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Hinsdale Holiday Rentals

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50 rentals in Hinsdale.
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Picturesque Cottage with Sunroom on Ashmere Lake!, holiday rental in Hinsdale

Picturesque Cottage with Sunroom on Ashmere Lake!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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New Timberframe House Rental in the Berkshire Mountains, Masschusetts, holiday rental in Hinsdale

New Timberframe House Rental in the Berkshire Mountains, Masschusetts

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Berkshire Village Carriage House, holiday rental in Hinsdale

Berkshire Village Carriage House

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Recently renovated 4 bedroom lakefront house in The Berkshires., holiday 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 Pontoosuc Lake Beauty Too-Brand new construction on the lake, holiday 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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Swiss Chalet Style Timber frame Home In Berkshires With All Modern Conveniences, holiday rental in Hinsdale

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

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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A-Frame in Sherwood Forest, holiday rental in Hinsdale

A-Frame in Sherwood Forest

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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A Beautiful Log Cabin In The Woods, On A Lake (Pontoosuc), Yet Near Everything, holiday 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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Warm your heart this holiday season in this cozy cottage next to downtown Lenox., holiday 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, holiday rental in Hinsdale

Tranquil Lake House Getaway on Onota Lake

5 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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RANKED #1 for 5 STAR REVIEWS covering 355 properties., holiday rental in Hinsdale

RANKED #1 for 5 STAR REVIEWS covering 355 properties.

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Berkshire Lake House Vacation Rental, holiday 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, holiday 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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Beautiful Waterfront home with deep water dock on Onota Lake, holiday 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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5 STAR! Lenox. Luxury. Location., holiday rental in Hinsdale

5 STAR! Lenox. Luxury. Location.

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

Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Freckled Hen's Berkshire Nest, holiday rental in Hinsdale

The Freckled Hen's Berkshire Nest

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Remote and Relaxing Cabin in the Berkshires, holiday rental in Hinsdale

Remote and Relaxing Cabin in the Berkshires

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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19th c. Renovated Barn in the Berkshires, holiday rental in Hinsdale

19th c. Renovated Barn in the Berkshires

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Large Immaculate Home, 10 Minute Walk To Lenox Center, Minutes To Tanglewood, holiday 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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Gartner House, a charming home in Lenox, holiday rental in Hinsdale

Gartner House, a charming home in Lenox

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

Grand Colonial Home in the Heart of The Berkshires

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Heart of Lenox Walk to Town Cozy Cottage!, holiday rental in Hinsdale

Heart of Lenox Walk to Town Cozy Cottage!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Newly Renovated Waterfront Lakehouse for rent, holiday rental in Hinsdale

Newly Renovated Waterfront Lakehouse for rent

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Scenic ByWay Waterfront Property, holiday rental in Hinsdale

Scenic ByWay Waterfront Property

3 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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2 Bedroom newly renovated townehouse, beautifully decorated at Garfield House, holiday 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, holiday 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, holiday 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, holiday 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, holiday rental in Hinsdale

Exquisite Apartment in Grand Victorian Home 1

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Charming Berkshire Getaway with Scenic Lake Views & Access, holiday rental in Hinsdale

Charming Berkshire Getaway with Scenic Lake Views & Access

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

Lake House

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

Heart of Lenox

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Cozy home, secluded sledding, snowshoe trails,babbling brook,waterfalls,23 acres, holiday rental in Hinsdale

Cozy home, secluded sledding, snowshoe trails,babbling brook,waterfalls,23 acres

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Berkshires Spacious Comfortable Charming Farmhouse, holiday 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, holiday 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, holiday 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, holiday rental in Hinsdale

Garfield House

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Private Guest House in Dtwn Lenox, Walk to Dining!, holiday 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!, holiday 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 Lenox Home, 3 Mi to Shakespeare & Co!, holiday 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, holiday rental in Hinsdale

The Gatehouse on Golden Hill

4 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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Restored 1881 Farm House, holiday rental in Hinsdale

Restored 1881 Farm House

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

NEW! Lakeside Berkshires Home Near Hiking & Skiing

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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