Title: Pittsfield Vacation Rentals from CA $158: Short-Term Rentals for 2025 | Expedia.ca

 

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# Pittsfield Vacation Rentals

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## Check prices for these dates

Tonight

[Nov 7 - Nov 8](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2025-11-07&endDate=2025-11-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Nov 8 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2025-11-08&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Vacation Rentals in Pittsfield

![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)

![Smart TV, fireplace, printers](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/811d3663.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)

![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 $380

CA $693 total

includes taxes & fees

Nov 8 - Nov 9

[](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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/34fa691f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/c189cee9.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

(15)

"Kids will love the fun bunk room setup, millennials will appreciate the big screen TV's and broadband Internet access, while parentals and grandparents enjoy the fully equipped kitchen and space to enjoy dinner together around a table for 12. Hot tub right outside the kitchen door, close proximity to Jiminy Peak makes it a breeze to shuttle the family back and forth . Extremely clean property.. Rent the extra suite if you have difficulty with stairs, and enjoy having the entire inn to...

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

Jim O.

CA $845

CA $1,568 total

includes taxes & fees

Nov 18 - Nov 19

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

![Smart TV](https://images.trvl-media.com/lodging/109000000/108500000/108496800/108496770/a1b50bde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/109000000/108500000/108496800/108496770/6718b83f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/109000000/108500000/108496800/108496770/70fb359a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/109000000/108500000/108496800/108496770/47beb459.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chic corporate apartment in wonderful Pittsfield with AC, WiFi

Pittsfield

2.0/10

(1)

"THIS. PLACE. IS. A. DUMP. Do NOT STAY HERE under any circumstances."

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

Michael

CA $212

CA $315 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Pittsfield-Hotels-Chic-Corporate-Apartment-In-Wonderful-Pittsfield-With-AC.h108496770.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107110000/107109200/107109194/220997f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/108000000/107110000/107109200/107109194/dd672984.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/108000000/107110000/107109200/107109194/1ebb7045.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107110000/107109200/107109194/837f847a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sugar Shack - 300 square feet of pure sweetness.

Chatham

10/10

Exceptional

(3)

"By far one of my favorite rentals. Everything was perfect and the details were amazing. Not only do I highly recommend, I amSURE I will be returning soon. "

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

Sue G.

CA $303

CA $509 total

includes taxes & fees

Nov 12 - Nov 13

[](https://www.expedia.ca/Chatham-Hotels-Sugar-Shack-300-Square-Feet-Of-Pure-Sweetness.h107109194.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/103000000/102810000/102806400/102806391/143defff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/103000000/102810000/102806400/102806391/f7d742eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/103000000/102810000/102806400/102806391/c465f1b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102810000/102806400/102806391/f7f03fbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### BLUSH: Boutique TINY home\*private spa\*walk to town

Chatham

10/10

Exceptional

(6)

"Perfect blend of decore, comfort, and function. We went to Tanglewood which was only a half hour away. Came back to hot tub and fire pit. Beds here are soooo comfy! This is our 2nd time here and won’t be our last."

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

Melissa D.

CA $303

CA $509 total

includes taxes & fees

Nov 18 - Nov 19

[](https://www.expedia.ca/Chatham-Hotels-BLUSH-Boutique-TINY-Home-W-Private-Spa-Walk-To-New-Yorks-Cutest-Village.h102806391.Hotel-Information)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/84000000/83780000/83773100/83773039/72279dd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/84000000/83780000/83773100/83773039/f53734be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/84000000/83780000/83773100/83773039/17688c80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83780000/83773100/83773039/1894b59b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### HunnyHAUS: Deluxe TINY\*private spa\*walk to town

Chatham

10/10

Exceptional

(9)

"We had the best time here. The house is even cuter and cozier in person (which says a lot because the pictures are great!). The hot tub was a great luxury and the house is literally a 3 minute walk to town. So convenient! We also had a fire in the Viking tent one night which was fun. Heidi was super helpful and quick to respond to any queries during our stay. She even left rose petals on the bed and a bottle of Prosecco chilling in the fridge for us upon our arrival. I would stay here again in a...

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

Megan H.

