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Berkshires Cottages

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245 rentals in Berkshires.
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Fox Hollow Laurel Lake Ranch, vacation rental in Berkshires

Fox Hollow Laurel Lake Ranch

4 bedrooms
5 bathrooms
Sleeps 11
Match: Sleeps
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'Too Good' With 11 Private Acres.  Contact us for Monthly Specials!, vacation rental in Berkshires

'Too Good' With 11 Private Acres. Contact us for Monthly Specials!

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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'The Mill River Cabin’ w/ Fireplace & River View!, vacation rental in Berkshires

'The Mill River Cabin’ w/ Fireplace & River View!

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Tranquil 3BR Stockbridge House w/Private Deck, vacation rental in Berkshires

Tranquil 3BR Stockbridge House w/Private Deck

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Unique People & Pet-Welcoming Country Haven, vacation rental in Berkshires

Unique People & Pet-Welcoming Country Haven

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Berkshire Farmhouse Vacation, vacation rental in Berkshires

Berkshire Farmhouse Vacation

5 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps
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Berkshires: Romantic Cottage with spectacular view, vacation rental in Berkshires

Berkshires: Romantic Cottage with spectacular view

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Gartner House, a charming home in Lenox, vacation rental in Berkshires

Gartner House, a charming home in Lenox

4 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Close To Skiing!  Beautiful +Family Friendly - W Tree House & Tennis Court, vacation rental in Berkshires

Close To Skiing! Beautiful +Family Friendly - W Tree House & Tennis Court

4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Berkshire Village Carriage House, vacation rental in Berkshires

Berkshire Village Carriage House

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Antique Farmhouse Totally Restored, vacation rental in Berkshires

Antique Farmhouse Totally Restored

4 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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New Rates! BEAUTIFUL Ski-In/Ski-Out - Jiminy Peak Mountain Resort - Berkshires, vacation rental in Berkshires

New Rates! BEAUTIFUL Ski-In/Ski-Out - Jiminy Peak Mountain Resort - Berkshires

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!, vacation rental in Berkshires

Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!

5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Beautiful 1920's Colonial 20 Minutes from Tanglewood, vacation rental in Berkshires

Beautiful 1920's Colonial 20 Minutes from Tanglewood

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Charming Downtown Williamstown Cottage - 5 Min Walk to Campus, vacation rental in Berkshires

Charming Downtown Williamstown Cottage - 5 Min Walk to Campus

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Recently renovated 4 bedroom lakefront house in The Berkshires., vacation rental in Berkshires

Recently renovated 4 bedroom lakefront house in The Berkshires.

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spring Break Special!  Stay two nights get one free for March and April!, vacation rental in Berkshires

Spring Break Special! Stay two nights get one free for March and April!

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Room to Roam. Modern home with all amenities + sep. cabin on 10+  wooded acres., vacation rental in Berkshires

Room to Roam. Modern home with all amenities + sep. cabin on 10+ wooded acres.

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Serene Lakefront Cottage, vacation rental in Berkshires

Serene Lakefront Cottage

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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COUPLE(S) PERFECT!! 2 BED/BATHS ; CENTRAL AC; FIREPL; ROMANTIC 'SKI LODGE' FEEL, vacation rental in Berkshires

COUPLE(S) PERFECT!! 2 BED/BATHS ; CENTRAL AC; FIREPL; ROMANTIC 'SKI LODGE' FEEL

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Huge Luxe Williamstown Updated Victorian,  All Ensuite Baths, Walk to Spring St!, vacation rental in Berkshires

Huge Luxe Williamstown Updated Victorian, All Ensuite Baths, Walk to Spring St!

5 bedrooms
6 bathrooms
Sleeps 15
Match: Sleeps
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Great Barrington Retreat ! Booking for the Fall & Winter Now!, vacation rental in Berkshires

Great Barrington Retreat ! Booking for the Fall & Winter Now!

