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

Pittsfield Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Pittsfield vacation homes

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

1. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
8.6 out of 10, Excellent, (11 reviews)
"Very comfortable and clean accommodations in a nice neighborhood, and a great deck to appreciate the view."
United States
Stephen L.
The price is CA $377
CA $697 total
includes taxes & fees
Oct 31 - Nov 1
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
A wooden deck with outdoor furniture, including chairs and a table, surrounded by a lush garden and trees.

2. Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (22 reviews)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is CA $810
CA $1,521 total
includes taxes & fees
Nov 4 - Nov 5
Hancock Village Inn Near Jiminy Peak
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

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

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
United States
Joanna P.
The price is CA $98
CA $284 total
includes taxes & fees
Nov 1 - Nov 2
NEW RENO - Chalet-style farm loft near Tanglewood
A spacious living room with a dining area, a kitchen, and a large window.

4. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley
New Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
United States
Leslie H.
The price is CA $119
CA $316 total
includes taxes & fees
Nov 5 - Nov 6
1800s Carriage house in Berkshires / Hudson Valley
A white two-story house with a porch, surrounded by trees and a hill.

5. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, Exceptional, (5 reviews)
"We had a wonderful stay. The house was spacious and the owner was readily available for all questions. It’s a really nice location. "
United States
Christine C.
The price is CA $230
CA $609 total
includes taxes & fees
Nov 9 - Nov 10
1789 Shaker Farmhouse in Berkshires/Hudson Valley
A dining area with a wooden table and chairs, a view of greenery and mountains through large windows, and a balcony with a railing.

6. Ellie’s Overlook, best view in the Berkshires!

Ellie’s Overlook, best view in the Berkshires!
Richmond
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful stay in the Berkshires! The house was lovely, very clean, and such a cozy place to spend a fall weekend. The overlook was absolutely stunning, especially with all the beautiful fall foliage! We loved that the property felt peaceful and tucked away while still being a short drive to Lenox, nearby towns, and plenty of great hiking trails. The host was so kind and always quick to respond, which made everything easy from start to finish. We really enjoyed our stay and would...
United States
Delaney M.
The price is CA $441
CA $975 total
includes taxes & fees
Nov 2 - Nov 3
Ellie’s Overlook, best view in the Berkshires!
Pool

7. Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.8 out of 10, Excellent, (12 reviews)
"Host was proactive in communication and answer each and every question."
United States
Amit
The price is CA $226
CA $757 total
includes taxes & fees
Nov 1 - Nov 2
Comfortable Berkshires retreat on mtn resort, SISO
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

8. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.2 out of 10, Wonderful, (10 reviews)
"A lovely house! Very convenient for a Tanglewood weekend."
United States
Robert B.
The price is CA $284
CA $845 total
includes taxes & fees
Oct 29 - Oct 30
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
A living room with a sofa, armchairs, a coffee table, and a television.

9. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
10.0 out of 10, Exceptional, (12 reviews)
"We had a lovely stay! The home was so well equipped and comfortable. Beautiful area, great restaurant choices and staying here made our Miraval experience perfect."
United States
Patricia O.
The price is CA $445
CA $890 total
includes taxes & fees
Oct 31 - Nov 1
Sun Filled Lenox Retreat - Minutes to Tanglewood!
A modern living room with a sofa, armchair, coffee table, and TV.

10. Spacious Central Berkshires Home for Groups

Spacious Central Berkshires Home for Groups
Lee
9.6 out of 10, Exceptional, (4 reviews)
"house was very clean, spacious and well equipped with everything we needed. Great communication with the host. Perfect location for our trip to Tanglewood."
United States
neil s.
The price is CA $410
CA $841 total
includes taxes & fees
Nov 1 - Nov 2
Spacious Central Berkshires Home for Groups
A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

11. Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods
Stockbridge
10.0 out of 10, Exceptional, (30 reviews)
"We had a wonderful time, we’d be happy to come back again "
United States
Ofer C.
The price is CA $478
CA $905 total
includes taxes & fees
Nov 2 - Nov 3
Secluded Family Home in Serene Stockbridge Woods
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

12. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.4 out of 10, Exceptional, (3 reviews)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
The price is CA $77
CA $412 total
includes taxes & fees
Nov 3 - Nov 4
Real Estate: Therapy - Lake, Laundry, Love it
A room with a large window, two sofas, and a small table.

