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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Stockbridge holiday homes

Exterior

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

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (36 reviews)
"Charming house in a wonderful setting in the Berkshires. "
United States
Mark Cristen J.
The price is HK$2,809
HK$5,682 total
includes taxes & fees
21 Apr - 22 Apr
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Interior

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is HK$1,141
HK$2,944 total
includes taxes & fees
20 Apr - 21 Apr
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Smart TV, books

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (14 reviews)
"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"
United States
Matthew F.
The price is HK$1,254
HK$3,087 total
includes taxes & fees
19 Apr - 20 Apr
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (29 reviews)
"The house was pristine, bright, with everything we needed. We hope to come back again to enjoy the area. "
United States
maureen k.
The price is HK$1,585
HK$2,513 total
includes taxes & fees
20 Apr - 21 Apr
Home in Great Barrington
Interior

Modern Victorian Walk to Main Street

Modern Victorian Walk to Main Street
Great Barrington
10.0 out of 10, Exceptional, (26 reviews)
"The house and location both perfect for a girls weekend away! "
United States
karen b.
The price is HK$2,308
HK$5,944 total
includes taxes & fees
19 Apr - 20 Apr
Modern Victorian Walk to Main Street
Interior

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries
Lebanon Springs
9.0 out of 10, Wonderful, (21 reviews)
"Comfy beds, clean, great big deck with a view. "
United States
Corinne T.
The price is HK$1,754
HK$3,752 total
includes taxes & fees
20 Apr - 21 Apr
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.2 out of 10, Wonderful, (14 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is HK$1,585
HK$2,452 total
includes taxes & fees
26 Apr - 27 Apr
Cozy Riverside Berkshires Retreat
Exterior

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.4 out of 10, Exceptional, (26 reviews)
"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."
United States
Paul S.
The price is HK$1,236
HK$3,094 total
includes taxes & fees
3 May - 4 May
Near Tanglewood: Historic Summer Retreat
Property grounds

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (42 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is HK$1,855
HK$3,951 total
includes taxes & fees
21 Apr - 22 Apr
Cheerful 3-bedroom cottage with woodstove
Outdoor dining

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

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
7.8 out of 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."
United States
Liz V.
The price is HK$2,106
HK$3,856 total
includes taxes & fees
19 Apr - 20 Apr
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
TV, fireplace

Artists’ Hideaway in Old Chatham

Artists’ Hideaway in Old Chatham
Old Chatham
The price is HK$1,262
HK$3,964 total
includes taxes & fees
5 May - 6 May
Artists’ Hideaway in Old Chatham
A heated pool

Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.8 out of 10, Excellent, (8 reviews)
"Kind and responsive host."
United States
Javier
The price is HK$1,260
HK$4,236 total
includes taxes & fees
26 Apr - 27 Apr
Comfortable Berkshires retreat on mtn resort, SISO
Property grounds

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.4 out of 10, Exceptional, (3 reviews)
"Great experience! Only there for one night because our son had a wrestling tournament. Wish we would have had more time at property. "
United States
Rochelle F.
The price is HK$1,369
HK$2,401 total
includes taxes & fees
20 Apr - 21 Apr
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Fridge, microwave, stovetop, dishwasher

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

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.4 out of 10, Exceptional, (3 reviews)
"excellent communication with property manager."
United States
Nancy H.
The price is HK$1,369
HK$4,348 total
includes taxes & fees
19 Apr - 20 Apr
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Exterior

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is HK$754
HK$1,017 total
includes taxes & fees
12 May - 13 May
Real Estate: Therapy - Lake, Laundry, Love it
TV

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is HK$2,066
HK$4,367 total
includes taxes & fees
22 Apr - 23 Apr
Treetop Hideaway in Tyringham
Private kitchen

NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet

NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet
New Lebanon
8.0 out of 10, Very good, (1 review)
"This location is great as an overnight trip. It’s centralized between ski resorts, restaurants near Pittsfield, MA and local NY. "
United States
Luz A.
The price is HK$1,183
HK$3,069 total
includes taxes & fees
19 Apr - 20 Apr
NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet
TV, fireplace, printers

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

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (4 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!"
United States
Roberta
The price is HK$4,430
HK$10,394 total
includes taxes & fees
19 Apr - 20 Apr
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.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (1 review)
"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.
The price is HK$2,230
HK$4,030 total
includes taxes & fees
19 Apr - 20 Apr
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Smart TV, books

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
9.8 out of 10, Exceptional, (6 reviews)
"Very charming, comfortable, and clean. It was in a great location and only minutes away from a lot of sightseeing locations. House management was very accommodating and friendly. I would stay here again."
United States
Paulo I.
The price is HK$2,486
HK$4,936 total
includes taxes & fees
28 Apr - 29 Apr
Sun Filled Lenox Retreat - Minutes to Tanglewood!
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

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent
"Cleanest and nicest room ever. Renovations ongoing but not disruptive. Excellent service."
Oleh 1-night trip
Posted 8 hours ago
Hampton Inn & Suites Berkshires-Lenox

Find out more about Stockbridge

Stockbridge Vacation Homes information

Number of reviews
247
Accommodation
415 Vacation Homes
Lowest Price
HK$1,017
Highest Price
HK$10,394

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