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Holiday Rentals in Charlemont

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

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

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
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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, holiday rental in Charlemont
Charming New England House Surrounded By Trees, Field And Pond, holiday rental in Charlemont

Charming New England House Surrounded By Trees, Field And Pond

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
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Hidden gem at base of ski mountain., holiday rental in Charlemont
Hidden gem at base of ski mountain., holiday rental in Charlemont
Hidden gem at base of ski mountain., holiday 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, holiday rental in Charlemont
StrautmanHaus - All-Season Chalet at Berkshire East, holiday rental in Charlemont
StrautmanHaus - All-Season Chalet at Berkshire East, holiday rental in Charlemont

StrautmanHaus - All-Season Chalet at Berkshire East

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Charming 2022 renovated 1867 farmhouse in Charlemont MA, holiday rental in Charlemont
Charming 2022 renovated 1867 farmhouse in Charlemont MA, holiday rental in Charlemont
Charming 2022 renovated 1867 farmhouse in Charlemont MA, holiday rental in Charlemont

Charming 2022 renovated 1867 farmhouse in Charlemont MA

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Unique People & Pet-Welcoming Country Haven, holiday rental in Charlemont
Unique People & Pet-Welcoming Country Haven, holiday rental in Charlemont
Unique People & Pet-Welcoming Country Haven, holiday rental in Charlemont

Unique People & Pet-Welcoming Country Haven

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

Lake Front Log Cabin Close to Mt. Snow

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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, holiday rental in Charlemont
In town, newly remodeled studio with private balcony, holiday rental in Charlemont

In town, newly remodeled studio with private balcony

Holiday Rental House
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!, holiday rental in Charlemont
This is it! Stunning Vermont Views w/ 25 Acres to Explore.  It's Almost Heaven!, holiday rental in Charlemont
This is it! Stunning Vermont Views w/ 25 Acres to Explore.  It's Almost Heaven!, holiday rental in Charlemont

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

Holiday Rental House
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, holiday rental in Charlemont
1810 Brook Side Mill/House - Enjoy a Fall/Holiday Season Getaway in Western MA, holiday rental in Charlemont
1810 Brook Side Mill/House - Enjoy a Fall/Holiday Season Getaway in Western MA, holiday rental in Charlemont

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

Holiday Rental House
3 bedrooms
3 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, holiday rental in Charlemont
Modern rustic house overlooking the Deerfield River, holiday rental in Charlemont

Modern rustic house overlooking the Deerfield River

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

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

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

Stunning views on 545 acres at end of dirt road

Holiday Rental House
3 bedrooms
0 bathrooms
Sleeps 8
Match: Sleeps
More info
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Retreat In The Woods, holiday rental in Charlemont
Retreat In The Woods, holiday rental in Charlemont
Retreat In The Woods, holiday rental in Charlemont

Retreat In The Woods

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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, holiday rental in Charlemont
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

Holiday Rental House
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, holiday rental in Charlemont
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, holiday rental in Charlemont

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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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The Green Mountain Roost, Very Private & Quiet Country House Sleeps 4, holiday rental in Charlemont
The Green Mountain Roost, Very Private & Quiet Country House Sleeps 4, holiday rental in Charlemont
The Green Mountain Roost, Very Private & Quiet Country House Sleeps 4, holiday rental in Charlemont

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

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
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Private Suite with a Sweet View. Spacious, close to town, great views., holiday rental in Charlemont
Private Suite with a Sweet View. Spacious, close to town, great views., holiday rental in Charlemont
Private Suite with a Sweet View. Spacious, close to town, great views., holiday rental in Charlemont

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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
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200 Year old updated Farmhouse on 12 acres - near Berkshire East Mountain Resort, holiday rental in Charlemont
200 Year old updated Farmhouse on 12 acres - near Berkshire East Mountain Resort, holiday rental in Charlemont
200 Year old updated Farmhouse on 12 acres - near Berkshire East Mountain Resort, holiday rental in Charlemont

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

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

HawleyHaus - Log Cabin in the Berkshires!

