Pittsfield Vacation Rentals from ￥12,263: Search Short-Term Rentals

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

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Our top choices for Pittsfield vacation rentals

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

1. Berkshire Mountain Lodge

Pittsfield

Susan J

￥17,266 total

includes taxes & fees

Dec 6 - Dec 7

A wooden deck with a table and chairs, surrounded by a white railing.

2. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Pittsfield

Stephen L.

￥75,151 total

includes taxes & fees

Nov 14 - Nov 15

A wooden deck with outdoor furniture, including chairs and a table, surrounded by a lush garden and trees.

3. Hancock Village Inn Near Jiminy Peak

Hancock

Price F.

￥174,293 total

includes taxes & fees

Nov 17 - Nov 18

4. Vacation Village in the Berkshires

Williamstown

Carol

￥16,093 total

includes taxes & fees

Nov 15 - Nov 16

A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

5. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

Dalton

Marcia O.

￥47,739 total

includes taxes & fees

Nov 17 - Nov 18

A cozy living room with a large window, wooden walls, and a television.

6. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Hancock

Maura D.

￥33,784 total

includes taxes & fees

Nov 15 - Nov 16

A porch with two Adirondack chairs, a welcome mat, and a door labeled "Apartment 2".

7. Berkshires Apartment at the Stephentown Hotel

Stephentown

Nicole O.

￥33,390 total

includes taxes & fees

Nov 15 - Nov 16

A wooden bed in a room with a sloped ceiling and a window overlooking a forest.

8. Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway

Sand Lake

Trena

￥28,020 total

includes taxes & fees

Nov 14 - Nov 15

A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

9. NEW RENO - Chalet-style farm loft near Tanglewood

New Lebanon

Joanna P.

￥30,906 total

includes taxes & fees

Nov 16 - Nov 17

A bedroom with a large bed, a brick wall, a window with curtains, and a wall clock.

10. Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor

Hancock

Dana

￥33,784 total

includes taxes & fees

Nov 15 - Nov 16

A bedroom with a wooden bed frame, a large window, and a painting of mountains on the wall.

11. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Hancock

patricia f.

￥33,784 total

includes taxes & fees

Nov 15 - Nov 16

A fire pit with chairs, a ski lift, and a building with a sign that reads "Mountain Resort".

12. Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Hancock

Ann

￥33,784 total

includes taxes & fees

Nov 15 - Nov 16

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

13. Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Hancock

David

￥36,049 total

includes taxes & fees

Nov 16 - Nov 17

A snow-covered outdoor area with a fire pit, seating, and a building in the background.

14. Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

Hancock

Neil J.

￥33,784 total

includes taxes & fees

Nov 15 - Nov 16

A gazebo with a stone floor and a grassy area with trees in the background.

15. 1800s Carriage house in Berkshires / Hudson Valley

New Lebanon

Leslie H.

￥33,839 total

includes taxes & fees

Nov 17 - Nov 18

A wooden cabin with a porch and multiple windows.

16. Taborton Harvest Boulder Pines Cabin in the woods

Sand Lake

Nathan

￥25,627 total

includes taxes & fees

Nov 17 - Nov 18

A bedroom with a bed, a small bedside table, a lamp, a window, and a picture on the wall.

17. Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center

Lenox

￥46,221 total

includes taxes & fees

Nov 14 - Nov 15

A bedroom with a large bed, a nightstand, a dresser, a window with curtains, and a wall with a deer painting.

18. Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base

Hancock

Eileen O.

￥33,784 total

includes taxes & fees

Nov 15 - Nov 16

19. Comfortable Berkshires retreat on mtn resort, SISO

Hancock

Amit

￥106,508 total

includes taxes & fees

Nov 19 - Nov 20

A garden with various plants, a brick wall, and a cactus in pots.

20. Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

North Adams

Ruthie K.

￥30,897 total

includes taxes & fees

Nov 15 - Nov 16

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Find vacation rentals that suit your style

Top Pittsfield Hotel Reviews

A multi-story hotel with a classic facade, large windows, and a prominent entrance.

Hotel On North

Pittsfield

10/10 Excellent

The Hotel on North is a thoughtful and beautiful transformation of 2 old contiguous buildings, a store and factory, into a hip and fun hotel. The spaces are extremely large and open from the common spaces to the guest rooms, including the bathrooms. The aesthetic is colorful and friendly rather than the cookie cutter faux luxury I usually find in expensive hotels. The quirky design features such as vintage furniture and painted floors are a great juxtaposition to the perfect bed linens and...