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Berkshire Pontoosuc Lake Beauty Too-Brand new construction on the lake, vacation rental in Berkshires

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

5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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A-Frame in Sherwood Forest, vacation rental in Berkshires

A-Frame in Sherwood Forest

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Private rustic cottage with lake access, vacation rental in Berkshires

Private rustic cottage with lake access

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Lovingly restored Victorian in Lee's Historic District **Spring:3rd nt 1/2 off, vacation rental in Berkshires

Lovingly restored Victorian in Lee's Historic District **Spring:3rd nt 1/2 off

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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PRIVATE LAKEFRONT BEACH PROPERTY ON GOOSE POND  near TANGLEWOOD, vacation rental in Berkshires

PRIVATE LAKEFRONT BEACH PROPERTY ON GOOSE POND near TANGLEWOOD

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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A Grand Estate in Historic Stockbridge, vacation rental in Berkshires

A Grand Estate in Historic Stockbridge

6 bedrooms
8 bathrooms
Sleeps 12
Match: Sleeps
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RANKED #1 for 5 STAR REVIEWS covering 355 properties., vacation rental in Berkshires

RANKED #1 for 5 STAR REVIEWS covering 355 properties.

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Elegant 19th Century New England 2BR Vacation Rental at Garfield House, vacation rental in Berkshires

Elegant 19th Century New England 2BR Vacation Rental at Garfield House

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Gorgeous Log Cabin in the Berkshires, vacation rental in Berkshires

Gorgeous Log Cabin in the Berkshires

3 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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The perfect getaway: 5 bd, 3 ba, 3 acres. Booking for fall, winter & 2021!, vacation rental in Berkshires

The perfect getaway: 5 bd, 3 ba, 3 acres. Booking for fall, winter & 2021!

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Vacation in a  Berkshire Farmhouse, vacation rental in Berkshires

Vacation in a Berkshire Farmhouse

5 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps
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General Williams Estate House Lenox/Stockbridge, vacation rental in Berkshires

General Williams Estate House Lenox/Stockbridge

6 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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A Beautiful Log Cabin In The Woods, On A Lake (Pontoosuc), Yet Near Everything, vacation rental in Berkshires

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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Spacious, Modern House 5 Bedrooms, 2.5 Bathrooms, Sleep 12 on small horse farm., vacation rental in Berkshires

Spacious, Modern House 5 Bedrooms, 2.5 Bathrooms, Sleep 12 on small horse farm.

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Retreat in the Woods, vacation rental in Berkshires

Retreat in the Woods

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful Waterfront home with deep water dock on Onota Lake, vacation rental in Berkshires

Beautiful Waterfront home with deep water dock on Onota Lake

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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4 BR home w/ beautiful gardens on pond in Berkshires. Walking distance to town., vacation rental in Berkshires

4 BR home w/ beautiful gardens on pond in Berkshires. Walking distance to town.

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Historic Red Schoolhouse featured in the 2015 Home & Garden TV Special, vacation rental in Berkshires

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

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tranquil Lake House Getaway on Onota Lake, vacation rental in Berkshires

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 Berkshires

Berkshire Lake House Vacation Rental

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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2 bedroom Riverhouse in the Heart of the Berkshires, vacation rental in Berkshires

2 bedroom Riverhouse in the Heart of the Berkshires

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy Monterey Family Chalet, Minutes From Lake & 10 Minutes From Butternut!, vacation rental in Berkshires

Cozy Monterey Family Chalet, Minutes From Lake & 10 Minutes From Butternut!

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

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

8 bedrooms
3 bathrooms
Sleeps 21
Match: Sleeps
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Warm your heart this holiday season in this cozy cottage next to downtown Lenox., vacation rental in Berkshires

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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Modern Secluded Home In Wooded Setting, vacation rental in Berkshires

Modern Secluded Home In Wooded Setting

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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5 STAR! Lenox. Luxury. Location., vacation rental in Berkshires

5 STAR! Lenox. Luxury. Location.

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful home with all amenities. Close to everything. Fiber optic internet., vacation rental in Berkshires

Beautiful home with all amenities. Close to everything. Fiber optic internet.

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Peace And Quiet On The Lake, vacation rental in Berkshires

Peace And Quiet On The Lake

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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