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

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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
8.4 out of 10, Very good, (10 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 $423
CA $749 total
includes taxes & fees
Oct 13 - Oct 14
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 $815
CA $1,531 total
includes taxes & fees
Sep 29 - Sep 30
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)
"Awesome location went for a solo trip w the purpose of spending time alone in nature with myself and god got exactly that calm quiet beautiful scenic area great room and service would book again"
United States
Varun M.
The price is CA $99
CA $294 total
includes taxes & fees
Sep 28 - Sep 29
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 $122
CA $320 total
includes taxes & fees
Sep 28 - Sep 29
1800s Carriage house in Berkshires / Hudson Valley

5. Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.4 out of 10, Very good, (10 reviews)
"The owner was responsive. The heater worked well. The living spaces are as advertised. Traveling with 5 adults and a toddler; the layout is great. Convenient location for day trips and hiking."
United States
Maura L.
The price is CA $228
CA $772 total
includes taxes & fees
Sep 28 - Sep 29
Comfortable Berkshires retreat on mtn resort, SISO
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

6. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.8 out of 10, Exceptional, (7 reviews)
"The host was extremely communicative and went above and beyond to ensure guest comfort."
United States
Diego G.
The price is CA $249
CA $804 total
includes taxes & fees
Oct 5 - Oct 6
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
A white two-story house with a porch, surrounded by trees and a hill.

7. 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 $280
CA $669 total
includes taxes & fees
Sep 30 - Oct 1
1789 Shaker Farmhouse in Berkshires/Hudson Valley
A modern living room with a grey sectional sofa, a brown leather ottoman, a woven rug, a dining table with chairs, and a view through large windows.

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

Ellie’s Overlook, best view in the Berkshires!
Richmond
The price is CA $445
CA $984 total
includes taxes & fees
Oct 4 - Oct 5
Ellie’s Overlook, best view 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.

9. 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, (9 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is CA $206
CA $532 total
includes taxes & fees
Sep 28 - Sep 29
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A wooden kitchen with a central island, bar stools, and a dining table with chairs.

10. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (9 reviews)
"This home is super cozy and had all the amenities I needed after a long drive. I will be staying here again."
United States
Jess M.
The price is CA $164
CA $290 total
includes taxes & fees
Oct 8 - Oct 9
Cozy Home in Pownal VT
A hot tub with a string of lights above it, set against a dark night sky.

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

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (17 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is CA $227
CA $558 total
includes taxes & fees
Sep 29 - Sep 30
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

12. Riverside Retreat in the Berkshires

Riverside Retreat in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (27 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 $286
CA $448 total
includes taxes & fees
Sep 28 - Sep 29
Riverside Retreat in the Berkshires
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
8.0 out of 10, Very good, (1 review)
"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 $137
CA $483 total
includes taxes & fees
Oct 5 - Oct 6
Real Estate: Therapy - Lake, Laundry, Love it
A modern living room with a sofa, armchair, coffee table, and TV.

14. Spacious Central Berkshires Home for Groups

Spacious Central Berkshires Home for Groups
Lee
9.4 out of 10, Exceptional, (3 reviews)
"This older home was beautifully renovated and was able to easily accommodate our large group."
United States
Beth S.
The price is CA $414
CA $835 total
includes taxes & fees
Oct 5 - Oct 6
Spacious Central Berkshires Home for Groups
A camping setup with a metal chair and a table by a river in a forest.

15. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
10.0 out of 10, Exceptional, (15 reviews)
"Super lovely house and host was helpful and communicative. Absolutely recommend if you are looking for a place in this area!"
United States
Jess S.
The price is CA $283
CA $486 total
includes taxes & fees
Sep 28 - Sep 29
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A modern building with a wooden deck and a door.

16. 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Old Chatham
10.0 out of 10, Exceptional, (5 reviews)
"We enjoyed our stay at this property. The hot tub was great and the home was immaculate!"
United States
Terri E.
The price is CA $327
CA $822 total
includes taxes & fees
Sep 28 - Sep 29
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
A patio with a wooden table and benches, a grill, and a garden with trees and flowers.

17. 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, (7 reviews)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
United States
Anonymous traveller
The price is CA $351
CA $768 total
includes taxes & fees
Sep 29 - Sep 30
NEW RENO Historic Creamery in Berkshires w/hot tub
A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

18. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
United States
Samantha G.
The price is CA $400
CA $806 total
includes taxes & fees
Oct 28 - Oct 29
Treetop Hideaway in Tyringham
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)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
The price is CA $283
CA $493 total
includes taxes & fees
Oct 8 - Oct 9
Sweet Cozy Victorian in Housatonic. Close to everything.
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

20. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (39 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is CA $300
CA $469 total
includes taxes & fees
Oct 26 - Oct 27
Home in Great Barrington
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"It was a well appointed suite with kitchen, dining area, living room with a fireplace and the bedroom and a nice quiet corner of the property. I did sit out on the balcony and watch the sun go down and I had the best night sleep. I’ve had in a long time I would definitely go back. I didn’t use any of the amenities that they charge extra for, but because I was traveling, it was nice to just have a quiet night in."
Rachel Elion 1-night trip
Posted 14 hours ago
Vacation Village in the Berkshires

Find out more about Pittsfield

Pittsfield Vacation Homes information

Number of reviews
204
Accommodation
420 Vacation Homes
Lowest Price
CA $290
Highest Price
CA $1,531

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