Pittsfield Holiday Rentals, Massachusetts: Private House Rentals

A historic building with classical architecture, a traffic light, and a yellow taxi.

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Our top choices for Pittsfield hotels

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

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

A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

A garden with wooden Adirondack chairs and a stone pathway.

1. Berkshire Mountain Lodge

Pittsfield

marilyn

2.223.129 ₫

3.062.601 ₫ total

includes taxes & fees

9 Nov - 10 Nov

A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.

A spacious living room with a large sofa, a coffee table, and a fireplace.

A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.

A hotel patio with outdoor seating and a fire pit.

2. Hilton Garden Inn Lenox Pittsfield

Pittsfield

James

3.316.440 ₫

3.704.413 ₫ total

includes taxes & fees

1 Nov - 2 Nov

An indoor swimming pool with clear water, tiled floors, and a blue wall.

A snack bar with shelves of snacks and a refrigerated display.

A modern hotel with a large entrance, multiple floors, and a well-lit facade.

A modern cafe with a counter, seating area, and large windows.

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

Pittsfield

Sheldon

2.567.466 ₫

2.867.860 ₫ total

includes taxes & fees

9 Nov - 10 Nov

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.

4. Hotel On North

Pittsfield

Lawrence

3.477.749 ₫

3.884.646 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

A hotel room with a patterned carpet, a sofa, a chair, a small table, a lamp, a television on a cabinet, and two framed pictures on the wall.

A reception area with grey upholstered chairs, a wooden reception desk, and a colorful pear painting on the wall.

A Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.

5. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

Joe

2.424.310 ₫

2.707.955 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A hotel room with a large bed, a desk with a lamp, a television, and a view of the city.

An indoor swimming pool with clear pool rules signage, multiple seating areas, and a view of the outdoors through large windows.

A conference room with a whiteboard, tables, and chairs.

6. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

Mark

2.541.532 ₫

2.838.891 ₫ total

includes taxes & fees

7 Nov - 8 Nov

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

A swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.

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

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

7. Berkshire Inn

Pittsfield

Kristina

2.230.065 ₫

2.490.982 ₫ total

includes taxes & fees

12 Oct - 13 Oct

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

A compact living space with a kitchenette, a dining area, and a sofa.

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

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

8. The Central Downtown Inn & Suites

Pittsfield

Rena

2.567.466 ₫

2.867.782 ₫ total

includes taxes & fees

14 Oct - 15 Oct

A hotel room with a large bed, a separate sitting area, a bathtub, and a large mirror.

A hotel room with a desk, computer, TV, and a chair.

A dining area with wooden tables and chairs, a television, and a door with a sign.

A hotel room with a TV, microwave, mini-fridge, desk, chair, mirror, and a coat rack.

9. FairBridge Inn Express

Pittsfield

William

1.610.501 ₫

1.798.930 ₫ total

includes taxes & fees

11 Oct - 12 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 cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.

A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

10. The Yankee Inn

Lenox

Basil

2.749.004 ₫

3.070.637 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A spacious hotel lobby with multiple seating areas, large windows, and a television.

A large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.

A hotel room with a large bed, wooden nightstands, a lamp, and a telephone.

11. Hampton Inn & Suites Berkshires-Lenox

Lenox

Thomas

2.953.883 ₫

3.299.487 ₫ total

includes taxes & fees

7 Nov - 8 Nov

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

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

A hotel room with a dining area, a sofa, a coffee station, and a TV mounted on the wall.

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

12. Howard Johnson by Wyndham Lenox

Lenox

Mark

2.048.786 ₫

2.288.494 ₫ total

includes taxes & fees

18 Oct - 19 Oct

A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

A covered outdoor area with stone pillars and a view of a road and green hills.

A modern restaurant with wooden flooring, bar area, and seating arrangements.

An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.

13. Courtyard by Marriott Lenox Berkshires

Lenox

Tracy

3.257.570 ₫

3.638.706 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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.

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

A cozy library with bookshelves, a fireplace, and comfortable seating.

14. Berkshires Untold

Lenox

Madhavi R

3.376.327 ₫

3.771.357 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

15. Vacation Village in the Berkshires

Williamstown

Denton

2.083.590 ₫

2.611.867 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

A hotel room with a bed, a desk, a television, a microwave, and a sofa.

