Title: Pittsfield Vacation Home Rentals from CA $339: Search Top Private Vacation Homes for Rent | Expedia.ca

 

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# Pittsfield Vacation Rentals

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## Check prices for these dates

Next weekend

[Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2025-12-12&endDate=2025-12-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Pittsfield Vacation Homes

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/a38bbe4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/44aa4835.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/adca2c72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/3fc8dc3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Pittsfield

7.8/10

Good

(6)

"Very clean and spacious! We enjoyed our stay with our small pup!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ann C.

CA $376

CA $690 total

includes taxes & fees

Dec 3 - Dec 4

[](https://www.expedia.ca/Pittsfield-Hotels-3-Bedroom-Home-W-Lake-And-Mountain-Views-Near-Skiing.h106650307.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/5d0aa061.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/ed3ffaa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/w1440h1084x0y1-9f76bc91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/c8837e7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hancock Village Inn Near Jiminy Peak

Hancock

10/10

Exceptional

(16)

"Amazing Inn. Cozy and everything we needed. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Price F.

CA $767

CA $1,398 total

includes taxes & fees

Dec 2 - Dec 3

[](https://www.expedia.ca/Pittsfield-Hotels-Hancock-Village-Inn-At-Jiminy-Peak.h89806253.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/ecdea449.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/51a25809.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/162d61f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/4bbc4f9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Sherwood Forest

10/10

Exceptional

(4)

"We loved it! Lots of local hiking trails and a wonderful relaxing place."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sharon K.

CA $204

CA $526 total

includes taxes & fees

Dec 2 - Dec 3

[](https://www.expedia.ca/Becket-Hotels-Dog-Friendly-A-Frame-In-The-Berkshires-Walk-To-Lake-With-Beach-Access.h115469906.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/af01e53f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/347359ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/dba15cbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/c04d3199.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Sherwood Forest

9.6/10

Exceptional

(10)

"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

James D.

CA $224

CA $551 total

includes taxes & fees

Dec 2 - Dec 3

[](https://www.expedia.ca/Becket-Hotels-Dog-Friendly2B1B-In-The-Berkshires-Private-Lake-Community-Whot-Tub-Canoe.h105230373.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/91000000/90260000/90251100/90251080/5dc2bebc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90260000/90251100/90251080/12b81391.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90260000/90251100/90251080/ade792b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/91000000/90260000/90251100/90251080/14ecae77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Florida Mountain Log Cabin

Florida

10/10

Exceptional

(4)

"Place was super clean. Beds were comfortable. Location was great."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Tristan e.

CA $257

CA $474 total

includes taxes & fees

Dec 2 - Dec 3

[](https://www.expedia.ca/North-Adams-Hotels-Florida-Mountain-Log-Cabin.h90251080.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/52bc41a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/dcb799f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/e0f691bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/caf5dd09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Home in Great Barrington

Great Barrington

9.8/10

Exceptional

(25)

"Enjoyed our stay!!!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Fred W.

CA $226

CA $379 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Great-Barrington-Hotels-Home-In-Great-Barrington.h84672833.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/61000000/60770000/60763800/60763766/w907h683x58y0-59aad182.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/61000000/60770000/60763800/60763766/w507h683x259y0-1d5f8c7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books, printers](https://images.trvl-media.com/lodging/61000000/60770000/60763800/60763766/w919h683x60y0-f3238385.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/61000000/60770000/60763800/60763766/w510h683x258y0-04b5e846.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### North Getaway Cottage

Williamstown

9.2/10

Wonderful

(24)

"The cottage was the perfect accommodations for our overnight stay in town for a funeral. Thank you Claudia. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Mary Alice H.

CA $283

CA $630 total

includes taxes & fees

Dec 2 - Dec 3

[](https://www.expedia.ca/Williamstown-Hotels-Vacation-Getaway-Or-Remote-Workschool-Location.h60763766.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/6339dfc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/3bd0d6d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/a7e5baab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/333900eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Housatonic

10/10

Exceptional

(3)

"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Cheryl F.

