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Hinsdale Vacation Rentals

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50 rentals in Hinsdale.
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New Timberframe House Rental in the Berkshire Mountains, Masschusetts, vacation rental in Hinsdale

New Timberframe House Rental in the Berkshire Mountains, Masschusetts

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ashmere Lake Log Cabin with privacy / 2 Bedrooms, vacation rental in Hinsdale

Ashmere Lake Log Cabin with privacy / 2 Bedrooms

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Picturesque Cottage with Sunroom on Ashmere Lake!, vacation rental in Hinsdale

Picturesque Cottage with Sunroom on Ashmere Lake!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Recently renovated 4 bedroom lakefront house in The Berkshires., vacation rental in Hinsdale

Recently renovated 4 bedroom lakefront house in The Berkshires.

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Berkshire Village Carriage House, vacation rental in Hinsdale

Berkshire Village Carriage House

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Berkshire Pontoosuc Lake Beauty Too-Brand new construction on the lake, vacation rental in Hinsdale

Berkshire Pontoosuc Lake Beauty Too-Brand new construction on the lake

5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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A Beautiful Log Cabin In The Woods, On A Lake (Pontoosuc), Yet Near Everything, vacation rental in Hinsdale

A Beautiful Log Cabin In The Woods, On A Lake (Pontoosuc), Yet Near Everything

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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RANKED #1 for 5 STAR REVIEWS covering 355 properties., vacation rental in Hinsdale

RANKED #1 for 5 STAR REVIEWS covering 355 properties.

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Warm your heart this holiday season in this cozy cottage next to downtown Lenox., vacation rental in Hinsdale

Warm your heart this holiday season in this cozy cottage next to downtown Lenox.

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Tranquil Lake House Getaway on Onota Lake, vacation rental in Hinsdale

Tranquil Lake House Getaway on Onota Lake

5 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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Berkshire Lake House Vacation Rental, vacation rental in Hinsdale

Berkshire Lake House Vacation Rental

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Historic Red Schoolhouse featured in the 2015 Home & Garden TV Special, vacation rental in Hinsdale

Historic Red Schoolhouse featured in the 2015 Home & Garden TV Special

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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The Freckled Hen's Berkshire Nest, vacation rental in Hinsdale

The Freckled Hen's Berkshire Nest

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Waterfront home with deep water dock on Onota Lake, vacation rental in Hinsdale

Beautiful Waterfront home with deep water dock on Onota Lake

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Remote and Relaxing Cabin in the Berkshires, vacation rental in Hinsdale

Remote and Relaxing Cabin in the Berkshires

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow, vacation rental in Hinsdale

Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Heart of Lenox Walk to Town Cozy Cottage!, vacation rental in Hinsdale

Heart of Lenox Walk to Town Cozy Cottage!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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5 STAR! Lenox. Luxury. Location., vacation rental in Hinsdale

5 STAR! Lenox. Luxury. Location.

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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19th c. Renovated Barn in the Berkshires, vacation rental in Hinsdale

19th c. Renovated Barn in the Berkshires

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Gartner House, a charming home in Lenox, vacation rental in Hinsdale

Gartner House, a charming home in Lenox

4 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Large Immaculate Home, 10 Minute Walk To Lenox Center, Minutes To Tanglewood, vacation rental in Hinsdale

Large Immaculate Home, 10 Minute Walk To Lenox Center, Minutes To Tanglewood

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Charming 1860 Farmhouse, Completely Renovated, Convenient Location, Central AC, vacation rental in Hinsdale

Charming 1860 Farmhouse, Completely Renovated, Convenient Location, Central AC

4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b, vacation rental in Hinsdale

Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Lakefront Cottage In The Berkshires In Western Massachusetts, vacation rental in Hinsdale

Lakefront Cottage In The Berkshires In Western Massachusetts

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Grand Colonial Home in the Heart of The Berkshires, vacation rental in Hinsdale

