Photo by The Curious Zephyr

Search Condos Rentals in Charlestown from CA $73

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 8 - Aug 10
In two weeks
Aug 15 - Aug 17
In one month
Aug 29 - Aug 31
In two months
Sep 26 - Sep 28

Browse Select Charlestown Condo Rentals

Coveted Ski-In/Ski-Out Winterplace Condo with Hot Tubs, Indoor Pool & Fireplace
Exterior

Coveted Ski-In/Ski-Out Winterplace Condo with Hot Tubs, Indoor Pool & Fireplace

9.2 out of 10, Wonderful, (17)
"We loved our stay at the Winterplace condo. It was clean and so easy to find, park and best of all ski out of!"
Coveted Ski-In/Ski-Out Winterplace Condo with Hot Tubs, Indoor Pool & Fireplace
Inviting condo with a fireplace, hot tubs, pool, tennis & washer/dryer
Property grounds

Inviting condo with a fireplace, hot tubs, pool, tennis & washer/dryer

9.2 out of 10, Wonderful, (51)
"The stay itself was wonderful. The apartment is fantastic for its location, cleanliness, and amenities. Unfortunately, being on the second floor with people above you there can be a lot of noise. Pool was wonderful. Walk to skiing is fantastic. Would happily come back"
Inviting condo with a fireplace, hot tubs, pool, tennis & washer/dryer
Dog-friendly & riverfront condo one mile from Okemo with wood fireplace
Terrace/patio

Dog-friendly & riverfront condo one mile from Okemo with wood fireplace

8.8 out of 10, Excellent, (19)
"Great Location. Inside of place was great. "
Dog-friendly & riverfront condo one mile from Okemo with wood fireplace
Ski-in/out mountainside condo with pool, hot tub, game room & washer/dryer
Fridge, microwave, oven, stovetop

Ski-in/out mountainside condo with pool, hot tub, game room & washer/dryer

9.6 out of 10, Exceptional, (14)
"This was a great place to stay. Clean, spacious, and gorgeous. I love the fully stocked kitchen, the games for the family, and relaxing spa like bathrooms."
Ski-in/out mountainside condo with pool, hot tub, game room & washer/dryer
Ski-in/out condo with fireplace, hot tubs. pool, tennis & washer/dryer
Property grounds

Ski-in/out condo with fireplace, hot tubs. pool, tennis & washer/dryer

9.4 out of 10, Exceptional, (25)
"Great ski in ski out location. Lift is right next to condo"
Ski-in/out condo with fireplace, hot tubs. pool, tennis & washer/dryer
Mountainside Luxury 2-Level Condo at Okemo. Ski-In/Out.
Property grounds

Mountainside Luxury 2-Level Condo at Okemo. Ski-In/Out.

10.0 out of 10, Exceptional, (34)
"We loved staying here. Such a wonderful experience. "
Mountainside Luxury 2-Level Condo at Okemo. Ski-In/Out.
Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!
Exterior

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

10.0 out of 10, Exceptional, (57)
"We had a great time at the wonderful Winterplace condo. The host was very responsive . "
Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!
Ski-In/Ski-out Condo: Most accessible location on Okemo Mountain
TV, fireplace

Ski-In/Ski-out Condo: Most accessible location on Okemo Mountain

9.8 out of 10, Exceptional, (8)
"Family had a great trip thanks"
Ski-In/Ski-out Condo: Most accessible location on Okemo Mountain
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Microwave, oven, stovetop, dishwasher

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

10.0 out of 10, Exceptional, (96)
"Convenient 2 BR space with comfy beds right in the heart of Ludlow. Would definitely stay there again."
The price is CA $168
CA $369 total
includes taxes & fees
Aug 4 - Aug 5
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Fridge, microwave, oven, stovetop

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

7.6 out of 10, Good, (53)
"Great location! Small walk to the trails but easy to get to! Definitely needed some improvements with the amount of sheets and cleanliness but other than that a great stay for an affordable rate!"
The price is CA $73
CA $361 total
includes taxes & fees
Aug 3 - Aug 4
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Ski-in/out, dog-friendly condo with prime location for skiing & hiking
Fridge, microwave, oven, stovetop

Ski-in/out, dog-friendly condo with prime location for skiing & hiking

10.0 out of 10, Exceptional, (6)
"This is a particularly quiet place"
Ski-in/out, dog-friendly condo with prime location for skiing & hiking
Newly renovated ski-in/out slope side condo
Exterior

