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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Compare 386 Vacation Homes in Pittsfield State Forest with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (243)
"What a great spot to stay for the few days we were there Can’t wait to come back! "
The price is AED 551
AED 841 total
includes taxes & fees
4 May - 5 May
Berkshire Village Carriage House - Super Private!!
Hancock Village Inn at Jiminy Peak
Miscellaneous

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (10)
"Very kinda hosts, and wonderful house."
The price is AED 2,016
AED 3,810 total
includes taxes & fees
5 May - 6 May
Hancock Village Inn at Jiminy Peak
Spectacular views and close to Great Barrington.
Smart TV, fireplace

Spectacular views and close to Great Barrington.

10.0 out of 10, Exceptional, (1)
"A beautiful place for our grown family to congregate. Easy commute to Tanglewood, a pool to keep us cool, and a wonderful kitchen to cook in. There are lots of other houses within view but not bothersome. Had a great stay here."
Spectacular views and close to Great Barrington.
Lakeside Oasis Just You, The Lake & The View!
Exterior

Lakeside Oasis Just You, The Lake & The View!

9.8 out of 10, Exceptional, (70)
"Perfect location for a peaceful, scenic vacation."
Lakeside Oasis Just You, The Lake & The View!
Secluded Lux Mansion Pool Home with Amazing Views
Fridge, microwave, oven, stovetop

Secluded Lux Mansion Pool Home with Amazing Views

10.0 out of 10, Exceptional, (1)
"We had a great time staying in the house for the weekend as a group of 10. Kitchen and bathrooms are well-stocked. The living room couch is enormous. All of the bedrooms are bright and cozy. The views and property are absolutely stunning. Had we been fewer, we probably would have used the outdoor firepits. Barry and Alisha are lovely and helpful hosts -- they sent along a great list of food reccs ahead of time, responded quickly when I couldn't find a few things, etc. "
Secluded Lux Mansion Pool Home with Amazing Views
Heart of Lenox Walk to Town Cozy Cottage!
Fridge, microwave, oven, stovetop

Heart of Lenox Walk to Town Cozy Cottage!

10.0 out of 10, Exceptional, (71)
"Going to the Berkshires this is a great place to stay. It is within walking distance to over 8 restaurants in downtown Lenox. Great gas stove and comfortable bed. Owner makes sure your stay is great. Would stay here again. "
Heart of Lenox Walk to Town Cozy Cottage!
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna
Fridge, microwave, oven, stovetop

Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

10.0 out of 10, Exceptional, (24)
"Great house that has everything for the family vacation "
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna
Perfect Nature Haven In Great Barrington
Exterior

Perfect Nature Haven In Great Barrington

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had a great time at the house. We had everything we needed. It was close to town. The space is very comfortable."
Perfect Nature Haven In Great Barrington
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
Property grounds

Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

10.0 out of 10, Exceptional, (4)
"Elise was an excellent host and super easy to work with. The property was even bigger, nicer, and cleaner than we expected. Plenty of room for a family getaway. "
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
Mountain Blossom Retreat by Evergreen Home
A heated pool

Mountain Blossom Retreat by Evergreen Home

10.0 out of 10, Exceptional, (5)
"We spent a wonderful weekend at this truly stunning property! The house is incredible, so well equipped, every detail has been thought of and the interior is beautiful. The outdoor spaces are amazing, the pool, hot tub, fire pit, outdoor seating, beautiful gardens are stunning! The location of the house is perfect, so close to lots of farms and orchards. We so look forward to making a return visit I!"
Mountain Blossom Retreat by Evergreen Home
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Terrace/patio

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

9.4 out of 10, Exceptional, (9)
"Lots of cozy relaxation by the fire and fun meals at the spacious dinning table. We had plenty of room to spread out and enjoy ourselves. "
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Exclusive Estate, Heated Yearround Outdoor Pool
Fridge, microwave, oven, stovetop

Exclusive Estate, Heated Yearround Outdoor Pool

9.6 out of 10, Exceptional, (19)
"Beautiful property, well-appointed, and comfortable for extended family of 12."
Exclusive Estate, Heated Yearround Outdoor Pool
Quintessential 6-BR Berkshires Lodge
Exterior

Quintessential 6-BR Berkshires Lodge

10.0 out of 10, Exceptional, (11)
"The house was perfect for our group of couples and young kids. Large bedrooms and beautiful property "
Quintessential 6-BR Berkshires Lodge
Near Tanglewood: Historic Summer Retreat
Fridge, microwave, oven, stovetop

Near Tanglewood: Historic Summer Retreat

9.4 out of 10, Exceptional, (20)
"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"
Near Tanglewood: Historic Summer Retreat
Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring
Exterior

Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring

10.0 out of 10, Exceptional, (10)
"The location is absolutely beautiful, the pool was great, and there was plenty of room for everyone. This was our second time staying at this house and we will be back."
Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Dining

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

10.0 out of 10, Exceptional, (121)
"Property as described. Great location to towns. Larger interior space than anticipated. Great Kitchen for a group of 5 to cook, chat and enjoy! Overall a warm and spacious home for old college friends to reunite. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
Interior

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

10.0 out of 10, Exceptional, (46)
"There is a game room that provided lots of fun. The linens were luxurious, the kitchen had every utensil. The yard is fenced in, the hot tub was great, we loved it!"
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Interior

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

9.6 out of 10, Exceptional, (42)
"Absolutely no complaints. Great place to stay, great host! Happy 2025 wishes from our family to everyone reading this post! "
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Home in Great Barrington
Fridge, microwave, oven, stovetop

Home in Great Barrington

9.6 out of 10, Exceptional, (20)
"Our family had a wonderful experience and stay. "
The price is AED 808
AED 1,231 total
includes taxes & fees
12 May - 13 May
Home in Great Barrington
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
Fridge, microwave, oven, stovetop

Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

10.0 out of 10, Exceptional, (54)
"We were taking our first family ski trip and were lucky to stay at this great house which is only 10 minutes from Butternut. Super convenient, very comfortable and the huge kitchen was a perfect place for our family to gather after a day on the slopes. We loved it and would happily return next year!"
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
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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Other property types in Pittsfield State Forest

Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1802)
"The property was clean and the staff very accommodated."
The price is AED 418
AED 507 total
includes taxes & fees
6 May - 7 May
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (928)
"Staff was exceptionally helpful and friendly."
The price is AED 493
AED 550 total
includes taxes & fees
4 May - 5 May
Jiminy Peak Mountain Resort
The Ponds at Foxhollow
Property grounds

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow
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.