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Check prices for these dates

In two weeks
Mar 20 - Mar 22
In two months
May 1 - May 3
In three months
May 29 - May 31
In four months
Jun 26 - Jun 28

Our top choices for Chester condo rentals

Interior

Condo in Ludlow

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
7.6 out of 10, Good, (56 reviews)
"Irish Bar nearby was a plus on St. Patrick’s Day !"
United States
Warren
$289 nightly
The price is $327
Apr 7 - Apr 8
Total with taxes and fees
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Property grounds

Condo in Clock Tower Base Area

Ski-in/out mountainside condo close to everything with full kitchen - tranquil
9.0 out of 10, Wonderful, (78 reviews)
"Perfect location for a quick ski trip. "
United States
Michael D.
$248 nightly
The price is $280
Apr 7 - Apr 8
Total with taxes and fees
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Property grounds

Condo in Stratton

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
7.4 out of 10, Good, (21 reviews)
"A great weekend. The property was clean and comfortable."
United States
Joan P.
$356 nightly
The price is $402
Mar 10 - Mar 11
Total with taxes and fees
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Outdoor dining

Condo in Clock Tower Base Area

Ski-in/out mountainside condo with balcony, washer/dryer & high-speed WiFi
8.6 out of 10, Excellent, (14 reviews)
"Great stay at Okemo. Super convenient to get to the lifts and unit was well maintained. Couldn’t find pillow cases for the pull out couch but otherwise everything was well appointed. Check in/check out was super easy. Thank you!"
United States
Kristin S.
$283 nightly
The price is $320
Mar 8 - Mar 9
Total with taxes and fees
Ski-in/out mountainside condo with balcony, washer/dryer & high-speed WiFi
Exterior

Condo in Ludlow

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
9.0 out of 10, Wonderful, (24 reviews)
"Great rate for a place with all the basics!"
United States
Macgregor
$237 nightly
The price is $268
Mar 8 - Mar 9
Total with taxes and fees
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Beach

Condo in West Dover

Cozy 3 bedroom condo 2.5 miles to Mount Snow
9.2 out of 10, Wonderful, (50 reviews)
"Lovely condo set against the trees in the heart of Mt. Snow apres. It have everything needed for a family of 4 - 6. "
United States
Alan S.
$267 nightly
The price is $302
Mar 23 - Mar 24
Total with taxes and fees
Cozy 3 bedroom condo 2.5 miles to Mount Snow
Exterior

Condo in Ludlow

Condo in the heart of town near skiing - less than a mile to Okemo Mountain
9.0 out of 10, Wonderful, (14 reviews)
"Great place!"
United States
Darcie L.
$285 nightly
The price is $322
Mar 8 - Mar 9
Total with taxes and fees
Condo in the heart of town near skiing - less than a mile to Okemo Mountain
Smart TV, fireplace

Condo in Clock Tower Base Area

Ski Haven: 1-Bed Ski-in/out Condo, Okemo Base Area
10.0 out of 10, Exceptional, (13 reviews)
"Great communication, ski in/out location"
United States
Robin
$463 nightly
The price is $523
Mar 11 - Mar 12
Total with taxes and fees
Ski Haven: 1-Bed Ski-in/out Condo, Okemo Base Area
Lobby

Condo in Dover

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
8.6 out of 10, Excellent, (35 reviews)
"Great place with great amenities! "
United States
Rachel R.
$289 nightly
The price is $327
Apr 7 - Apr 8
Total with taxes and fees
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Property grounds

Condo in Stratton

Lovely ski-in/out condo steps from ski lift with trails and amazing views
8.4 out of 10, Very Good, (31 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.
$294 nightly
The price is $332
Mar 18 - Mar 19
Total with taxes and fees
Lovely ski-in/out condo steps from ski lift with trails and amazing views
Exterior

Condo in Ludlow

2nd-floor downtown Ludlow studio condo with kitchenette, streaming
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.
$235 nightly
The price is $265
Apr 7 - Apr 8
Total with taxes and fees
2nd-floor downtown Ludlow studio condo with kitchenette, streaming
Smart TV, fireplace, books