Steve

A spacious kitchen with wooden beams, a dining area with a large table and chairs, and a view of the outdoors through large windows.

Inn at Silver Maple Farm

East Chatham

10/10 Excellent

Michelle

A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

Devonfield Inn B&B

Lee

10/10 Excellent

Anonymous traveler

A restaurant with multiple dining tables, chairs, and a large Buddha statue centerpiece.

Hilton Garden Inn Lenox Pittsfield

Pittsfield

10/10 Excellent

Shaker Mill Inn

West Stockbridge

10/10 Excellent

This was the most comfortable B&B I have every heard of let alone stayed at. It does not have the awkwardness of eating breakfast in a community room of strangers. All the breakfast amenities are in you room, including the food that is stock daily by the inn keepers, so you get to enjoy in the comforts of your room (which is a cozy as home). The room was so spacious and well kept. Every detail is thought of by the innkeepers and if they forgot something they are accessible and gracious to...

Joe

A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

Brook Farm Inn

Lenox

10/10 Excellent

roberta

A breakfast setting with a plate of food, a glass of orange juice, and a cup of tea.

Harbour House Inn

Cheshire

10/10 Excellent

Anonymous traveler

Two Adirondack chairs facing a river with a forested hill in the background.

The Yankee Inn

Lenox

10/10 Excellent

We had a fantastic stay at the Yankee! Our adjoining rooms were clean, large and comfortable. We loved that the rooms had a fireplace and balcony! All the amenities were appreciated. The breakfast had so many offerings, including fresh fruit and two kinds of eggs. The front desk staff (especially George) were professional, helpful and friendly. This was our first stay at the Yankee, but it won't be the last!

Colleen

The Inn at Stockbridge

Stockbridge

10/10 Excellent

Kevin

A vintage turquoise Ford truck parked in front of a building labeled "CHAMBÉRY INN."

Chambery Inn

Lee

10/10 Excellent

Elaine

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

Maple Terrace Motel

Williamstown

10/10 Excellent

Eric

Berkshire Mountain Lodge

Pittsfield

10/10 Excellent

Elliott

An outdoor patio area with a circular fire pit surrounded by wicker furniture and a stone fire table.

Courtyard by Marriott Lenox Berkshires

Lenox

10/10 Excellent

Alyssa

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

The Cornell Inn, Lenox & The Berkshires

Lenox

10/10 Excellent

Lawrence

Find out more about Pittsfield

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Frequently Asked Questions

Can I find vacation rentals in Pittsfield?

Yes, we give you a choice of vacation rentals in Pittsfield near Berkshire Museum, or you can choose a more secluded option if you want a relaxing stay. Travelers who like culture and the arts say Pittsfield is known for its entertainment venues. Make sure you have time to check out the baseball games and museums during your trip.

What's the top vacation rental that Pittsfield has to offer?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: You might want to consider this vacation home rental near Pittsfield, which is located near skiing and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Pittsfield?

With 35 Expedia vacation rentals, you're sure to find just the right place for your Pittsfield stay.

What can I see and do in Pittsfield?

Family-friendly attractions include Berkshire Museum and Bousquet Ski Area, whereas Housatonic River and Onota Lake are a couple of great spots to enjoy the outdoors. Other places in town to visit include Colonial Theater and Hancock Shaker Village.

What are vacation rentals like in Pittsfield?

Vacation rentals are privately owned properties you can reserve for several days or more in Pittsfield. Vacation rentals feature amenities such as patios, hot tubs, and fire pits to help you enjoy your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for a family trip or a small group gathering.

Pittsfield Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Pittsfield vacation rentals

1. Berkshire Mountain Lodge

2. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3. Hancock Village Inn Near Jiminy Peak

4. Vacation Village in the Berkshires

5. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

6. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

7. Berkshires Apartment at the Stephentown Hotel

8. Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway

9. NEW RENO - Chalet-style farm loft near Tanglewood

10. Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor

11. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

12. Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

13. Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

14. Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

15. 1800s Carriage house in Berkshires / Hudson Valley

16. Taborton Harvest Boulder Pines Cabin in the woods

17. Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center

18. Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base

19. Comfortable Berkshires retreat on mtn resort, SISO

20. Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

Find vacation rentals that suit your style

Top Pittsfield Hotel Reviews

Hotel On North

10/10 Excellent

Find out more about Pittsfield

Frequently Asked Questions

Can I find vacation rentals in Pittsfield?

What's the top vacation rental that Pittsfield has to offer?

How many vacation rentals are there in Pittsfield?

What can I see and do in Pittsfield?

What are vacation rentals like in Pittsfield?