 12:00 pm. Otherwise we enjoyed our stay and proximity to the slope is unparallel."
United States
Indrajit A.
$236 nightly
The price is $266
Oct 12 - Oct 13
Total with taxes and fees
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
A two-story house with a porch, a staircase, and a front door.

4. Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Ludlow
8.8 out of 10, Excellent, (27 reviews)
"Great location - walkable to small town. Very close drive to slopes"
United States
Keath
$240 nightly
The price is $271
Oct 6 - Oct 7
Total with taxes and fees
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
A modern living room with a fireplace, a television, and a ceiling fan.

5. Ski-In/Out Condo with Mountain Views, and Washer/Dryer

Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Ludlow
9.6 out of 10, Exceptional, (18 reviews)
"Very clean and comfortable for our family of 4. Great ski-in/ski-out location - easily accessible to all lifts. Highly recommend. "
United States
Carey S.
$446 nightly
The price is $503
Oct 6 - Oct 7
Total with taxes and fees
Ski-In/Out Condo with Mountain Views, and Washer/Dryer
A rectangular pool with a glass enclosure, surrounded by lounge chairs and umbrellas, set in a landscaped area with trees.

6. Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Cavendish
10.0 out of 10, Exceptional, (24 reviews)
"Great location, and comfortable for the whole family. Everyone in the enjoyed the open living room and dining room, plus the privacy of their own bedroom space. "
United States
Ania H.
$479 nightly
The price is $536
Oct 6 - Oct 7
Total with taxes and fees
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
A two-story house with a covered porch, a staircase, and a front door with a wreath.

7. 2nd-floor downtown Ludlow studio condo with kitchenette, streaming

2nd-floor downtown Ludlow studio condo with kitchenette, streaming
Ludlow
8.6 out of 10, Excellent, (4 reviews)
"Great location and convenient to all local businesses. I enjoyed it very much. Would stay here anytime and plan to again. "
United States
Kevin C.
$233 nightly
The price is $264
Oct 6 - Oct 7
Total with taxes and fees
2nd-floor downtown Ludlow studio condo with kitchenette, streaming
A two-story house with a covered porch, a staircase, and a front door with a wreath.

8. Condo in the heart of town near skiing - less than a mile to Okemo Mountain

Condo in the heart of town near skiing - less than a mile to Okemo Mountain
Ludlow
9.0 out of 10, Wonderful, (14 reviews)
"Great place!"
United States
Darcie L.
$286 nightly
The price is $323
Oct 6 - Oct 7
Total with taxes and fees
Condo in the heart of town near skiing - less than a mile to Okemo Mountain
A living room with a sofa, a television, a fireplace, and a dining area with chairs and a table.

9. Lovely ski-in/out condo steps from ski lift with trails and amazing views

Lovely ski-in/out condo steps from ski lift with trails and amazing views
Stratton
8.4 out of 10, Very good, (36 reviews)
"I have stayed in this condo a few times now, and for my needs it is a great value; affordable, comfortable and ideal location. "
United States
eric m.
$278 nightly
The price is $314
Oct 6 - Oct 7
Total with taxes and fees
Lovely ski-in/out condo steps from ski lift with trails and amazing views
A spacious living room with a stone fireplace, wooden furniture, and large windows.

10. Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck

Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
Plymouth
9.8 out of 10, Exceptional, (24 reviews)
"convenient to okemo"
United States
marcus l.
$616 nightly
The price is $689
Oct 31 - Nov 1
Total with taxes and fees
Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
A modern living room with a fireplace, a dining area, and a kitchen in the background.

11. Ground Floor ski-in/out condo, full kitchen & high-speed WiFi

Ground Floor ski-in/out condo, full kitchen & high-speed WiFi
Clock Tower Base Area
9.4 out of 10, Exceptional, (27 reviews)
"No interaction with host but all amenities were excellent "
United States
Dan M.
$361 nightly
The price is $408
Oct 6 - Oct 7
Total with taxes and fees
Ground Floor ski-in/out condo, full kitchen & high-speed WiFi
A multi-story building with a red and yellow facade, surrounded by lush greenery and flowering plants.

12. Okemo | Charming 1BR Condo + Close to Amenities

Okemo | Charming 1BR Condo + Close to Amenities
Jackson Gore Base Area
$350 nightly
The price is $387
Oct 26 - Oct 27
Total with taxes and fees
Okemo | Charming 1BR Condo + Close to Amenities
A calm lake with a wooden boat on the shore.

