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Search and Rent Charlestown Condos

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Our top choices for Charlestown condo rentals

9.0 out of 10, Wonderful, (74)
"Perfect location for a quick ski trip. "
United States
Michael D.
$283 nightly
The price is $320
Jan 11 - Jan 12, 2026
Total with taxes and fees
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
7.6 out of 10, Good, (53)
"Irish Bar nearby was a plus on St. Patrick’s Day !"
United States
Warren
$328 nightly
The price is $370
Jan 12 - Jan 13, 2026
Total with taxes and fees
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
9.2 out of 10, Wonderful, (26)
"Loved the location"
United States
Steven W.
$367 nightly
The price is $414
Jan 28 - Jan 29, 2026
Total with taxes and fees
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
10.0 out of 10, Exceptional, (19)
"Amazing place! "
United States
Tara
$481 nightly
The price is $539
Jan 4 - Jan 5, 2026
Total with taxes and fees
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
8.6 out of 10, Excellent, (4)
"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.
$268 nightly
The price is $303
Jan 5 - Jan 6, 2026
Total with taxes and fees
2nd-floor downtown Ludlow studio condo with kitchenette, streaming
8.6 out of 10, Excellent, (14)
"Excellent Location.. "
United States
Juan Carlos L.
$300 nightly
The price is $339
Jan 4 - Jan 5, 2026
Total with taxes and fees
Ski-in/out mountainside condo with balcony, washer/dryer & high-speed WiFi
10.0 out of 10, Exceptional, (102)
"Convenient 2 BR space with comfy beds right in the heart of Ludlow. Would definitely stay there again."
United States
Andrew L.
$326 nightly
The price is $356
Jan 12 - Jan 13, 2026
Total with taxes and fees
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
9.4 out of 10, Exceptional, (22)
"Enjoy our stay !!!!! Awesome in and out right on the slope feet away for deck."
United States
Dan G.
$390 nightly
The price is $441
Jan 8 - Jan 9, 2026
Total with taxes and fees
Ground Floor ski-in/out condo, full kitchen & high-speed WiFi
9.0 out of 10, Wonderful, (14)
"Great location and very comfortable."
United States
Richard J.
$313 nightly
The price is $353
Jan 12 - Jan 13, 2026
Total with taxes and fees
Condo in the heart of town near skiing - less than a mile to Okemo Mountain
9.0 out of 10, Wonderful, (22)
"Great rate for a place with all the basics!"
United States
Macgregor
$268 nightly
The price is $303
Jan 5 - Jan 6, 2026
Total with taxes and fees
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
9.8 out of 10, Exceptional, (16)
"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.
$855 nightly
The price is $966
Jan 4 - Jan 5, 2026
Total with taxes and fees
Ski-In/Out Condo with Mountain Views, and Washer/Dryer
$894 nightly
The price is $987
Jan 13 - Jan 14, 2026
Total with taxes and fees
Okemo | 1BR + Loft Condo + Close to All Amenities
10.0 out of 10, Exceptional, (15)
"The condo is great for ski in ski out"
United States
Nanette P.
$1,341 nightly
The price is $1,515
Jan 19 - Jan 20, 2026
Total with taxes and fees
OKEMO WINTERPLACE Best Location, Ski-In/Ski-Out 4BR/3BATH + LOFT. Spacious.
10.0 out of 10, Exceptional, (1)
"This was an excellent Okemo stay for our family. The proximity to the mountain is hard to beat — an easy 2-minute walk to the trail — and the home itself is beautifully designed and fully stocked. Everything felt intentional and comfortable, making it easy to settle in right away. Our family had a great time, and the host was extremely responsive and helpful whenever we had questions. Highly recommend."
United States
Rana K.
$1,154 nightly
The price is $1,304
Jan 22 - Jan 23, 2026
Total with taxes and fees
Okemo Ridge Retreat - Slopeside 3-bdrm. Steps to Kettlebrook Trail.
$708 nightly
The price is $781
Jan 13 - Jan 14, 2026
Total with taxes and fees
Okemo | Charming 1BR Condo + Close to Amenities
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 Charlestown Hotel Reviews

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Charlestown Condo Rentals information

Number of reviews
272
Accommodation
255 Condo Rentals
Lowest Price
$303
Highest Price
$1,515

Frequently asked questions

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How can I find cheap condos in Charlestown?
The easiest way to compare cheap condos in Charlestown is with Expedia's easy-to-use filter tool. Narrow down your search by star rating, budget and amenities to take advantage of awesome bargains with only a few clicks.
What is there to do in Charlestown near my condo?
The best travel accessory is a well-thought-out travel plan. The Fort at No.4 Open Air Museum is a wonderful spot to begin your exploration of Charlestown.

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