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

16. Quality Inn Lee - Lenox South

Lee

Christine

2.402.785 ₫

2.683.911 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A snow-covered outdoor area with a patio, seating, and a covered dining area.

A snow-covered outdoor area with a small bridge over a stream, surrounded by trees and illuminated by string lights.

A two-story house with a balcony, a brick chimney, and a porch with Adirondack chairs.

A modern living room with a fireplace, comfortable seating, and a large window with curtains.

17. The Cornell Inn, Lenox & The Berkshires

Lenox

Rosann

3.986.787 ₫

4.572.845 ₫ total

includes taxes & fees

27 Oct - 28 Oct

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

A lakeside lodge with a dock, fishing rods, and outdoor seating.

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

A lakeside dock with kayaks and a covered boat ramp.

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

Lee

Bob

3.086.146 ₫

3.447.226 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.

A reception area with a wooden reception desk, modern pendant lighting, and a vertical garden wall.

An outdoor seating area with Adirondack chairs and a fire feature.

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.

19. Element by Marriott Lenox Berkshires

Lenox

Kirsty

3.708.562 ₫

4.142.464 ₫ total

includes taxes & fees

8 Nov - 9 Nov

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

A sunlit room with large windows, a stone floor, and two rocking chairs.

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

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

20. The Whitlock

Lenox

Michael

3.786.364 ₫

4.229.369 ₫ total

includes taxes & fees

2 Nov - 3 Nov

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Stay near popular Pittsfield attractions

A snow-covered town with buildings, a ski lift, and a mountain in the background.

Bousquet Ski Area

8.2/10 (48 reviews)

This historic ski area pioneered night skiing in America and offers 23 trails across 200 acres. Glide down gentle slopes or challenge yourself on expert runs, then warm up at the lodge with panoramic mountain views.

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A historic stone building with a yellow roof, surrounded by a white fence and lush green grass.

Hancock Shaker Village

9.2/10 (101 reviews)

Step back in time at this living history museum showcasing Shaker life and craftsmanship. Marvel at the iconic Round Stone Barn and explore 20 historic buildings filled with over 22,000 authentic artefacts.

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A town with historic buildings, a prominent yellow church, and a mountainous backdrop.

Berkshire Museum

8.4/10 (26 reviews)

The Berkshire Museum blends art, history, and natural science in one captivating collection. Explore ancient fossils, contemporary art, and the popular aquarium featuring diverse marine life.

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Colonial Theater

8.0/10 (19 reviews)

This historic 1903 venue showcases ornate plasterwork and a painted ceiling mural in an intimate setting. Experience performances surrounded by the Colonial Theatre's exceptional acoustics and architectural splendour.

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Guido's Marketplace

9.6/10 (31 reviews)

This beloved Berkshire marketplace offers European-inspired local produce and gourmet specialities. Browse artisanal cheeses, fresh-baked breads, and seasonal fruits while enjoying a coffee from the café.

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Barrington Stage Company

8.0/10 (16 reviews)

This acclaimed theatre company launched "The 25th Annual Putnam County Spelling Bee" before its Tony-winning Broadway run. Experience innovative productions in BSC's intimate venues during their vibrant summer season.

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Herman Melville's Arrowhead

8.2/10 (18 reviews)

The farmhouse where Herman Melville wrote "Moby-Dick" offers a window into literary genius. Tour his study overlooking Mount Greylock—the inspiration for his legendary white whale.

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Onota Lake

Commune with nature and explore the great outdoors at Onota Lake during your travels in Pittsfield. Experience the area's entertainment venues or attend a sporting event.

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Learn more about Pittsfield

Nestled in the heart of the Berkshires, this cultural hub boasts the renowned Berkshire Museum and historic Colonial Theatre. Outdoor enthusiasts can hike nearby Pittsfield State Forest trails before exploring the vibrant downtown's farm-to-table restaurants and local art galleries.

See all hotels in Pittsfield

A historic building with a clock, a flag, and a street lamp.

Top Pittsfield Hotel Reviews

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent

"it was beautiful, centrally located, perfect getaway"

Hotel On North

10/10 Excellent

"This is a great hotel. Large rooms, great amenities and a steak house restaurant that is superb. We like it so much we are staying an extra night."

