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Charlemont Holiday Rentals

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50 rentals in Charlemont.
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Unique People & Pet-Welcoming Country Haven, holiday rental in Charlemont

Unique People & Pet-Welcoming Country Haven

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Charming Downtown Williamstown Cottage - 5 Min Walk to Campus, holiday rental in Charlemont

Charming Downtown Williamstown Cottage - 5 Min Walk to Campus

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Ski Mt. Snow! 25 Private Acres - Almost Heaven in Rustic Vermont!  Come Explore!, holiday rental in Charlemont

Ski Mt. Snow! 25 Private Acres - Almost Heaven in Rustic Vermont! Come Explore!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Swiss Chalet Style Timber frame Home In Berkshires With All Modern Conveniences, holiday rental in Charlemont

Swiss Chalet Style Timber frame Home In Berkshires With All Modern Conveniences

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Modern Rustic House Overlooking The Deerfield River, holiday rental in Charlemont

Modern Rustic House Overlooking The Deerfield River

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Spectacular 4 Season Home On Spruce Lake Near Mt. Snow, holiday rental in Charlemont

Spectacular 4 Season Home On Spruce Lake Near Mt. Snow

5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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In town, newly remodeled studio with private balcony, holiday rental in Charlemont

In town, newly remodeled studio with private balcony

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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19th c. Renovated Barn in the Berkshires, holiday rental in Charlemont

19th c. Renovated Barn in the Berkshires

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Mount Snow opening November 25! Reserve your stay now!, holiday rental in Charlemont

Mount Snow opening November 25! Reserve your stay now!

6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Charming New England House Surrounded By Trees, Field And Pond, holiday rental in Charlemont

Charming New England House Surrounded By Trees, Field And Pond

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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LITTLE BIT OF HEAVEN in Southern VT - Mt Snow, Berkshires, Bennington, Mass Moca, holiday rental in Charlemont

LITTLE BIT OF HEAVEN in Southern VT - Mt Snow, Berkshires, Bennington, Mass Moca

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Sweet Spot in a Region that Shines in Every Season, holiday rental in Charlemont

Sweet Spot in a Region that Shines in Every Season

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cozy renovated cabin in Williamstown, steps from hiking trails, holiday rental in Charlemont

Cozy renovated cabin in Williamstown, steps from hiking trails

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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1810 Brook Side Mill/House / Winter Fun Getaway in Western MA, holiday rental in Charlemont

1810 Brook Side Mill/House / Winter Fun Getaway in Western MA

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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A roomy remodeled retreat close to MassMoCA, holiday rental in Charlemont

A roomy remodeled retreat close to MassMoCA

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Mountain Log Cabin Getaway, holiday rental in Charlemont

Mountain Log Cabin Getaway

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Charming Rural Cottage in the Heart of the Scenic Mohawk Trail, holiday rental in Charlemont

Charming Rural Cottage in the Heart of the Scenic Mohawk Trail

2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Waterfront Lake Raponda Vacation Paradise, holiday rental in Charlemont

Waterfront Lake Raponda Vacation Paradise

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming Affordable  Home for groups up to 14, holiday rental in Charlemont

Charming Affordable Home for groups up to 14

7 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Retreat in the Woods, holiday rental in Charlemont

Retreat in the Woods

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Vermont Log Cabin available for weekend and weekly, holiday rental in Charlemont

Vermont Log Cabin available for weekend and weekly

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Cozy and quaint country cottage, walk to downtown Williamstown, holiday rental in Charlemont

Cozy and quaint country cottage, walk to downtown Williamstown

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Lake Raponda Lakefront - 4 Seasons of fun, holiday rental in Charlemont

Lake Raponda Lakefront - 4 Seasons of fun

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Berkshire house w/ fireplace, A/C, WiFi & laundry, holiday rental in Charlemont

Berkshire house w/ fireplace, A/C, WiFi & laundry

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Mountain View Retreat - Close to all year round activities, holiday rental in Charlemont

Mountain View Retreat - Close to all year round activities

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Mt. Snow/Lake Raponda, holiday rental in Charlemont

