A grassy field with a wooden fence, surrounded by autumn-colored trees and a hill in the background.

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Charlestown condo rentals

A living room with a sofa, a bench, a fireplace, a TV, and a large window.

1. Ground-floor ski-in/ski-out condo facing the Clock Tower base lodge

Ground-floor ski-in/ski-out condo facing the Clock Tower base lodge
Clock Tower Base Area
9.2 out of 10, Wonderful, (30 reviews)
"Great property, clean and close to the slope"
United States
tiliger01
$205 nightly
The price is $232
Oct 23 - Oct 24
Total with taxes and fees
Ground-floor ski-in/ski-out condo facing the Clock Tower base lodge
A building with multiple floors, a red curved structure, and a flower bed with purple flowers.

2. Okemo ski-in/ski-out condo a few feet from the A and B Quad lifts

Okemo ski-in/ski-out condo a few feet from the A and B Quad lifts
Clock Tower Base Area
8.8 out of 10, Excellent, (81 reviews)
"It was a perfect location and had everything we needed for a great stay."
United States
Danna K.
$236 nightly
The price is $266
Oct 23 - Oct 24
Total with taxes and fees
Okemo ski-in/ski-out condo a few feet from the A and B Quad lifts
A two-story house with a porch, a staircase, and a front door.

3. Downtown Ludlow condo with electric fireplace, shuttle stop across the street

Downtown Ludlow condo with electric fireplace, shuttle stop across the street
Ludlow
8.8 out of 10, Excellent, (27 reviews)
"Great location - walkable to small town. Very close drive to slopes"
United States
Keath
$240 nightly
The price is $271
Oct 23 - Oct 24
Total with taxes and fees
Downtown Ludlow condo with electric fireplace, shuttle stop across the street
A cozy cabin interior with a sofa, dining table, chairs, wooden cabinets, and a kitchen area.

4. Condo a short walk to the Sachem trail with seasonal pool and tennis

Condo a short walk to the Sachem trail with seasonal pool and tennis
Ludlow
$262 nightly
The price is $296
Oct 25 - Oct 26
Total with taxes and fees
Condo a short walk to the Sachem trail with seasonal pool and tennis
A rectangular pool with a glass enclosure, surrounded by lounge chairs and umbrellas, set in a landscaped area with trees.

5. 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, (25 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.
$479 nightly
The price is $536
Oct 23 - Oct 24
Total with taxes and fees
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
A cozy living room with a fireplace, a black leather sofa, and a television mounted above it.

6. 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 right in town and close to Okemo."
United States
Justin P.
$401 nightly
The price is $432
Nov 18 - Nov 19
Total with taxes and fees
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
A two-story house with a covered porch, a staircase, and a front door with a wreath.

7. Second-floor downtown Ludlow studio in a historic ski town

Second-floor downtown Ludlow studio in a historic ski town
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.
$233 nightly
The price is $264
Oct 23 - Oct 24
Total with taxes and fees
Second-floor downtown Ludlow studio in a historic ski town
A modern living room with a fireplace, a television, and a ceiling fan.

8. Ground-floor ski-in/ski-out condo near the Sachem trail, ski to Sunburst

Ground-floor ski-in/ski-out condo near the Sachem trail, ski to Sunburst
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.
$446 nightly
The price is $503
Oct 25 - Oct 26
Total with taxes and fees
Ground-floor ski-in/ski-out condo near the Sachem trail, ski to Sunburst
A two-story house with a covered porch, a staircase, and a front door with a wreath.

9. First-floor downtown condo, less than a mile from Okemo Mountain

First-floor downtown condo, less than a mile from Okemo Mountain
Ludlow
9.0 out of 10, Wonderful, (14 reviews)
"Great place!"
United States
Darcie L.
$286 nightly
The price is $323
Oct 23 - Oct 24
Total with taxes and fees
First-floor downtown condo, less than a mile from Okemo Mountain
A modern living room with a fireplace, a dining area, and a kitchen in the background.

10. Building C ground-floor ski-in/ski-out condo with Clock Tower views

Building C ground-floor ski-in/ski-out condo with Clock Tower views
Clock Tower Base Area
9.4 out of 10, Exceptional, (27 reviews)
"No interaction with host but all amenities were excellent "
United States
Dan M.
$361 nightly
The price is $408
Oct 23 - Oct 24
Total with taxes and fees
Building C ground-floor ski-in/ski-out condo with Clock Tower views
A multi-story building with a red and yellow facade, surrounded by lush greenery and flowering plants.

11. Okemo | Charming 1BR Condo + Close to Amenities

Okemo | Charming 1BR Condo + Close to Amenities
Jackson Gore Base Area
$360 nightly
The price is $397
Oct 26 - Oct 27
Total with taxes and fees
Okemo | Charming 1BR Condo + Close to Amenities
An indoor swimming pool with clear blue water, surrounded by lounge chairs and tables, under a high ceiling with skylights.

12. Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!

Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!
Okemo Village
10.0 out of 10, Exceptional, (64 reviews)
"The host is extremely friendly and accommodating! The place is large and didn’t feel cramped with two adults and five male teenagers! Perfect in every way, clean, well stocked, and easy access to the slopes!"
United States
Nina
$800 nightly
The price is $904
Oct 23 - Oct 24
Total with taxes and fees
Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!
A multi-story building with a red and yellow facade, surrounded by lush greenery and flowering plants.

13. Okemo | 1BR + Loft Condo + Close to All Amenities

Okemo | 1BR + Loft Condo + Close to All Amenities
Jackson Gore Base Area
$453 nightly
The price is $500
Oct 26 - Oct 27
Total with taxes and fees
Okemo | 1BR + Loft Condo + Close to All 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

The Putney Inn

The Putney Inn

8/10 Good
"It was adequate"
Debbie 3-night trip
Posted 8 hours ago
The Putney Inn

Find out more about Charlestown

Charlestown Condo Rentals information

Number of reviews
372
Accommodation
228 Condo Rentals
Lowest Price
$232
Highest Price
$904

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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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