13. Cozy 3 bedroom condo 2.5 miles to Mount Snow

Cozy 3 bedroom condo 2.5 miles to Mount Snow
West Dover
9.2 out of 10, Wonderful, (52 reviews)
"The place was absolutely relaxing, clean, and one of the best host we’ve ever had an experience with. Will come back!!"
United States
Scott S.
$262 nightly
The price is $296
Oct 13 - Oct 14
Total with taxes and fees
Cozy 3 bedroom condo 2.5 miles to Mount Snow
A modern kitchen with dark cabinetry, stainless steel appliances, and a bar area with stools.

14. Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub

Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
Stratton Mountain
10.0 out of 10, Exceptional, (36 reviews)
"Great space, great location!"
United States
Jason S.
$466 nightly
The price is $527
Oct 26 - Oct 27
Total with taxes and fees
Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
A multi-story building with a stone facade, a central courtyard with a hot tub, and a stone pathway.

15. Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Stratton
8.0 out of 10, Very good, (1 review)
$360 nightly
The price is $406
Oct 6 - Oct 7
Total with taxes and fees
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
An indoor swimming pool with clear blue water, surrounded by lounge chairs and tables, under a high ceiling with skylights.

16. Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!

Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!
Okemo Village
10.0 out of 10, Exceptional, (64 reviews)
"The host is extremely friendly and accommodating! The place is large and didn’t feel cramped with two adults and five male teenagers! Perfect in every way, clean, well stocked, and easy access to the slopes!"
United States
Nina
$800 nightly
The price is $904
Oct 6 - Oct 7
Total with taxes and fees
Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!
A spacious living area with a high ceiling, wooden beams, a fireplace, and a large wooden coffee table.

17. Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Dover
8.6 out of 10, Excellent, (37 reviews)
"Location was fantastic! Great ski-in, ski-out location! Unit itself was very dated but location made up for it."
United States
Evan C.
$319 nightly
The price is $361
Oct 11 - Oct 12
Total with taxes and fees
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
A modern living room with a fireplace, a large sofa set, and a view through the glass doors.

18. New! Vermont Getaway! Stratton - close to skiing!

New! Vermont Getaway! Stratton - close to skiing!
Winhall
10.0 out of 10, Exceptional, (1 review)
"The place was perfect for us! Easy stay. Very clean and the wood burning fireplace was great. Would def recommend!"
United States
Carolyn K.
$518 nightly
The price is $526
Nov 3 - Nov 4
Total with taxes and fees
New! Vermont Getaway! Stratton - close to skiing!
A wooden cabin with multiple balconies and a stone chimney.

19. Trailside Village #1: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals

Trailside Village #1: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
Killington
9.2 out of 10, Wonderful, (59 reviews)
"Great stay. We really loved the ski in ski out feature. Host was responsive with any issues"
United States
Andrea W.
$542 nightly
The price is $612
Oct 6 - Oct 7
Total with taxes and fees
Trailside Village #1: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
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

The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

10/10 Excellent
"Great place to stay"
Joseph 1-night trip
Posted 4 hours ago
The Black Bear Lodge at Stratton Mountain Resort

Find out more about Chester

Chester Condo Rentals information

Number of reviews
507
Accommodation
496 Condo Rentals
Lowest Price
$232
Highest Price
$904

Frequently asked questions

How much do condos in Chester cost?
Condos in Chester range from $232 to $904 per night. This gives you lots of space for your whole family at a price that's easy on your wallet. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many condos are there in Chester?
Choose from 496 condos in Chester. No matter if you're traveling with the little ones or planning a getaway with friends, Expedia will help you find the perfect space for your squad.
Why book your condo in Chester with Expedia?
Getaways should be a piece of cake, so if you're in search of condos at a great price, Expedia has you covered. Keep the budget in check and go for something small and affordable, or book 5-star accommodations and treat your loved ones. Our search filters make it easy to find a stay in Chester that suits your needs.
How can I find cheap condos in Chester?
Expedia can help you look for cheap condos in Chester. To book your ideal stay in a few clicks, try out our handy filter tool to refine your search results by star rating, amenities and budget.
What is there to do in Chester near my condo?
Once you've unpacked your bags, set out and discover the awesome things Chester has on offer. DaVallia Art & Accents is a great attraction to add to your must-see list.

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