Condo in Ludlow

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
9.8 out of 10, Exceptional, (106 reviews)
"Great Condo. We had plenty of space. Wendi was very responsive and even accommodated us checking in an hour early when we arrived in town. We would definitely come back. "
United States
Barbara M.
$293 nightly
The price is $319
Apr 7 - Apr 8
Total with taxes and fees
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
TV

Condo in Ludlow

Ski-In/Out Condo with Mountain Views, and Washer/Dryer
9.8 out of 10, Exceptional, (16 reviews)
"Perfect spot to jump onto the mountain and ski. Two adults and 4 kids, and we had plenty of space for a long weekend."
United States
Allison T.
$437 nightly
The price is $494
Apr 7 - Apr 8
Total with taxes and fees
Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Property grounds

Condo in Clock Tower Base Area

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
9.2 out of 10, Wonderful, (28 reviews)
"Overall very clean and nice. Needs some updating like more spoons, only 2, bigger coffee cups. And a new coffee table that is very worn. "
United States
David A.
$233 nightly
The price is $263
Apr 7 - Apr 8
Total with taxes and fees
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Interior

Condo in Clock Tower Base Area

Ground Floor ski-in/out condo, full kitchen & high-speed WiFi
9.4 out of 10, Exceptional, (24 reviews)
"Clean room and very comfortable bed. Was ready for check in sooner than expected. "
United States
Wilson V.
$356 nightly
The price is $403
Apr 7 - Apr 8
Total with taxes and fees
Ground Floor ski-in/out condo, full kitchen & high-speed WiFi
Exterior

Condo in Killington

Trailside Village #1: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
9.4 out of 10, Exceptional, (58 reviews)
"Wonderful location…"
United States
David C.
$820 nightly
The price is $927
Mar 11 - Mar 12
Total with taxes and fees
Trailside Village #1: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
Fridge, microwave, oven, stovetop

Condo in Stratton Mountain

Stratton Mtn Studio | Renovated | Walk to Lifts
10.0 out of 10, Exceptional, (31 reviews)
"Great location."
United States
Jeffrey
$449 nightly
The price is $507
Apr 6 - Apr 7
Total with taxes and fees
Stratton Mtn Studio | Renovated | Walk to Lifts
Outdoor pool, a heated pool

Condo in Cavendish

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
10.0 out of 10, Exceptional, (21 reviews)
"Amazing place! "
United States
Tara
$478 nightly
The price is $535
Mar 23 - Mar 24
Total with taxes and fees
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Indoor pool

Condo in Okemo Village

Cozy Slopeside Escape - Ski-In/Out Condo at Okemo
10.0 out of 10, Exceptional, (11 reviews)
"Location was perfect for skiing. Hosts were responsive and the stay was pleasant. Would book again."
United States
Paul T.
$448 nightly
The price is $506
Mar 26 - Mar 27
Total with taxes and fees
Cozy Slopeside Escape - Ski-In/Out Condo at Okemo
Dining

Condo in Killington

Ski-In/Ski-Out Sunrise Village Condo | 2BR, Fireplace, Pool
10.0 out of 10, Exceptional, (35 reviews)
"Great ski-in, ski-out property."
United States
Kristi C.
$678 nightly
The price is $766
Mar 9 - Mar 10
Total with taxes and fees
Ski-In/Ski-Out Sunrise Village Condo | 2BR, Fireplace, 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.
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Top Chester Hotel Reviews

Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

10/10 Excellent
"Good "
Douglas 2-night trip
Posted 5 hours ago
Hampton Inn and Suites Manchester

Find out more about Chester

Chester Condo Rentals information

Number of reviews
579
Accommodation
494 Condo Rentals
Lowest Price
$263
Highest Price
$927

Frequently asked questions

How much do condos in Chester cost?
Condos in Chester range from $263 to $927 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 494 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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