Mt. Snow/Lake Raponda

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spring Escape, Get away in the falls❤️, holiday rental in Charlemont

Spring Escape, Get away in the falls❤️

5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Flight's End-A Country Home with Babbling Brook, holiday rental in Charlemont

Flight's End-A Country Home with Babbling Brook

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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A True Shangri-La-Country Retreat W/Pond, Gardens and Huge Deck and View, holiday rental in Charlemont

A True Shangri-La-Country Retreat W/Pond, Gardens and Huge Deck and View

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Secluded dog-friendly home w/ wood burning fireplace, Internet, & forest views!, holiday rental in Charlemont

Secluded dog-friendly home w/ wood burning fireplace, Internet, & forest views!

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Bright three-level home w/water views, jetted tub, firepit, and more!, holiday rental in Charlemont

Bright three-level home w/water views, jetted tub, firepit, and more!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stunning mountain top lodge, Ideal for groups of all kinds, 4 -season fun, holiday rental in Charlemont

Stunning mountain top lodge, Ideal for groups of all kinds, 4 -season fun

6 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Charming, rural house w/shared tennis, private Ping-Pong table, Foosball, & more, holiday rental in Charlemont

Charming, rural house w/shared tennis, private Ping-Pong table, Foosball, & more

4 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Wilmington / Mt. Snow/ Chimney Hill  Southern Vermont Home, holiday rental in Charlemont

Wilmington / Mt. Snow/ Chimney Hill Southern Vermont Home

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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PARADISE on EARTH! - Historic 4BR Farmhouse, holiday rental in Charlemont

PARADISE on EARTH! - Historic 4BR Farmhouse

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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New Lakefront Cedar Log Home, holiday rental in Charlemont

New Lakefront Cedar Log Home

3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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New Timberframe House Rental in the Berkshire Mountains, Masschusetts, holiday rental in Charlemont

New Timberframe House Rental in the Berkshire Mountains, Masschusetts

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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OWL'S NEST LODGING, holiday rental in Charlemont

OWL'S NEST LODGING

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Charming 'Swiss Chalet' Ski Cabin Near Mount Snow, holiday rental in Charlemont

Charming 'Swiss Chalet' Ski Cabin Near Mount Snow

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Serene Shelburne Studio Cabin w/Spring-Fed Pool!, holiday rental in Charlemont

Serene Shelburne Studio Cabin w/Spring-Fed Pool!

0 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Wilmington Home w/Pool Access- 20 Mins to Mt. Snow, holiday rental in Charlemont

Wilmington Home w/Pool Access- 20 Mins to Mt. Snow

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Spacious Wilmington Home w/ Game Room & Deck!, holiday rental in Charlemont

Spacious Wilmington Home w/ Game Room & Deck!

6 bedrooms
5 bathrooms
Sleeps 26
Match: Sleeps
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The Bear Den, holiday rental in Charlemont

The Bear Den

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Picturesque Cottage with Sunroom on Ashmere Lake!, holiday rental in Charlemont

Picturesque Cottage with Sunroom on Ashmere Lake!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Hidden Hoosic   Riverside Camp, holiday rental in Charlemont

Tentrr Signature Site - Hidden Hoosic Riverside Camp

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Jacksonville Cabin w/ Wraparound Deck & Views, holiday rental in Charlemont

Jacksonville Cabin w/ Wraparound Deck & Views

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Rural Berkshires Home, holiday rental in Charlemont

Rural Berkshires Home

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Crafts Inn in Vermont 1BR Suite, SATURDAY Check-In, holiday rental in Charlemont

Crafts Inn in Vermont 1BR Suite, SATURDAY Check-In

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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New listing! Sunny & secluded home w/ a gazebo plus mountain & reservoir views, holiday rental in Charlemont

New listing! Sunny & secluded home w/ a gazebo plus mountain & reservoir views

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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NEW! Kid-Friendly & Views! Hike, Bike, Grill, Swim, holiday rental in Charlemont

NEW! Kid-Friendly & Views! Hike, Bike, Grill, Swim

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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