Pittsfield State Forest Holiday Rentals, Pittsfield: Private House Rentals

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Our top choices for Pittsfield State Forest hotels

A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

A spacious living room with large windows, a fireplace, and a variety of seating options.

An outdoor patio area with tables and chairs, green umbrellas, and a building with large windows.

A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.

1. Vacation Village in the Berkshires

Williamstown

Jacob

Rp1.703.350

Rp2.099.038 total

includes taxes & fees

29 Sept - 30 Sept

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

A garden with wooden Adirondack chairs and a stone pathway.

A spacious lobby with a fireplace, seating area, and a bar.

An indoor swimming pool with a high ceiling, multiple windows, and seating areas.

2. Berkshire Mountain Lodge

Pittsfield

Jay

Rp1.425.067

Rp1.991.753 total

includes taxes & fees

1 Oct - 2 Oct

A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

A swimming pool with a surrounding deck, a stone wall, and a building in the background.

A cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.

3. The Yankee Inn

Lenox

William

Rp1.933.524

Rp2.159.818 total

includes taxes & fees

27 Oct - 28 Oct

A garden with a swing set, a blue chair, and a flower bed.

A swimming pool with lounge chairs and a fence.

A house with a porch, snow-covered ground, and a Christmas tree with lights.

A garden with a wooden pergola, potted plants, and a lawn with chairs.

4. Maple Terrace Motel

Williamstown

Deborah

Rp2.309.487

Rp2.579.643 total

includes taxes & fees

28 Sept - 29 Sept

A building entrance with a large planter with purple flowers and a small tree.

A spacious room with a large window, a brick wall, a sofa set, and a patterned carpet.

A restaurant with a large open dining area, wooden tables and chairs, and a brick wall with a colorful mural.

A lobby with a red sofa, two armchairs, a wooden table with a vase, brick walls, and an ornate ceiling.

5. Hotel On North

Pittsfield

Drew

Rp2.403.477

Rp2.684.685 total

includes taxes & fees

5 Oct - 6 Oct

A patio area with wooden chairs and tables, surrounded by dense greenery and trees.

A hay bale display with pumpkins and scarecrows.

A hotel room with a TV, a desk, a chair, a dresser, a bed with a patterned bedspread, and a microwave.

A hotel room with two blue upholstered chairs, a wooden table with a lamp, a TV mounted on the wall, and a wooden dresser with drawers.

6. Willows Motel Williamstown

Williamstown

Linda

Rp1.853.856

Rp2.070.661 total

includes taxes & fees

28 Sept - 29 Sept

A modern hotel lobby with seating areas, tables, and a reception desk.

A kitchenette with a microwave, coffee maker, and coffee cups.

A coffee station with two coffee machines and a variety of coffee pods and cups.

A breakfast area with a counter, coffee machine, and a display of pastries.

7. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Great Barrington

Maria Dulce

Rp2.130.457

Rp2.379.667 total

includes taxes & fees

19 Oct - 20 Oct

An outdoor seating area with Adirondack chairs and potted plants.

A hotel room with a large bed, two bedside lamps, a nightstand, a framed picture on the wall, and a window with curtains.

A reception area with a bulletin board, a 'no smoking' sign, a clock, and a 'STOP' sign.

A sign with the word "CLARM" on a grassy field with a road and trees in the background.

8. Cozy Corner Motel

Williamstown

Jonathan

Rp1.579.045

Rp1.856.004 total

includes taxes & fees

28 Sept - 29 Sept

A hotel room with a sofa, armchair, desk with lamp, television, mini-fridge, and patterned carpet.

A modern kitchen with a coffee machine, a refrigerator, and a dining area with chairs and tables.

A modern living room with a fireplace, two blue armchairs, and decorative vases on the mantel.

9. Quality Inn Lee - Lenox South

Lee

Christine

Rp1.963.064

Rp2.192.741 total

includes taxes & fees

19 Oct - 20 Oct

A dining table set for two with red plates, silverware, and a wine glass, viewed through a window overlooking a red building.

A cozy living room with a leather sofa, a wooden coffee table with a vase of flowers, and a staircase leading to an upper level.

A wooden sign for The Gregory House, County Inn and Restaurant, with a rustic design and a natural backdrop.

10. Gregory House Country Inn

Averill Park

Brian

Rp2.014.087

Rp2.235.636 total

includes taxes & fees

28 Sept - 29 Sept

A large, multi-story building with a prominent stone facade and a metal roof, surrounded by landscaped gardens and a pedestrian bridge.

