Search and Rent Chester Condos

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

In two weeks
In two months
In three months
In four months

Condo Rentals in Chester

Charming 1-bedroom condo in delightful Dover

Dover
9.6 out of 10, Exceptional, (7)
"Easy to find. Good communication helped, but the sliding door was a little wonky. Additional security for single female travelers would be nice. A bedside table would be useful. All the amenities you would ever need."
United States
Tia
$178 nightly
The price is $201
Nov 19 - Nov 20
Total with taxes and fees
Charming 1-bedroom condo in delightful Dover

Cozy 3 bedroom condo 2.5 miles to Mount Snow

West Dover
9.0 out of 10, Wonderful, (43)
"We loved the place. It was very homey and comfortable. My only suggestion would be to upgrade the towels and add a few more dish towels. "
United States
Kathy S.
$272 nightly
The price is $307
Nov 25 - Nov 26
Total with taxes and fees
Cozy 3 bedroom condo 2.5 miles to Mount Snow

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

Clock Tower Base Area
9.0 out of 10, Wonderful, (73)
"It was a perfect location and had everything we needed for a great stay."
United States
Danna K.
$224 nightly
The price is $253
Nov 10 - Nov 11
Total with taxes and fees
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

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

Dover
8.6 out of 10, Excellent, (31)
"Very nice accommodations and location!"
United States
Michael M.
$254 nightly
The price is $287
Nov 16 - Nov 17
Total with taxes and fees
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

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

Stratton
8.4 out of 10, Very Good, (26)
"Great location close to lift. Condo is clean and well appointed."
United States
Grace Ann B.
$246 nightly
The price is $278
Nov 9 - Nov 10
Total with taxes and fees
Lovely ski-in/out condo steps from ski lift with trails and amazing views

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

Ludlow
7.6 out of 10, Good, (53)
"Property great location but needs interior renovations"
United States
William D.
$278 nightly
The price is $314
Dec 1 - Dec 2
Total with taxes and fees
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

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

Ludlow
10.0 out of 10, Exceptional, (101)
"Pretty nice little condo in a nice location."
United States
jonathan H.
$256 nightly
The price is $277
Nov 11 - Nov 12
Total with taxes and fees
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

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

Ludlow
8.6 out of 10, Excellent, (4)
"Clean room. Glad that the text responses are quick. We weren't initially provided a room number and then the door code we were given would not work. Host responded and was able to reset code from afar. "
United States
Ana Maria C.
$207 nightly
The price is $234
Nov 12 - Nov 13
Total with taxes and fees
2nd-floor downtown Ludlow studio condo with kitchenette, streaming

Ski Haven: 1-Bed Ski-in/out Condo, Okemo Base Area

Clock Tower Base Area
9.8 out of 10, Exceptional, (10)
"The place was great. Exactly like the listing described. Ski lift right off the rear of the building. Great location. Walking distance to some nightlife and food. And just a short drive for all other needs. Place was clean and nicely equipped kitchen. Will definitely be looking to stay again in the future."
United States
ian w.
$311 nightly
The price is $351
Nov 12 - Nov 13
Total with taxes and fees
Ski Haven: 1-Bed Ski-in/out Condo, Okemo Base Area

Ski-in/out mountainside condo with balcony, washer/dryer & high-speed WiFi

Clock Tower Base Area
8.4 out of 10, Very Good, (13)
"Excellent Location.. "
United States
Juan Carlos L.
$279 nightly
The price is $315
Nov 20 - Nov 21
Total with taxes and fees
Ski-in/out mountainside condo with balcony, washer/dryer & high-speed WiFi

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

Ludlow
9.0 out of 10, Wonderful, (14)
"Great location and very comfortable."
United States
Richard J.
$232 nightly
The price is $262
Nov 12 - Nov 13
Total with taxes and fees
Condo in the heart of town near skiing - less than a mile to Okemo Mountain

