Stockbridge Holiday House Rentals from AU$373: Search Holiday Homes

Stockbridge Holiday Homes
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Linwood House at the Norman Rockwell Museum Stockbridge Massachusetts USA.

Significant collection of the artist's original work & memorabilia on display in his hometown.

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Our top choices for Stockbridge holiday homes

Holiday Home in Stockbridge

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

10.0 out of 10, Exceptional, (33 reviews)

10/10

Exceptional

(33 reviews)

"A college friends' retreat was fantastic, in part due to the location, cleanliness and amenities in this 3 bedroom house. Furniture was comfortable and kitchen was stocked with everything we needed. "

cathy c.

The price is AU$960

AU$960

includes taxes & fees

21 Jan - 22 Jan

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Holiday Home in Sherwood Forest

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

10.0 out of 10, Exceptional, (5 reviews)

10/10

Exceptional

(5 reviews)

"We loved it! Lots of local hiking trails and a wonderful relaxing place."

Sharon K.

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

2 bedrooms, desk, iron/ironing board, travel cot

Holiday Home in Sherwood Forest

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

9.6 out of 10, Exceptional, (10 reviews)

9.6/10

Exceptional

(10 reviews)

"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."

James D.

The price is AU$577

AU$577

includes taxes & fees

21 Jan - 22 Jan

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Holiday Home in Great Barrington

Home in Great Barrington

9.8 out of 10, Exceptional, (26 reviews)

9.8/10

Exceptional

(26 reviews)

"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "

Cameron M.

The price is AU$373

AU$373

includes taxes & fees

26 Jan - 27 Jan

Home in Great Barrington

Smart TV, fireplace, books, music library

Holiday Home in Lebanon Springs

Historic Berkshires Home Near Tanglewood, Trails & Wineries

9.0 out of 10, Wonderful, (21 reviews)

9.0/10

Wonderful

(21 reviews)

"Great stay in the Berkshires for a wedding. Amanda was very accommodating and communicative. "

Wendy D.

The price is AU$561

AU$561

includes taxes & fees

29 Jan - 30 Jan

Historic Berkshires Home Near Tanglewood, Trails & Wineries

3 bedrooms, iron/ironing board, free WiFi, bed sheets

Holiday Home in New Lebanon

Near Tanglewood: Historic Summer Retreat

9.2 out of 10, Wonderful, (25 reviews)

9.2/10

Wonderful

(25 reviews)

"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."

Paul S.

The price is AU$522

AU$522

includes taxes & fees

25 Jan - 26 Jan

Near Tanglewood: Historic Summer Retreat

Holiday Home in Lee

Sun Filled Lenox Retreat - Minutes to Tanglewood!

9.4 out of 10, Exceptional, (3 reviews)

9.4/10

Exceptional

(3 reviews)

"The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay."

Sarah D.

The price is AU$675

AU$675

includes taxes & fees

20 Jan - 21 Jan

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Holiday Home in Great Barrington

Family Ski Getaway in the Berkshires

9.2 out of 10, Wonderful, (7 reviews)

9.2/10

Wonderful

(7 reviews)

"Close to a great bakery and near to a farm market and shopping mall. "

Cristine C.

The price is AU$441

AU$441

includes taxes & fees

20 Jan - 21 Jan

Family Ski Getaway in the Berkshires

Holiday Home in Monterey

Hupi House: A Peaceful, Wooded, Lakeside Sanctuary

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Hupi House was the perfect location for our girls reunion weekend. It was a great mix of a quiet retreat in nature and good meals/shopping in town. The property and house are beautiful and updated. Beds and linens are top notch! Highly recommend."

Kim H.

Hupi House: A Peaceful, Wooded, Lakeside Sanctuary

Holiday Home in Housatonic

Sweet Cozy Victorian in Housatonic. Close to everything.

10.0 out of 10, Exceptional, (3 reviews)

10/10

Exceptional

(3 reviews)

"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."

Cheryl F.

The price is AU$389

AU$389

includes taxes & fees

1 Feb - 2 Feb

Sweet Cozy Victorian in Housatonic. Close to everything.

Holiday Home in Pittsfield

3-bedroom house in beautiful Berkshires, close to amenities!

The price is AU$509

AU$509

includes taxes & fees

16 Feb - 17 Feb

3-bedroom house in beautiful Berkshires, close to amenities!

Holiday Home in Stephentown

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

2.0 star property

8.0 out of 10, Very good, (1 review)

8.0/10

Very good

(1 review)

"excellent communication with property manager."

Nancy H.

The price is AU$843

AU$843

includes taxes & fees

20 Jan - 21 Jan

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

Holiday Home in Spencertown

Suite 3 - Quiet and private accommodations in a country setting.

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Fantastic place to stay!"

James

The price is AU$406

AU$406

includes taxes & fees

25 Jan - 26 Jan

Suite 3 - Quiet and private accommodations in a country setting.

Holiday Home in Chatham

Renovated house. Built in 1890s. No neighbors in sight.

2.0 star property

The price is AU$453

AU$453

includes taxes & fees

25 Jan - 26 Jan

Renovated house. Built in 1890s. No neighbors in sight.

Holiday Home in Great Barrington

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

10.0 out of 10, Exceptional, (3 reviews)

10/10

Exceptional

(3 reviews)

"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"

Roberta

The price is AU$1,962

AU$1,962

includes taxes & fees

20 Jan - 21 Jan

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Holiday Home in Old Chatham

Artists’ Hideaway in Old Chatham

The price is AU$769

AU$769

includes taxes & fees

2 Feb - 3 Feb

Artists’ Hideaway in Old Chatham

3 bedrooms, desk, iron/ironing board, WiFi

Holiday Home in Pittsfield

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

2.0 star property

7.8 out of 10, Good, (7 reviews)

7.8/10

Good

(7 reviews)

"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."

Liz V.

The price is AU$734

AU$734

includes taxes & fees

21 Jan - 22 Jan

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

1 bedroom, iron/ironing board, WiFi, bed sheets

Holiday Home in New Marlborough

Peaceful, Post and Beam Loft, Sleeps 9

9.8 out of 10, Exceptional, (22 reviews)

9.8/10

Exceptional

(22 reviews)

"A very nice post & beam Berkshire house, quiet, clean, great acerage and amenities.Lucas was very accessible to handle minor issues quickly."

HARRELL O.

Peaceful, Post and Beam Loft, Sleeps 9

Holiday Home in Great Barrington

Great Barrington Get Away

9.4 out of 10, Exceptional, (26 reviews)

9.4/10

Exceptional

(26 reviews)

"We stayed here for Memorial Day weekend and had a wonderful trip. Close to the downtown shops, and all the supplies a family needs staying in a home. Thanks for the great stay!"

Elizabeth G.

The price is AU$831

AU$831

includes taxes & fees

25 Jan - 26 Jan

Great Barrington Get Away

Holiday Home in Egremont

Catamount, Zip Line, Private Setting, Book Now!

10.0 out of 10, Exceptional, (7 reviews)

10/10

Exceptional

(7 reviews)

"This was a very lovely home to stay in for our family, everything you need is in the house (basic things minus food of course) We would definitely book this house again when we visit the Berkshires again."

Jason W.

Catamount, Zip Line, Private Setting, Book Now!

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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