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Charlemont Vacation Rentals

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50 rentals in Charlemont.
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Sfa Lodge Log Cabin 4 Bd - 2 Ba Nestled In The Woods 5 Mins From Berkshire East, vacation rental in Charlemont
Sfa Lodge Log Cabin 4 Bd - 2 Ba Nestled In The Woods 5 Mins From Berkshire East, vacation rental in Charlemont
Sfa Lodge Log Cabin 4 Bd - 2 Ba Nestled In The Woods 5 Mins From Berkshire East, vacation rental in Charlemont

Sfa Lodge Log Cabin 4 Bd - 2 Ba Nestled In The Woods 5 Mins From Berkshire East

Rental Home
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Charming New England House Surrounded By Trees, Field And Pond, vacation rental in Charlemont
Charming New England House Surrounded By Trees, Field And Pond, vacation rental in Charlemont
Charming New England House Surrounded By Trees, Field And Pond, vacation rental in Charlemont

Charming New England House Surrounded By Trees, Field And Pond

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Hidden gem at base of ski mountain., vacation rental in Charlemont
Hidden gem at base of ski mountain., vacation rental in Charlemont
Hidden gem at base of ski mountain., vacation rental in Charlemont

Hidden gem at base of ski mountain.

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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StrautmanHaus - All-Season Chalet at Berkshire East, vacation rental in Charlemont
StrautmanHaus - All-Season Chalet at Berkshire East, vacation rental in Charlemont
StrautmanHaus - All-Season Chalet at Berkshire East, vacation rental in Charlemont

StrautmanHaus - All-Season Chalet at Berkshire East

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Charming 2022 renovated 1867 farmhouse in Charlemont MA, vacation rental in Charlemont
Charming 2022 renovated 1867 farmhouse in Charlemont MA, vacation rental in Charlemont
Charming 2022 renovated 1867 farmhouse in Charlemont MA, vacation rental in Charlemont

Charming 2022 renovated 1867 farmhouse in Charlemont MA

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Unique People & Pet-Welcoming Country Haven, vacation rental in Charlemont
Unique People & Pet-Welcoming Country Haven, vacation rental in Charlemont
Unique People & Pet-Welcoming Country Haven, vacation rental in Charlemont

Unique People & Pet-Welcoming Country Haven

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Lake Front Log Cabin Close to Mt. Snow, vacation rental in Charlemont
Lake Front Log Cabin Close to Mt. Snow, vacation rental in Charlemont
Lake Front Log Cabin Close to Mt. Snow, vacation rental in Charlemont

Lake Front Log Cabin Close to Mt. Snow

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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In town, newly remodeled studio with private balcony, vacation rental in Charlemont
In town, newly remodeled studio with private balcony, vacation rental in Charlemont
In town, newly remodeled studio with private balcony, vacation rental in Charlemont

In town, newly remodeled studio with private balcony

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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This is it! Stunning Vermont Views w/ 25 Acres to Explore.  It's Almost Heaven!, vacation rental in Charlemont
This is it! Stunning Vermont Views w/ 25 Acres to Explore.  It's Almost Heaven!, vacation rental in Charlemont
This is it! Stunning Vermont Views w/ 25 Acres to Explore.  It's Almost Heaven!, vacation rental in Charlemont

This is it! Stunning Vermont Views w/ 25 Acres to Explore. It's Almost Heaven!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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1810 Brook Side Mill/House - Enjoy a Fall/Holiday Season Getaway in Western MA, vacation rental in Charlemont
1810 Brook Side Mill/House - Enjoy a Fall/Holiday Season Getaway in Western MA, vacation rental in Charlemont
1810 Brook Side Mill/House - Enjoy a Fall/Holiday Season Getaway in Western MA, vacation rental in Charlemont

1810 Brook Side Mill/House - Enjoy a Fall/Holiday Season Getaway in Western MA

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Modern rustic house overlooking the Deerfield River, vacation rental in Charlemont
Modern rustic house overlooking the Deerfield River, vacation rental in Charlemont
Modern rustic house overlooking the Deerfield River, vacation rental in Charlemont

Modern rustic house overlooking the Deerfield River

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort, vacation rental in Charlemont
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort, vacation rental in Charlemont
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort, vacation rental in Charlemont