Holiday Rental House
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, holiday rental in Charlemont
Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft, holiday rental in Charlemont
Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft, holiday rental in Charlemont

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

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

Secluded, Cozy Cabin on 10 Acres of Woods

Holiday Rental House
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., holiday rental in Charlemont
Secluded large country home for big groups with giant open yard for outdoor fun., holiday rental in Charlemont
Secluded large country home for big groups with giant open yard for outdoor fun., holiday rental in Charlemont

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

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

Charming Affordable Home for groups up to 14

Holiday Rental House
7 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
More info
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Retreat in the Woods, holiday rental in Charlemont
Retreat in the Woods, holiday rental in Charlemont
Retreat in the Woods, holiday rental in Charlemont

Retreat in the Woods

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

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

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

Flight's End-A Country Home with Babbling Brook

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Charlemont Outdoor Retreat on the Chickley River!, holiday rental in Charlemont
Charlemont Outdoor Retreat on the Chickley River!, holiday rental in Charlemont
Charlemont Outdoor Retreat on the Chickley River!, holiday rental in Charlemont

Charlemont Outdoor Retreat on the Chickley River!

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

Spacious Family Winter Retreat: Hot Tub & Fire Pit

Holiday Rental House
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, holiday rental in Charlemont
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, holiday rental in Charlemont

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

Holiday Rental House
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 ., holiday rental in Charlemont
Rustic 1850s barn, updated & funky, ideal for exploring Southern VT/Western MA ., holiday rental in Charlemont
Rustic 1850s barn, updated & funky, ideal for exploring Southern VT/Western MA ., holiday rental in Charlemont

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

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

Amazing Country Getaway / Buckland Retreat House

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

Serene Shelburne Studio Cabin w/Spring-Fed Pool!

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

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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The Bear Den, holiday rental in Charlemont
The Bear Den, holiday rental in Charlemont
The Bear Den, holiday rental in Charlemont

The Bear Den

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

Manapouri Pond House

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Commune with alpacas on 8 beautiful acres!, holiday rental in Charlemont
Commune with alpacas on 8 beautiful acres!, holiday rental in Charlemont
Commune with alpacas on 8 beautiful acres!, holiday rental in Charlemont

Commune with alpacas on 8 beautiful acres!

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

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

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

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

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

Tentrr Signature Site - Hawley Hideaway private campground

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

The Mohawk Cabin * Wigwam Western Summit

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

Tentrr Signature Site - Hawley Hideaway private campground

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

The Bear’s Den * America's Switzerland

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

Stylish cottage close to great hiking trails and great art museums

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Black Bear Mountain Cottage, holiday rental in Charlemont
Black Bear Mountain Cottage, holiday rental in Charlemont
Black Bear Mountain Cottage, holiday rental in Charlemont

Black Bear Mountain Cottage

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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The Wampanoag Cabin * The Wigwam Western Summit, holiday rental in Charlemont
The Wampanoag Cabin * The Wigwam Western Summit, holiday rental in Charlemont
The Wampanoag Cabin * The Wigwam Western Summit, holiday rental in Charlemont

The Wampanoag Cabin * The Wigwam Western Summit

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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Luxury log cabin with views to Mt. Monadnock, holiday rental in Charlemont
Luxury log cabin with views to Mt. Monadnock, holiday rental in Charlemont
Luxury log cabin with views to Mt. Monadnock, holiday rental in Charlemont

Luxury log cabin with views to Mt. Monadnock

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

The Pocumtuck Cabin * The Wigwam Western Summit

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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Hoosac Range Retreat, holiday rental in Charlemont
Hoosac Range Retreat, holiday rental in Charlemont
Hoosac Range Retreat, holiday 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, holiday rental in Charlemont
Sunny Chalet Nestled in the Woods of Ashfield, holiday rental in Charlemont
Sunny Chalet Nestled in the Woods of Ashfield, holiday rental in Charlemont

Sunny Chalet Nestled in the Woods of Ashfield

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
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