Grand Colonial Home in the Heart of The Berkshires

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Scenic ByWay Waterfront Property, vacation rental in Hinsdale

Scenic ByWay Waterfront Property

3 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Elegant 19th Century New England Newly Renovated 1BR Vacation Rental, vacation rental in Hinsdale

Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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2 Bedroom newly renovated townehouse, beautifully decorated at Garfield House, vacation rental in Hinsdale

2 Bedroom newly renovated townehouse, beautifully decorated at Garfield House

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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6BR Berkshire Bliss - 38 Acres of nature - minutes from Jiminy Peak Ski Resort, vacation rental in Hinsdale

6BR Berkshire Bliss - 38 Acres of nature - minutes from Jiminy Peak Ski Resort

6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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SPECTACULAR RENOVATED BERKSHIRE LAKEFRONT HOUSE ON RICHMOND POND, vacation rental in Hinsdale

SPECTACULAR RENOVATED BERKSHIRE LAKEFRONT HOUSE ON RICHMOND POND

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Garfield House Studio at 208, vacation rental in Hinsdale

Garfield House Studio at 208

0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Exquisite Apartment in Grand Victorian Home 1, vacation rental in Hinsdale

Exquisite Apartment in Grand Victorian Home 1

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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6BR Berkshire Bliss - 38 private acres - close to skiing and town, vacation rental in Hinsdale

6BR Berkshire Bliss - 38 private acres - close to skiing and town

6 bedrooms
5 bathrooms
Sleeps 15
Match: Sleeps
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Mounatin Getaway in the Heart of the Berkshires!, vacation rental in Hinsdale

Mounatin Getaway in the Heart of the Berkshires!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Lake House, vacation rental in Hinsdale

Lake House

5 bedrooms
6 bathrooms
Sleeps 9
Match: Sleeps
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Heart of Lenox, vacation rental in Hinsdale

Heart of Lenox

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Restored 1881 Farm House, vacation rental in Hinsdale

Restored 1881 Farm House

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Berkshires Spacious Comfortable Charming Farmhouse, vacation rental in Hinsdale

Berkshires Spacious Comfortable Charming Farmhouse

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Exquisite Apartment in Grand Victorian 2, vacation rental in Hinsdale

Exquisite Apartment in Grand Victorian 2

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Deluxe New Home, 2 Master Suites, Tanglewood Area, vacation rental in Hinsdale

Deluxe New Home, 2 Master Suites, Tanglewood Area

5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Garfield House, vacation rental in Hinsdale

Garfield House

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table, vacation rental in Hinsdale

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

8 bedrooms
3 bathrooms
Sleeps 21
Match: Sleeps
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Private Guest House in Dtwn Lenox, Walk to Dining!, vacation rental in Hinsdale

Private Guest House in Dtwn Lenox, Walk to Dining!

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Spacious, Lake View Condo Near Tanglewood in the Heart of the Berkshires!, vacation rental in Hinsdale

Spacious, Lake View Condo Near Tanglewood in the Heart of the Berkshires!

4 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Beautiful Jiminy Peak Mountainside Condo Near Lifts - Just Remodeled, vacation rental in Hinsdale

Beautiful Jiminy Peak Mountainside Condo Near Lifts - Just Remodeled

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Lenox Home, 3 Mi to Shakespeare & Co!, vacation rental in Hinsdale

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Gatehouse on Golden Hill, vacation rental in Hinsdale

The Gatehouse on Golden Hill

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Berkshires Summer Rental -  Lee/Lenox, vacation rental in Hinsdale

Berkshires Summer Rental - Lee/Lenox

3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Apartment Newly Remodeled Super Location, vacation rental in Hinsdale

Apartment Newly Remodeled Super Location

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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NEW! Lakeside Berkshires Home Near Hiking & Skiing, vacation rental in Hinsdale

NEW! Lakeside Berkshires Home Near Hiking & Skiing

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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