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Charlestown Holiday Rentals

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Holiday Rentals in Charlestown

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

9.8 out of 10, Exceptional, (164)
"The property is exactly like the pictures indicate. The house is in a friendly neighborhood outside of town. The house is very comfortable and spacious. The host responds to your messages in timely manner, and, she is very workable. Would definitely stay there again "
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly

9.0 out of 10, Wonderful, (26)
"The tiny houses were cute and well equipped. They were ideal for 2 friends traveling together having their own space. I would definitely rent this property again. Only negative was having 3 empty propane tanks when we wanted to use the fire table(something to be added to the maintenance checklust) however once i text them they dropped a fresh tank off that same evening."
The price is AU$796
includes taxes & fees
1 Jan - 2 Jan 2025
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

8.2 out of 10, Very good, (34)
"All in all it was a great trip. The place was very cute and as described. The upstairs bedrooms are not for light sleepers as the walls only go so far up so they are not really divided. I had read this in other reveiws but honestly for us it wasn't a problem. We went as a family group and it was kind of nice to be able to lay in bed and talk to the others in the room next to you. When we got there the hot tub was so hot that we were not able to get in. Maybe a problem with the thermostat but...
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

9.6 out of 10, Exceptional, (34)
"Great weekend! Beautiful location !!"
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

9.6 out of 10, Exceptional, (151)
"Never could get the wifi to work. I entered the code on the router 6 times but no luck. Would be helpful if you changed the password for the wifi to an easily entered name. The man who came to shovel unfortunately after we were stuck in the snow was very helpful and very nice.. He got us out."
The price is AU$594
includes taxes & fees
6 Jan - 7 Jan 2025
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Perfect Getaway! Cozy, Modern condo & Convenient to Everything you will need.

9.8 out of 10, Exceptional, (61)
"Great"
The price is AU$451
includes taxes & fees
9 Jan - 10 Jan 2025
Perfect Getaway! Cozy, Modern condo & Convenient to Everything you will need.

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

9.8 out of 10, Exceptional, (113)
"Terrific and comfortable place to stay! Amazing firepit!"
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views.

10.0 out of 10, Exceptional, (39)
"This property was beautiful, clean, well maintained, had everything we needed. Wish we could have stayed longer! Thank you for a weekend we’ll never forget! We hope to rent this house again in the future. "
Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views.

Efficient condo near slopes with kitchenette & great location

9.0 out of 10, Wonderful, (24)
"Stay was good. Couldn’t figure out the TV - Not sure if there was actually cable or not. Close to the main road so traffic was a bit loud. Other than that great stay. "
The price is AU$351
includes taxes & fees
2 Jan - 3 Jan 2025
Efficient condo near slopes with kitchenette & great location

Treehouse at Wise Pines- SoBo

9.8 out of 10, Exceptional, (19)
"Beautiful property and wonderful host. Very welcoming and cozy, and within a quick drive of lots of great activities. I would definitely stay here again!"
The price is AU$301
includes taxes & fees
6 Jan - 7 Jan 2025
Treehouse at Wise Pines- SoBo

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

9.2 out of 10, Wonderful, (15)
"Location was great. Couldn’t stay anywhere more convenient to the slopes. The unit was spacious for our group."
Coveted Ski-In/Ski-Out Winterplace Condo with Hot Tubs, Indoor Pool & Fireplace

Quaint lakefront home with a private deck, firepit, and dock

9.4 out of 10, Exceptional, (92)
"We wanted to visit VT and decided to rent this beautiful little home on quiet Lake Pauline in Ludlow. We were not disappointed in any way. Serene location, clean, cozy, and welcoming home, excellent nearby restaurants and other attractions.A great 50th anniversary getaway!"
Quaint lakefront home with a private deck, firepit, and dock

Cozy Creekside Chalet centrally located near 4 ski resorts

10.0 out of 10, Exceptional, (8)
"Nice location. Plenty of room for 6 adults. Pellet stove and Christmas movies after a day of shopping and exploring made for a perfect night. "
The price is AU$1,105
includes taxes & fees
8 Jan - 9 Jan 2025
Cozy Creekside Chalet centrally located near 4 ski resorts

Countryside, lakefront cabin with kayaks, stone fireplace, balcony, & fast WiFi

9.0 out of 10, Wonderful, (18)
"The house was clean. The kitchen and rooms worked great for our Thanksgiving celebration. "
Countryside, lakefront cabin with kayaks, stone fireplace, balcony, & fast WiFi

Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing

9.0 out of 10, Wonderful, (22)
"This is a great cabin with stunning views!"
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing

Eastman Home Sleeps 18 on Golf Course, Beach Access in Ski Country

9.6 out of 10, Exceptional, (14)
"Location with access to Eastman Lake is the gem of this property.We had 17 family members across three generations together. the host is responsive."
Eastman Home Sleeps 18 on Golf Course, Beach Access in Ski Country

Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt

10.0 out of 10, Exceptional, (126)
"Very clean and well stocked with all needs."
Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt

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

7.6 out of 10, Good, (50)
"This cozy cabin was perfect for a ski weekend with friends. We really enjoyed gathering by the stone fireplace after a couple long days out on the slopes."
The price is AU$481
includes taxes & fees
1 Jan - 2 Jan 2025
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

VT Cabin overlooking the West River and Village

10.0 out of 10, Exceptional, (27)
"We loved our stay! Such lovely cabin! We loved it so much that we were bummed we didn’t book a longer stay. It had everything we needed to make our stay comfortable."
The price is AU$631
includes taxes & fees
6 Jan - 7 Jan 2025
VT Cabin overlooking the West River and Village

Idyllic Lakefront House Suited Two Families

9.8 out of 10, Exceptional, (153)
"Our stay was wonderful, and the hosts were more than accomadating! Lovely home and very convenient to Ludlow and Okemo. "
Idyllic Lakefront House Suited Two Families
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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Other types of properties in Charlestown you may be interested in

Pointe at Castle Hill Resort

3.5 star property
8.8 out of 10, Excellent, (770)
"It was a very nice place and the staff was very friendly."
The price is AU$309
includes taxes & fees
8 Jan - 9 Jan 2025
Pointe at Castle Hill Resort

Days Inn by Wyndham Keene NH

2.0 star property
7.2 out of 10, Good, (973)
"Quiet. "
The price is AU$162
includes taxes & fees
28 Dec - 29 Dec
Days Inn by Wyndham Keene NH

Courtyard by Marriott Keene Downtown

3.0 star property
8.8 out of 10, Excellent, (1001)
"Lovely staff"
The price is AU$280
includes taxes & fees
31 Dec - 1 Jan 2025
Courtyard by Marriott Keene Downtown
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.

Frequently asked questions

Can I find a holiday rental in Charlestown?

Yes, there are holiday rentals close to the most popular sights in Charlestown, or you can select a more secluded option if you're looking for a relaxing stay. Charlestown is known for its university setting and museums.

What are some of the best holiday rentals that Charlestown has to offer?

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location: This holiday home rental outside of Charlestown is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a private garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

What’s there to see and do in Charlestown?

Cultural attractions include The Fort at No.4 Open Air Museum, whereas Connecticut River is a spot to enjoy nature. In the wider area, you’ll find Morningside Flight Park and Vermont Country Store.

What’s a holiday rental in Charlestown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Charlestown. Holiday rentals provide amenities such as laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from public hotel lifts and busy concierge desks while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for a small group gathering.