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Featured Holiday Homes in Charleston

Colorful Farmhouse just minutes from East Burke, Kingdom Trails and Burke Mtn

Colorful Farmhouse just minutes from East Burke, Kingdom Trails and Burke Mtn

Lyndon
Stay at this vacation home in East Burke. Enjoy free WiFi, a garden, and patios. Popular attractions Vermont Children's Theater and Kingdom Trails are located ...
Colorful Farmhouse just minutes from East Burke, Kingdom Trails and Burke Mtn
Brand New, Private Home with Nordic Hot Tub- Just .5mi to Jay Peak Ski Resort

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

Jay
Stay at this vacation home in North Troy. Enjoy patios, air conditioning, and a hot tub. Popular attractions Jay Peak Ski Resort and Jay Peak Resort Golf Course ...
Brand New, Private Home with Nordic Hot Tub- Just .5mi to Jay Peak Ski Resort
Charming Farmhouse: Walk to Village + Trails!

Charming Farmhouse: Walk to Village + Trails!

East Burke
Stay at this vacation home in East Burke. Enjoy an in-room coffeemaker. Popular attractions Kingdom Trails and Darling Memorial Park are located nearby.
Charming Farmhouse: Walk to Village + Trails!
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Adventurebrook, bike, ski & hike out your front door!

Adventurebrook, bike, ski & hike out your front door!

East Burke
Stay at this vacation home in East Burke. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Darling Memorial Park and Burke Mountain Ski ...
Adventurebrook, bike, ski & hike out your front door!
Charming 2nd floor lakeside townhome in brilliant Newport with WiFi. New listing

Charming 2nd floor lakeside townhome in brilliant Newport with WiFi. New listing

Newport
Stay at this vacation home in Newport. Enjoy an in-room coffeemaker. Popular attractions MAC Center for the Arts and Newport Bike Path are located nearby.
Charming 2nd floor lakeside townhome in brilliant Newport with WiFi. New listing
Waterfront Home At The End Of An Out Of The Way Dead End Street

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

Newport
Stay at this vacation home in Newport. Enjoy a water park, a fitness center, and a garden. Popular attractions Newport Bike Path and Lake Memphremagog are located ...
Waterfront Home At The End Of An Out Of The Way Dead End Street
Entire Home w/ Indoor Hot Tub - 5mi to Jay Peak. Discounted Lift Tix Included!

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

Jay
Book a stay at this family-friendly vacation home in North Troy. Enjoy free WiFi, a water park, and a garden. Popular attractions Jay Peak Ski Resort and Big ...
Entire Home w/ Indoor Hot Tub - 5mi to Jay Peak. Discounted Lift Tix Included!
Lakefront adventure home with kayaks, dock, & wood fireplace, - dog-friendly

Lakefront adventure home with kayaks, dock, & wood fireplace, - dog-friendly

Glover
Book a stay at this family-friendly vacation home in Barton. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Shadow Lake and Long ...
Lakefront adventure home with kayaks, dock, & wood fireplace, - dog-friendly
 Access to snowmobile trail thru secondary trail/100% Solar Powered

Access to snowmobile trail thru secondary trail/100% Solar Powered

Canaan
Book a stay at this family-friendly vacation home in Canaan. Enjoy free WiFi, a garden, and patios. Our guests praise the property condition in our reviews. ...
Access to snowmobile trail thru secondary trail/100% Solar Powered
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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.

Charleston Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Charleston vacation homes are the perfect way for you to wing it.

Holiday houses in Charleston let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Charleston in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Charleston adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Charleston with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Charleston vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Charleston Holiday Homes essential information

Accommodation
104 Holiday Homes
Lowest Price
NZ$193
Highest Price
NZ$314
Popular accommodation
Colorful Farmhouse just minutes from East Burke, Kingdom Trails and Burke Mtn, Brand New, Private Home with Nordic Hot Tub- Just .5mi to Jay Peak Ski Resort, Charming Farmhouse: Walk to Village + Trails!, Adventurebrook, bike, ski & hike out your front door!, Charming 2nd floor lakeside townhome in brilliant Newport with WiFi. New listing, Waterfront Home At The End Of An Out Of The Way Dead End Street , Entire Home w/ Indoor Hot Tub - 5mi to Jay Peak. Discounted Lift Tix Included!, Lakefront adventure home with kayaks, dock, & wood fireplace, - dog-friendly, Access to snowmobile trail thru secondary trail/100% Solar Powered

Top trending hotels in Charleston

The Jay Village Inn

The Jay Village Inn

3 out of 5
1078 Vermont Route 242, North Troy, VT
The price is NZ$193 per night from 6 May to 7 May
NZ$193
includes taxes & fees
6 May - 7 May
Stay at this 3-star inn in North Troy. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the restaurant in our reviews. Popular attractions ...
The Jay Village Inn
Pine Crest Motel And Cabins

Pine Crest Motel And Cabins

2.5 out of 5
1288 Barton Orleans Rd, Barton, VT
Fully refundableReserve now, pay when you stay
The price is NZ$206 per night from 18 May to 19 May
NZ$206
includes taxes & fees
18 May - 19 May
Stay at this motel in Barton. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions ...
Pine Crest Motel And Cabins
Burke Mountain Hotel & Conference Center

Burke Mountain Hotel & Conference Center

3 out of 5
2259 Mountain Rd, East Burke, VT
The price is NZ$314 per night from 18 May to 19 May
NZ$314
includes taxes & fees
18 May - 19 May
Stay at this 3-star ski hotel in East Burke. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Burke Mountain Ski Area and Darling Memorial ...
Burke Mountain Hotel & Conference Center
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Lake Willoughby Views and access.  Boat Dock and Beach  Wood fired hot tub

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

Westmore
Stay at this cabin in Orleans. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Lake Willoughby and North Beach are located nearby.
Lake Willoughby Views and access. Boat Dock and Beach Wood fired hot tub
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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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^Subject to availability and chosen travel dates.