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Our top choices for Pittsfield vacation homes

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

3-bedroom house in beautiful Berkshires, close to amenities!
Pittsfield
The price is ¥28,684
¥48,607 total
includes taxes & fees
Mar 9 - Mar 10
3-bedroom house in beautiful Berkshires, close to amenities!

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 ¥42,459
¥77,917 total
includes taxes & fees
Mar 9 - Mar 10
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (18 reviews)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is ¥90,952
¥170,801 total
includes taxes & fees
Mar 11 - Mar 12
Hancock Village Inn Near Jiminy Peak

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (27 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 ¥26,128
¥43,285 total
includes taxes & fees
Mar 15 - Mar 16
Home in Great Barrington

Florida Mountain Log Cabin

Florida Mountain Log Cabin
Florida
10.0 out of 10, Exceptional, (4 reviews)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
The price is ¥28,992
¥53,819 total
includes taxes & fees
Mar 8 - Mar 9
Florida Mountain Log Cabin

North Getaway Cottage

North Getaway Cottage
Williamstown
9.2 out of 10, Wonderful, (24 reviews)
"We stayed here on a beautiful fall weekend so that my son could tour William's college. It was perfect!"
United States
Carole S.
The price is ¥31,950
¥70,759 total
includes taxes & fees
Mar 16 - Mar 17
North Getaway Cottage

Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires
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 ¥31,950
¥49,612 total
includes taxes & fees
Mar 8 - Mar 9
Family Ski Getaway in the Berkshires

Berkshires Cottage! Dog friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires Cottage! Dog 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 ¥25,276
¥62,247 total
includes taxes & fees
Mar 12 - Mar 13
Berkshires Cottage! Dog friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Treat yourself at the stunning June Farms Wellness Huts!

Treat yourself at the stunning June Farms Wellness Huts!
West Sand Lake
10.0 out of 10, Exceptional, (8 reviews)
"The wellness hut was an amazing getaway. Beautiful interior and design. Loved the little outdoor sauna. Loved the front porch/deck. Would definitely return for another stay."
United States
SteveS
The price is ¥39,193
¥70,650 total
includes taxes & fees
Mar 9 - Mar 10
Treat yourself at the stunning June Farms Wellness Huts!

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 ¥17,466
¥53,492 total
includes taxes & fees
Mar 8 - Mar 9
Near Tanglewood: Historic Summer Retreat

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, (34 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 ¥35,382
¥87,107 total
includes taxes & fees
Mar 9 - Mar 10
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

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 ¥25,560
¥61,859 total
includes taxes & fees
Apr 1 - Apr 2
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (1 review)
"This home is super cozy and had all the amenities I needed after a long drive. I will be staying here again."
United States
Jess M.
The price is ¥16,283
¥29,724 total
includes taxes & fees
Mar 10 - Mar 11
Cozy Home in Pownal VT

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 ¥21,300
¥58,315 total
includes taxes & fees
Mar 17 - Mar 18
Historic Berkshires Home Near Tanglewood, Trails & Wineries

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 ¥52,856
¥98,959 total
includes taxes & fees
Mar 9 - Mar 10
Luxury Barn Retreat — All-Season Escape Awaits!

Artists’ Hideaway in Old Chatham

Artists’ Hideaway in Old Chatham
Old Chatham
The price is ¥25,453
¥80,990 total
includes taxes & fees
Mar 8 - Mar 9
Artists’ Hideaway in Old Chatham

Riverbend Berkshire East Basecamp - 3 bedrooms available

Riverbend Berkshire East Basecamp - 3 bedrooms available
Charlemont
10.0 out of 10, Exceptional, (2 reviews)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
The price is ¥27,570
¥70,038 total
includes taxes & fees
Mar 8 - Mar 9
Riverbend Berkshire East Basecamp - 3 bedrooms available

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 ¥89,319
¥209,568 total
includes taxes & fees
Mar 8 - Mar 9
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

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)
"Howie was a great host, very responsive and accommodating. If we find ourselves in the area in the future , will def try to stay here again "
United States
jon e.
The price is ¥41,654
¥87,238 total
includes taxes & fees
Mar 10 - Mar 11
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 Pittsfield Hotel Reviews

Find out more about Pittsfield

Pittsfield Vacation Homes information

Number of reviews
276
Accommodation
417 Vacation Homes
Lowest Price
¥29,724
Highest Price
¥209,568