Holiday Homes in Pittsfield

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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Holiday Homes in Pittsfield

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Fridge, microwave, oven, stovetop

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

2.0 star property
9.0 out of 10, Wonderful, (4)
"Very clean and spacious! We enjoyed our stay with our small pup!"
The price is NZ$884
includes taxes & fees
11 Sept - 12 Sept
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
NEW RENO Historic Creamery in Berkshires w/hot tub
Terrace/patio

NEW RENO Historic Creamery in Berkshires w/hot tub

10.0 out of 10, Exceptional, (1)
"Absolutely AMAZING house beautiful inside and out the features are absolutely amazing!! Carl the host is super nice. Definitely 100% recommend staying here! "
The price is NZ$846
includes taxes & fees
17 Aug - 18 Aug
NEW RENO Historic Creamery in Berkshires w/hot tub
3-bedroom house in beautiful Berkshires, close to amenities!
Property grounds

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

The price is NZ$537
includes taxes & fees
26 Aug - 27 Aug
3-bedroom house in beautiful Berkshires, close to amenities!
Hancock Village Inn at Jiminy Peak
Exterior

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (12)
"Very kinda hosts, and wonderful house."
The price is NZ$1,768
includes taxes & fees
20 Aug - 21 Aug
Hancock Village Inn at Jiminy Peak
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Outdoor dining

Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

10.0 out of 10, Exceptional, (3)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
The price is NZ$667
includes taxes & fees
1 Sept - 2 Sept
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Smart TV, books

Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

9.8 out of 10, Exceptional, (7)
"My wife, two kids, and chocolate lab spent a few days at the cottage to enjoy the snow and hot tub. Everything was set up exactly as described and Nicole was very friendly and proactive. We had a great time and would do it again "
The price is NZ$695
includes taxes & fees
1 Sept - 2 Sept
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Home in Great Barrington
Fridge, microwave, oven, stovetop

Home in Great Barrington

9.8 out of 10, Exceptional, (23)
"Our family had a wonderful experience and stay. "
The price is NZ$532
includes taxes & fees
19 Aug - 20 Aug
Home in Great Barrington
North Getaway Cottage
Exterior

North Getaway Cottage

9.6 out of 10, Exceptional, (20)
"Claudia is such a considerate and thoughtful host! We felt so welcome and at ease."
The price is NZ$747
includes taxes & fees
18 Aug - 19 Aug
North Getaway Cottage
Hummingbird Haven is a Berkshires Retreat surrounded by Nature and Local Charm.
Property grounds

Hummingbird Haven is a Berkshires Retreat surrounded by Nature and Local Charm.

10.0 out of 10, Exceptional, (4)
"The property was spacious and very comfortable, had everything we needed. The area was also nice and fun to explore. "
Hummingbird Haven is a Berkshires Retreat surrounded by Nature and Local Charm.
Comfortable Berkshires retreat on mtn resort, SISO
A heated pool

Comfortable Berkshires retreat on mtn resort, SISO

8.8 out of 10, Excellent, (6)
"Kind and responsive host."
The price is NZ$805
includes taxes & fees
10 Sept - 11 Sept
Comfortable Berkshires retreat on mtn resort, SISO
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Fridge, microwave, oven, stovetop

Sun Filled Lenox Retreat - Minutes to Tanglewood!

10.0 out of 10, Exceptional, (1)
"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."
The price is NZ$867
includes taxes & fees
1 Sept - 2 Sept
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Perfect House In Hillsdale, Brings Friends & Fam
Exterior

Perfect House In Hillsdale, Brings Friends & Fam

8.6 out of 10, Excellent, (4)
"As a group of 10 friends, this house was everything we could have wanted. 5 bedrooms, a very large living room, and a dining table to fit all of us at once. Very close to Catamount, Hy’s Fried, Roe Jan brewery and more. Very clean for such an old house. "
The price is NZ$881
includes taxes & fees
25 Aug - 26 Aug
Perfect House In Hillsdale, Brings Friends & Fam
Near Tanglewood: Historic Summer Retreat
Fridge, microwave, oven, stovetop

Near Tanglewood: Historic Summer Retreat

9.6 out of 10, Exceptional, (22)
"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"
The price is NZ$866
includes taxes & fees
18 Aug - 19 Aug
Near Tanglewood: Historic Summer Retreat
Bungalow in the Berkshires
Exterior

Bungalow in the Berkshires

10.0 out of 10, Exceptional, (1)
"Renting this house was very last minute because the place we initially booked fell through - and we're so glad it did! The house was charming, cozy, up-to-date, and beautifully decorated. The neighborhood was nice and quiet, and the drive to downtown was short. I highly recommend this house!"
The price is NZ$865
includes taxes & fees
24 Aug - 25 Aug
Bungalow in the Berkshires
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Terrace/patio

Historic Berkshires Home Near Tanglewood, Trails & Wineries

9.0 out of 10, Wonderful, (17)
"Of all the properties I have stayed at, this home is my favorite! Excited to be able to stay in a such a historical home in a rich historical area! Amanda was a wonderful host! Provided a comfortable stay. The home had all the necessities! The town has delicious places to eat. Grocery store is great! My hope is to return and spend more time here."
The price is NZ$716
includes taxes & fees
10 Sept - 11 Sept
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Great Barrington Get Away
Fridge, microwave, oven, stovetop

Great Barrington Get Away

9.4 out of 10, Exceptional, (23)
"Nice, cozy, clean house with character. Great location as we could walk to town. Would stay again for sure."
The price is NZ$938
includes taxes & fees
11 Sept - 12 Sept
Great Barrington Get Away
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Exterior

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

9.8 out of 10, Exceptional, (71)
"We had a wonderful stay, thank you! "
The price is NZ$918
includes taxes & fees
18 Aug - 19 Aug
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Experience Timeless Elegance in The Edith Wharton Room!
1 bedroom, bed sheets, wheelchair access

Experience Timeless Elegance in The Edith Wharton Room!

The price is NZ$505
includes taxes & fees
8 Sept - 9 Sept
Experience Timeless Elegance in The Edith Wharton Room!
Glass Lake Cottage
Outdoor dining

Glass Lake Cottage

10.0 out of 10, Exceptional, (1)
"Glass lake cottage was the perfect relaxing retreat while I was visiting for a wedding at the Old Daley Inn! The place was clean, had a well stocked kitchen and everything I needed. We were lucky to catch a fantastic sunset and enjoyed the view from the large deck. Will definitely be back! "
The price is NZ$1,141
includes taxes & fees
26 Aug - 27 Aug
Glass Lake Cottage
The Lakeshore House
Property grounds

The Lakeshore House

10.0 out of 10, Exceptional, (1)
"Excellent stay!"
The price is NZ$1,355
includes taxes & fees
9 Sept - 10 Sept
The Lakeshore House
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
"Great value for families! The welcoming staff, location (Lenox/Pittsfield border), spacious suite, and ample amenities made for a fantastic vacation. No free breakfast but there are several dining options and markets nearby. Gorgeous view of the sunset from the upper floors. There was a note of upcoming renovations so looking forward to what else they have in store. "
Anonymous traveller 2-night trip
Posted 1 day ago
Berkshire Mountain Lodge