Pittsfield Holiday Rentals, Massachusetts: Private House Rentals

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Pittsfield

Pet friendly

Pool

Apartment

Hot tub

Condo

Family friendly

Cottage

Waterpark

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Pittsfield hotels

A hotel patio with outdoor seating and a fire pit.

A modern reception area with a green textured wall, a reception desk, and a coffee machine.

A modern kitchen with a marble countertop, stainless steel appliances, and a variety of food items displayed on the counter.

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

1. Hilton Garden Inn Lenox Pittsfield

Pittsfield

James

3.311.836 ₫

3.699.270 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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

A garden with wooden Adirondack chairs and a stone pathway.

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

2. Berkshire Mountain Lodge

Pittsfield

Joel

2.239.037 ₫

3.079.076 ₫ total

includes taxes & fees

12 Nov - 13 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 cafe with a counter, seating area, and large windows.

A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.

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

Pittsfield

Ginger

2.458.220 ₫

2.745.832 ₫ total

includes taxes & fees

19 Nov - 20 Nov

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

A library with bookshelves, a television, and two armchairs.

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

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

4. Hotel On North

Pittsfield

Devon

3.469.972 ₫

3.875.959 ₫ total

includes taxes & fees

4 Nov - 5 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 reception area with grey upholstered chairs, a wooden reception desk, and a colorful pear painting on the wall.

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 a coffee machine, a water dispenser, and a sign indicating the fitness center.

5. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

James

2.524.980 ₫

2.820.402 ₫ total

includes taxes & fees

16 Nov - 17 Nov

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

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

6. Berkshire Inn

Pittsfield

cheryl

2.225.077 ₫

2.485.411 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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

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

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.

7. The Central Downtown Inn & Suites

Pittsfield

Debra

2.561.724 ₫

2.861.368 ₫ total

includes taxes & fees

22 Oct - 23 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.

8. FairBridge Inn Express

Pittsfield

Richard

1.839.784 ₫

2.055.038 ₫ total

includes taxes & fees

22 Oct - 23 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 hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

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

9. The Yankee Inn

Lenox

Basil

2.745.188 ₫

3.066.375 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

10. Howard Johnson by Wyndham Lenox

Lenox

Aleksandr

2.044.204 ₫

2.283.376 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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

A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.

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

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

11. Courtyard by Marriott Lenox Berkshires

Lenox

Vandhana

3.250.284 ₫

3.630.567 ₫ total

includes taxes & fees

15 Nov - 16 Nov

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

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

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

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

12. Berkshires Untold

Lenox

Madhavi R

3.368.776 ₫

3.762.922 ₫ 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 spacious living room with large windows, a fireplace, and a variety of seating options.

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

13. Vacation Village in the Berkshires

Williamstown

Adrianne

2.078.929 ₫

2.606.023 ₫ total

includes taxes & fees

2 Nov - 3 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 dining area with a glass table, red walls, and framed artwork.

14. The Cornell Inn, Lenox & The Berkshires

Lenox

judith

3.970.827 ₫

4.554.538 ₫ total

includes taxes & fees

28 Oct - 29 Oct

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

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

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

15. Quality Inn Lee - Lenox South

Lee

Lucinda

2.397.411 ₫

2.677.909 ₫ total

includes taxes & fees

11 Nov - 12 Nov

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

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.

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

16. The Whitlock

Lenox

Michelle

3.596.764 ₫

4.017.586 ₫ total

includes taxes & fees

17 Nov - 18 Nov

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 lakeside dock with kayaks and a covered boat ramp.

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

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

Lee

Gustavo

2.903.287 ₫

3.242.972 ₫ total

includes taxes & fees

15 Nov - 16 Nov

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

A hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.

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

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

18. Element by Marriott Lenox Berkshires

Lenox

Francis

3.496.230 ₫

3.905.289 ₫ total

includes taxes & fees

8 Nov - 9 Nov

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

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

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

A wooden cabin with a porch and steps leading to a door, surrounded by snow.

19. Jiminy Peak Mountain Resort

Hancock

Olga

3.469.972 ₫

3.875.960 ₫ total

includes taxes & fees

22 Oct - 23 Oct

A hotel room with a bed, a sofa, a TV, and a bathroom visible through an open door.

