Holiday Homes in Stockbridge

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Check prices for these dates

In two weeks
6 Feb - 8 Feb
In two months
20 Mar - 22 Mar
In three months
17 Apr - 19 Apr
In four months
15 May - 17 May

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, (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. "
United States
cathy c.
The price is NZ$1,091
includes taxes & fees
22 Jan - 23 Jan
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Smart TV, books

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

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Sherwood Forest
9.6 out of 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."
United States
James D.
The price is NZ$666
includes taxes & fees
21 Jan - 22 Jan
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 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. "
United States
Cameron M.
The price is NZ$429
includes taxes & fees
26 Jan - 27 Jan
Home in Great Barrington
Interior

Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires
Great Barrington
9.2 out of 10, Wonderful, (7 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is NZ$504
includes taxes & fees
21 Jan - 22 Jan
Family Ski Getaway in the Berkshires
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
2.0 star property
Stephentown
8.0 out of 10, Very good, (1 review)
"excellent communication with property manager."
United States
Nancy H.
The price is NZ$950
includes taxes & fees
21 Jan - 22 Jan
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Smart TV, books

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
9.6 out of 10, Exceptional, (4 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."
United States
Sarah D.
The price is NZ$779
includes taxes & fees
21 Jan - 22 Jan
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Exterior

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.2 out of 10, Wonderful, (25 reviews)
"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."
United States
Paul S.
The price is NZ$587
includes taxes & fees
21 Jan - 22 Jan
Near Tanglewood: Historic Summer Retreat
Interior

Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
10.0 out of 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."
United States
Cheryl F.
The price is NZ$458
includes taxes & fees
1 Feb - 2 Feb
Sweet Cozy Victorian in Housatonic. Close to everything.
Interior

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

Suite 3 - Quiet and private accommodations in a country setting.
Spencertown
10.0 out of 10, Exceptional, (1 review)
"Fantastic place to stay!"
United States
James
The price is NZ$467
includes taxes & fees
25 Jan - 26 Jan
Suite 3 - Quiet and private accommodations in a country setting.
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!
2.0 star property
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 NZ$845
includes taxes & fees
21 Jan - 22 Jan
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Exterior detail

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

3-bedroom house in beautiful Berkshires, close to amenities!
Pittsfield
The price is NZ$594
includes taxes & fees
17 Feb - 18 Feb
3-bedroom house in beautiful Berkshires, close to amenities!
Property grounds

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

Renovated house. Built in 1890s. No neighbors in sight.
2.0 star property
Chatham
The price is NZ$522
includes taxes & fees
25 Jan - 26 Jan
Renovated house. Built in 1890s. No neighbors in sight.
Interior

Luxury Barn Retreat — All-Season Escape Awaits!

Luxury Barn Retreat — All-Season Escape Awaits!
2.0 star property
East Chatham
10.0 out of 10, Exceptional, (2 reviews)
"Accommodations were even better than we expected. The rooms were very clean, and there are unique (and sometimes whimsical, other times thought-provoking) decorations/pictures throughout the barn. The kitchen was basically a chef’s kitchen- all appliances were top notch. The backyard was spacious, and even contained a (non-working) pay phone booth! My wife loved the swinging two-seat chair on the porch! "
United States
Timothy S.
Luxury Barn Retreat — All-Season Escape Awaits!
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)
"Great stay in the Berkshires for a wedding. Amanda was very accommodating and communicative. "
United States
Wendy D.
The price is NZ$640
includes taxes & fees
21 Jan - 22 Jan
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Property grounds

The Lakeshore House

The Lakeshore House
Niverville
10.0 out of 10, Exceptional, (1 review)
"Excellent stay!"
United States
KEITARO A.
The price is NZ$1,348
includes taxes & fees
23 Jan - 24 Jan
The Lakeshore House
TV, fireplace

Artists’ Hideaway in Old Chatham

Artists’ Hideaway in Old Chatham
Old Chatham
The price is NZ$867
includes taxes & fees
27 Jan - 28 Jan
Artists’ Hideaway in Old Chatham
Outdoor dining

Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (16 reviews)
"Great place for a family reunion. Lots of bedrooms and bathrooms. Kitchen is large & well equipped"
United States
Veronica and Mark W.
The price is NZ$1,939
includes taxes & fees
21 Jan - 22 Jan
Hancock Village Inn Near Jiminy Peak
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, (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!"
United States
Roberta
The price is NZ$2,094
includes taxes & fees
31 Jan - 1 Feb
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Smart TV, DVD player, books, stereo

Great Barrington Get Away

Great Barrington Get Away
Great Barrington
9.4 out of 10, Exceptional, (26 reviews)
"Nice large kitchen and yard, walking distance to downtown, friendly neighborhood- we enjoyed our stay! "
United States
Deb W.
The price is NZ$943
includes taxes & fees
3 Feb - 4 Feb
Great Barrington Get Away
Fridge, microwave, oven, stovetop

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 NZ$1,450
includes taxes & fees
12 Feb - 13 Feb
Spacious 5-bedroom house in charming Lee with WiFi
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

Hotel On North

Hotel On North

10/10 Excellent
"It can be hard trying to choose a place to stay lately, especially since AI has blown up. I'm so happy I gave this place a chance. The staff was extremely friendly and helpful. Not once did I feel like they didn't want to be there. When we checked out at noon (which is an amazing checkout time), they held our luggage and bags for us. When we came back many hours later they offered to let us use the restroom before going to the train station. Most places in NYC don't want anything to do with you once you're checked out. The rooms were clean, and everything worked, including the wifi and heat/ac. I would definitely take my family back to stay here on another NYC trip. The room price was also very reasonable for the city. "
Sarah 1-night trip
Posted 2 days ago
Hotel On North

Find out more about Stockbridge

Stockbridge Holiday Homes information

Number of reviews
179
Accommodation
419 Holiday Homes
Lowest Price
NZ$429
Highest Price
NZ$2,094