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Holiday Homes in Berkshires

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214 rentals in Berkshires.
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Gartner House, a charming home in Lenox, holiday rental in Berkshires

Gartner House, a charming home in Lenox

4 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Unique People & Pet-Welcoming Country Haven, holiday rental in Berkshires

Unique People & Pet-Welcoming Country Haven

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

Berkshire Farmhouse Vacation

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

Berkshires: Romantic Cottage with spectacular view

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Close To Skiing!  Beautiful +Family Friendly - W Tree House & Tennis Court, holiday 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, holiday rental in Berkshires

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 Berkshires

Recently renovated 4 bedroom lakefront house in The Berkshires.

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!, holiday 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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Room to Roam. Modern home with all amenities + sep. cabin on 10+  wooded acres., holiday 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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COUPLE(S) PERFECT!! 2 BED/BATHS ; CENTRAL AC; FIREPL; ROMANTIC 'SKI LODGE' FEEL, holiday 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!, holiday 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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Charming Downtown Williamstown Cottage - 5 Min Walk to Campus, holiday rental in Berkshires

Charming Downtown Williamstown Cottage - 5 Min Walk to Campus

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Beautiful 1920's Colonial 20 Minutes from Tanglewood, holiday rental in Berkshires

Beautiful 1920's Colonial 20 Minutes from Tanglewood

4 bedrooms
2 bathrooms
Sleeps 8
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New Rates! BEAUTIFUL Ski-In/Ski-Out - Jiminy Peak Mountain Resort - Berkshires, holiday 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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Antique Farmhouse Totally Restored, holiday rental in Berkshires

Antique Farmhouse Totally Restored

4 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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Private rustic cottage with lake access, holiday rental in Berkshires

Private rustic cottage with lake access

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Berkshire Pontoosuc Lake Beauty Too-Brand new construction on the lake, holiday 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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Spring Break Special!  Stay two nights get one free for March and April!, holiday 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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Gorgeous Log Cabin in the Berkshires, holiday rental in Berkshires

Gorgeous Log Cabin in the Berkshires

3 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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A-Frame in Sherwood Forest, holiday rental in Berkshires

A-Frame in Sherwood Forest

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Lovingly restored Victorian in Lee's Historic District **Spring:3rd nt 1/2 off, holiday 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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Elegant 19th Century New England 2BR Vacation Rental at Garfield House, holiday 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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Cozy Monterey Family Chalet, Minutes From Lake & 10 Minutes From Butternut!, holiday 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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PRIVATE LAKEFRONT BEACH PROPERTY ON GOOSE POND  near TANGLEWOOD, holiday rental in Berkshires

PRIVATE LAKEFRONT BEACH PROPERTY ON GOOSE POND near TANGLEWOOD

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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The perfect getaway: 5 bd, 3 ba, 3 acres. Booking for fall, winter & 2021!, holiday 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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Downtown GB apartment walk to shops and restaurants, holiday rental in Berkshires

Downtown GB apartment walk to shops and restaurants

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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A Grand Estate in Historic Stockbridge, holiday rental in Berkshires

A Grand Estate in Historic Stockbridge

6 bedrooms
8 bathrooms
Sleeps 12
Match: Sleeps
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A Beautiful Log Cabin In The Woods, On A Lake (Pontoosuc), Yet Near Everything, holiday 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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General Williams Estate House Lenox/Stockbridge, holiday rental in Berkshires

General Williams Estate House Lenox/Stockbridge

6 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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RANKED #1 for 5 STAR REVIEWS covering 355 properties., holiday rental in Berkshires

RANKED #1 for 5 STAR REVIEWS covering 355 properties.

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Vacation in a  Berkshire Farmhouse, holiday rental in Berkshires

Vacation in a Berkshire Farmhouse

5 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps
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Tranquil Lake House Getaway on Onota Lake, holiday 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, holiday rental in Berkshires

Berkshire Lake House Vacation Rental

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Newly Renovated 1910 Farmhouse - Walk To Town - Perfect Berkshire Retreat, holiday rental in Berkshires

Newly Renovated 1910 Farmhouse - Walk To Town - Perfect Berkshire Retreat

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Woodland Cottage-NEW! Convenient, private, family friendly- see CLEANING DETAILS, holiday rental in Berkshires

Woodland Cottage-NEW! Convenient, private, family friendly- see CLEANING DETAILS

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Spacious, Modern House 5 Bedrooms, 2.5 Bathrooms, Sleep 12 on small horse farm., holiday 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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Beautiful Waterfront home with deep water dock on Onota Lake, holiday 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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2 bedroom Riverhouse in the Heart of the Berkshires, holiday rental in Berkshires

2 bedroom Riverhouse in the Heart of the Berkshires

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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4 BR home w/ beautiful gardens on pond in Berkshires. Walking distance to town., holiday 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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Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table, holiday 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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Historic Red Schoolhouse featured in the 2015 Home & Garden TV Special, holiday 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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Retreat in the Woods, holiday rental in Berkshires

Retreat in the Woods

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful four season lakeside log home close to all Berkshires attractions., holiday rental in Berkshires

Beautiful four season lakeside log home close to all Berkshires attractions.

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Spacious waterfront Berkshire home family private get-away, holiday rental in Berkshires

Spacious waterfront Berkshire home family private get-away

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Southfield Village!, holiday rental in Berkshires

Beautiful Southfield Village!

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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The Freckled Hen's Berkshire Nest, holiday rental in Berkshires

The Freckled Hen's Berkshire Nest

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Peace And Quiet On The Lake, holiday rental in Berkshires

Peace And Quiet On The Lake

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Warm your heart this holiday season in this cozy cottage next to downtown Lenox., holiday 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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19th c. Renovated Barn in the Berkshires, holiday rental in Berkshires

19th c. Renovated Barn in the Berkshires

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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5 STAR! Lenox. Luxury. Location., holiday rental in Berkshires

5 STAR! Lenox. Luxury. Location.

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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