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Check prices for these dates

In two weeks
Apr 24 - Apr 26
In two months
Jun 5 - Jun 7
In three months
Jul 3 - Jul 5
In four months
Jul 31 - Aug 2

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, (79 reviews)
"Unit was as advertised. Clean and comfortable."
United States
Ralph D.
$230 nightly
The price is $259
Apr 12 - Apr 13
Total with taxes and fees
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
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.
$260 nightly
The price is $293
Apr 12 - Apr 13
Total with taxes and fees
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
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
$197 nightly
The price is $223
Apr 12 - Apr 13
Total with taxes and fees
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
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, (108 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.
$246 nightly
The price is $265
Apr 12 - Apr 13
Total with taxes and fees
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
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)
"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.
$372 nightly
The price is $420
Apr 16 - Apr 17
Total with taxes and fees
Ski-In/Out Condo with Mountain Views, and Washer/Dryer
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
8.8 out of 10, Excellent, (36 reviews)
"Great place with great amenities! "
United States
Rachel R.
$272 nightly
The price is $307
Apr 12 - Apr 13
Total with taxes and fees
Ski-in/ski-out condo with deck, wood-burning fireplace, & community 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)
"Clean room and very comfortable bed. Was ready for check in sooner than expected. "
United States
Wilson V.
$341 nightly
The price is $385
Apr 12 - Apr 13
Total with taxes and fees
Ground Floor ski-in/out condo, full kitchen & high-speed WiFi
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)
"A great weekend. The property was clean and comfortable."
United States
Joan P.
$343 nightly
The price is $387
Apr 13 - Apr 14
Total with taxes and fees
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
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, (25 reviews)
"Easy stay. Great location."
United States
Zach S.
$223 nightly
The price is $252
Apr 12 - Apr 13
Total with taxes and fees
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Exterior

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
9.4 out of 10, Exceptional, (58 reviews)
"We had an amazing stay at this Vrbo in Killington, Vermont! The ski-in/ski-out location right next to the trail was absolutely perfect and made skiing with our family of four incredibly easy and enjoyable. The place was spotless, well maintained, and had everything we needed for a comfortable stay. We especially loved the wood-burning fireplace—it made the evenings cozy and memorable after long days on the slopes. The outdoor jacuzzi was the highlight for us, the perfect spot to relax and unwind...
United States
Rhemuel V.
$508 nightly
The price is $574
Apr 12 - Apr 13
Total with taxes and fees
Trailside Village #1: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
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)
"Great cozy apartment right next to a ski resort"
United States
Mikhail S.
$257 nightly
The price is $290
Apr 20 - Apr 21
Total with taxes and fees
Cozy 3 bedroom condo 2.5 miles to Mount Snow
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, (32 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.
$271 nightly
The price is $306
Apr 14 - Apr 15
Total with taxes and fees
Lovely ski-in/out condo steps from ski lift with trails and amazing views
Microwave, oven, stovetop, dishwasher

NEW Ski in/out condo with Mt views, hot tub, porch, gym & wifi!

NEW Ski in/out condo with Mt views, hot tub, porch, gym & wifi!
Dover
9.4 out of 10, Exceptional, (9 reviews)
"rented for a ski trip, was nice clean and accommodating. "
United States
yehuda t.
$269 nightly
The price is $304
Apr 13 - Apr 14
Total with taxes and fees
NEW Ski in/out condo with Mt views, hot tub, porch, gym & wifi!
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.
$277 nightly
The price is $313
Apr 15 - Apr 16
Total with taxes and fees
Magic Mountain Trailside Condo - Ski In / Ski Out
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)
"Great place!"
United States
Darcie L.
$269 nightly
The price is $304
Apr 13 - Apr 14
Total with taxes and fees
Condo in the heart of town near skiing - less than a mile to Okemo Mountain
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.
$237 nightly
The price is $268
May 12 - May 13
Total with taxes and fees
2nd-floor downtown Ludlow studio condo with kitchenette, streaming
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 location."
United States
Jeffrey
$372 nightly
The price is $420
May 3 - May 4
Total with taxes and fees
Stratton Mtn Studio | Renovated | Walk to Lifts
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)
"Amazing place! "
United States
Tara
$480 nightly
The price is $538
Apr 12 - Apr 13
Total with taxes and fees
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
TV

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)
"The Nest at Hawk Ledges was a perfect summer getaway. The home provides comfort in a tranquil setting while being close enough to many summer adventures. We enjoyed relaxing in the bright, open home after taking many day trips to explore the area. What a gem!"
United States
Ben N.
$610 nightly
The price is $683
Apr 16 - Apr 17
Total with taxes and fees
Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
Interior

SunBear-Ski on Ski off, Pool, HotTub, Game Room!

SunBear-Ski on Ski off, Pool, HotTub, Game Room!
Killington
10.0 out of 10, Exceptional, (29 reviews)
"Clean and perfect"
United States
Cyle D.
$503 nightly
The price is $569
Apr 12 - Apr 13
Total with taxes and fees
SunBear-Ski on Ski off, Pool, HotTub, Game Room!
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

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

10/10 Excellent
"Yes"
Beverly 1-night trip
Posted 2 hours ago
Best Western Plus Keene Hotel

Find out more about Chester

Chester Condo Rentals information

Number of reviews
348
Accommodation
494 Condo Rentals
Lowest Price
$223
Highest Price
$683

Frequently asked questions

How much do condos in Chester cost?
Condos in Chester range from $223 to $683 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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