Search Condo Rentals in Chester

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
23 Jan - 25 Jan
In two weeks
30 Jan - 1 Feb
In one month
13 Feb - 15 Feb
In two months
13 Mar - 15 Mar

Our top choices for Chester condo rentals

Beach

Condo in West Dover

Cozy 3 bedroom condo 2.5 miles to Mount Snow
9.0 out of 10, Wonderful, (46 reviews)
"Great quiet location, kitchen had enough essentials for basic cooking to be easy. The king bed was comfortable and the living room is a great hangout spot."
United States
Franklin C.
The price is SAR 375
SAR 1,144 total
includes taxes & fees
3 Feb - 4 Feb
Cozy 3 bedroom condo 2.5 miles to Mount Snow
Lobby

Condo in Dover

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
8.8 out of 10, Excellent, (32 reviews)
"Very nice accommodations and location!"
United States
Michael M.
The price is SAR 386
SAR 1,428 total
includes taxes & fees
1 Feb - 2 Feb
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Interior

Condo in Ludlow

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
7.4 out of 10, Good, (55 reviews)
"Irish Bar nearby was a plus on St. Patrick’s Day !"
United States
Warren
The price is SAR 390
SAR 1,494 total
includes taxes & fees
3 Feb - 4 Feb
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
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)
"Excellent Location.. "
United States
Juan Carlos L.
The price is SAR 424
SAR 1,261 total
includes taxes & fees
26 Jan - 27 Jan
Ski-in/out mountainside condo with balcony, washer/dryer & high-speed WiFi
Property grounds

Condo in Stratton

Lovely ski-in/out condo steps from ski lift with trails and amazing views
8.6 out of 10, Excellent, (27 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 SAR 540
SAR 1,651 total
includes taxes & fees
28 Jan - 29 Jan
Lovely ski-in/out condo steps from ski lift with trails and amazing views
Indoor pool

Condo in Okemo Village

Cozy Slopeside Escape - Ski-In/Out Condo at Okemo
3.0 star property
10.0 out of 10, Exceptional, (7 reviews)
"Location was perfect for skiing. Hosts were responsive and the stay was pleasant. Would book again."
United States
Paul T.
The price is SAR 1,121
SAR 2,398 total
includes taxes & fees
26 Jan - 27 Jan
Cozy Slopeside Escape - Ski-In/Out Condo at Okemo
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)
"Loved the location"
United States
Steven W.
The price is SAR 949
SAR 2,005 total
includes taxes & fees
9 Feb - 10 Feb
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
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.
The price is SAR 506
SAR 1,193 total
includes taxes & fees
26 Jan - 27 Jan
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
10.0 out of 10, Exceptional, (102 reviews)
"Ideal location, clean and comfortable condo, and kind, responsive host! The larger bedroom could benefit from blackout curtains, but if you like to wake up to bright sunlight then it's a non-issue!"
United States
Jessica C.
The price is SAR 889
SAR 1,564 total
includes taxes & fees
4 Feb - 5 Feb
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Property grounds

Condo in Stratton

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
7.4 out of 10, Good, (20 reviews)
"A great weekend. The property was clean and comfortable."
United States
Joan P.
The price is SAR 551
SAR 1,628 total
includes taxes & fees
20 Jan - 21 Jan
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
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, (75 reviews)
"Perfect location for a quick ski trip. "
United States
Michael D.
The price is SAR 780
SAR 1,768 total
includes taxes & fees
2 Feb - 3 Feb
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
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.
The price is SAR 529
SAR 1,325 total
includes taxes & fees
26 Jan - 27 Jan
Condo in the heart of town near skiing - less than a mile to Okemo Mountain
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, (20 reviews)
"Amazing place! "
United States
Tara
The price is SAR 1,125
SAR 2,020 total
includes taxes & fees
19 Jan - 20 Jan
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Exterior

Condo in Ludlow

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
9.0 out of 10, Wonderful, (23 reviews)
"Great rate for a place with all the basics!"
United States
Macgregor
The price is SAR 506
SAR 1,193 total
includes taxes & fees
26 Jan - 27 Jan
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Condo, 3 Bedrooms | Marina

Condo in Ludlow

Okemo Westwood Condo 3 Bedroom Condo by RedAwning
3.5 star property
The price is SAR 1,670
SAR 4,428 total
includes taxes & fees
3 Feb - 4 Feb
Okemo Westwood Condo 3 Bedroom Condo by RedAwning
Fridge, microwave, oven, stovetop

Condo in Stratton Mountain

Stratton Mtn Studio | Renovated | Walk to Lifts
10.0 out of 10, Exceptional, (30 reviews)
"Great location."
United States
Jeffrey
The price is SAR 928
SAR 1,896 total
includes taxes & fees
19 Jan - 20 Jan
Stratton Mtn Studio | Renovated | Walk to Lifts
Indoor pool

Condo in Killington

Cozy 2 BR Ski On Ski Off Condo in Killington's Sunrise Mountain Village. Pool. Hot Tub.
2.0 star property
9.4 out of 10, Exceptional, (3 reviews)
"Great location for skiing!!!"
United States
Pawel B.
Cozy 2 BR Ski On Ski Off Condo in Killington's Sunrise Mountain Village. Pool. Hot Tub.
Interior

Condo in Ludlow

Ski Okemo! Walk to the slopes from your modern 2 bed/2 bath condo at Winterplace
10.0 out of 10, Exceptional, (12 reviews)
"Great ski weekend at Okemo - thanks for the great place to stay!"
United States
Catherine S.
Ski Okemo! Walk to the slopes from your modern 2 bed/2 bath condo at Winterplace
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.
The price is SAR 1,871
SAR 3,579 total
includes taxes & fees
19 Jan - 20 Jan
Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Interior

Condo in Killington

SunBear-Ski on Ski off, Pool, HotTub, Game Room!
10.0 out of 10, Exceptional, (29 reviews)
"Stayed 3 nights in early summer. Location was quiet and away from most killington activity.Condo was comfortable and clean. A/C was portable unit type and adequate but a little noisy."
United States
James R.
The price is SAR 1,098
SAR 2,783 total
includes taxes & fees
26 Jan - 27 Jan
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chester Hotel Reviews

The Manchester View

The Manchester View

10/10 Excellent
"Excellent "
Rebecca 2-night trip
Posted 21 hours ago
The Manchester View

Frequently asked questions

How much do condos in Chester cost?
Condos in Chester range from SAR 1,144 to SAR 4,428 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.

Explore a world of travel with Expedia