Title: Pittsfield Vacation Rentals from CA $174: Short-Term Rentals for 2026 | Expedia.ca

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![Pittsfield showing a city](https://images.trvl-media.com/place/9478/b5f5430c-dc51-405d-9103-478c33e1bf14.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Pittsfield vacation rentals

![Exterior detail](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/f9227a2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/079bb1c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/54590b16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/411deb16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 3-bedroom house in beautiful Berkshires, close to amenities!

[](https://www.expedia.ca/Pittsfield-Hotels-3-Bedroom-House-In-Beautiful-Berkshires.h119322276.Hotel-Information)

Pittsfield

CA $254

CA $427 total

includes taxes & fees

Feb 24 - Feb 25

[](https://www.expedia.ca/Pittsfield-Hotels-3-Bedroom-House-In-Beautiful-Berkshires.h119322276.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/bdc7550f.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!

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

Pittsfield

7.8/10

Good

(7 reviews)

"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."

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

Liz V.

CA $368

CA $677 total

includes taxes & fees

Feb 20 - Feb 21

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

![Outdoor dining](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/c8837e7e.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)

![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)

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

### Hancock Village Inn Near Jiminy Peak

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

Hancock

10/10

Exceptional

(16 reviews)

"Amazing Inn. Cozy and everything we needed. "

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

Price F.

CA $848

CA $1,558 total

includes taxes & fees

Feb 9 - Feb 10

[](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)

![Interior](https://images.trvl-media.com/lodging/109000000/108500000/108496800/108496770/4dc5b6f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Pittsfield

2.0/10

(1 review)

"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 $185

CA $276 total

includes taxes & fees

Feb 14 - Feb 15

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

![Exterior](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/cd7fa5fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Bungalow](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/a965b40f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Bungalow | Private kitchen](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/2d5c8478.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Bungalow](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/65ba1b08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Huttopia Berkshires 

[](https://www.expedia.ca/Williamstown-Hotels-Huttopia-Berkshires.h113777287.Hotel-Information)

Williamstown

9.4/10

Exceptional

(8 reviews)

"Healthy food too!"

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

GEORGINA

CA $230

CA $257 total

includes taxes & fees

Mar 8 - Mar 9

[](https://www.expedia.ca/Williamstown-Hotels-Huttopia-Berkshires.h113777287.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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102810000/102806400/102806391/dd92adc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102810000/102806400/102806391/21a1823e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/103000000/102810000/102806400/102806391/2da92659.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Chatham

10/10

Exceptional

(6 reviews)

"We loved this property. All the bells and whistles as far as amenities go for a Vrbo! Great location and place to unwind, unplug ,and reconnect!"

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

scott B.

CA $294

CA $490 total

includes taxes & fees

Feb 23 - Feb 24

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

![Dining](https://images.trvl-media.com/lodging/108000000/107110000/107109200/107109194/aba54efe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107110000/107109200/107109194/504a6d5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107110000/107109200/107109194/ece507a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107110000/107109200/107109194/4fcbd214.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Chatham

10/10

Exceptional

(3 reviews)

"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 $294

CA $490 total

includes taxes & fees

Feb 24 - Feb 25

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

![Exterior](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/db44d375.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/03675fdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/8168a5fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

### Vacation Village in the Berkshires

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

Williamstown

8.8/10

Excellent

(2,229 reviews)

"I great place to stay!!"

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

Maricel

CA $142

CA $174 total

includes taxes & fees

Feb 8 - Feb 9

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

![Exterior](https://images.trvl-media.com/lodging/90000000/89510000/89505500/89505416/d4e277cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/90000000/89510000/89505500/89505416/2e432a1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, toaster](https://images.trvl-media.com/lodging/90000000/89510000/89505500/89505416/604150ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/90000000/89510000/89505500/89505416/3e8858f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Getaway Near Mass MoCA, Great Hiking, Scenic Views

[](https://www.expedia.ca/Stamford-Hotels-Getaway-Near-Mass-MoCA.h89505416.Hotel-Information)

Stamford

10/10

Exceptional

(28 reviews)

"Nice property for a quick and simple check-in. Near MassMOCA, the Clark Art Institute and much more."

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

Mario R.

CA $93

CA $196 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Stamford-Hotels-Getaway-Near-Mass-MoCA.h89505416.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)

![Exterior](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/af01e53f.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)

![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/8c55822c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

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

Sherwood Forest

9.8/10

Exceptional

(11 reviews)

"My wife and I wanted a quick get away in the Berkshires with our dog and this property couldn't have been more perfect. The house was wonderful, clean, cozy, and had everything we needed from towels, to kitchen utensils and appliances, to smart TVs. The location is set back in the woods in an already very quiet town, giving plenty of peace, quiet, and privacy. The hot tub was the highlight of the stay. The host is excellent with communication and was eager to be of assistance if needed. We...

