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Our top choices for Chester condo rentals

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
8.8 out of 10, Excellent, (81 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.
$236 nightly
The price is $266
Jun 30 - Jul 1
Total with taxes and fees
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

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)
"The slope side condo was wonderful, warm and had everything we needed. Thank you, Amy"
United States
AMY K.
$205 nightly
The price is $232
Jun 30 - Jul 1
Total with taxes and fees
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

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)
"Appeared dated"
United States
John B.
$281 nightly
The price is $317
Jun 30 - Jul 1
Total with taxes and fees
Lovely ski-in/out condo steps from ski lift with trails and amazing views

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.
$383 nightly
The price is $433
Jun 30 - Jul 1
Total with taxes and fees
Ski-In/Out Condo with Mountain Views, and Washer/Dryer

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
$234 nightly
The price is $265
Jun 30 - Jul 1
Total with taxes and fees
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

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

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Ludlow
$331 nightly
The price is $374
Jul 1 - Jul 2
Total with taxes and fees
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

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, (52 reviews)
"Fire place was awesome! Great place to stay! Had everything in the kitchen we needed. All the beds were comfy! "
United States
Susan S.
$250 nightly
The price is $283
Jul 8 - Jul 9
Total with taxes and fees
Cozy 3 bedroom condo 2.5 miles to Mount Snow

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
Jun 30 - Jul 1
Total with taxes and fees
Magic Mountain Trailside Condo - Ski In / Ski Out

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)
"Great location, "
United States
Bryan R J.
$240 nightly
The price is $259
Jun 30 - Jul 1
Total with taxes and fees
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

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

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Stratton
$351 nightly
The price is $396
Jun 30 - Jul 1
Total with taxes and fees
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities

Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub

Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
Stratton Mountain
10.0 out of 10, Exceptional, (31 reviews)
"Great space, great location!"
United States
Jason S.
$352 nightly
The price is $397
Jun 30 - Jul 1
Total with taxes and fees
Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub

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.
$281 nightly
The price is $317
Jun 30 - Jul 1
Total with taxes and fees
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

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)
"convenient to okemo"
United States
marcus l.
$618 nightly
The price is $692
Jul 15 - Jul 16
Total with taxes and fees
Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck

Sunrise Timberline I7 Quaint 2 bedroom Sunrise Timberline I7 Ski to/from. Pets welcome

Sunrise Timberline I7 Quaint 2 bedroom Sunrise Timberline I7 Ski to/from. Pets welcome
Killington
10.0 out of 10, Exceptional, (8 reviews)
"The condo had everything we needed for a great ski vacation! We loved the ski in/ski out location to the Sunrise lift."
United States
Gary A.
Sunrise Timberline I7 Quaint 2 bedroom Sunrise Timberline I7 Ski to/from. Pets welcome

Charming 3BR/2BA Condo in Sunrise Village at Killington. Pool. Hot Tub. Sports Center.

Charming 3BR/2BA Condo in Sunrise Village at Killington. Pool. Hot Tub. Sports Center.
Killington
9.6 out of 10, Exceptional, (4 reviews)
"We had a special ski weekend with friends. "
United States
Adam C.
$434 nightly
The price is $490
Jul 1 - Jul 2
Total with taxes and fees
Charming 3BR/2BA Condo in Sunrise Village at Killington. Pool. Hot Tub. Sports Center.

Trailside Village #3: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals

Trailside Village #3: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
Killington
9.6 out of 10, Exceptional, (24 reviews)
"The host was well organized and communicative. The location of the property is excellent and really convenient to maximize skiing time."
United States
Justin G.
$509 nightly
The price is $575
Jun 30 - Jul 1
Total with taxes and fees
Trailside Village #3: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals

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.
$503 nightly
The price is $569
Jun 30 - Jul 1
Total with taxes and fees
SunBear- AC, Pool, Game Room, Fireplace, Hiking!

Mountain condo by Okemo w/ hot tub

Mountain condo by Okemo w/ hot tub
Ludlow
9.4 out of 10, Exceptional, (24 reviews)
"Good Communication, condo was clean and well stocked. Washer was out of service during our stay, but host reached out prior to notify and confirm it wouldn’t be an issue. No complaints, would stay again. "
United States
P H.
Mountain condo by Okemo w/ hot tub

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 location, and comfortable for the whole family. Everyone in the enjoyed the open living room and dining room, plus the privacy of their own bedroom space. "
United States
Ania H.
$485 nightly
The price is $543
Jun 30 - Jul 1
Total with taxes and fees
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

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.
$529 nightly
The price is $537
Jul 14 - Jul 15
Total with taxes and fees
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

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Chester Condo Rentals information

Number of reviews
533
Accommodation
498 Condo Rentals
Lowest Price
$232
Highest Price
$692

Frequently asked questions

How much do condos in Chester cost?
Condos in Chester range from $232 to $692 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 498 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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