CA $189

CA $339 total

includes taxes & fees

Dec 4 - Dec 5

[](https://www.expedia.ca/Housatonic-Hotels-Sweet-Cozy-Victorian-In-Housatonic-Close-To-Everything.h102018223.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/94000000/93410000/93402500/93402422/61c037e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/94000000/93410000/93402500/93402422/d3440e57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/94000000/93410000/93402500/93402422/fe54d0f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/94000000/93410000/93402500/93402422/60a24c7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Treat yourself at the stunning June Farms Wellness Huts!

West Sand Lake

10/10

Exceptional

(8)

"The wellness hut was an amazing getaway. Beautiful interior and design. Loved the little outdoor sauna. Loved the front porch/deck. Would definitely return for another stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

SteveS

CA $385

CA $551 total

includes taxes & fees

Dec 2 - Dec 3

[](https://www.expedia.ca/Treat-Yourself-At-The-Stunning-June-Farms-Wellness-Huts.h93402422.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/101000000/100060000/100053100/100053078/ffa8b349.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/101000000/100060000/100053100/100053078/59725e4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, offices](https://images.trvl-media.com/lodging/101000000/100060000/100053100/100053078/b650005a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100060000/100053100/100053078/db74a893.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Perfect House In Hillsdale, Brings Friends & Fam

Hillsdale

8.4/10

Very good

(5)

"As a group of 10 friends, this house was everything we could have wanted. 5 bedrooms, a very large living room, and a dining table to fit all of us at once. Very close to Catamount, Hy’s Fried, Roe Jan brewery and more. Very clean for such an old house. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Stefanie K.

CA $260

CA $731 total

includes taxes & fees

Dec 6 - Dec 7

[](https://www.expedia.ca/Hillsdale-Hotels-Perfect-House-In-Hillsdale.h100053078.Hotel-Information)

![Game room](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/406cc767.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/c57b8d60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/862ec0e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/59edf6fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pet Friendly Riverfront Home in Great Barrington

Great Barrington

9.4/10

Exceptional

(6)

CA $283

CA $416 total

includes taxes & fees

Dec 2 - Dec 3

[](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Riverfront-Escape-In-Great-Barrington-Whiskers-On-The-Water.h120304823.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119140000/119137900/119137863/5858308d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119140000/119137900/119137863/fa499ab5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119140000/119137900/119137863/c910a979.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/120000000/119140000/119137900/119137863/f2b309c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Greylock Cabin

Florida

10/10

Exceptional

(4)

"Wonderful view, peaceful quiet area, cosy cabin."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Anonymous traveller

CA $367

CA $611 total

includes taxes & fees

Dec 8 - Dec 9

[](https://www.expedia.ca/North-Adams-Hotels-True-Cabin-In-The-Woods-New-Log-Cabin-With-View-Of-Mt-Greylock.h119137863.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/fbef3554.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/65181381.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/f0ba5959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/6d1211ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Historic Berkshires Home Near Tanglewood, Trails & Wineries

Lebanon Springs

8.8/10

Excellent

(20)

"It was great - just what we were looking for. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kaye S.

CA $189

CA $520 total

includes taxes & fees

Dec 2 - Dec 3

[](https://www.expedia.ca/New-Lebanon-Hotels-Historic-Berkshires-Home-Near-Tanglewood.h84357520.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/121000000/120470000/120461900/120461825/f305b62e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120470000/120461900/120461825/d80b29aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/121000000/120470000/120461900/120461825/037efde9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120470000/120461900/120461825/76291106.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Riverbend Berkshire East Basecamp - 3 bedrooms available

Charlemont

CA $224

CA $578 total

includes taxes & fees

Dec 2 - Dec 3

[](https://www.expedia.ca/Charlemont-Hotels-Riverbend-Berkshire-East-Basecamp-3-Bedrooms-Available.h120461825.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/505c31c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/53261c35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player, books, stereo](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/8d87241a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/1bcf2f0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Great Barrington Get Away

Great Barrington

9.4/10

Exceptional

(25)

"We stayed here for Memorial Day weekend and had a wonderful trip. Close to the downtown shops, and all the supplies a family needs staying in a home. Thanks for the great stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Elizabeth G.