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Stunning views on 545 acres at end of dirt road, vacation rental in Charlemont
Stunning views on 545 acres at end of dirt road, vacation rental in Charlemont
Stunning views on 545 acres at end of dirt road, vacation rental in Charlemont

Stunning views on 545 acres at end of dirt road

Rental Home
3 bedrooms
0 bathrooms
Sleeps 8
Match: Sleeps
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Retreat In The Woods, vacation rental in Charlemont
Retreat In The Woods, vacation rental in Charlemont
Retreat In The Woods, vacation rental in Charlemont

Retreat In The Woods

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Charming Rural Cottage in the Heart of the Scenic Mohawk Trail, vacation rental in Charlemont
Charming Rural Cottage in the Heart of the Scenic Mohawk Trail, vacation rental in Charlemont
Charming Rural Cottage in the Heart of the Scenic Mohawk Trail, vacation rental in Charlemont

Charming Rural Cottage in the Heart of the Scenic Mohawk Trail

Rental Home
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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A True Shangri-La-Country Retreat W/Pond, Gardens and Huge Deck and View, vacation rental in Charlemont
A True Shangri-La-Country Retreat W/Pond, Gardens and Huge Deck and View, vacation rental in Charlemont
A True Shangri-La-Country Retreat W/Pond, Gardens and Huge Deck and View, vacation rental in Charlemont

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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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The Green Mountain Roost, Very Private & Quiet Country House Sleeps 4, vacation rental in Charlemont
The Green Mountain Roost, Very Private & Quiet Country House Sleeps 4, vacation rental in Charlemont
The Green Mountain Roost, Very Private & Quiet Country House Sleeps 4, vacation rental in Charlemont

The Green Mountain Roost, Very Private & Quiet Country House Sleeps 4

Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Private Suite with a Sweet View. Spacious, close to town, great views., vacation rental in Charlemont
Private Suite with a Sweet View. Spacious, close to town, great views., vacation rental in Charlemont
Private Suite with a Sweet View. Spacious, close to town, great views., vacation rental in Charlemont

Private Suite with a Sweet View. Spacious, close to town, great views.

Rental Home
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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200 Year old updated Farmhouse on 12 acres - near Berkshire East Mountain Resort, vacation rental in Charlemont
200 Year old updated Farmhouse on 12 acres - near Berkshire East Mountain Resort, vacation rental in Charlemont
200 Year old updated Farmhouse on 12 acres - near Berkshire East Mountain Resort, vacation rental in Charlemont

200 Year old updated Farmhouse on 12 acres - near Berkshire East Mountain Resort

Rental Home
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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HawleyHaus - Log Cabin in the Berkshires!, vacation rental in Charlemont
HawleyHaus - Log Cabin in the Berkshires!, vacation rental in Charlemont
HawleyHaus - Log Cabin in the Berkshires!, vacation rental in Charlemont

HawleyHaus - Log Cabin in the Berkshires!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft, vacation rental in Charlemont
Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft, vacation rental in Charlemont
Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft, vacation rental in Charlemont

Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Secluded, Cozy Cabin on 10 Acres of Woods, vacation rental in Charlemont
Secluded, Cozy Cabin on 10 Acres of Woods, vacation rental in Charlemont
Secluded, Cozy Cabin on 10 Acres of Woods, vacation rental in Charlemont

Secluded, Cozy Cabin on 10 Acres of Woods

Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
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Secluded large country home for big groups with giant open yard for outdoor fun., vacation rental in Charlemont
Secluded large country home for big groups with giant open yard for outdoor fun., vacation rental in Charlemont
Secluded large country home for big groups with giant open yard for outdoor fun., vacation rental in Charlemont

Secluded large country home for big groups with giant open yard for outdoor fun.

