Charleston Holiday Rentals

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Holiday Rentals in Charleston

Vermont Vacation Rental ~ 11 Mi to Lake Willoughby

9.6 out of 10, Exceptional, (5)
"The house was perfect for our needs"
Vermont Vacation Rental ~ 11 Mi to Lake Willoughby

The Hamblett at Hinton Hill

9.8 out of 10, Exceptional, (7)
"A great little cabin in the woods...I recommend it highly "
The Hamblett at Hinton Hill

Waterfront Home At The End Of An Out Of The Way Dead End Street

9.8 out of 10, Exceptional, (146)
"We loved everything about this place! The view was amazing! The host was very nice and communicated with us about things to see during our trip, including the northern lights! It was a relaxing, beautiful visit with hopefully many more to come!"
Waterfront Home At The End Of An Out Of The Way Dead End Street

Just Like Being At Home- Newly Renovated Unit

9.8 out of 10, Exceptional, (17)
"It was exactly as Caitlyn described. A lot of extra things provided you don’t expect rentals to include. I’m happy I didn’t have to pay an extra fee for my pup and she even felt comfortable there. A small hiccup at check out but it was a nice rental for the $. "
Just Like Being At Home- Newly Renovated Unit

Gorgeous, secluded home with private deck & WiFi

9.2 out of 10, Wonderful, (30)
"Wonderful property in a great area. Highly reccomend"
Gorgeous, secluded home with private deck & WiFi

AMAZING! LAKESHORE HOME w/DOCK; Sleeps 7

10.0 out of 10, Exceptional, (19)
"The home is located in a very quiet area with a beautiful view of the lake. Very clean and communication was excellent. "
AMAZING! LAKESHORE HOME w/DOCK; Sleeps 7

Lake Willoughby Views and access. Boat Dock and Beach Wood fired hot tub

10.0 out of 10, Exceptional, (11)
"Rented the place in mid-oct for a second-marriage honeymoon. The place was easy to find and was set up perfectly for a two person cozy stay. House faces the sunset and has a deck and sitting porch. Brought my little boat and the boating access is across the street. We had zero issues. We would definitely come back!! Definitely worth it. 👌 "
Lake Willoughby Views and access. Boat Dock and Beach Wood fired hot tub

2bdrm East Burke Apt *Great Location*

9.8 out of 10, Exceptional, (157)
"It was everything we wanted and Amy was a great host. "
The price is NZ$339
includes taxes & fees
31 Dec - 1 Jan 2025
2bdrm East Burke Apt *Great Location*

Beautifully Renovated Classic Vermont Lake View Cottage

9.6 out of 10, Exceptional, (94)
"We had a really nice stay. Tim was very kind and inviting, made sure check in was a breeze, and was helpful with recommendations. The kitchen had everything we needed. The location is great, as is the view. Bed was comfortable but is also on wheels which was a problem for our dog going under the bed. We also discovered a lot of dust bunnies under the bed and arm chair as a result. Lastly, you should know that the water is sulfurous. It didn't bother us but it's worth knowing. We would...
Beautifully Renovated Classic Vermont Lake View Cottage

Brand New, Private Home with Nordic Hot Tub- Just .5mi to Jay Peak Ski Resort

10.0 out of 10, Exceptional, (5)
"The house is brand new, set up well and very clean and has all amenities that you need for a week stay. It is less than 5 mins to the mountain and a 5 min drive to the small Jay Village. We will definitely return."
Brand New, Private Home with Nordic Hot Tub- Just .5mi to Jay Peak Ski Resort

Home Away From Home, Newly Renovated Apartment

9.8 out of 10, Exceptional, (23)
"Had myself a quick weekend getaway. Caitlyn was wonderful and the property was perfect for myself and my dog "
Home Away From Home, Newly Renovated Apartment

Sweet Escape Cottage on River

9.4 out of 10, Exceptional, (10)
"We stayed in the cottage during the third weekend of October, yet the foliage was still beautiful. We were located just a few minutes away from Crystal Lake State Park, Lake Willoughby, and wonderful local restaurants like Roberto's Pizza and Barton Baking. The cottage was very clean and had everything we needed, including heating and a nice fireplace. Highly recommend!"
Sweet Escape Cottage on River

Entire Home w/ Indoor Hot Tub - 5mi to Jay Peak. Discounted Lift Tix Included!