A modern interior with a large window, a wooden table, and bar stools.

A reception area with a large landscape painting, a dark reception desk, and a potted plant.

A modern cafe with a wooden accent wall, a coffee machine, and black chairs.

20. Hotel Downstreet, an Ascend Collection Hotel

North Adams

mary ellen

3.084.419 ₫

3.445.296 ₫ total

includes taxes & fees

15 Nov - 16 Nov

View all properties

Save an average of 15% on thousands of hotels when you're signed in

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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 On North

10/10 Excellent

"Staff is awesome and this dog friendly hotel doesn’t feel dirty or different than any other boutique hotel."

Berkshire Mountain Lodge

10/10 Excellent

"Hot tub did not work"

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent

"Breakfast was great ... coffee available early!"

Vacation Village in the Berkshires

10/10 Excellent

"Great apartment. Large pool. Comfortable bed. Everything we needed for a great stay."

Berkshires Untold

10/10 Excellent

"Great service"

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"This place was an excellent deal. I thought I was getting a hotel room, but what I got was a 2-story townhouse. The facility includes lots to do indoors (clubhouse, movie theater) and outside (sports courts, trails along the river)"

Berkshire Inn

10/10 Excellent

"Very clean room and apparently the room had been upgraded recently by real craftsmen. Well done. You don't expect this quality from an older motel, but the owners obviously take pride in the property."

The Williams Inn

10/10 Excellent

"Fantastic hotel! Would definitely stay again."

The Yankee Inn

10/10 Excellent

"The old fashioned touches like real glasses in the rooms. The flower selections around the property. The condition of the indoor pool and whirlpool were great.The pond and surrounding land are great. Nicest motor lodge I've been to."

More cheap stays in Pittsfield

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

1.839.784 ₫

2.055.038 ₫ total

22 Oct - 23 Oct

includes taxes & fees

5.4/10 (925 reviews)

Quality Inn Great Barrington

372 Main Street Great Barrington MA

1.957.519 ₫

2.186.549 ₫ total

11 Nov - 12 Nov

includes taxes & fees

8.6/10 Excellent! (1,000 reviews)

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA

2.044.204 ₫

2.283.376 ₫ total

25 Oct - 26 Oct

includes taxes & fees

7.6/10 Good! (929 reviews)

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

1055 South Street Pittsfield MA

2.458.220 ₫

2.745.832 ₫ total

19 Nov - 20 Nov

includes taxes & fees

The Yankee Inn

461 Pittsfield Rd Lenox MA

2.745.188 ₫

3.066.375 ₫ total

1 Nov - 2 Nov

includes taxes & fees

9.2/10 Wonderful! (1,010 reviews)

Comfort Inn & Suites East Greenbush - Albany

99 Miller Rd Castleton-on-Hudson NY

2.839.716 ₫

3.152.086 ₫ total

10 Nov - 11 Nov

includes taxes & fees

8.8/10 Excellent! (1,002 reviews)

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.

Explore a world of travel with Expedia

More ways to book

Book Hotels in Pittsfield on Expedia.com

Find hotels in Pittsfield, MA from 2.055.038 ₫

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. Hilton Garden Inn Lenox Pittsfield

2. Berkshire Mountain Lodge

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

4. Hotel On North

5. Best Western Plus Berkshire Hills Inn & Suites

6. Berkshire Inn

7. The Central Downtown Inn & Suites

8. FairBridge Inn Express

9. The Yankee Inn

10. Howard Johnson by Wyndham Lenox

11. Courtyard by Marriott Lenox Berkshires

12. Berkshires Untold

13. Vacation Village in the Berkshires

14. The Cornell Inn, Lenox & The Berkshires

15. Quality Inn Lee - Lenox South

16. The Whitlock

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

18. Element by Marriott Lenox Berkshires

19. Jiminy Peak Mountain Resort

20. Hotel Downstreet, an Ascend Collection Hotel

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 On North

Berkshire Mountain Lodge

Comfort Inn & Suites East Greenbush - Albany

Vacation Village in the Berkshires

Berkshires Untold

Holiday Inn Club Vacations Oak 'n Spruce Resort

Berkshire Inn

The Williams Inn

The Yankee Inn

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

Explore a world of travel with Expedia

Go further with the Expedia app