CA $317

CA $582 total

includes taxes & fees

Nov 16 - Nov 17

[](https://www.expedia.ca/Chatham-Hotels-HunnyHAUS-Deluxe-TINYprivate-Spawalk-To-Town.h83773039.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/cf8c8830.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/a8f10f60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/662f1ebe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 Bedroom Condo 1/2 mile from base | In-room dining](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/40940c35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Jiminy Peak Mountain Resort

Hancock

8.2/10

Very good

(984)

"It was a fun place to stay. Rooms were clean and dishes well stocked in the kitchenette. "

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

Sandhya

CA $210

CA $235 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information)

![Indoor pool, outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/5c348ca4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/f251fc45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property - evening/night](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/eda478dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/f5477a61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Ponds at Foxhollow

Lenox

8.6/10

Excellent

(132)

"Perfect location "

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

krystle

[](https://www.expedia.ca/Lenox-Hotels-The-Ponds-At-Foxhollow-By-Capital-Vacations.h18109961.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)

![Property grounds](https://images.trvl-media.com/lodging/91000000/90260000/90251100/90251080/f0c8191e.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)

### Florida Mountain Log Cabin

Florida

10/10

Exceptional

(4)

"We loved our 1 night stay here - it is a super cute log cabin with comfortable beds and very clean! Our favorite part was the fire pit for smores and the kids especially loved the cozy swings! Host was very accessible. Definitely recommend!"

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

Kate R.

CA $259

CA $478 total

includes taxes & fees

Nov 12 - Nov 13

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

![Lobby](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining room](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/16150550.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/64adfbe5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool, outdoor pool, pool umbrellas](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/18127ca3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Village in the Berkshires

Williamstown

8.8/10

Excellent

(2124)

"Clean and great pool and hot tub facilities "

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

Alyce

CA $128

CA $158 total

includes taxes & fees

Nov 25 - Nov 26

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73730000/73729000/73728934/19f12f1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/74000000/73730000/73729000/73728934/99fcbf69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/74000000/73730000/73729000/73728934/5e98ee8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/74000000/73730000/73729000/73728934/b5789346.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Rustic Apt in 18th c Berkshire Farmhouse

Lanesborough

9.6/10

Exceptional

(67)

"Perfect take out cafe across the street, was very comfortable would stay again for sure"

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

Christopher

CA $190

CA $291 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Lanesborough-Hotels-Cozy-Rustic-Apt-In-18th-C-Berkshire-Farmhouse.h73728934.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)

![Interior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/83d3f833_edited_d758.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)

![Smart TV, DVD player](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/77e07421.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

(3)

"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 $206

CA $533 total

includes taxes & fees

Nov 12 - Nov 13

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

![Exterior detail](https://images.trvl-media.com/lodging/102000000/101310000/101301800/101301745/a78d5e6a_edited_6c49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/102000000/101310000/101301800/101301745/d249528d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/102000000/101310000/101301800/101301745/2c4a26d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/102000000/101310000/101301800/101301745/02d3bd96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Taborton Harvest Boulder Pines Cabin in the woods

Sand Lake

10/10

Exceptional

(13)

"We LOVED our stay! Cabins were spotless and the main building was just great! Waking up to a picture window behind us with all the fall colors in their glory was such a highlight. "

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

Barb W.

CA $176

CA $260 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Sand-Lake-Hotels-Cabin-In-The-Woods.h101301745.Hotel-Information)

![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/106000000/105240000/105230400/105230373/2278baae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/4e64ac0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/80124d14.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

(9)

"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 $226

CA $554 total

includes taxes & fees

Nov 12 - Nov 13

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

![Exterior](https://images.trvl-media.com/lodging/90000000/89720000/89714400/89714351/ec8e2057.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89720000/89714400/89714351/0ab9f2e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89720000/89714400/89714351/edecce8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/90000000/89720000/89714400/89714351/4fb8018b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Hinsdale

9.8/10

Exceptional

(33)

"Great cottage - well appointed and very clean. No air conditioning so a bit warm when it’s hot out, but all in all a great stay"

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

Lindsey E.

CA $229

CA $591 total

includes taxes & fees

Nov 10 - Nov 11

[](https://www.expedia.ca/Hinsdale-Hotels-Beautiful-2-Bedroom-Loft-With-Hot-Tub-At-Lake-Ashmere.h89714351.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/74000000/73420000/73412800/73412761/48dd5672.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/74000000/73420000/73412800/73412761/b7925219.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hair dryer](https://images.trvl-media.com/lodging/74000000/73420000/73412800/73412761/45b221b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/74000000/73420000/73412800/73412761/c41e3cef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bright Boho Apt in 18th c Berkshire Farmhouse

Lanesborough

9.0/10

Wonderful

(22)

"Very nice. Attending a wedding in the area and really needed a place to get dressed and return to sleep. This fit the bill perfectly. Clean and comfortable we enjoyed our visit. Need to come back and visit the many sites in the area."

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

Margaret K.

CA $205

CA $309 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Lanesborough-Hotels-Bright-Boho-Apt-In-18th-C-Berkshire-Farmhouse.h73412761.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/92000000/91630000/91621600/91621591/w1024h593x0y45-2966e99d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/92000000/91630000/91621600/91621591/4fcb5611.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91630000/91621600/91621591/4e9408e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91630000/91621600/91621591/730ec918.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bear Creek Cabin

Charlemont

10/10

Exceptional

(41)

"We enjoyed our stay!!"