A spacious interior with a wooden staircase, a seating area with patterned cushions, and large windows allowing natural light.

An outdoor seating area with stone fire pit, chairs, and a red building in the background.

A bar area with wooden beams, red chairs, and a long wooden table.

11. The Williams Inn

Williamstown

William

Rp3.477.657

Rp3.884.544 total

includes taxes & fees

28 Sept - 29 Sept

A large house with a covered patio area featuring outdoor seating and a fire pit.

A corner dining area with a wooden table set for four, surrounded by upholstered chairs.

A cozy lounge area with plush seating, a fireplace, and large windows offering a view of the outdoors.

A well-lit room with a large window, a clock, and a fireplace. There are several chairs and a table with a vase.

12. The Whitlock

Lenox

Michael

Rp2.480.998

Rp2.771.275 total

includes taxes & fees

28 Sept - 29 Sept

A hotel with a covered entrance, stone facade, and arched windows.

A spacious living area with a blue sofa, yellow armchair, and a coffee table. A staircase leads to an upper level with a balcony.

A spacious living room with a stone fireplace, large windows, and modern furniture.

A spacious living area with a high ceiling, a staircase with a wooden railing, a large blue patterned rug, and a white sofa.

13. Comfort Inn & Suites East Greenbush - Albany

Castleton-on-Hudson

Abram J

Rp2.039.152

Rp2.263.459 total

includes taxes & fees

18 Oct - 19 Oct

A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".

A cozy library with bookshelves, a sofa, a coffee table, and a large window with a view of trees.

A spacious bar area with a long counter and multiple stools, a seating area with a sofa and chairs, and a view through large windows to the outdoors.

14. Berkshires Untold

Lenox

Drue

Rp2.505.202

Rp2.798.310 total

includes taxes & fees

28 Sept - 29 Sept

A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

A gazebo with a metal roof and wooden benches, surrounded by a white fence and lush greenery.

A hotel room with a dining area featuring a table and chairs, a kitchenette with a coffee machine, and a television on the wall.

A multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.

15. Howard Johnson by Wyndham Lenox

Lenox

COLLEEN

Rp1.414.337

Rp1.579.815 total

includes taxes & fees

28 Sept - 29 Sept

A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

A lodge with a large building and a dock by a lake, surrounded by forest.

A dining area with large windows, wooden furniture, and a view of a lake.

A lakeside dock with kayaks and a covered boat ramp.

16. The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

Ann M

Rp2.466.138

Rp2.754.676 total

includes taxes & fees

29 Sept - 30 Sept

A hotel room with a large bed, two bedside lamps, a chair, and a window with curtains.

A motel with a parking lot, a swimming pool, and outdoor seating.

A residential street with a paved road, a lamp post, and flowering trees.

A fenced outdoor area with a pool, lounge chairs, and umbrellas.

17. Berkshire Inn

Pittsfield

Kristina

Rp1.539.479

Rp1.719.597 total

includes taxes & fees

28 Sept - 29 Sept

A resort with multiple buildings, a parking area, and a mountainous backdrop.

A cozy living room with a stone fireplace, comfortable seating, and a welcoming sign.

A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

A restaurant interior with wooden tables and chairs, hanging light fixtures, and large windows allowing natural light.

18. Jiminy Peak Mountain Resort

Hancock

Karen

Rp2.667.547

Rp2.979.650 total

includes taxes & fees

18 Oct - 19 Oct

A small, single-story building with a green roof and a white exterior. There are two large trees in front of the building, each with a flower pot on top. The surrounding area has grass, a few pumpkins, and a small garden with red flowers.

A kitchen with a fireplace, dining area, and a large window with curtains.

A blue wooden deck with white picket railings, surrounded by a well-maintained lawn and colorful autumn foliage.

A living room with a sofa, coffee table, and fireplace. There is a kitchen area with cabinets and a refrigerator.

19. Williamstown Motel

Williamstown

Ahmet

Rp1.915.621

Rp2.139.749 total

includes taxes & fees

28 Sept - 29 Sept

A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

A modern apartment with a living room, kitchenette, and dining area.

A hotel room with two beds, a nightstand with a lamp, and a window with curtains.

A covered porch with a wooden floor and white railing, overlooking a green lawn and a clear blue sky.