10.0 out of 10, Exceptional, (61)
"We really enjoyed our time at the house. We were two familles of three with a dog and everybody was comfortable. The house is spacious, cozy, clean and has a big garden for kids(and dogs) to run about. It is well equipped. We also appreciated the jacuzzi after our days on the slopes and the discount tickets Asia had kindly left for us to use at the resort (ski and Pumphouse). We recommend for a group of 6 to 8 people."
Entire Home w/ Indoor Hot Tub - 5mi to Jay Peak. Discounted Lift Tix Included!

Lakeside Isbell Cottage and Isbellita Guest Cottage

9.8 out of 10, Exceptional, (25)
"Fantastic location. Hose had everything we needed for our family visiting for a family wedding. We enjoyed hanging out on the porch, swimming and relaxing at the dock and gathering together for dinner. Thanks for a lovely stay. Stunning fall foliage too!"
Lakeside Isbell Cottage and Isbellita Guest Cottage

Renovated historic cabin with mountain views, lake access, & electric fireplace

10.0 out of 10, Exceptional, (11)
"Beautiful scenery. Cabin was amazing and had everything we needed to enjoy a quiet weekend away from everything. The views out every window were great. Will definitely be looking to stay again. "
Renovated historic cabin with mountain views, lake access, & electric fireplace

Updated Condo Next to Burke Mountain Bike Trails!

9.6 out of 10, Exceptional, (22)
"We had a fantastic and comfortable stay at this wonderful condo! It is gorgeous and there’s so much room. A wonderful stay and we would love to return one day. Thank you!"
Updated Condo Next to Burke Mountain Bike Trails!

Great Location, new lower rates on access road to Burke Mountain Ski Area .

9.0 out of 10, Wonderful, (81)
"A little bit tight for more than 5 but with good weather and a fire pit quite comfortable. Great entry room for bikes and work shop. Ping pong in the garage was a plus. It's a great location. "
The price is NZ$525
includes taxes & fees
1 Jan - 2 Jan 2025
Great Location, new lower rates on access road to Burke Mountain Ski Area .

Country Cottage Near Kingdom Trails + Burke Mountain, Farm Setting

9.8 out of 10, Exceptional, (82)
"Roomy, comfortable, excellent value. We will return. "
Country Cottage Near Kingdom Trails + Burke Mountain, Farm Setting

Jay River Front Three Bedroom. 2 miles to Jay Peak

9.8 out of 10, Exceptional, (7)
"Great place to stay for a Jay Peak visit. It's 5 minutes from the mountain. It's clean with plenty of space and sleeping arrangements, and Jesse is super nice and quick and efficient with communication. Highly recommend."
Jay River Front Three Bedroom. 2 miles to Jay Peak

Charming ski chalet nestled in Vermont's Northeast Kingdom

10.0 out of 10, Exceptional, (3)
"Nice place, will visit again. "
Charming ski chalet nestled in Vermont's Northeast Kingdom
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 Charleston you may be interested in

Vermont Vacation Rental ~ 11 Mi to Lake Willoughby

9.6 out of 10, Exceptional, (5)
"The house was perfect for our needs"
Vermont Vacation Rental ~ 11 Mi to Lake Willoughby

The Hamblett at Hinton Hill

9.8 out of 10, Exceptional, (7)
"A great little cabin in the woods...I recommend it highly "
The Hamblett at Hinton Hill

The Jay Village Inn

3.0 star property
8.0 out of 10, Very good, (306)
"Everyone was so friendly. Room was very clean and comfortable "
The price is NZ$236
includes taxes & fees
7 Jan - 8 Jan 2025
The Jay Village Inn
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 holiday rentals in Charleston?

Yes, there are holiday rentals close to the most popular sights in Charleston, or you can select a more secluded option if you're looking for a relaxing stay.

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

Waterfront Home At The End Of An Out Of The Way Dead End Street : This holiday home rental outside of Charleston is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of books.

How many holiday rentals are there in Charleston?

Choose from 4 Expedia holiday rentals in Charleston for a memorable holiday.

What’s there to see and do in Charleston?

Seymour Lake and Echo Lake are a couple of lovely local spots to get outside and enjoy nature. Seymour Lake and Lake Willoughby are a couple of places you'll find in the wider area.

What’s a holiday rental in Charleston like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Charleston. Holiday rentals feature amenities like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great choice for a small group gathering.