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

Hillary S.

CA $564

CA $844 total

includes taxes & fees

Nov 12 - Nov 13

[](https://www.expedia.ca/Charlemont-Hotels-Bear-Creek-Cabin.h91621591.Hotel-Information)

![1 bedroom, iron/ironing board, bed sheets](https://images.trvl-media.com/lodging/123000000/122140000/122136900/122136838/a0875211.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/123000000/122140000/122136900/122136838/185f4743.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122140000/122136900/122136838/dabbf205.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/123000000/122140000/122136900/122136838/cef2db6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Penthouse Apartment on Park Street

Adams

9.6/10

Exceptional

(13)

"We had a wonderful relaxing stay in this gorgeous place. The listing is just as described, natural light filled, high ceilings, on the top floor, comfortable bedding, and a thoughtful host. Lea left the A/C on, a bottle of water in the fridge, lots of good coffee, and even some hot cocoa packets for our son. The boba shop right downstairs was awesome and had fun gift items. There is a diner next door and some fantastic restaurants 15-20 minutes away. Very convenient to Mass MOCA and...

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

Teresa M.

CA $164

CA $345 total

includes taxes & fees

Nov 13 - Nov 14

[](https://www.expedia.ca/Adams-Hotels-Penthouse-Apartment-On-Park-Street.h122136838.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/91000000/90190000/90182200/90182167/70501210.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/91000000/90190000/90182200/90182167/w515h679x0y4-9a7cc624.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, DVD player](https://images.trvl-media.com/lodging/91000000/90190000/90182200/90182167/32688657.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90190000/90182200/90182167/805904c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Hancock

10/10

Exceptional

(8)

"Perfect place to stay for a quick ski trip. Host was super helpful & accommodating. Suite was comfortable & well-equipped. We’ll be back "

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

Kevin K.

CA $148

CA $331 total

includes taxes & fees

Nov 12 - Nov 13

[](https://www.expedia.ca/Hancock-Hotels-Must-See-Cabin-Suite-Jiminy-Sleeps-4-Mountainview-Ski-OnOff-Country-Inn-Redone.h90182167.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/102000000/101740000/101733900/101733845/dfd30b97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/102000000/101740000/101733900/101733845/34328d90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/102000000/101740000/101733900/101733845/49cd1317.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/102000000/101740000/101733900/101733845/26d89405.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2-Bdr Apt In Town, By the Water

Williamstown

9.4/10

Exceptional

(10)

"Lovely property, in good shape. Close to many Williamstown attractions."

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

Scott M.

CA $169

CA $381 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Williamstown-Hotels-Newley-Renovated-2-Bdr-Apt-In-Town.h101733845.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=2025-11-21&endDate=2025-11-22&regionId=9478&adults=2&sort=RECOMMENDED&openPlayBack=true)

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

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

## Top Pittsfield Hotel Reviews

![Quality Inn](//images.trvl-media.com/lodging/1000000/130000/128300/128208/62e9a326_y.jpg)

### Quality Inn

10/10 Excellent

"The staff was amazing, so kind and accommodating. The room was clean, the beds were very comfortable. Nice breakfast options. We were in town for a concert at Mahaiwe and we didn’t use our car once we checked in… a great home base for the weekend. Will definitely be back. "

[](https://expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information)

![The Red Lion Inn](//images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg)

### The Red Lion Inn

10/10 Excellent

"I love the ambience - historic and comfortable and excellent food. "

[](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information)

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

### Hotel On North

10/10 Excellent

"Perfect Stay in the Berkshire This hotel was spacious, clean, and had everything needed for a comfortable stay. The room was well-maintained, and the location was ideal—close to local attractions and easy to get around. Smooth check-in process and great access throughout. Highly recommend! "

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

![The Central Downtown Inn & Suites](//images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/fdeb3407_y.jpg)

### The Central Downtown Inn & Suites

10/10 Excellent

"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."

[](https://expedia.ca/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.Hotel-Information)

![Best Western Plus Berkshire Hills Inn & Suites](//images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387_y.jpg)

### Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent

"Everything was fine just no shampoo in the dispencer"

[](https://expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information)

![Berkshires Untold](//images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg)

### Berkshires Untold

10/10 Excellent

"Great staff and the room was awesome!! Would definitely come again!"