20. The Central Downtown Inn & Suites

Pittsfield

Rena

Rp1.772.397

Rp1.979.714 total

includes taxes & fees

28 Sept - 29 Sept

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Top Pittsfield State Forest Hotel Reviews

Vacation Village in the Berkshires

10/10 Excellent

"Everything clean!"

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent

"Great staff"

The Yankee Inn

10/10 Excellent

"There was a nice set up for the complimentary breakfast."

Quality Inn Great Barrington

10/10 Excellent

"Front desk guy was great very helpful.. rooms were clean,good location"

The Red Lion Inn

10/10 Excellent

"Another unforgettable experience at the Red Lion. My family has been coming up for 50 years, we’re happy to continue the tradition. Wether Fall, Spring, Summer or Winter, the 4 seasons at the Red Lion are always a favorite!"

Berkshires Untold

10/10 Excellent

"Love the property, room seemed a little tired since I was there last, about 3 years ago. Wish we could stay just one night instead of minimum two, as we often come just for a Tanglewood concert and stay only one night in town."

Holiday Inn Club Vacations Oak 'n Spruce Resort

8/10 Good

"I stayed in a townhouse, an upgrade from the room I booked. It was quiet and private, which I enjoyed, and more room than I needed. If my family's schedule had been different, I could have invited them over for a cookout (they live nearby). The townhouse was rather dated and I am afraid a bit dreary, with a lot of browns and beiges. But well-outfitted and convenient."

The Whitlock

10/10 Excellent

"The hotel staff were very friendly and helpful. There is ample parking and the location in town is great for walking to shops and restaurants. This is a very nice property."

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent

"Great location; walkable to restaurants. Spacious 7th floor room had a nice town and mountain view. All staff friendly and helpful. Bed was comfortable; room very clean. Breakfast was minimal and uninspiring."

More cheap stays in Pittsfield State Forest

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

Rp1.111.776

Rp1.241.853 total

28 Sept - 29 Sept

includes taxes & fees

5.4/10 (911 reviews)

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA

Rp1.414.337

Rp1.579.815 total

28 Sept - 29 Sept

includes taxes & fees

7.6/10 Good! (917 reviews)

Quality Inn Great Barrington

372 Main Street Great Barrington MA

Rp1.810.888

Rp2.022.761 total

18 Oct - 19 Oct

includes taxes & fees

8.6/10 Excellent! (1,003 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

Rp1.933.524

Rp2.159.818 total

27 Oct - 28 Oct

includes taxes & fees

9.2/10 Wonderful! (1,014 reviews)

Comfort Inn & Suites East Greenbush - Albany

99 Miller Rd Castleton-on-Hudson NY

Rp2.039.152

Rp2.263.459 total

18 Oct - 19 Oct

includes taxes & fees

8.8/10 Excellent! (1,006 reviews)

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

1055 South Street Pittsfield MA

Rp2.040.942

Rp2.279.768 total

20 Oct - 21 Oct

includes taxes & fees

Find hotels in Pittsfield State Forest, MA from Rp1.241.853

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Pittsfield State Forest

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Pittsfield State Forest hotels

1. Vacation Village in the Berkshires

2. Berkshire Mountain Lodge

3. The Yankee Inn

4. Maple Terrace Motel

5. Hotel On North

6. Willows Motel Williamstown

7. Holiday Inn Express Hotel & Suites Great Barrington by IHG

8. Cozy Corner Motel

9. Quality Inn Lee - Lenox South

10. Gregory House Country Inn

11. The Williams Inn

12. The Whitlock

13. Comfort Inn & Suites East Greenbush - Albany

14. Berkshires Untold

15. Howard Johnson by Wyndham Lenox

16. The Black Swan Lee - Lenox, an Ascend Collection Hotel

17. Berkshire Inn

18. Jiminy Peak Mountain Resort

19. Williamstown Motel

20. The Central Downtown Inn & Suites

Top Pittsfield State Forest Hotel Reviews

Vacation Village in the Berkshires

Comfort Inn & Suites East Greenbush - Albany

The Yankee Inn

Quality Inn Great Barrington

The Red Lion Inn

Berkshires Untold

Holiday Inn Club Vacations Oak 'n Spruce Resort

The Whitlock

Hotel Downstreet, an Ascend Collection Hotel

More cheap stays in Pittsfield State Forest

FairBridge Inn Express

Howard Johnson by Wyndham Lenox

Quality Inn Great Barrington

The Yankee Inn

Comfort Inn & Suites East Greenbush - Albany

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

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