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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Pittsfield holiday homes

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!
Pittsfield
8.4 out of 10, Very good, (9 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 HK$2,463
HK$4,318 total
includes taxes & fees
26 Jul - 27 Jul
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Outdoor dining

Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (22 reviews)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is HK$4,519
HK$8,487 total
includes taxes & fees
21 Jul - 22 Jul
Hancock Village Inn Near Jiminy Peak
Exterior

White Lily Lodge 50 acre estate with private lake

White Lily Lodge 50 acre estate with private lake
Cropseyville
The price is HK$5,645
HK$7,162 total
includes taxes & fees
31 Jul - 1 Aug
White Lily Lodge 50 acre estate with private lake
Property grounds

Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts

Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts
Cummington
10.0 out of 10, Exceptional, (1 review)
"Staff was super friendly, host was also amazing!"
United States
Connor
The price is HK$855
HK$1,069 total
includes taxes & fees
20 Jul - 21 Jul
Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts
Coffee/tea maker, fridge, microwave, stovetop

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.6 out of 10, Exceptional, (5 reviews)
"excellent communication with property manager."
United States
Nancy H.
The price is HK$1,380
HK$4,456 total
includes taxes & fees
21 Jul - 22 Jul
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
A heated pool

Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.4 out of 10, Very good, (10 reviews)
"The location was excellent, within walking distance of ski trail. Wonderful view of the ski area and surrounding mountains. The fireplace was perfect for the end of the day. Our large family had plenty of space to have fun together or chill alone. We had concerns about the cleanliness and working conditions of some electronics. Our concerns were communicated with the owner, and the response was positive. I am sure with corrections this Comfortable Berkshire Retreat will be a 5 star stay. "
United States
Russell R.
The price is HK$1,262
HK$4,279 total
includes taxes & fees
21 Jul - 22 Jul
Comfortable Berkshires retreat on mtn resort, SISO
Smart TV

stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.0 out of 10, Wonderful, (2 reviews)
"Property was just as described, clean and well equipped. Had excellent communication with the host. Would highly recommend staying here."
United States
Donna K.
The price is HK$1,581
HK$3,298 total
includes taxes & fees
21 Jul - 22 Jul
stylish Berkshires Retreat
Interior

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
Real Estate: Therapy - Lake, Laundry, Love it
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.4 out of 10, Exceptional, (18 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is HK$1,799
HK$2,745 total
includes taxes & fees
26 Jul - 27 Jul
Cozy Riverside Berkshires Retreat
Interior

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
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 HK$1,672
HK$3,619 total
includes taxes & fees
26 Jul - 27 Jul
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Pool

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)
"Helpful host, lovely condo. Great location. Clean, tons of games and movies in unit. Also plenty of coffee pods included!"
United States
Christy F.
The price is HK$1,898
HK$4,117 total
includes taxes & fees
21 Jul - 22 Jul
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Dining

Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (4 reviews)
"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 HK$910
HK$1,599 total
includes taxes & fees
30 Jul - 31 Jul
Cozy Home in Pownal VT
Outdoor spa tub

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, (15 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is HK$1,803
HK$3,774 total
includes taxes & fees
17 Aug - 18 Aug
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Coffee/tea maker, fridge, microwave, oven

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.6 out of 10, Exceptional, (34 reviews)
"Adorable guest home in Great Barrington! Light and bright. Perfect space for our family of 4. Well equipped kitchen and easy walk to downtown and groceries at the co-op. Would definitely stay here again!"
United States
Julie J.
The price is HK$2,509
HK$3,678 total
includes taxes & fees
6 Aug - 7 Aug
Home in Great Barrington
Exterior detail

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Old Chatham
10.0 out of 10, Exceptional, (3 reviews)
"We enjoyed our stay at this property. The hot tub was great and the home was immaculate!"
United States
Terri E.
The price is HK$1,835
HK$4,338 total
includes taxes & fees
21 Jul - 22 Jul
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Exterior

The Greylock Cabin

The Greylock Cabin
Florida
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful cabin in a beautiful location. Host is amazing, very responsive. "
United States
Anonymous traveller
The price is HK$2,037
HK$3,439 total
includes taxes & fees
17 Aug - 18 Aug
The Greylock Cabin
Dining

A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
10.0 out of 10, Exceptional, (57 reviews)
"Comfortable lovely home with everything we needed to have a great weekend. "
United States
Margaret C.
The price is HK$1,795
HK$3,774 total
includes taxes & fees
21 Jul - 22 Jul
A roomy remodeled retreat close to MassMoCA
Property grounds

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.8 out of 10, Exceptional, (9 reviews)
"Mark was very accommodating and always available immediately if I had a question. The place was very clean and comfortable. Perfect location. We would love to come back in the summer when we can use the fire pit and the creek in the back. "
United States
Jessica V.
The price is HK$1,803
HK$2,977 total
includes taxes & fees
2 Aug - 3 Aug
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Interior

Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (7 reviews)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
The price is HK$1,568
HK$2,724 total
includes taxes & fees
20 Jul - 21 Jul
Sweet Cozy Victorian in Housatonic. Close to everything.
Property grounds

Enjoy comfortable elegance in this secluded grand home located in town

Enjoy comfortable elegance in this secluded grand home located in town
Lenox
10.0 out of 10, Exceptional, (83 reviews)
"Amazing property, close to town "
United States
Tricia E.
The price is HK$5,488
HK$7,006 total
includes taxes & fees
20 Jul - 21 Jul
Enjoy comfortable elegance in this secluded grand home located in town
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

Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent
"Clean room. Good location. Hot breakfast."
Amy 1-night trip
Posted less than an hour ago
Comfort Inn & Suites East Greenbush - Albany

Find out more about Pittsfield

Pittsfield Vacation Homes information

Number of reviews
11,095
Accommodation
449 Vacation Homes
Lowest Price
HK$544
Highest Price
HK$2,181

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