CA $398

CA $732 total

includes taxes & fees

Dec 2 - Dec 3

[](https://www.expedia.ca/Great-Barrington-Hotels-Great-Barrington-Get-Away.h29615546.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/33000000/32810000/32807400/32807378/e3e0e9fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/33000000/32810000/32807400/32807378/094a3cc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/33000000/32810000/32807400/32807378/52f8efbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/33000000/32810000/32807400/32807378/8e812ffc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

Valatie

10/10

Exceptional

(57)

"Great spot on the lake. Super quiet and relaxing."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

vincent m.

CA $377

CA $751 total

includes taxes & fees

Dec 2 - Dec 3

[](https://www.expedia.ca/Albany-Hotels-Escape-To-Lakefront-Leisurehudson.h32807378.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/122000000/121090000/121082600/121082559/98889bac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace](https://images.trvl-media.com/lodging/122000000/121090000/121082600/121082559/b572a747.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/122000000/121090000/121082600/121082559/42550a03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/122000000/121090000/121082600/121082559/d94e7ffd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Artists’ Hideaway in Old Chatham

Old Chatham

CA $267

CA $659 total

includes taxes & fees

Dec 3 - Dec 4

[](https://www.expedia.ca/Old-Chatham-Hotels-Artists-Hideaway-In-Old-Chatham.h121082559.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/772f14ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/2cdfc6fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/b2f15e32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/61aeb8a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Great Barrington

10/10

Exceptional

(1)

"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Roberta

CA $791

CA $1,856 total

includes taxes & fees

Dec 2 - Dec 3

[](https://www.expedia.ca/Great-Barrington-Hotels-Berkshires-Best-Large-Deck-With-Hotub.h120149051.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/58b0972d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/fb68a83f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/8b34823f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/636f9a34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious 5-bedroom house in charming Lee with WiFi

Lee

8.0/10

Very good

(1)

"House was large, clean, and comfortable. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

John Z.

CA $535

CA $1,039 total

includes taxes & fees

Dec 8 - Dec 9

[](https://www.expedia.ca/Lee-Hotels-Spacious-5-Bedroom-House-In-Charming-Lee-With-WiFi.h117382215.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/68000000/67640000/67635500/67635438/8a26cf53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/68000000/67640000/67635500/67635438/d4f0c0c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/68000000/67640000/67635500/67635438/976ef973.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/68000000/67640000/67635500/67635438/11a36f07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Hancock

9.8/10

Exceptional

(72)

"Great communication. Lots of games for the kids. Comfortable beds. Great living and game room. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Samuel R.

CA $369

CA $765 total

includes taxes & fees

Dec 2 - Dec 3

[](https://www.expedia.ca/Hancock-Hotels-Spacious-3BR-3BA-Ski-OnOff-Jiminy-Mountain-Resort.h67635438.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-15&endDate=2025-12-16&regionId=9478&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

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Limited-time deals: save up to 50% on select hotels

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[Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FPittsfield-Private-Vacation-Homes.d9478-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FPittsfield-Private-Vacation-Homes.d9478-aaPrivateVacationHomes.Travel-Guide-Accommodation)

## Top Pittsfield Hotel Reviews

![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg)

### Berkshire Mountain Lodge

10/10 Excellent

"Friendly staff, room was very clean. Pool area well maintained. Overall a great place to stay"

[](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information)

![The Black Swan Lee - Lenox, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9_y.jpg)

### The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"Great service. Attentive staff. Great location. Rooms clean and comfortable. Thanks for another great stay! "

[](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information)

![Hotel Downstreet, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/73bb1216_y.jpg)

### Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent

"Great property, nice staff, lovely rooms, awesome location."

[](https://expedia.ca/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information)

![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg)

### The Yankee, Trademark Collection by Wyndham

10/10 Excellent

"Everything was a great experience "

[](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information)

![Comfort Inn & Suites East Greenbush - Albany](https://images.trvl-media.com/lodging/2000000/1060000/1052400/1052319/ea181a79_y.jpg)

### Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent

"Good waffles"

[](https://expedia.ca/Albany-Hotels-Comfort-Inn-Suites-East-Greenbush-Albany.h1052319.Hotel-Information)

![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/e153ce9c_y.jpg)

### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent

"Great"

[](https://expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information)

![Holiday Inn & Suites Pittsfield-Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg)

### Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent

"Everything was great. "

[](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information)

![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg)

### Vacation Village in the Berkshires

10/10 Excellent

"Nice place to stay, off season. Price was very reasonable. Room was comfortable, (1st floor, Building 5), entire building was very quiet, hardly anyone on the property. Nice amenities, but we only walked through, did not use (pool, locker rooms, hot tub, fire pit). Room was nicely appointed and comfortable. Gas fireplace worked well, hot water was plentiful, water pressure was good. Kitchen was stocked with just about anything you'd need to cook simple meals. Great option when in the area, would recommend and would stay again."

