Berkshire County Cottages
Massachusetts
United States of America
Cottages
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Berkshire County Hotels Vacation Rentals in Berkshire County Berkshire County Car Rentals Berkshire County Vacations

The Berkshires showing snow as well as a family

Cottages in Berkshire County

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Cottages in Berkshire County

A-frame Cabin w/ Furnished Deck in Becket!

3.0 star property

Becket

A-frame Cabin w/ Furnished Deck in Becket!

Luxury Vacation Rental in the Berkshires!

3.0 star property

Williamstown

Luxury Vacation Rental in the Berkshires!

Cottage (4 Bedrooms) | Front of property

1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge

3.0 star property

Glendale

10.0 out of 10, Exceptional, (1)

10/10

Exceptional

(1)

1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge

Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

3.0 star property

Lee

Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

Skiing & Hiking: Water-view Home in the Berkshires

3.0 star property

Sheffield

Skiing & Hiking: Water-view Home in the Berkshires

Spacious Historic Home in the Berkshires!

3.0 star property

Pittsfield

Spacious Historic Home in the Berkshires!

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

3.0 star property

Great Barrington

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Lakefront Otis Home w/ Stunning Views & Boats!

3.0 star property

Otis

Lakefront Otis Home w/ Stunning Views & Boats!

Cozy Stockbridge Cabin - Walk to Beach & Lake!

3.0 star property

Stockbridge

2.0 out of 10, (1)

2.0/10

(1)

Cozy Stockbridge Cabin - Walk to Beach & Lake!

Whitney by Avantstay Private Berkshires Estate

3.0 star property

Sheffield

Whitney by Avantstay Private Berkshires Estate

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

3.0 star property

Great Barrington

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

Stockbridge Home: Walk to Town Beach!

3.0 star property

Stockbridge

Stockbridge Home: Walk to Town Beach!

Picturesque Cottage With Sunroom on Ashmere Lake!

3.0 star property

Hinsdale

Picturesque Cottage With Sunroom on Ashmere Lake!

Cozy Becket Cottage Escape w/ Lake Access!

3.0 star property

Sherwood Forest

Cozy Becket Cottage Escape w/ Lake Access!

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

3.0 star property

Lenox

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

Massachusetts Vacation Rental w/ Deck & Grill

3.0 star property

Windsor

Massachusetts Vacation Rental w/ Deck & Grill

Stockbridge Retreat w/ Pool & Hot Tub!

3.0 star property

Glendale

Stockbridge Retreat w/ Pool & Hot Tub!

Renovated Lakefront House w/ Dock: Pets Welcome!

3.0 star property

Great Barrington

Renovated Lakefront House w/ Dock: Pets Welcome!

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

3.0 star property

Sandisfield

10.0 out of 10, Exceptional, (1)

10/10

Exceptional

(1)

"We had an amazing experience! Such a beautiful home and amazing host! We loved it! Definitely staying here again. Highly recommend! Thank you! "

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

4 Mi to Great Barrington: Berkshires Retreat!

3.0 star property

Great Barrington

4 Mi to Great Barrington: Berkshires Retreat!

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Top Berkshire County Hotel Reviews

Vacation Village in the Berkshires

10/10 Excellent

"Clean room and friendly staff. No issues at all. Will definitely stay again."

Yang 2-night trip

Posted 6 hours ago

Vacation Village in the Berkshires

Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent

"Staff is friendly and accommodating "

Karol 1-night trip

Posted 4 days ago

Best Western Plus Berkshire Hills Inn & Suites

Berkshire Mountain Lodge

10/10 Excellent

"Clean and spacious one bedroom suite with well stocked kitchen. Large indoor pool and outdoor year round Jacuzzi are wonderful. Also very affordable. Second time staying here and will stay here again. "

Melinda 2-night trip

Posted 4 days ago

Berkshire Mountain Lodge

Berkshires Untold

10/10 Excellent

"What a beautiful place. I wish I could have stayed longer. Top notch!"

Jennifer 1-night trip

Posted 5 days ago

Berkshires Untold

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

10/10 Excellent

"Very nice hotel"

Shawn 2-night trip

Posted 5 days ago

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

The Yankee, Trademark Collection by Wyndham

10/10 Excellent

"It's just a nice place and the staff is very nice "

Robin 5-night trip

Posted 5 days ago

The Yankee, Trademark Collection by Wyndham

The Porches Inn at Mass MoCA

10/10 Excellent

"True to its historic character, the attention to detail was splendid! "

Paul 1-night trip

Posted 6 days ago

The Porches Inn at Mass MoCA

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent

"Excellent hotel. Great staff. "

David 2-night trip

Posted 6 days ago

Hampton Inn & Suites Berkshires-Lenox

Hotel On North

10/10 Excellent

"Great property! Very large clean room in a unique hotel! "

michelle 2-night trip

Posted 7 days ago

Hotel On North

Find out more about Berkshire County

Berkshire County Cottages information

Number of reviews	3
Accommodation	57 Cottages
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RV Parks in Berkshire County
Condo Rentals in Berkshire County
Country Houses in Berkshire County
Resorts in Berkshire County
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Cottages in Berkshire County

Compare and save

Change your mind

Treat yourself

Be picky

Check prices for these dates

Cottages in Berkshire County

A-frame Cabin w/ Furnished Deck in Becket!

A-frame Cabin w/ Furnished Deck in Becket!

Luxury Vacation Rental in the Berkshires!

Luxury Vacation Rental in the Berkshires!

1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge

1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge

Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

Skiing & Hiking: Water-view Home in the Berkshires

Skiing & Hiking: Water-view Home in the Berkshires

Spacious Historic Home in the Berkshires!

Spacious Historic Home in the Berkshires!

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Lakefront Otis Home w/ Stunning Views & Boats!

Lakefront Otis Home w/ Stunning Views & Boats!

Cozy Stockbridge Cabin - Walk to Beach & Lake!

Cozy Stockbridge Cabin - Walk to Beach & Lake!

Whitney by Avantstay Private Berkshires Estate

Whitney by Avantstay Private Berkshires Estate

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

Stockbridge Home: Walk to Town Beach!

Stockbridge Home: Walk to Town Beach!

Picturesque Cottage With Sunroom on Ashmere Lake!

Picturesque Cottage With Sunroom on Ashmere Lake!

Cozy Becket Cottage Escape w/ Lake Access!

Cozy Becket Cottage Escape w/ Lake Access!

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

Massachusetts Vacation Rental w/ Deck & Grill

Massachusetts Vacation Rental w/ Deck & Grill

Stockbridge Retreat w/ Pool & Hot Tub!

Stockbridge Retreat w/ Pool & Hot Tub!

Renovated Lakefront House w/ Dock: Pets Welcome!

Renovated Lakefront House w/ Dock: Pets Welcome!

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

4 Mi to Great Barrington: Berkshires Retreat!

4 Mi to Great Barrington: Berkshires Retreat!

Top Berkshire County Hotel Reviews

Vacation Village in the Berkshires

Find out more about Berkshire County

Find out more about Berkshire County

Berkshire County Cottages information

Explore a world of travel with Expedia

Explore a world of travel with Expedia

More Accommodation Types in Berkshire County

All Accommodation Types

More ways to book

Expedia's Latest Trends