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Our top choices for Stockbridge vacation homes

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

Vacation Home in Sherwood Forest

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
$335 nightly
The price is $374
Jan 5 - Jan 6, 2026
Total with taxes and fees
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Fridge, microwave, oven, stovetop
Home in Great Barrington

Vacation Home in Great Barrington

Home in Great Barrington
9.8 out of 10, Exceptional, (26)
"Enjoyed our stay!!!"
United States
Fred W.
$230 nightly
The price is $257
Jan 5 - Jan 6, 2026
Total with taxes and fees
Home in Great Barrington
Smart TV, books
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Vacation Home in Sherwood Forest

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
9.6 out of 10, Exceptional, (10)
"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."
United States
James D.
$351 nightly
The price is $392
Jan 5 - Jan 6, 2026
Total with taxes and fees
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Interior
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Vacation Home in Lebanon Springs

Historic Berkshires Home Near Tanglewood, Trails & Wineries
8.8 out of 10, Excellent, (20)
"It was great - just what we were looking for. "
United States
Kaye S.
$329 nightly
The price is $368
Jan 8 - Jan 9, 2026
Total with taxes and fees
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Property grounds
Cheerful 3-bedroom cottage with woodstove

Vacation Home in Sheffield

Cheerful 3-bedroom cottage with woodstove
10.0 out of 10, Exceptional, (41)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
$450 nightly
The price is $503
Jan 5 - Jan 6, 2026
Total with taxes and fees
Cheerful 3-bedroom cottage with woodstove
Exterior
Near Tanglewood: Historic Summer Retreat

Vacation Home in New Lebanon

Near Tanglewood: Historic Summer Retreat
9.4 out of 10, Exceptional, (23)
"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."
United States
Paul S.
$431 nightly
The price is $483
Dec 27 - Dec 28
Total with taxes and fees
Near Tanglewood: Historic Summer Retreat
Interior
Family Ski Getaway in the Berkshires

Vacation Home in Great Barrington

Family Ski Getaway in the Berkshires
9.4 out of 10, Exceptional, (6)
$253 nightly
The price is $283
Jan 4 - Jan 5, 2026
Total with taxes and fees
Family Ski Getaway in the Berkshires
Exterior detail
3-bedroom house in beautiful Berkshires, close to amenities!

Vacation Home in Pittsfield

3-bedroom house in beautiful Berkshires, close to amenities!
$285 nightly
The price is $318
Jan 12 - Jan 13, 2026
Total with taxes and fees
3-bedroom house in beautiful Berkshires, close to amenities!
Outdoor dining
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Vacation 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, (6)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
$442 nightly
The price is $494
Jan 3 - Jan 4, 2026
Total with taxes and fees
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Interior
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

Vacation Home in Valatie

Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!
10.0 out of 10, Exceptional, (60)
"Great spot on the lake. Super quiet and relaxing."
United States
vincent m.
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!
Smart TV, DVD player, books, stereo
Great Barrington Get Away

Vacation Home in Great Barrington

Great Barrington Get Away
9.4 out of 10, Exceptional, (25)
"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!"
United States
Elizabeth G.
$496 nightly
The price is $554
Jan 4 - Jan 5, 2026
Total with taxes and fees
Great Barrington Get Away
TV, fireplace, printers
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Vacation Home in Great Barrington

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
10.0 out of 10, Exceptional, (3)
"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!"
United States
Roberta
$1,189 nightly
The price is $1,328
Dec 25 - Dec 26
Total with taxes and fees
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
3 bedrooms, iron/ironing board, WiFi, bed sheets
Cozy. Clean. Free bagel shop. 3 Fireplaces.

Vacation Home in Great Barrington

Cozy. Clean. Free bagel shop. 3 Fireplaces.
10.0 out of 10, Exceptional, (1)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
$526 nightly
The price is $588
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cozy. Clean. Free bagel shop. 3 Fireplaces.
TV, fireplace
Artists’ Hideaway in Old Chatham

Vacation Home in Old Chatham

Artists’ Hideaway in Old Chatham
$448 nightly
The price is $502
Jan 4 - Jan 5, 2026
Total with taxes and fees
Artists’ Hideaway in Old Chatham
Outdoor dining
Hancock Village Inn Near Jiminy Peak

Vacation Home in Hancock

Hancock Village Inn Near Jiminy Peak
10.0 out of 10, Exceptional, (16)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
$971 nightly
The price is $1,050
Jan 6 - Jan 7, 2026
Total with taxes and fees
Hancock Village Inn Near Jiminy Peak
Property grounds
The Lakeshore House

Vacation Home in Niverville

The Lakeshore House
10.0 out of 10, Exceptional, (1)
"Excellent stay!"
United States
KEITARO A.
$716 nightly
The price is $802
Dec 23 - Dec 24
Total with taxes and fees
The Lakeshore House
Fridge, microwave, oven, stovetop
Spacious 5-bedroom house in charming Lee with WiFi

Vacation Home in Lee

Spacious 5-bedroom house in charming Lee with WiFi
8.0 out of 10, Very Good, (2)
"House was clean and made our Thanksgiving great with it's size and amenities. "
United States
Khalil S.
$819 nightly
The price is $915
Jan 5 - Jan 6, 2026
Total with taxes and fees
Spacious 5-bedroom house in charming Lee with WiFi
Terrace/patio
Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room

Vacation Home in Hillsdale

Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room
10.0 out of 10, Exceptional, (1)
"Beautiful house! It was a big house and we loved all the rooms and how they were decorated! When we first arrived the heat wasn’t working and the host had someone there with the half hour fixing the problem. Beautiful quite area as well "
United States
Gabrielle T.
$1,156 nightly
The price is $1,295
Jan 19 - Jan 20, 2026
Total with taxes and fees
Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room
Pool
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Vacation Home in Hancock

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
9.8 out of 10, Exceptional, (72)
"We had a wonderful stay, thank you! "
United States
Gary L.
$568 nightly
The price is $634
Dec 23 - Dec 24
Total with taxes and fees
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Property grounds
Hupi House: A Peaceful, Wooded, Lakeside Sanctuary

Vacation Home in Monterey

Hupi House: A Peaceful, Wooded, Lakeside Sanctuary
10.0 out of 10, Exceptional, (1)
"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."
United States
Kim H.
$1,587 nightly
The price is $1,773
Jan 18 - Jan 19, 2026
Total with taxes and fees
Hupi House: A Peaceful, Wooded, Lakeside Sanctuary
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 Stockbridge Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"While waiting for our vallet car due to construction. The hotel staff were engaging and had personal conversations with us. Rooms were good and all staff treated us exceptional. Give them an atta boy on proformance"
Nathan 1-night trip
Posted 18 hours ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Find out more about Stockbridge

Stockbridge Vacation Homes information

Number of reviews
306
Accommodation
419 Vacation Homes
Lowest Price
$257
Highest Price
$1,773

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