Holiday Homes in West Stockbridge

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Our top choices for West Stockbridge holiday homes

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 NZ$659
includes taxes & fees
18 Mar - 19 Mar
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (28 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 NZ$503
includes taxes & fees
30 Mar - 31 Mar
Home in Great Barrington

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

3-bedroom house in beautiful Berkshires, close to amenities!
Pittsfield
The price is NZ$577
includes taxes & fees
23 Mar - 24 Mar
3-bedroom house in beautiful Berkshires, close to amenities!

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (31 reviews)
"Good for a quick overnight - host was very accommodating when we needed an early check-in."
United States
Katie B.
The price is NZ$242
includes taxes & fees
26 Mar - 27 Mar
All the comforts of home

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 NZ$827
includes taxes & fees
19 Mar - 20 Mar
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.0 out of 10, Wonderful, (12 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is NZ$532
includes taxes & fees
18 Mar - 19 Mar
Cozy Riverside Berkshires Retreat

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 NZ$639
includes taxes & fees
18 Mar - 19 Mar
Near Tanglewood: Historic Summer Retreat

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

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
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 NZ$679
includes taxes & fees
16 Apr - 17 Apr
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Luxury Spa Retreat with Sauna, Hot Tub & Swimming Pool in the Heart of Hudson

Luxury Spa Retreat with Sauna, Hot Tub & Swimming Pool in the Heart of Hudson
Hudson
9.8 out of 10, Exceptional, (30 reviews)
"The home was as described. Exceptional. It was immaculate and well stocked."
United States
judy h.
The price is NZ$1,842
includes taxes & fees
18 Mar - 19 Mar
Luxury Spa Retreat with Sauna, Hot Tub & Swimming Pool in the Heart of Hudson

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 NZ$625
includes taxes & fees
19 Mar - 20 Mar
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Artists’ Hideaway in Old Chatham

Artists’ Hideaway in Old Chatham
Old Chatham
The price is NZ$864
includes taxes & fees
28 Mar - 29 Mar
Artists’ Hideaway in Old Chatham

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, (35 reviews)
"Julie was an excellent host. She responded quickly to my questions and provided us with a long list of local restaurants and activities.The house is lovely! It was very clean and had everything that we would need for our stay. We appreciated the big kitchen and the open living room- dining room space. "
United States
Kathleen E.
The price is NZ$1,210
includes taxes & fees
20 Mar - 21 Mar
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

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 NZ$2,174
includes taxes & fees
18 Mar - 19 Mar
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

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 NZ$851
includes taxes & fees
29 Mar - 30 Mar
Cheerful 3-bedroom cottage with woodstove

Luxury Barn Retreat — All-Season Escape Awaits!

Luxury Barn Retreat — All-Season Escape Awaits!
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.
The price is NZ$1,047
includes taxes & fees
18 Mar - 19 Mar
Luxury Barn Retreat — All-Season Escape Awaits!

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.0 out of 10, Wonderful, (10 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 NZ$936
includes taxes & fees
24 Mar - 25 Mar
Treetop Hideaway in Tyringham

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
9.6 out of 10, Exceptional, (4 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 NZ$765
includes taxes & fees
19 Mar - 20 Mar
Sun Filled Lenox Retreat - Minutes to Tanglewood!

Hudson Hot Tub & Pet Escape

Hudson Hot Tub & Pet Escape
Stottville
10.0 out of 10, Exceptional, (2 reviews)
The price is NZ$482
includes taxes & fees
22 Mar - 23 Mar
Hudson Hot Tub & Pet Escape

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$1,140
includes taxes & fees
24 Mar - 25 Mar
Spacious 5-bedroom house in charming Lee with WiFi

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)
"Had the best weekend skiing and enjoying family time in this amazing 3 story condo. Plenty of room for kids and grandkids to spread out. Short walk to the slopes made it so convenient for the skiers and a short ride down the mountain for the Littles in ski school. The unit was fully equipped with everything we needed. The views of the mountain breathtaking and the cozy fire at night was a nice bonus! Howie is an amazing host. Very responsive and helpful with all my questions. We will for sure be...
United States
Kim
The price is NZ$924
includes taxes & fees
18 Mar - 19 Mar
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
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 West Stockbridge Hotel Reviews

Find out more about West Stockbridge

West Stockbridge Holiday Homes information

Number of reviews
341
Accommodation
480 Holiday Homes
Lowest Price
NZ$242
Highest Price
NZ$2,174