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Check prices for these dates

Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov
In one month
21 Nov - 23 Nov
In two months
19 Dec - 21 Dec

Vacation Homes in Pittsfield

Fridge, microwave, oven, stovetop
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
7.8 out of 10, Good, (6)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
The price is AEDĀ 988
AEDĀ 1,806 total
includes taxes & fees
26 Oct - 27 Oct
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Exterior
Spacious 6BR Near Jiminy Peak ā€“ Hot Tub, Game Room & Ski Lift Ticket Discount
Spacious 6BR Near Jiminy Peak ā€“ Hot Tub, Game Room & Ski Lift Ticket Discount
10.0 out of 10, Exceptional, (15)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is AEDĀ 2,200
AEDĀ 4,081 total
includes taxes & fees
28 Oct - 29 Oct
Spacious 6BR Near Jiminy Peak ā€“ Hot Tub, Game Room & Ski Lift Ticket Discount
Outdoor dining
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
10.0 out of 10, Exceptional, (3)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AEDĀ 536
AEDĀ 1,386 total
includes taxes & fees
28 Oct - 29 Oct
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
Smart TV, books
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
9.6 out of 10, Exceptional, (8)
"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 AEDĀ 588
AEDĀ 1,441 total
includes taxes & fees
27 Oct - 28 Oct
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Terrace/patio
Charming 2-bedroom house in beautiful countryside of Cummington, Ma
Charming 2-bedroom house in beautiful countryside of Cummington, Ma
2.0 star property
The price is AEDĀ 716
AEDĀ 1,044 total
includes taxes & fees
25 Oct - 26 Oct
Charming 2-bedroom house in beautiful countryside of Cummington, Ma
Fridge, microwave, oven, stovetop
Home in Great Barrington
Home in Great Barrington
9.8 out of 10, Exceptional, (24)
"Crisp and clean with a great location.Wonderful choice."
United States
Richard B.
The price is AEDĀ 698
AEDĀ 1,120 total
includes taxes & fees
23 Nov - 24 Nov
Home in Great Barrington
Exterior
North Getaway Cottage
North Getaway Cottage
9.2 out of 10, Wonderful, (22)
"Claudia is such a considerate and thoughtful host! We felt so welcome and at ease."
United States
Caroline J.
The price is AEDĀ 744
AEDĀ 1,614 total
includes taxes & fees
27 Oct - 28 Oct
North Getaway Cottage
Fridge, microwave, oven, stovetop
Near Tanglewood: Historic Summer Retreat
Near Tanglewood: Historic Summer Retreat
9.6 out of 10, Exceptional, (22)
"Very cozy and comfortable with everything we needed to make our stay enjoyable. The kitchen was well stocked, the bedrooms a good size with comfortable mattresses. The deck and the yard were lovely. This location is gem!"
United States
Patty W.
The price is AEDĀ 628
AEDĀ 1,534 total
includes taxes & fees
26 Oct - 27 Oct
Near Tanglewood: Historic Summer Retreat
Fridge, microwave, oven, stovetop
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Sun Filled Lenox Retreat - Minutes to Tanglewood!
9.4 out of 10, Exceptional, (3)
"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 AEDĀ 698
AEDĀ 1,698 total
includes taxes & fees
30 Oct - 31 Oct
Sun Filled Lenox Retreat - Minutes to Tanglewood!
A heated pool
Comfortable Berkshires retreat on mtn resort, SISO
Comfortable Berkshires retreat on mtn resort, SISO
8.8 out of 10, Excellent, (6)
"Kind and responsive host."
United States
Javier
The price is AEDĀ 591
AEDĀ 1,792 total
includes taxes & fees
26 Oct - 27 Oct
Comfortable Berkshires retreat on mtn resort, SISO
Fridge, microwave, oven, stovetop
Great Barrington Get Away
Great Barrington Get Away
9.4 out of 10, Exceptional, (24)
"The host was very communicative and responsive during our arrival and check out. The listing and everything was as it said we were very pleased with both the location of the home and the actual home itself and the property walking distance to town truly cannot say enough. Thank you for Your hospitality. Our family is very grateful. "
United States
Amy B.
The price is AEDĀ 937
AEDĀ 1,764 total
includes taxes & fees
27 Oct - 28 Oct
Great Barrington Get Away
Property grounds
Riverbend Berkshire East Basecamp - 3 bedrooms available
Riverbend Berkshire East Basecamp - 3 bedrooms available
The price is AEDĀ 588
AEDĀ 1,551 total
includes taxes & fees
27 Oct - 28 Oct
Riverbend Berkshire East Basecamp - 3 bedrooms available
Game room
Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"
Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"
9.0 out of 10, Wonderful, (2)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is AEDĀ 702
AEDĀ 900 total
includes taxes & fees
5 Nov - 6 Nov
Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"
Terrace/patio
Treat yourself at the stunning June Farms Wellness Huts!
Treat yourself at the stunning June Farms Wellness Huts!
10.0 out of 10, Exceptional, (8)
"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 AEDĀ 972
AEDĀ 1,711 total
includes taxes & fees
5 Nov - 6 Nov
Treat yourself at the stunning June Farms Wellness Huts!
Smart TV, fireplace, books
Cozy. Clean. Free bagel shop.
Cozy. Clean. Free bagel shop.
10.0 out of 10, Exceptional, (10)
"The perfect location for a stay in Great Barrington. The house is so well done and very comfortable!"
United States
Carly F.
The price is AEDĀ 1,322
AEDĀ 2,232 total
includes taxes & fees
4 Nov - 5 Nov
Cozy. Clean. Free bagel shop.
Exterior
Bungalow in the Berkshires
Bungalow in the Berkshires
10.0 out of 10, Exceptional, (3)
"We had a lovely stay. Easy check in and communication was great. "
United States
Dale G.
The price is AEDĀ 1,102
AEDĀ 1,534 total
includes taxes & fees
26 Oct - 27 Oct
Bungalow in the Berkshires
Exterior
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
9.8 out of 10, Exceptional, (72)
"We had a wonderful stay, thank you! "
United States
Gary L.
The price is AEDĀ 962
AEDĀ 2,019 total
includes taxes & fees
26 Oct - 27 Oct
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Outdoor spa tub
Escape to Lakefront Leisureā€”Hudson, Berkshires, Amazing Views!!!
Escape to Lakefront Leisureā€”Hudson, Berkshires, Amazing Views!!!
10.0 out of 10, Exceptional, (54)
"Great spot on the lake. Super quiet and relaxing."
United States
vincent m.
The price is AEDĀ 992
AEDĀ 1,975 total
includes taxes & fees
26 Oct - 27 Oct
Escape to Lakefront Leisureā€”Hudson, Berkshires, Amazing Views!!!
Fireplace
Artistsā€™ Hideaway in Old Chatham
Artistsā€™ Hideaway in Old Chatham
The price is AEDĀ 739
AEDĀ 1,651 total
includes taxes & fees
26 Oct - 27 Oct
Artistsā€™ Hideaway in Old Chatham
Microwave, oven, stovetop, dishwasher
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Cozy. Clean. Free bagel shop. 3 Fireplaces.
The price is AEDĀ 1,249
AEDĀ 2,158 total
includes taxes & fees
4 Nov - 5 Nov
Cozy. Clean. Free bagel shop. 3 Fireplaces.
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"We loved this place. Quiet, very clean,attractive. Loved that it had a kitchen area. Second story, sliding glass doors overlooked the fall foliage in the back of the building. Very peaceful.."
Steven 4-night trip
Posted 1 day ago
Berkshire Mountain Lodge