Landoll's Mohican Castle, Christmas lights.

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Our top choices for Stockbridge holiday homes

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is HK$635
HK$2,556 total
includes taxes & fees
17 Jun - 18 Jun
Real Estate: Therapy - Lake, Laundry, Love it

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$1,143
HK$2,948 total
includes taxes & fees
15 Jun - 16 Jun
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

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, (15 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is HK$1,319
HK$3,145 total
includes taxes & fees
23 Jun - 24 Jun
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
The price is HK$1,389
HK$3,154 total
includes taxes & fees
16 Jun - 17 Jun
stylish Berkshires Retreat

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.2 out of 10, Wonderful, (15 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is HK$1,601
HK$2,489 total
includes taxes & fees
16 Jun - 17 Jun
Cozy Riverside Berkshires Retreat

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (32 reviews)
"Perfect space for an overnight stay. Very clean and well appointed. Communication from host was great and check in was a breeze. 2 minute drive from downtown Great Barrington."
United States
Anonymous traveller
The price is HK$1,869
HK$2,858 total
includes taxes & fees
14 Jun - 15 Jun
Home in Great Barrington

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$1,371
HK$4,354 total
includes taxes & fees
14 Jun - 15 Jun
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.4 out of 10, Exceptional, (26 reviews)
"Very clean, fully stocked kitchen,great location "
United States
Karen H.
The price is HK$1,135
HK$2,983 total
includes taxes & fees
15 Jun - 16 Jun
Near Tanglewood: Historic Summer Retreat

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

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.8 out of 10, Exceptional, (6 reviews)
"Mark was very communicative and helpful, answering all questions quickly and accurately"
United States
Jim S.
The price is HK$1,802
HK$2,975 total
includes taxes & fees
14 Jun - 15 Jun
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

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$2,320
HK$4,663 total
includes taxes & fees
15 Jun - 16 Jun
Treetop Hideaway in Tyringham

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$1,375
HK$3,278 total
includes taxes & fees
15 Jun - 16 Jun
Historic Berkshires Home Near Tanglewood, Trails & Wineries

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$1,411
HK$3,361 total
includes taxes & fees
14 Jun - 15 Jun
NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (43 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is HK$1,857
HK$3,956 total
includes taxes & fees
14 Jun - 15 Jun
Cheerful 3-bedroom cottage with woodstove

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Old Chatham
10.0 out of 10, Exceptional, (2 reviews)
"We enjoyed our stay at this property. The hot tub was great and the home was immaculate!"
United States
Terri E.
The price is HK$2,006
HK$4,502 total
includes taxes & fees
16 Jun - 17 Jun
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

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$2,461
HK$4,307 total
includes taxes & fees
14 Jun - 15 Jun
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

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$2,351
HK$4,175 total
includes taxes & fees
17 Jun - 18 Jun
Cozy. Clean. Free bagel shop. 3 Fireplaces.

Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.4 out of 10, Very good, (10 reviews)
"Kind and responsive host."
United States
Javier
The price is HK$1,262
HK$4,260 total
includes taxes & fees
14 Jun - 15 Jun
Comfortable Berkshires retreat on mtn resort, SISO

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Hancock
9.8 out of 10, Exceptional, (74 reviews)
"Helpful host, lovely condo. Great location. Clean, tons of games and movies in unit. Also plenty of coffee pods included!"
United States
Christy F.
The price is HK$2,069
HK$4,324 total
includes taxes & fees
15 Jun - 16 Jun
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi
Lee
8.8 out of 10, Excellent, (3 reviews)
"House was clean and made our Thanksgiving great with it's size and amenities. "
United States
Khalil S.
The price is HK$3,722
HK$6,749 total
includes taxes & fees
23 Jun - 24 Jun
Spacious 5-bedroom house in charming Lee with WiFi

Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (19 reviews)
"Really great host - communication was great. House is so close to skiing, can’t beat it "
United States
Stephanie B.
The price is HK$4,929
HK$9,004 total
includes taxes & fees
16 Jun - 17 Jun
Hancock Village Inn Near Jiminy Peak
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

Find out more about Stockbridge

Stockbridge Vacation Homes information

Number of reviews
269
Accommodation
471 Vacation Homes
Lowest Price
HK$2,489
Highest Price
HK$9,004

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