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

Stratton
7.6 out of 10, Good, (18)
"Great clean, modern condo with in a short walk to Stratton Village and the chair lifts. Upgraded huge TV in the living room. Great place to relax after a long day of skiing. Parking spot located under the complex that is heated. The parking area also has carts to bring all your stuff up the condo in one trip. We would definitely book this place again on our next trip to Stratton to Ski."
United States
John M.
$314 nightly
The price is $355
Nov 9 - Nov 10
Total with taxes and fees
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities

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

Clock Tower Base Area
9.4 out of 10, Exceptional, (21)
"A great spot for an early season weekend celebration. The listing is inaccurate unfortunately. It only sleeps 4 in beds. There is only one sleeper sofa in the living area and there weren’t any sheets for it."
United States
Kristen C.
$325 nightly
The price is $368
Nov 9 - Nov 10
Total with taxes and fees
Ground Floor ski-in/out condo, full kitchen & high-speed WiFi

Sunrise Bear Ridge C4 4 Bedroom Condo

3.0 star property
Killington
$716 nightly
The price is $796
Nov 9 - Nov 10
Total with taxes and fees
Sunrise Bear Ridge C4 4 Bedroom Condo

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

Ludlow
9.0 out of 10, Wonderful, (22)
"This modest property was super clean and convenient to Okemo ski resort. Access was simple as the door codes were emailed. I do wish there was an interior deadbolt/chain-lock for security in addition to just the exterior access combo.This whole unit was freshly painted. The all purpose room was spacious. The kitchen corner was modestly equipped but offered the necessities. The couch was comfortable and the TV was average. The bathroom was spacious but had a dated floor and shower. The...
United States
John
$207 nightly
The price is $234
Nov 12 - Nov 13
Total with taxes and fees
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

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

Ludlow
9.8 out of 10, Exceptional, (16)
"Location location location!"
United States
Britt H.
$398 nightly
The price is $450
Nov 9 - Nov 10
Total with taxes and fees
Ski-In/Out Condo with Mountain Views, and Washer/Dryer

Cozy 2 BR Ski On Ski Off Condo in Killington's Sunrise Mountain Village. Pool. Hot Tub.

2.0 star property
Killington
9.4 out of 10, Exceptional, (3)
"Absolutely perfect spot. Kids and parents loved it. Everything you’re looking for in an on mountain condo. Pool and hot tub are a short drive away but we still used it. "
United States
nicholas d.
$473 nightly
The price is $535
Nov 10 - Nov 11
Total with taxes and fees
Cozy 2 BR Ski On Ski Off Condo in Killington's Sunrise Mountain Village. Pool. Hot Tub.

Stratton Mtn Studio | Renovated | Walk to Lifts

Stratton Mountain
10.0 out of 10, Exceptional, (30)
"Great location."
United States
Jeffrey
$371 nightly
The price is $419
Nov 9 - Nov 10
Total with taxes and fees
Stratton Mtn Studio | Renovated | Walk to Lifts

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

Killington
10.0 out of 10, Exceptional, (29)
"House was great"
United States
Alex G.
$540 nightly
The price is $610
Nov 11 - Nov 12
Total with taxes and fees
SunBear-Ski on Ski off, Pool, HotTub, Game Room!

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

Dover
9.4 out of 10, Exceptional, (18)
"Close to the mountain, great for a bigger group!"
United States
Alexa G.
$508 nightly
The price is $574
Nov 9 - Nov 10
Total with taxes and fees
Mount Snow Condo: 4 min Walk to Sundance Lift (High Speed - 6 Seat)
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chester Hotel Reviews

Find out more about Chester

Chester Condo Rentals information

Number of reviews
408
Accommodation
475 Condo Rentals
Lowest Price
$201
Highest Price
$796

Frequently asked questions

How much do condos in Chester cost?
Condos in Chester range from $201 to $796 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 475 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.

Explore a world of travel with Expedia