Search Condos Rentals in Chester from CA $308

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Check prices for these dates

In two weeks
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

Our top choices for Chester condo rentals

Property grounds

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
9.0 out of 10, Wonderful, (80 reviews)
"Our stay was perfectly pleasant but the parking was far from the unit and the ski school and daycare was on a different part of the mountain which made the location inconvenient for having little kids with us."
United States
Teresa W.
The price is CA $103
CA $357 total
includes taxes & fees
May 26 - May 27
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Property grounds

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
The price is CA $68
CA $308 total
includes taxes & fees
May 26 - May 27
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Interior

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

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Ludlow
7.6 out of 10, Good, (56 reviews)
"The place was very dirty. The linens were dirty, the pots/pans and all of the cooking utensils were dirty. There was a rubber band on the floor in bathroom that didn't belong to us.There was only 3 forks and a few spoons. Very little silverwear."
United States
Leigh-Ellen F.
The price is CA $165
CA $534 total
includes taxes & fees
May 28 - May 29
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
TV

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.
The price is CA $172
CA $582 total
includes taxes & fees
May 28 - May 29
Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Beach

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, (51 reviews)
"Cozy place, very close to the moover and Mount Snow. Host was very responsive. Would definitely book again!"
United States
dory p.
The price is CA $112
CA $392 total
includes taxes & fees
May 29 - May 30
Cozy 3 bedroom condo 2.5 miles to Mount Snow
Smart TV, fireplace, books

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (109 reviews)
The price is CA $188
CA $395 total
includes taxes & fees
May 27 - May 28
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Lobby

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.
The price is CA $98
CA $425 total
includes taxes & fees
May 26 - May 27
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Sauna

Magic Mountain Trailside Condo - Ski In / Ski Out

Magic Mountain Trailside Condo - Ski In / Ski Out
Londonderry
9.8 out of 10, Exceptional, (14 reviews)
"Nice and we enjoyed our stay"
United States
Gretchen H.
The price is CA $172
CA $434 total
includes taxes & fees
May 31 - Jun 1
Magic Mountain Trailside Condo - Ski In / Ski Out
Exterior

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.
The price is CA $131
CA $338 total
includes taxes & fees
May 26 - May 27
2nd-floor downtown Ludlow studio condo with kitchenette, streaming
Property grounds

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, (35 reviews)
"We loved staying at the townhome. It was a welcome place to stay while we traveled around, enjoying fall. It was very comfortable and the village amenities were great."
United States
John N.
The price is CA $98
CA $425 total
includes taxes & fees
May 26 - May 27
Lovely ski-in/out condo steps from ski lift with trails and amazing views
Exterior

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

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Ludlow
9.0 out of 10, Wonderful, (26 reviews)
"Great location - walkable to small town. Very close drive to slopes"
United States
Keath
The price is CA $138
CA $347 total
includes taxes & fees
May 28 - May 29
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Property grounds

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

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Stratton
7.4 out of 10, Good, (21 reviews)
"Poor management company. Great lodge. "
United States
Billy W.
The price is CA $183
CA $534 total
includes taxes & fees
May 26 - May 27
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Interior

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)
"This condo is a true ski-in, ski-out experience! Literally walked out the back door and skied to the lift. (A/B lifts) The kitchen was well appointed, the bed comfortable, and was perfectly set up for a ski vacation. The entire space had a comfortable, rustic vibe. Would definitely stay here again when returning to Okemo."
United States
Patricia D.
The price is CA $207
CA $539 total
includes taxes & fees
May 26 - May 27
Ground Floor ski-in/out condo, full kitchen & high-speed WiFi
Exterior

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)
The price is CA $173
CA $421 total
includes taxes & fees
May 26 - May 27
Condo in the heart of town near skiing - less than a mile to Okemo Mountain
Fridge, microwave, oven, stovetop

Stratton Mtn Studio | Renovated | Walk to Lifts

Stratton Mtn Studio | Renovated | Walk to Lifts
Stratton Mountain
10.0 out of 10, Exceptional, (31 reviews)
"Great space, great location!"
United States
Jason S.
The price is CA $185
CA $503 total
includes taxes & fees
May 26 - May 27
Stratton Mtn Studio | Renovated | Walk to Lifts
Interior

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

SunBear- AC, Pool, Game Room, Fireplace, Hiking!
Killington
9.8 out of 10, Exceptional, (31 reviews)
"Clean and perfect"
United States
Cyle D.
The price is CA $296
CA $783 total
includes taxes & fees
May 25 - May 26
SunBear- AC, Pool, Game Room, Fireplace, Hiking!
Outdoor pool, a heated pool

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, (23 reviews)
"Great communication without host. The property is clean, well stocked and well maintained. Would definitely stay again! Thanks for letting us share your space."
United States
Steve G.
The price is CA $413
CA $747 total
includes taxes & fees
May 24 - May 25
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Outdoor dining

Okemo | Charming 1BR Condo + Close to Amenities

Okemo | Charming 1BR Condo + Close to Amenities
Jackson Gore Base Area
The price is CA $331
CA $419 total
includes taxes & fees
May 25 - May 26
Okemo | Charming 1BR Condo + Close to Amenities
Interior

Mount Snow Condo: 4 min Walk to Sundance Lift (High Speed - 6 Seat)

Mount Snow Condo: 4 min Walk to Sundance Lift (High Speed - 6 Seat)
Dover
9.4 out of 10, Exceptional, (23 reviews)
"Place was great, perfect location, super clean! Owner had coffee k-cups available, single-use toothbrushes, etc. Great weekend!"
United States
Jim D.
The price is CA $298
CA $825 total
includes taxes & fees
May 25 - May 26
Mount Snow Condo: 4 min Walk to Sundance Lift (High Speed - 6 Seat)
Smart TV, fireplace

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.
The price is CA $344
CA $637 total
includes taxes & fees
Jun 8 - Jun 9
New! Vermont Getaway! Stratton - close to skiing!
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 Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

8/10 Good
"Always enjoy our stay there"
Jason 3-night trip
Posted 11 hours ago
The Palmer House Resort, an Ascend Collection Hotel

Find out more about Chester

Chester Condo Rentals information

Number of reviews
433
Accommodation
518 Condo Rentals
Lowest Price
CA $308
Highest Price
CA $825

Frequently asked questions

How much do condos in Chester cost?
Condos in Chester range from CA $308 to CA $825 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 518 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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