Book Holiday Homes in Charlestown

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Featured Holiday Homes in Charlestown

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

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

Ludlow
With a stay at this vacation home, you'll be centrally located in Ludlow, within a 5-minute drive of Okemo Mountain Resort and Red Lot.
Opens in a new windowClassic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
Idyllic Lakefront House Suited Two  Families

Idyllic Lakefront House Suited Two Families

Ludlow
With a stay at this vacation home in Ludlow, you'll be on the waterfront, within a 10-minute drive of Okemo Mountain Resort and Green Mountain Sugar House.
Opens in a new windowIdyllic Lakefront House Suited Two Families
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

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

Ludlow
With a stay at this vacation home in Ludlow, you'll be on a lake, within a 5-minute drive of Okemo Mountain Resort and Sunshine Ski Lift.
Opens in a new windowFabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
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Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing

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

Andover
Located in Ludlow, this vacation home is on the waterfront, within a 15-minute drive of Green Mountain National Forest and Mill Museum.
Opens in a new windowSecluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

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

Ludlow
With a stay at this vacation home, you'll be centrally located in Ludlow, within a 10-minute drive of Okemo Mountain Resort and Fletcher Farm School for the ...
Opens in a new windowTraveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

Townshend
Located in Townshend, this vacation home is on the waterfront, a 1-minute drive from West River and 8 minutes from Townshend State Forest.
Opens in a new windowModern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
The Green Mountain Chapel // Old Church repositioned into 3 BR

The Green Mountain Chapel // Old Church repositioned into 3 BR

2 out of 5
Londonderry
With a stay at this vacation home in South Londonderry, you'll be within a 5-minute walk of West River and West River Farmers Market.
Opens in a new windowThe Green Mountain Chapel // Old Church repositioned into 3 BR
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

Ludlow
With a stay at this vacation home in Ludlow, you'll be on the waterfront, within a 5-minute drive of Okemo Mountain Resort and Green Mountain Sugar House.
Opens in a new windowLake front house about 1 mile from Okemo's Jackson Gore Base Lodge
Private Home Walk to Okemo Lifts! Hot Tub/Fire Pit

Private Home Walk to Okemo Lifts! Hot Tub/Fire Pit

Ludlow
When you stay at this vacation home in Ludlow, you'll be in the mountains, within a 10-minute walk of Okemo Mountain Resort and General Parking.
Opens in a new windowPrivate Home Walk to Okemo Lifts! Hot Tub/Fire Pit
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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.

Charlestown 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 Charlestown vacation homes are the perfect way for you to wing it.

Holiday houses in Charlestown 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 Charlestown 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 Charlestown adventures, obvs.

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

Charlestown Holiday Homes essential information

Accommodation
482 Holiday Homes
Lowest Price
AU$189
Highest Price
AU$227
Popular accommodation
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable, Idyllic Lakefront House Suited Two Families, Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location, Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing, Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo, Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns, The Green Mountain Chapel // Old Church repositioned into 3 BR, Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge, Private Home Walk to Okemo Lifts! Hot Tub/Fire Pit

Top trending hotels in Charlestown

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 out of 5
175 Key Rd, Keene, NH
Fully refundableReserve now, pay when you stay
The price is AU$189 per night from 25 Sept to 26 Sept
AU$189
25 Sept - 26 Sept
includes taxes & fees
With a stay at Keene Elm City Hotel, an Ascend Collection Hotel in Keene, you'll be within a 5-minute drive of Cheshire Children's Museum and Historic Main ...
Opens in a new windowKeene Elm City Hotel, an Ascend Collection Hotel
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St, Keene, NH
Fully refundableReserve now, pay when you stay
The price is AU$227 per night from 21 Sept to 22 Sept
AU$227
21 Sept - 22 Sept
includes taxes & fees
Located in Keene, Best Western Plus Keene Hotel is in the suburbs, within a 5-minute drive of Cheshire Children's Museum and Keene State College.
Opens in a new windowBest Western Plus Keene Hotel
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103, Cavendish, VT
The price is AU$219 per night from 19 Oct to 20 Oct
AU$219
19 Oct - 20 Oct
includes taxes & fees
With a stay at Pointe at Castle Hill Resort in Cavendish, you'll be near ski lifts, within a 10-minute drive of Okemo Mountain Resort and Fletcher Farm School ...
Opens in a new windowPointe at Castle Hill Resort
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The Putney Inn

The Putney Inn

2.5 out of 5
57 Putney Landing Rd, Putney, VT
Fully refundableReserve now, pay when you stay
With a stay at The Putney Inn in Putney, you'll be a 4-minute walk from Connecticut River and 8 minutes by foot from Yellow Barn.
Opens in a new windowThe Putney Inn
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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.