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

Zack D.

CA $219

CA $540 total

includes taxes & fees

Feb 11 - Feb 12

[](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/102000000/101310000/101301800/101301745/30153bc5.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)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101310000/101301800/101301745/8d5d0ff1.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

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

Sand Lake

10/10

Exceptional

(13 reviews)

"Loved the earthiness and serenity of the cabin and great room. Everything built and made and maintained by the Adamos- truly a haven "

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

Joanna R.

CA $171

CA $250 total

includes taxes & fees

Feb 8 - Feb 9

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

![Daily to-go breakfast for a fee](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/7f42759d.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)

![Lobby](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/b35035ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/71df138f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Jiminy Peak Mountain Resort

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

Hancock

8.2/10

Very good

(989 reviews)

"nice and clean, good customer service, but the room is smell. "

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

Huang

CA $259

CA $289 total

includes taxes & fees

Mar 8 - Mar 9

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

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

![Living area](https://images.trvl-media.com/lodging/121000000/120470000/120461900/120461825/38972098.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)

### Riverbend Berkshire East Basecamp - 3 bedrooms available

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

Charlemont

10/10

Exceptional

(2 reviews)

"Very nice house and the stay was unproblematic!"

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

Noah K.

CA $219

CA $582 total

includes taxes & fees

Feb 24 - Feb 25

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

![TV](https://images.trvl-media.com/lodging/91000000/90260000/90251100/90251080/6c6cf45f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/91000000/90260000/90251100/90251080/972c3b08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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)

### Florida Mountain Log Cabin

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

Florida

10/10

Exceptional

(4 reviews)

"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 $251

CA $465 total

includes taxes & fees

Feb 22 - Feb 23

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

![TV, offices](https://images.trvl-media.com/lodging/102000000/101740000/101733900/101733845/c5241605.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101740000/101733900/101733845/74627ad9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/102000000/101740000/101733900/101733845/e51abd89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Williamstown-Hotels-2-Bdr-Apt-In-Town.h101733845.Hotel-Information)

Williamstown

9.6/10

Exceptional

(11 reviews)

"Clean, close to town, very convenient. On a busy road, so just be aware of that. But overall a good place to stay. "

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

Brian L.

CA $164

CA $385 total

includes taxes & fees

Mar 1 - Mar 2

[](https://www.expedia.ca/Williamstown-Hotels-2-Bdr-Apt-In-Town.h101733845.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/101000000/100960000/100959100/100959022/9c2c97d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/101000000/100960000/100959100/100959022/27a0e81a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/101000000/100960000/100959100/100959022/ea4a2ad0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100960000/100959100/100959022/917cabfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Berkshires Apartment at the Stephentown Hotel

[](https://www.expedia.ca/Stephentown-Hotels-Berkshires-Apartment-At-The-Stephentown-Hotel.h100959022.Hotel-Information)

Stephentown

10/10

Exceptional

(3 reviews)

"Dillon was very helpful and detailed in his communication and the apartment was as advertised. We loved the small deck to enjoy our morning coffee. The kitchen setup was helpful as well."

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

Matt E.

CA $150

CA $313 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Stephentown-Hotels-Berkshires-Apartment-At-The-Stephentown-Hotel.h100959022.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/90000000/89720000/89714400/89714351/w4000h2662x0y5-f1ed56ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/90000000/89720000/89714400/89714351/7d4bb1aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89720000/89714400/89714351/669a10ae.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)

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

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

Hinsdale

9.8/10

Exceptional

(36 reviews)

"Amazing, peaceful, immaculately clean property. "

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

Cec C.

CA $354

CA $744 total

includes taxes & fees

Mar 4 - Mar 5

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

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/c50e9e6c.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/85000000/84680000/84672900/84672833/6137aab0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Home in Great Barrington

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

Great Barrington

9.8/10

Exceptional

(27 reviews)

"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "

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

Cameron M.

CA $220

CA $368 total

includes taxes & fees

Feb 24 - Feb 25

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

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122170000/122165500/122165421/c0b1b1ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/123000000/122170000/122165500/122165421/4d94624e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122170000/122165500/122165421/c1a3192b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122170000/122165500/122165421/0800588d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

[](https://www.expedia.ca/Stephentown-Hotels-8-Mi-To-Jiminy-Peak-Resort-Mtn-View-Home-W-Deck.h122165421.Hotel-Information)

Stephentown

CA $268

CA $757 total

includes taxes & fees

Feb 21 - Feb 22

[](https://www.expedia.ca/Stephentown-Hotels-8-Mi-To-Jiminy-Peak-Resort-Mtn-View-Home-W-Deck.h122165421.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/102000000/101740000/101733900/101733841/53935e7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/102000000/101740000/101733900/101733841/c3b9e910.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/102000000/101740000/101733900/101733841/751785ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101740000/101733900/101733841/5619200c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Downtown | Waterfront | Walk to Shops

[](https://www.expedia.ca/Williamstown-Hotels-Downtown-Waterfront-Walk-To-Shops.h101733841.Hotel-Information)

Williamstown

10/10

Exceptional

(7 reviews)

"Perfect setup for anyone visiting Williamstown."

