Pittsfield State Forest holiday homes

We found 439 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Pittsfield State Forest

Showing deals for:1 Jan - 8 Jan

Open plan dining area with water views and access to the sunroom
view from the 2nd bedroom
View from the lawn by the water
View of the lower deck from the sunroom
Exceptional
(66 reviews)

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Pittsfield

8% off
NZ$8,660
for 7 nights, 1 home
NZ$1,237 per night
includes taxes & fees
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Interior
Living area
Exterior detail
Outdoor dining
Exceptional
(35 reviews)

Renovated Pittsfield Colonial by Evergreen Home

Pittsfield

11% off
NZ$7,513
for 7 nights, 1 home
NZ$1,073 per night
includes taxes & fees
Renovated Pittsfield Colonial by Evergreen Home
Private kitchen
Terrace/patio
Dining
Room
Exceptional
(20 reviews)

Family-friendly, private three bedroom cottage in the beautiful Berkshires

Williamstown

12% off
NZ$5,349
for 7 nights, 1 cottage
NZ$764 per night
includes taxes & fees
Family-friendly, private three bedroom cottage in the beautiful Berkshires
Living area
Interior
Property grounds
Exterior
Exceptional
(8 reviews)

Serene rustic cabin in the Berkshires!

West Stockbridge

8% off
NZ$4,866
for 7 nights, 1 cabin
NZ$695 per night
includes taxes & fees
Serene rustic cabin in the Berkshires!
Queen bedroom
Terrace/patio
Property grounds
Screened in porch
Exceptional
(103 reviews)

Vacation in a Berkshire Farmhouse

West Stockbridge

8% off
NZ$5,142
for 7 nights, 1 home
NZ$735 per night
includes taxes & fees
Vacation in a Berkshire Farmhouse
Dining
Outdoor dining
Property grounds
Renovated kitchen
Exceptional
(39 reviews)

Large, family-friendly farmhouse located in the beautiful Berkshires

Williamstown

20% off
NZ$7,102
for 7 nights, 1 home
NZ$1,015 per night
includes taxes & fees
Large, family-friendly farmhouse located in the beautiful Berkshires
Living area
Interior
Interior
Exterior
Exceptional
(44 reviews)

A MAGIC SPOT: Booking all year. A perfect, private, quiet mountaintop location.

Stephentown

8% off
NZ$3,013
for 7 nights, 1 home
NZ$430 per night
includes taxes & fees
A MAGIC SPOT: Booking all year. A perfect, private, quiet mountaintop location.
Interior
Interior
Kitchen
Property grounds
Excellent
(14 reviews)

Canary Lodge - Berkshires Mountain Retreat - 6 Guests

West Stockbridge

8% off
NZ$6,871
for 7 nights, 1 home
NZ$982 per night
includes taxes & fees
Canary Lodge - Berkshires Mountain Retreat - 6 Guests
another view of same bedroom as well as makeup table
new backyard table
Beaver Pond Pool/clubhouse
kitchen and laundry room area
Exceptional
(17 reviews)

3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY

Lanesborough

22% off
NZ$6,454
for 7 nights, 1 apartment
NZ$922 per night
includes taxes & fees
3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY
Living area
Private kitchen
Living area
Room
Exceptional
(14 reviews)

Spacious 7 bedroom house, Near jiminy Peak in Hancock ma , In the Berkshires

New Lebanon

17% off
NZ$12,027
for 7 nights, 1 home
NZ$1,718 per night
includes taxes & fees
Spacious 7 bedroom house, Near jiminy Peak in Hancock ma , In the Berkshires
Bathroom
Interior
Interior
Property grounds
Exceptional
(6 reviews)

Historic Stone Church in The Berkshires

Lanesborough

8% off
NZ$4,939
for 7 nights, 1 home
NZ$706 per night
includes taxes & fees
Historic Stone Church in The Berkshires
Living Room, wow!
Dining
Interior
view into large bathroom
Exceptional
(17 reviews)

New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.

Richmond

17% off
NZ$4,403
for 7 nights, 1 apartment
NZ$629 per night
includes taxes & fees
New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.
Quarter & Rift sawn white oak floors
Private kitchen
Gorgeous open concept living room
Dining
Exceptional
(11 reviews)

The Penthouse, Downtown Lenox by Evergreen Home

Lenox

11% off
NZ$8,322
for 7 nights, 1 apartment
NZ$1,189 per night
includes taxes & fees
The Penthouse, Downtown Lenox by Evergreen Home
Exterior
Interior
Interior
Interior
Exceptional
(18 reviews)

UNIQUE - 1BR Country Condo @ Jiminy Peak

Hancock

8% off
NZ$5,166
for 7 nights, 1 apartment
NZ$738 per night
includes taxes & fees
UNIQUE - 1BR Country Condo @ Jiminy Peak
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Find the perfect holiday rental for your Pittsfield State Forest getaway

The parks and surrounding scenery provide a peaceful ambience to your holiday home in Pittsfield State Forest. This city is well-known for its restaurants and shopping. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in and around Pittsfield State Forest

Are you hoping to discover things to do in the city? Venture out of your cosy holiday rental and experience everything that makes Pittsfield State Forest a fun place to get away to. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Jiminy Peak Mountain Resort (5.2 mi / 8.3 km)
  • Bousquet Ski Area (5.4 mi / 8.7 km)
  • Kennedy Park (7.7 mi / 12.4 km)
  • Wyndhurst Golf & Club (10.3 mi / 16.6 km)
  • Waubeeka Golf Links (12.7 mi / 20.4 km)
  • Zema's Nursery (4.1 mi / 6.5 km)

Exploring the natural features in Pittsfield State Forest

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Pittsfield State Forest is a great place to spend some time outside. These are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Lenox Mountain (5.9 mi / 9.5 km)
  • Queechy Lake (7 mi / 11.3 km)
  • Mount Greylock State Reservation Visitor Center (7.5 mi / 12 km)
  • Kennedy Park (7.7 mi / 12.4 km)
  • Stockbridge Bowl (10.4 mi / 16.7 km)
  • The Mount (10.6 mi / 17 km)

More holiday ideas