Holiday Rentals in Charleston

  • Plan, book, stay with confidence
    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Charleston

Vermont Vacation Rental ~ 11 Mi to Lake Willoughby
Terrace/patio

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
Outdoor dining

The Hamblett at Hinton Hill

9.8 out of 10, Exceptional, (6)
"Absolutely charming little cabin for no more than 2 people and perfectly appointed. Beautiful, like something you would see in a travel magazine. Just about everything you need is already there: towels, kitchen supplies, cleaning supplies, grill, etc. The deck and grounds are well done with chairs and tables, a hammock is outside too. When the sun goes down the solar lights add sparkle to the perimeter of the property. A very nice touch! What you don't know from the listing is that the Hamblett...
The Hamblett at Hinton Hill
Brand New, Private Home with Nordic Hot Tub- Just .5mi to Jay Peak Ski Resort
Outdoor spa tub

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

10.0 out of 10, Exceptional, (4)
"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
Come stay at the Kirby Hideaway!
Smart TV, video games, DVD player, books

Come stay at the Kirby Hideaway!

10.0 out of 10, Exceptional, (82)
"We had a fabulous weekend here to celebrate a family birthday. The place was comfortable, spacious and clean, the views are better than the pictures, and it was the perfect spot for our family including two toddlers, a baby, and a couple of dogs! I'd love to come back one day. Todd was a wonderful and gracious communicator when I reached out to him directly, and he responded immediately for a question I had after our stay had ended. For future visitors, I would recommend checking in with him if...
Come stay at the Kirby Hideaway!
Entire Family-Friendly Home w/ Indoor Hot Tub Near Bike Trails & 5mi to Jay Peak
Miscellaneous

Entire Family-Friendly Home w/ Indoor Hot Tub Near Bike Trails & 5mi to Jay Peak

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 Family-Friendly Home w/ Indoor Hot Tub Near Bike Trails & 5mi to Jay Peak
Ski, Bike and family fun at "The Future" cottage.
Property grounds

Ski, Bike and family fun at "The Future" cottage.

Ski, Bike and family fun at "The Future" cottage.
Lake Willoughby Views and access. Boat Dock and Beach Wood fired hot tub
Beach nearby

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

10.0 out of 10, Exceptional, (10)
"It was a perfect getaway for a weekend. Within walking distance to Mt. Pisgah and its own dock access for Lake Willoughby. Couldn't have asked for more. I was actually surprised how well the kitchen worked. Only downside was thr shower was a bit small for a 6 ft guy."
Lake Willoughby Views and access. Boat Dock and Beach Wood fired hot tub
Great Location, new lower rates on access road to Burke Mountain Ski Area .
Outdoor dining

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 €295
includes taxes & fees
25 Nov - 26 Nov
Great Location, new lower rates on access road to Burke Mountain Ski Area .
2bdrm East Burke Apt *Great Location*
Property grounds

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 €188
includes taxes & fees
29 Nov - 30 Nov
2bdrm East Burke Apt *Great Location*
Beautifully Renovated Classic Vermont Lake View Cottage
On the beach

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
Charming dog-friendly riverside escape with deck, firepit & EV charger
Exterior

Charming dog-friendly riverside escape with deck, firepit & EV charger

9.6 out of 10, Exceptional, (16)
"We had a lovely stay. The house is just as shown and described, though the water is not accessible from the property. There were also two unannounced visits by groundskeepers, who while pleasant and professional, were unexpected."
Charming dog-friendly riverside escape with deck, firepit & EV charger
Journeys End Chalet - Minutes to Jay Peak!
Exterior

Journeys End Chalet - Minutes to Jay Peak!

10.0 out of 10, Exceptional, (48)
"This place is amazing! We had a great time and enjoyed our stay to the last minute. The house is spacious, with a vary well stocked kitchen, comfy beds and a huge deck where we ate all our meals. We also had a lot of fun playing pool in the basement. There is tons of activities around, so it's really hard to get bored. We recommend a visit to the Jay Peak Resort and a cab ride to the mountain top. The views from there are stunning. We would give this property 6 stars if possible. We will gladly...
The price is €360
includes taxes & fees
25 Nov - 26 Nov
Journeys End Chalet - Minutes to Jay Peak!
Lakeside Isbell Cottage and Isbellita Guest Cottage
Terrace/patio

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
Fridge, microwave, oven, stovetop

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
Gorgeous, secluded home with private deck & WiFi
Property grounds

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

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
Gebhardt Getaway - Charming LAKEFRONT Cottage on Lake Willoughby
On the beach, sun-loungers

Gebhardt Getaway - Charming LAKEFRONT Cottage on Lake Willoughby

9.6 out of 10, Exceptional, (37)
"We loved the cabin and location. Willoughby lake right across the street. I will go back next year."
Gebhardt Getaway - Charming LAKEFRONT Cottage on Lake Willoughby
Home Away From Home, Newly Renovated Apartment
Fridge, microwave, oven, stovetop

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
Entire Lake House on Lake Memphremagog, dead end RD, private. 30 min to Jay Peak
Property grounds

Entire Lake House on Lake Memphremagog, dead end RD, private. 30 min to Jay Peak

10.0 out of 10, Exceptional, (13)
"Wonderful clean place in a cute VT town right by the Canadian border. Love "
Entire Lake House on Lake Memphremagog, dead end RD, private. 30 min to Jay Peak
Jay River Front Three Bedroom. 2 miles to Jay Peak
Interior

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
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.
Don't see what you're looking for?
See all available properties in Charleston
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other types of properties in Charleston you may be interested in

Vermont Vacation Rental ~ 11 Mi to Lake Willoughby
Terrace/patio

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
Outdoor dining

The Hamblett at Hinton Hill

9.8 out of 10, Exceptional, (6)
"Absolutely charming little cabin for no more than 2 people and perfectly appointed. Beautiful, like something you would see in a travel magazine. Just about everything you need is already there: towels, kitchen supplies, cleaning supplies, grill, etc. The deck and grounds are well done with chairs and tables, a hammock is outside too. When the sun goes down the solar lights add sparkle to the perimeter of the property. A very nice touch! What you don't know from the listing is that the Hamblett...
The Hamblett at Hinton Hill
The Jay Village Inn
Seasonal outdoor pool

The Jay Village Inn

3.0 star property
8.0 out of 10, Very good, (302)
"People great. Dining was a plus. Prices very reasonable. "
The price is €110
includes taxes & fees
25 Nov - 26 Nov
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?

Come stay at the Kirby Hideaway!: This holiday home rental outside of Charleston is located in the mountains, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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 Seymour Lake are a couple of lovely local spots to get outside and enjoy nature. Echo 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.