Newly renovated ski-in/out slope side condo

9.0 out of 10, Wonderful, (21)
"Loved the cozy and updated condo."
Newly renovated ski-in/out slope side condo
Three-level ski-in/out condo with sauna, washer/dryer & mountain view
TV, books

Three-level ski-in/out condo with sauna, washer/dryer & mountain view

9.0 out of 10, Wonderful, (12)
"Loved skiing out our back door. This place was the perfect vacation getaway for our group!"
Three-level ski-in/out condo with sauna, washer/dryer & mountain view
Serene 1-BR Ski-In/Ski-Out Retreat on Okemo Mtn.
Exterior

Serene 1-BR Ski-In/Ski-Out Retreat on Okemo Mtn.

9.4 out of 10, Exceptional, (3)
"My family of four stayed here for 3 days and enjoyed our visit. The unit is clean and the beds are comfy. The hot tub was nice on a cold night. And being able to come back for lunch is great. "
Serene 1-BR Ski-In/Ski-Out Retreat on Okemo Mtn.
Enjoy our ski in ski out condo. Located mid-mountain at Solitude Peak!
Property grounds

Enjoy our ski in ski out condo. Located mid-mountain at Solitude Peak!

10.0 out of 10, Exceptional, (48)
"Always a great stay! It's easy to communicate with Jeff and check-in/out is seamless. Great condo that feels personal and not corporate. "
Enjoy our ski in ski out condo. Located mid-mountain at Solitude Peak!
Okemo Ski in-Ski out @ Winterplace, 3 bdr, 2 ba Condo with Pool, Hot Tub, W/D
Fridge, microwave, oven, stovetop

Okemo Ski in-Ski out @ Winterplace, 3 bdr, 2 ba Condo with Pool, Hot Tub, W/D

10.0 out of 10, Exceptional, (27)
"My family really enjoyed our stay at Ellen's condo at Okemo. The location was excellent and so convenient being at the top of the A/B Quad. The condo was clean, spacious, and well appointed. Thank you so much Ellen, we can't wait to go back again!"
Okemo Ski in-Ski out @ Winterplace, 3 bdr, 2 ba Condo with Pool, Hot Tub, W/D
Ski-In/Ski-Out Hike and Swim Okemo Luxury Rustic Condo
Exterior

Ski-In/Ski-Out Hike and Swim Okemo Luxury Rustic Condo

10.0 out of 10, Exceptional, (1)
"The condo was very comfortable and a short walk to the trail. We had a great ski vacation. "
Ski-In/Ski-Out Hike and Swim Okemo Luxury Rustic Condo
The Lodge-Modern Ski-Out/Ski-Out. Serene retreat Condo for the Outdoorsy type!
Fridge, microwave, oven, stovetop

The Lodge-Modern Ski-Out/Ski-Out. Serene retreat Condo for the Outdoorsy type!

10.0 out of 10, Exceptional, (3)
"Kerry's condo was immaculate and comfortable and in an awesome location right on the mountain. She was very easy to communicate with and a great host. My son and I had a great time. Thank you Kerry!"
The Lodge-Modern Ski-Out/Ski-Out. Serene retreat Condo for the Outdoorsy type!
Okemo Ski-In/Ski-Out: Modern, Cozy 2-BR Retreat
TV, fireplace, offices

Okemo Ski-In/Ski-Out: Modern, Cozy 2-BR Retreat

10.0 out of 10, Exceptional, (4)
"Great property as advertised. Responsive host. Beautiful ski in ski out condo!! Woulstay here again. "
Okemo Ski-In/Ski-Out: Modern, Cozy 2-BR Retreat
Modern & Updated Winterplace 3Br- Sleeps 12
Microwave, oven, dishwasher, coffee/tea maker

Modern & Updated Winterplace 3Br- Sleeps 12

8.0 out of 10, Very good, (4)
"They place was great. The only issue was the heat wouldn't turn off so it was very hot, even with windows open. Called the contacts given and they said they would send maintenance and they never came. Also couldn't find any of the wifi information."
Modern & Updated Winterplace 3Br- Sleeps 12
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Charlestown Hotel Reviews

Newport Motel

Newport Motel

10/10 Excellent
"The owner and staff were amazing. They accommodated a late check in and the room was clean and spacious. I’ll be back. "
Anthony 1-night trip
Posted 1 day ago
Newport Motel