October Mountain State Forest holiday homes

We found 533 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – October Mountain State Forest

Showing deals for:18 Dec - 25 Dec

View from the lawn by the water
view from the 2nd bedroom
Open plan dining area with water views and access to the sunroom
Workstation with a view!
Exceptional
(65 reviews)

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Pittsfield

8% off
NZ$10,095
for 7 nights, 1 home
NZ$1,442 per night
includes taxes & fees
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Dining
The great room with wonderful water views and working fireplace
Open kitchen to great room, wonderful for cooking and entertaining
Sunroom has Queen pull out sofa bed
Exceptional
(86 reviews)

Spectacular setting on your own private lake close to it all!

Lee

8% off
NZ$8,170
for 7 nights, 1 home
NZ$1,167 per night
includes taxes & fees
Spectacular setting on your own private lake close to it all!
Outdoor dining
Living area
Exterior detail
Interior
Exceptional
(35 reviews)

Renovated Pittsfield Colonial by Evergreen Home

Pittsfield

11% off
NZ$7,990
for 7 nights, 1 home
NZ$1,141 per night
includes taxes & fees
Renovated Pittsfield Colonial by Evergreen Home
Reading nook with natural lighting
Fully screened porch!
Front Staircase
Dining Room w/ Doors to Screened Porch Dining Area
Exceptional
(8 reviews)

Berkshires Colonial on 2 Acres by Evergreen Home

Richmond

12% off
NZ$6,521
for 7 nights, 1 home
NZ$932 per night
includes taxes & fees
Berkshires Colonial on 2 Acres by Evergreen Home
Living area
Interior
Dining
Exterior
Exceptional
(8 reviews)

Serene rustic cabin in the Berkshires!

West Stockbridge

8% off
NZ$4,783
for 7 nights, 1 cabin
NZ$683 per night
includes taxes & fees
Serene rustic cabin in the Berkshires!
Open and bright main floor living space with stunning views of Laurel Lake.
Open kitchen area with bar seating, great for socializing while you meal prep.
Living room with fireplace and forest views
Second story deck with lake views, dining table for 8, sitting area and grill
Exceptional
(31 reviews)

Lake View Berkshires Retreat - Private & Minutes to Lenox

Lee

15% off
NZ$6,887
for 7 nights, 1 home
NZ$984 per night
includes taxes & fees
Lake View Berkshires Retreat - Private & Minutes to Lenox
Dining room with butcher block table
Terrace/patio
Screened in porch
Queen bedroom
Exceptional
(103 reviews)

Vacation in a Berkshire Farmhouse

West Stockbridge

9% off
NZ$5,015
for 7 nights, 1 home
NZ$716 per night
includes taxes & fees
Vacation in a Berkshire Farmhouse
Blue House side entry from driveway
River view from window
Alfresco dining
Great room river view
Exceptional
(44 reviews)

Renovated Colonial on the River! Fantastic Views

Housatonic

8% off
NZ$4,869
for 7 nights, 1 home
NZ$696 per night
includes taxes & fees
Renovated Colonial on the River! Fantastic Views
Kitchen
Interior
Interior
Property grounds
Excellent
(14 reviews)

Canary Lodge - Berkshires Mountain Retreat - 6 Guests

West Stockbridge

8% off
NZ$6,846
for 7 nights, 1 home
NZ$978 per night
includes taxes & fees
Canary Lodge - Berkshires Mountain Retreat - 6 Guests
Interior
Dining
view into large bathroom
Living Room, wow!
Exceptional
(17 reviews)

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

Richmond

17% off
NZ$4,417
for 7 nights, 1 apartment
NZ$631 per night
includes taxes & fees
New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.
Interior
Interior
Bathroom
Room
Exceptional
(6 reviews)

Historic Stone Church in The Berkshires

Lanesborough

8% off
NZ$4,863
for 7 nights, 1 home
NZ$695 per night
includes taxes & fees
Historic Stone Church in The Berkshires
Our hanging egg chair is the most popular seat in the house #Instagram yourself!
Private entry is with the parking in the rear of the house.
Our combination living/dining room is a great size for four people.
Exterior
Exceptional
(24 reviews)

New Reno, New Everything! Crisp and Clean 2 Bedroom in Stockbridge Center.

Stockbridge

24% off
NZ$3,312
for 7 nights, 1 apartment
NZ$473 per night
includes taxes & fees
New Reno, New Everything! Crisp and Clean 2 Bedroom in Stockbridge Center.
Quarter & Rift sawn white oak floors
Private kitchen
Custom Chef's Kitchen with high end appliances from Bertazzoni and Fisher & Paykel
Dining
Exceptional
(11 reviews)

The Penthouse, Downtown Lenox by Evergreen Home

Lenox

11% off
NZ$9,286
for 7 nights, 1 apartment
NZ$1,327 per night
includes taxes & fees
The Penthouse, Downtown Lenox by Evergreen Home
  • 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

Explore the majestic setting in October Mountain State Forest

The mountains and parks provide a pleasant backdrop to your holiday home in October Mountain State Forest. This city is well-known for its shopping and restaurants. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Sightseeing in and around October Mountain State Forest

Are you hoping to find things to do while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes October Mountain 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:

  • Wyndhurst Golf & Club (5.4 mi / 8.7 km)
  • Bousquet Ski Area (8 mi / 12.8 km)
  • Otis Ridge (10.4 mi / 16.8 km)
  • Ski Butternut (13.5 mi / 21.8 km)
  • Jiminy Peak Mountain Resort (16.3 mi / 26.3 km)
  • Kennedy Park (6.5 mi / 10.5 km)

Exploring the natural landscape of October Mountain State Forest

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in October Mountain State Forest. Here are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Goose Pond Reservation (4.2 mi / 6.7 km)
  • The Mount (6.2 mi / 10 km)
  • Stockbridge Bowl (8 mi / 12.9 km)
  • Lenox Mountain (8.5 mi / 13.7 km)
  • Naumkeag Museum (8.6 mi / 13.9 km)
  • Berkshire Botanical Garden (9.3 mi / 15 km)

More holiday ideas