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

Michael P.

CA $178

CA $394 total

includes taxes & fees

Feb 24 - Feb 25

[](https://www.expedia.ca/Williamstown-Hotels-Downtown-Waterfront-Walk-To-Shops.h101733841.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=2026-02-21&endDate=2026-02-22&regionId=9478&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Cabins

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Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Pittsfield%2C+Massachusetts%2C+United+States+of+America&regionId=9478&latLong=42.44846%2C-73.253891&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=COTTAGE)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Pittsfield%2C+Massachusetts%2C+United+States+of+America&regionId=9478&latLong=42.44846%2C-73.253891&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=VACATION_HOME)

Apartments

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Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Pittsfield%2C+Massachusetts%2C+United+States+of+America&regionId=9478&latLong=42.44846%2C-73.253891&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=APART_HOTEL)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Pittsfield%2C+Massachusetts%2C+United+States+of+America&regionId=9478&latLong=42.44846%2C-73.253891&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=CONDO)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Pittsfield%2C+Massachusetts%2C+United+States+of+America&regionId=9478&latLong=42.44846%2C-73.253891&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=CHALET)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Pittsfield%2C+Massachusetts%2C+United+States+of+America&regionId=9478&latLong=42.44846%2C-73.253891&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=VILLA)

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## Top Pittsfield Hotel Reviews

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

### Berkshires Untold

10/10 Excellent

"loved "

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

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

### Berkshire Mountain Lodge

10/10 Excellent

"We had a lovely extended family weekend here. The staff was outstanding, every staff member was helpful, friendly and courteous. The large room in back of the lobby was especially helpful for our large group to hang out in and be comfortable. Everyone enjoyed the pool and hot tub despite it being so cold out. The hotel is well maintained. The only small complaint I had was that the bathroom in our room needs to be refreshed. We have already started talking about coming back in the warmer weather to enjoy some of the outdoor activities in in the area."

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

"Room was cozy and clean. Staff was very responsive and courteous. The entire place was great from location to feel."

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

![The Williams Inn](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2_y.jpg)

### The Williams Inn

10/10 Excellent

"Clean"

[](https://expedia.ca/Williamstown-Hotels-The-Williams-Inn.h35658765.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

"Immaculately clean and friendly staff. Easy parking and great breakfast"

[](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

"Quiet, clean,"

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

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

### The Red Lion Inn

10/10 Excellent

"Great stay. The only thing I would say - and I’ve been staying at the hotel since the 80s - it might be time for a few updates here and there. It runs the risk of going from rustic charm to grandma’s house in the not tooooo distant future. "

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

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

### Hotel On North

10/10 Excellent

"Great staff, beautiful hotel. Would definitely recommend "

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

"Everything was great, the staff, the room, and the amenities. We will be coming back. "

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

## Find out more about Pittsfield

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Pittsfield. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Vacation Homes in Pittsfield ](https://expedia.ca/Pittsfield-Private-Vacation-Homes.d9478-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cottages in Pittsfield ](https://expedia.ca/Pittsfield-Cottages.d9478-aaCottages.Travel-Guide-Accommodation)
- [Apartments in Pittsfield ](https://expedia.ca/Pittsfield-Apartments.d9478-aaApartments.Travel-Guide-Accommodation)
- [Condo Rentals in Pittsfield ](https://expedia.ca/Pittsfield-Condos.d9478-aaCondos.Travel-Guide-Accommodation)
- [Motels in Pittsfield ](https://expedia.ca/Pittsfield-Motels.d9478-aaMotels.Travel-Guide-Accommodation)
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- [Cabin Rentals in Pittsfield ](https://expedia.ca/Pittsfield-Cabins.d9478-aaCabins.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)
- [Chalets in Pittsfield ](https://expedia.ca/Pittsfield-Chalets.d9478-aaChalets.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)
- [Villas in Pittsfield ](https://expedia.ca/Pittsfield-Villas.d9478-aaVillas.Travel-Guide-Accommodation)
- [Lodges in Pittsfield ](https://expedia.ca/Pittsfield-Lodges.d9478-aaLodges.Travel-Guide-Accommodation)
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