Holiday Inn Club Vacations Oak 'n Spruce Resort

8/10 Good

"no comment"

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

10/10 Excellent

"This hotel was clean and in a good location. The staff was friendly and helpful. I loved their nice pool and jacuzzi and enjoyed it. Breakfast was OK. Rooms are clean and big enough to make your money worth for it. One more important thing for us was its free and big parking lot."

The Yankee Inn

10/10 Excellent

"Not enough bath clothes towels not enough outlets around the bed for people who have cpap or breathing problems."

The Red Lion Inn

8/10 Good

"Would go there again but would request to be in the main Inn, they have properties all over the town center that are considered the Inn. That was disappointing. A very unique property and super cute!"

Berkshire Inn

10/10 Excellent

"We stayed one night after a concert at Tanglewood, and the hotel was perfectly fine for our purpose: clean and comfortable."

Quality Inn Great Barrington

8/10 Good

"The staff was very pleasant and helpful. Breakfast was good. They had delicious and fresh muffins. Parking was right outside our door."

The Central Downtown Inn & Suites

8/10 Good

"The staff were helpful and the room was clean. Overall the experience was good"

More cheap stays in Pittsfield

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

1.610.501 ₫

1.798.930 ₫ total

11 Oct - 12 Oct

includes taxes & fees

5.4/10 (919 reviews)

Quality Inn Great Barrington

372 Main Street Great Barrington MA

1.961.907 ₫

2.191.451 ₫ total

1 Nov - 2 Nov

includes taxes & fees

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA

2.048.786 ₫

2.288.494 ₫ total

18 Oct - 19 Oct

includes taxes & fees

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

1055 South Street Pittsfield MA

2.567.466 ₫

2.867.860 ₫ total

9 Nov - 10 Nov

includes taxes & fees

9.2/10 Wonderful! (230 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

2.749.004 ₫

3.070.637 ₫ total

1 Nov - 2 Nov

includes taxes & fees

9.2/10 Wonderful! (1,000 reviews)

Comfort Inn & Suites East Greenbush - Albany

99 Miller Rd Castleton-on-Hudson NY

2.953.883 ₫

3.278.812 ₫ total

30 Oct - 31 Oct

includes taxes & fees

Hotels in Pittsfield with star rating

Frequently asked questions

What's the seasonal weather like in Pittsfield?

The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Pittsfield are January, March, February and November, with each month seeing an average of 18 cm of snowfall.

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Book Hotels in Pittsfield on Expedia.com

Find hotels in Pittsfield, MA from 1.798.930 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Pittsfield

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Pittsfield hotels

1. Berkshire Mountain Lodge

2. Hilton Garden Inn Lenox Pittsfield

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

4. Hotel On North

5. Best Western Plus Berkshire Hills Inn & Suites

6. Holiday Inn & Suites Pittsfield-Berkshires by IHG

7. Berkshire Inn

8. The Central Downtown Inn & Suites

9. FairBridge Inn Express

10. The Yankee Inn

11. Hampton Inn & Suites Berkshires-Lenox

12. Howard Johnson by Wyndham Lenox

13. Courtyard by Marriott Lenox Berkshires

14. Berkshires Untold

15. Vacation Village in the Berkshires

16. Quality Inn Lee - Lenox South

17. The Cornell Inn, Lenox & The Berkshires

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

19. Element by Marriott Lenox Berkshires

20. The Whitlock

Stay near popular Pittsfield attractions

Bousquet Ski Area

Hancock Shaker Village

Berkshire Museum

Colonial Theater

Guido's Marketplace

Barrington Stage Company

Herman Melville's Arrowhead

Onota Lake

Learn more about Pittsfield

Top Pittsfield Hotel Reviews

Hotel Downstreet, an Ascend Collection Hotel

Hotel On North

Holiday Inn Club Vacations Oak 'n Spruce Resort

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

The Yankee Inn

The Red Lion Inn

Berkshire Inn

Quality Inn Great Barrington

The Central Downtown Inn & Suites

More cheap stays in Pittsfield

FairBridge Inn Express

Quality Inn Great Barrington

Howard Johnson by Wyndham Lenox

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

The Yankee Inn

Comfort Inn & Suites East Greenbush - Albany

Hotels in Pittsfield with star rating

Frequently asked questions

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