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Berkshires Vacation Rentals

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199 rentals in Berkshires.
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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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Tentrr Signature Site - Hidden Hoosic   Riverside Camp, vacation rental in Berkshires

Tentrr Signature Site - Hidden Hoosic Riverside Camp

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Berkshire Mountain Hideaway, vacation rental in Berkshires

Tentrr Signature Site - Berkshire Mountain Hideaway

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

Berkshire Farmhouse Vacation

5 bedrooms
2 bathrooms
Sleeps 15
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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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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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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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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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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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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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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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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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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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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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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Antique Farmhouse Totally Restored, vacation rental in Berkshires

Antique Farmhouse Totally Restored

4 bedrooms
3 bathrooms
Sleeps 16
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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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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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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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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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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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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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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Newly Renovated 1910 Farmhouse - Walk To Town - Perfect Berkshire Retreat, vacation 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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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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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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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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Downtown GB apartment walk to shops and restaurants, vacation rental in Berkshires

Downtown GB apartment walk to shops and restaurants

2 bedrooms
1 bathroom
Sleeps 5
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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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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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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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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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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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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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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Woodland Cottage-NEW! Convenient, private, family friendly- see CLEANING DETAILS, vacation 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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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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Stunning Renovated Victorian, vacation rental in Berkshires

Stunning Renovated Victorian

5 bedrooms
5 bathrooms
Sleeps 12
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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Cozy renovated cabin in Williamstown, steps from hiking trails, vacation rental in Berkshires

Cozy renovated cabin in Williamstown, steps from hiking trails

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Beautiful four season lakeside log home close to all Berkshires attractions., vacation 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, vacation 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!, vacation rental in Berkshires

Beautiful Southfield Village!

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

The Freckled Hen's Berkshire Nest

3 bedrooms
2 bathrooms
Sleeps 6
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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