[](https://expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information)

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

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

10/10 Excellent

"Spotless and friendly staff"

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

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

### Berkshire Mountain Lodge

10/10 Excellent

"Clean, convenience, great staff, quiet, beautiful and secluded yet close to everything! Thank you"

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

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

### Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent

"Room was clean, comfortable and right next to the pool as requested. Pool was clean, breakfast was good and well stocked, all staff was friendly and accommodating. Would definitely stay here again. "

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

## Find out more about Pittsfield

**Everything you need to know about** **Pittsfield** **vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pittsfield vacation rental for you. At Expedia, you can take your pick from [private vacation homes](https://www.expedia.ca/aa/PrivateVacationHomes), [apartments](https://www.expedia.ca/aa/Apartments), cottages, [cabins](https://www.expedia.ca/aa/Cabins), villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pittsfield vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

**Pittsfield vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Pittsfield. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pittsfield vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pittsfield vacation rentals we have selected for you start as low as CA $158 per night. Entering your travel dates in the search wizard you might find even better deals!

**How to find incredible deals on Pittsfield rentals**

At Expedia, we put the best Pittsfield vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Pittsfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pittsfield vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pittsfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

## Explore a world of travel with Expedia

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-   [Vacation Homes in Pittsfield](https://expedia.ca/Pittsfield-Private-Vacation-Homes.d9478-aaPrivateVacationHomes.Travel-Guide-Accommodation)
-   [Apartments in Pittsfield](https://expedia.ca/Pittsfield-Apartments.d9478-aaApartments.Travel-Guide-Accommodation)
-   [Cottages in Pittsfield](https://expedia.ca/Pittsfield-Cottages.d9478-aaCottages.Travel-Guide-Accommodation)
-   [Condo Rentals in Pittsfield](https://expedia.ca/Pittsfield-Condos.d9478-aaCondos.Travel-Guide-Accommodation)
-   [Cabin Rentals in Pittsfield](https://expedia.ca/Pittsfield-Cabins.d9478-aaCabins.Travel-Guide-Accommodation)
-   [Motels in Pittsfield](https://expedia.ca/Pittsfield-Motels.d9478-aaMotels.Travel-Guide-Accommodation)
-   [B&B in Pittsfield](https://expedia.ca/Pittsfield-Bed-And-Breakfast.d9478-aaBedAndBreakfast.Travel-Guide-Accommodation)
-   [Resorts in Pittsfield](https://expedia.ca/Pittsfield-Resort-Hotels.d9478-aaResortHotels.Travel-Guide-Accommodation)
-   [Farmstay in Pittsfield](https://expedia.ca/Pittsfield-Agritourism.d9478-aaAgritourism.Travel-Guide-Accommodation)
-   [Guest Houses in Pittsfield](https://expedia.ca/Pittsfield-Guest-Houses.d9478-aaGuestHouses.Travel-Guide-Accommodation)
-   [Aparthotels in Pittsfield](https://expedia.ca/Pittsfield-Apart-Hotels.d9478-aaApartHotels.Travel-Guide-Accommodation)
-   [Inns in Pittsfield](https://expedia.ca/Pittsfield-Inns.d9478-aaInns.Travel-Guide-Accommodation)
-   [Chalets in Pittsfield](https://expedia.ca/Pittsfield-Chalets.d9478-aaChalets.Travel-Guide-Accommodation)
-   [Villas in Pittsfield](https://expedia.ca/Pittsfield-Villas.d9478-aaVillas.Travel-Guide-Accommodation)
-   [RV Parks in Pittsfield](https://expedia.ca/Pittsfield-RV-Parks.d9478-aaRVParks.Travel-Guide-Accommodation)
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-   [Castles in Pittsfield](https://expedia.ca/Pittsfield-Castles.d9478-aaCastles.Travel-Guide-Accommodation)
-   [Country Houses in Pittsfield](https://expedia.ca/Pittsfield-Country-House.d9478-aaCountryHouse.Travel-Guide-Accommodation)

## 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?

> [Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table](https://www.expedia.ca/Pittsfield-Hotels-Beautiful-8-Bedroom.h33492239.Hotel-Information): Visitors give good reviews to this Pittsfield vacation home rental, which is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation. Our travelers also rate [Hancock Village Inn Near Jiminy Peak](https://www.expedia.ca/Pittsfield-Hotels-Hancock-Village-Inn-At-Jiminy-Peak.h89806253.Hotel-Information) as a favorite home for rent in Pittsfield.

### How many vacation rentals are there in Pittsfield?

> With 39 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 Canoe Meadows Wildlife Sanctuary are a couple of great spots to enjoy the outdoors. Other places in town to visit include Colonial Theater and Barrington Stage Company.

### 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.

![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg)

## Go further with the Expedia app

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Scan the QR code with your device camera and download our app

![QR code to download the app](data:image/png;base64,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)