[](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information)

![Hotel On North](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934_y.jpg)

### Hotel On North

10/10 Excellent

"Wonderful stay, as usual. I have business in the Pittsfield area, 3 or 4 times a year and wouldn’t think of staying anywhere else. Quiet, comfortable….staff is always helpful and friendly….restaurant in the building is just another plus."

[](https://expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information)

## Find out more about Pittsfield

## Pittsfield Vacation Homes information

| Number of reviews | 272 |
| --- | --- |
| Accommodation | 421 Vacation Homes |
| Lowest Price | CA $339 |
| Highest Price | CA $1,856 |

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-   [Flights from Ithaca (ITH) to Pittsfield (PSF)](https://www.expedia.ca/lp/flights/ith/psf/ithaca-to-pittsfield)
-   [Flights from Plattsburgh (PBG) to Pittsfield (PSF)](https://www.expedia.ca/lp/flights/pbg/psf/plattsburgh-to-pittsfield)
-   [Flights from Phoenix (PHX) to Pittsfield (PSF)](https://www.expedia.ca/lp/flights/phx/psf/phoenix-to-pittsfield)
-   [Flights from Richmond (RIC) to Pittsfield (PSF)](https://www.expedia.ca/lp/flights/ric/psf/richmond-to-pittsfield)
-   [Flights from Seattle (SEA) to Pittsfield (PSF)](https://www.expedia.ca/lp/flights/sea/psf/seattle-to-pittsfield)
-   [Flights from Toronto (YYZ) to Pittsfield (PSF)](https://www.expedia.ca/lp/flights/yyz/psf/toronto-to-pittsfield)

-   [Canoe Meadows Wildlife Sanctuary](https://www.expedia.ca/Canoe-Meadows-Wildlife-Sanctuary-Pittsfield.d553248621532665285.Vacation-Attraction)
-   [Hancock Shaker Village](https://www.expedia.ca/Hancock-Shaker-Village-Pittsfield.d6091849.Vacation-Attraction)
-   [Lenox Library](https://www.expedia.ca/Lenox-Library-Lenox.d553248621532665268.Vacation-Attraction)
-   [Richmond Vacations](https://www.expedia.ca/Richmond.d151138.Destination-Travel-Guides)
-   [Ventfort Hall Mansion and Gilded Age Museum](https://www.expedia.ca/Ventfort-Hall-Mansion-And-Gilded-Age-Museum-Lenox.d553248621532665270.Vacation-Attraction)

-   [Avis Rental Cars in Lenox](https://www.expedia.ca/Avis-Car-Rentals-In-Lenox.d8587-c41.Car-Rental-Guide-Suppliers)
-   [Car rental Hancock](https://www.expedia.ca/Car-Rentals-In-Hancock.d112303.Car-Rental-Guide)
-   [Car rentals near Jiminy Peak Mountain Resort](https://www.expedia.ca/Car-Rentals-In-Jiminy-Peak-Mountain-Resort.d553248621532665536.Car-Rental-Guide)
-   [Car rental Lenox](https://www.expedia.ca/Car-Rentals-In-Lenox.d8587.Car-Rental-Guide)
-   [Rental cars Pittsfield Municipal airport](https://www.expedia.ca/Car-Rentals-In-Pittsfield-Municipal.d6031274.Car-Rental-Guide)

-   [Dalton Vacation Rentals](https://www.expedia.ca/Dalton-Vacation-Rentals.d6911.Travel-Guide-VacationRentals)

-   [Book Vacation Homes in Pittsfield on Expedia.com](https://www.expedia.com/Pittsfield-Private-Vacation-Homes.d9478-aaPrivateVacationHomes.Travel-Guide-Accommodation)