Charlestown Condo Rentals from CA $318

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

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Our top choices for Charlestown condo rentals

1. Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

Cavendish

Ania H.

CA $740 total

includes taxes & fees

Sep 4 - Sep 5

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

Ludlow

Keath

CA $376 total

includes taxes & fees

Sep 8 - Sep 9

3. Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Clock Tower Base Area

AMY K.

CA $318 total

includes taxes & fees

Sep 8 - Sep 9

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

Clock Tower Base Area

serena m.

CA $369 total

includes taxes & fees

Sep 8 - Sep 9

5. 2nd-floor downtown Ludlow studio condo with kitchenette, streaming

Ludlow

Kevin C.

CA $365 total

includes taxes & fees

Sep 8 - Sep 9

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

Ludlow

Darcie L.

CA $447 total

includes taxes & fees

Sep 8 - Sep 9

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

Ludlow

CA $407 total

includes taxes & fees

Sep 30 - Oct 1

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

Ludlow

Carey S.

CA $599 total

includes taxes & fees

Sep 8 - Sep 9

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Top Charlestown Hotel Reviews

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent

"The room was large and comfortable."

Best Western Springfield Hotel

10/10 Excellent

"We had a wonderful stay at this hotel and would definitely recommend it. The property was very clean and well maintained, which made us feel comfortable from the moment we arrived. The staff were exceptionally friendly, welcoming, and always willing to help with any questions or requests. We also appreciated the complimentary drinks and fresh fruit, which were a thoughtful touch. Breakfast has a good variety of options to choose from. Another highlight of our stay was the indoor pool, which was clean, relaxing, and very enjoyable. Overall, this hotel exceeded our expectations, and we would be happy to stay here again."

Mountain Edge Suites at Sunapee, an Ascend Collection Hotel

8/10 Good

"First, the service was amazing. The afternoon/evening front desk gentlemen was extremely kind and helpful as we navigated an issue with the room we were originally given (that turned out to not be an issue so won’t bother mentioning). The rooms were slightly dated but clean and well maintained. The only downside of the room was the carpet - it wasn’t awful but was old and a bit musty. We are very sensitive to smells and allergens so others may not notice. That said it didn’t affect our allergies too much so it wasn’t that bad. Room comes with basic cooking equipment, plates and silverware. The room we got was a two bedroom but the queen bedroom doesn’t have a door that closes - it’s a separate room but is open to the living room/kitchen. This wasn’t an issue for us but worth noting for others. Beds were clean and looked new but weren’t the nicest mattresses. Same with the pillows. We did go to the indoor pools - it was pretty well maintained. They had locker rooms and a dry sauna but we didn’t use either. Continental breakfast was as you’d expect. Nothing hot was served but lots of options - including a whole gluten free section which you NEVER see at hotels and I great appreciated. The hotel was nice and the staff great but it definitely had “we were a reeeallly nice hotel before the pandemic and then we lost a lot of our extras” vibes. They used to have a spa, a bar, an outdoor pool and a restaurant but those are all gone. It was fine as is though."

Find out more about Charlestown

Charlestown Condo Rentals information

Number of reviews	296
Accommodation	239 Condo Rentals
Lowest Price	CA $318
Highest Price	CA $1,162

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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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Search Condos Rentals in Charlestown from CA $318

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Charlestown condo rentals

1. Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

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

3. Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

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

5. 2nd-floor downtown Ludlow studio condo with kitchenette, streaming

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

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

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

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

10. Cozy Slopeside Escape - Ski-In/Out Condo at Okemo

11. Modern Ski-in/Ski-Out Winterplace Condo

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

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

14. True Ski in/Ski out with Pool, Hot tubs & Firepits

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

16. Okemo | 2BR + Exec Loft Condo w/ Washer & Dryer

17. 2BR Exec Condo + Close to All Amenities | Biking

18. Okemo | 2BR + Loft Condo + Close to All Amenities

19. Pool + Hot Tubs! Charming Condo at Jackson Gore

20. Okemo | 3BR Condo & Close to Amenities + Slopes!

Find vacation rentals that suit your style

Top Charlestown Hotel Reviews

Keene Elm City Hotel, an Ascend Collection Hotel

Find out more about Charlestown

Charlestown Condo Rentals information

Frequently asked questions

Explore a world of travel with Expedia