Rental Home
4 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps
More info
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Charming Affordable  Home for groups up to 14, vacation rental in Charlemont
Charming Affordable  Home for groups up to 14, vacation rental in Charlemont
Charming Affordable  Home for groups up to 14, vacation rental in Charlemont

Charming Affordable Home for groups up to 14

Rental Home
7 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Retreat in the Woods, vacation rental in Charlemont
Retreat in the Woods, vacation rental in Charlemont
Retreat in the Woods, vacation rental in Charlemont

Retreat in the Woods

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Berkshire house w/ fireplace, A/C, WiFi & laundry, vacation rental in Charlemont
Berkshire house w/ fireplace, A/C, WiFi & laundry, vacation rental in Charlemont
Berkshire house w/ fireplace, A/C, WiFi & laundry, vacation rental in Charlemont

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Flight's End-A Country Home with Babbling Brook, vacation rental in Charlemont
Flight's End-A Country Home with Babbling Brook, vacation rental in Charlemont
Flight's End-A Country Home with Babbling Brook, vacation rental in Charlemont

Flight's End-A Country Home with Babbling Brook

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Charlemont Outdoor Retreat on the Chickley River!, vacation rental in Charlemont
Charlemont Outdoor Retreat on the Chickley River!, vacation rental in Charlemont
Charlemont Outdoor Retreat on the Chickley River!, vacation rental in Charlemont

Charlemont Outdoor Retreat on the Chickley River!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Spacious Family Winter Retreat: Hot Tub & Fire Pit, vacation rental in Charlemont
Spacious Family Winter Retreat: Hot Tub & Fire Pit, vacation rental in Charlemont
Spacious Family Winter Retreat: Hot Tub & Fire Pit, vacation rental in Charlemont

Spacious Family Winter Retreat: Hot Tub & Fire Pit

Rental Home
5 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
More info
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Stunning mountain top lodge, Ideal for groups of all kinds, 4 -season fun, vacation rental in Charlemont
Stunning mountain top lodge, Ideal for groups of all kinds, 4 -season fun, vacation rental in Charlemont
Stunning mountain top lodge, Ideal for groups of all kinds, 4 -season fun, vacation rental in Charlemont

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

Rental Home
7 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Rustic 1850s barn, updated & funky, ideal for exploring Southern VT/Western MA ., vacation rental in Charlemont
Rustic 1850s barn, updated & funky, ideal for exploring Southern VT/Western MA ., vacation rental in Charlemont
Rustic 1850s barn, updated & funky, ideal for exploring Southern VT/Western MA ., vacation rental in Charlemont

Rustic 1850s barn, updated & funky, ideal for exploring Southern VT/Western MA .

Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Amazing Country Getaway / Buckland Retreat House, vacation rental in Charlemont
Amazing Country Getaway / Buckland Retreat House, vacation rental in Charlemont
Amazing Country Getaway / Buckland Retreat House, vacation rental in Charlemont

Amazing Country Getaway / Buckland Retreat House

Rental Home
5 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
More info
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Serene Shelburne Studio Cabin w/Spring-Fed Pool!, vacation rental in Charlemont
Serene Shelburne Studio Cabin w/Spring-Fed Pool!, vacation rental in Charlemont
Serene Shelburne Studio Cabin w/Spring-Fed Pool!, vacation rental in Charlemont

Serene Shelburne Studio Cabin w/Spring-Fed Pool!

Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
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The Lodge * America's Switzerland - The Mountains Are Calling!, vacation rental in Charlemont
The Lodge * America's Switzerland - The Mountains Are Calling!, vacation rental in Charlemont
The Lodge * America's Switzerland - The Mountains Are Calling!, vacation rental in Charlemont

The Lodge * America's Switzerland - The Mountains Are Calling!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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The Bear Den, vacation rental in Charlemont
The Bear Den, vacation rental in Charlemont
The Bear Den, vacation rental in Charlemont

The Bear Den

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Manapouri Pond House, vacation rental in Charlemont
Manapouri Pond House, vacation rental in Charlemont
Manapouri Pond House, vacation rental in Charlemont

Manapouri Pond House

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Commune with alpacas on 8 beautiful acres!, vacation rental in Charlemont
Commune with alpacas on 8 beautiful acres!, vacation rental in Charlemont
Commune with alpacas on 8 beautiful acres!, vacation rental in Charlemont

Commune with alpacas on 8 beautiful acres!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Rural VT Retreat—Complete Privacy on 140 Acres! Long-term rental specials!, vacation rental in Charlemont
Rural VT Retreat—Complete Privacy on 140 Acres! Long-term rental specials!, vacation rental in Charlemont
Rural VT Retreat—Complete Privacy on 140 Acres! Long-term rental specials!, vacation rental in Charlemont

Rural VT Retreat—Complete Privacy on 140 Acres! Long-term rental specials!