13. Mayas Shangrila - A 200-year-old historic farmhouse on 4 secluded acres in the Berkshires

Mayas Shangrila - A 200-year-old historic farmhouse on 4 secluded acres in the Berkshires
Richmond
The price is CA $1,261
CA $1,761 total
includes taxes & fees
Nov 3 - Nov 4
Mayas Shangrila - A 200-year-old historic farmhouse on 4 secluded acres in the Berkshires
A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

14. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (10 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is CA $204
CA $530 total
includes taxes & fees
Nov 2 - Nov 3
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A dining area with a wooden table, chairs, and a ceiling fan.

15. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (29 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
United States
Kelly B.
The price is CA $284
CA $444 total
includes taxes & fees
Nov 2 - Nov 3
Leaf-Peeper Paradise in the Berkshires
A wooden kitchen with a central island, bar stools, and a dining table with chairs.

16. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (13 reviews)
"Absolutely wonderful place to stay. Quiet, clean, comfortable and close to a lot of things while feeling secluded. Owner communicated quickly and entry was easy. Loved every minute of our stay."
United States
Jeri R.
The price is CA $163
CA $284 total
includes taxes & fees
Nov 1 - Nov 2
Cozy Home in Pownal VT
A hot tub with a string of lights above it, set against a dark night sky.

17. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.6 out of 10, Exceptional, (19 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is CA $225
CA $556 total
includes taxes & fees
Nov 1 - Nov 2
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A patio with a wooden table and benches, a grill, and a garden with trees and flowers.

18. NEW RENO Historic Creamery in Berkshires w/hot tub

NEW RENO Historic Creamery in Berkshires w/hot tub
New Lebanon
10.0 out of 10, Exceptional, (8 reviews)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
United States
Anonymous traveller
The price is CA $416
CA $841 total
includes taxes & fees
Nov 9 - Nov 10
NEW RENO Historic Creamery in Berkshires w/hot tub
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

19. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (12 reviews)
"This was an easy house to stay in—simply decorated, but comfortable and with clear consideration of all the things guests might need to feel at home. Very clean and tidy. Communication and check-in/-out were seamless. I would happily stay here again."
United States
Eric H.
The price is CA $280
CA $493 total
includes taxes & fees
Nov 1 - Nov 2
Sweet Cozy Victorian in Housatonic. Close to everything.
A cozy living room with a sofa, a fireplace, and large windows.

20. Luxury Barn Near Hudson With New Private Sauna

Luxury Barn Near Hudson With New Private Sauna
East Chatham
10.0 out of 10, Exceptional, (4 reviews)
"Peaceful weekend spot"
United States
Michael T.
The price is CA $536
CA $965 total
includes taxes & fees
Nov 1 - Nov 2
Luxury Barn Near Hudson With New Private Sauna
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Pittsfield Hotel Reviews

The Yankee Inn

The Yankee Inn

10/10 Excellent
"We had a wonderful stay over the weekend. Bed VERY comfortable. Quiet, except one early am with kids running in the halls! Parents issue! Breakfast was good. Several items needing to be replenished each am. Had to go and ask the girls a few times. They were in the back room eating, seemingly unaware of restocking needed items. The bar on the weekend was an extra perk! Loved Carl 💕, the bartender , quite a conversationalist. Overall beautiful location , walking path in the back was nice, in the back of the hotel."
Erin 3-night trip
Posted 1 hour ago
The Yankee Inn

Find out more about Pittsfield

Pittsfield Vacation Homes information

Number of reviews
199
Accommodation
420 Vacation Homes
Lowest Price
CA $284
Highest Price
CA $1,761

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