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Classic home on 300 acres w/ incredible views, firepit & fireplace - 2 dogs OK!, vacation rental in Charlemont
Classic home on 300 acres w/ incredible views, firepit & fireplace - 2 dogs OK!, vacation rental in Charlemont
Classic home on 300 acres w/ incredible views, firepit & fireplace - 2 dogs OK!, vacation rental in Charlemont

Classic home on 300 acres w/ incredible views, firepit & fireplace - 2 dogs OK!

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Tentrr Signature Site - Hawley Hideaway private campground, vacation rental in Charlemont
Tentrr Signature Site - Hawley Hideaway private campground, vacation rental in Charlemont
Tentrr Signature Site - Hawley Hideaway private campground, vacation rental in Charlemont

Tentrr Signature Site - Hawley Hideaway private campground

Rental Home
2 bedrooms
1 bathroom
Sleeps 12
Match: Sleeps
More info
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The Mohawk Cabin * Wigwam Western Summit, vacation rental in Charlemont
The Mohawk Cabin * Wigwam Western Summit, vacation rental in Charlemont
The Mohawk Cabin * Wigwam Western Summit, vacation rental in Charlemont

The Mohawk Cabin * Wigwam Western Summit

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Tentrr Signature Site - Hawley Hideaway private campground, vacation rental in Charlemont
Tentrr Signature Site - Hawley Hideaway private campground, vacation rental in Charlemont
Tentrr Signature Site - Hawley Hideaway private campground, vacation rental in Charlemont

Tentrr Signature Site - Hawley Hideaway private campground

Rental Home
2 bedrooms
1 bathroom
Sleeps 12
Match: Sleeps
More info
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The Bear’s Den * America's Switzerland, vacation rental in Charlemont
The Bear’s Den * America's Switzerland, vacation rental in Charlemont
The Bear’s Den * America's Switzerland, vacation rental in Charlemont

The Bear’s Den * America's Switzerland

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Stylish cottage close to great hiking trails and great art museums, vacation rental in Charlemont
Stylish cottage close to great hiking trails and great art museums, vacation rental in Charlemont
Stylish cottage close to great hiking trails and great art museums, vacation rental in Charlemont

Stylish cottage close to great hiking trails and great art museums

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Black Bear Mountain Cottage, vacation rental in Charlemont
Black Bear Mountain Cottage, vacation rental in Charlemont
Black Bear Mountain Cottage, vacation rental in Charlemont

Black Bear Mountain Cottage

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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The Wampanoag Cabin * The Wigwam Western Summit, vacation rental in Charlemont
The Wampanoag Cabin * The Wigwam Western Summit, vacation rental in Charlemont
The Wampanoag Cabin * The Wigwam Western Summit, vacation rental in Charlemont

The Wampanoag Cabin * The Wigwam Western Summit

Rental Home
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Luxury log cabin with views to Mt. Monadnock, vacation rental in Charlemont
Luxury log cabin with views to Mt. Monadnock, vacation rental in Charlemont
Luxury log cabin with views to Mt. Monadnock, vacation rental in Charlemont

Luxury log cabin with views to Mt. Monadnock

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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The Pocumtuck Cabin * The Wigwam Western Summit, vacation rental in Charlemont
The Pocumtuck Cabin * The Wigwam Western Summit, vacation rental in Charlemont
The Pocumtuck Cabin * The Wigwam Western Summit, vacation rental in Charlemont

The Pocumtuck Cabin * The Wigwam Western Summit

Rental Home
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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Hoosac Range Retreat, vacation rental in Charlemont
Hoosac Range Retreat, vacation rental in Charlemont
Hoosac Range Retreat, vacation rental in Charlemont

Hoosac Range Retreat

Condo/Apartment
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Sunny Chalet Nestled in the Woods of Ashfield, vacation rental in Charlemont
Sunny Chalet Nestled in the Woods of Ashfield, vacation rental in Charlemont
Sunny Chalet Nestled in the Woods of Ashfield, vacation rental in Charlemont

Sunny Chalet Nestled in the Woods of Ashfield

Rental Home
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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