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

[The Berkshires Travel Guide](https://expedia.ca/The-Berkshires.dx6047665)[Hotels in The Berkshires](https://expedia.ca/The-Berkshires-Hotels.d6047665.Travel-Guide-Hotels)[Flights to The Berkshires](https://expedia.ca/Cheap-Flights-To-The-Berkshires.d6047665.Travel-Guide-Flights)[The Berkshires Car Rentals](https://expedia.ca/Car-Rentals-In-The-Berkshires.d6047665.Car-Rental-Guide)[The Berkshires Vacation Packages](https://expedia.ca/The-Berkshires.d6047665.Destination-Travel-Guides)

![The Berkshires which includes flowers](https://images.trvl-media.com/place/6047665/e95ad08c-cd3f-48ea-b01c-31171bbd50b7.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Photo courtesy of Berkshire Visitors Bureau

![](https://images.trvl-media.com/place/6047665/e95ad08c-cd3f-48ea-b01c-31171bbd50b7.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 15 - May 17](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 12 - Jun 14](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2026-06-12&endDate=2026-06-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for The Berkshires vacation rentals

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

![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/9e460e0a.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)

### Vacation Village in the Berkshires

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

Williamstown

8.8/10

Excellent

(2,248 reviews)

"Excellent location and terrific space and amenities."

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

Michelle

CA $142

CA $174 total

includes taxes & fees

Feb 22 - Feb 23

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

![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)

![Lobby](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/b35035ab.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 16 - Mar 17

[](https://www.expedia.ca/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.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 | Living area](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/1e2d02da.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)

![Family Bungalow](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/a965b40f.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

(9 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 17 - Mar 18

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

![Property grounds](https://images.trvl-media.com/lodging/99000000/98520000/98512800/98512708/bae121bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/99000000/98520000/98512800/98512708/c5fd4f84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/99000000/98520000/98512800/98512708/ffe021cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, DVD player, books](https://images.trvl-media.com/lodging/99000000/98520000/98512800/98512708/69ce761a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

[](https://www.expedia.ca/Hancock-Hotels-Must-See-Pirate-Suite-Ski-OnOff-Jiminy-Mtn-View-Fully-Redone-Decor.h98512708.Hotel-Information)

Hancock

10/10

Exceptional

(5 reviews)

"It was great experience and we loved the ammenities."

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

Carrie C.

CA $188

CA $378 total

includes taxes & fees

Feb 23 - Feb 24

[](https://www.expedia.ca/Hancock-Hotels-Must-See-Pirate-Suite-Ski-OnOff-Jiminy-Mtn-View-Fully-Redone-Decor.h98512708.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/75000000/74320000/74312900/74312811/w1075h808x0y2-de6afae7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/75000000/74320000/74312900/74312811/w1075h804x0y7-b7678d93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/75000000/74320000/74312900/74312811/w1075h806x0y5-6945b1ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/75000000/74320000/74312900/74312811/w1080h783x0y5-9ee375ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### UNIQUE - 1BR Country Condo @ Jiminy Peak

[](https://www.expedia.ca/Hancock-Hotels-UNIQUE-Gnome-Themed-1BR-Condo.h74312811.Hotel-Information)

Hancock

10/10

Exceptional

(15 reviews)

"lovely place to stay"

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

Nancy P.

CA $221

CA $537 total

includes taxes & fees

Feb 26 - Feb 27

[](https://www.expedia.ca/Hancock-Hotels-UNIQUE-Gnome-Themed-1BR-Condo.h74312811.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)

![Exterior](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/6137aab0.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

[](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 $221

CA $366 total

includes taxes & fees

Feb 25 - Feb 26

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

![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)

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101740000/101733900/101733841/7239287a.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 23 - Feb 24

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

![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)

![Exterior](https://images.trvl-media.com/lodging/91000000/90260000/90251100/90251080/e012bbab.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)

### 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 $252

CA $467 total

includes taxes & fees

Feb 22 - Feb 23

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

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90190000/90182200/90182167/27b1a758.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90190000/90182200/90182167/w1333h900x16y0-62588f79.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

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

Hancock

10/10

Exceptional

(10 reviews)

"Room was perfect location for skiing. Able to see slopes and a few of the chairlifts from room. Beds were super comfortable. Parking was close by and in private area which helped avoid parking in huge resort parking lot. Owner was very responsive."

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

Charles

[](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)

![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)

![TV, offices](https://images.trvl-media.com/lodging/102000000/101740000/101733900/101733845/26d89405.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

(12 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 $386 total

includes taxes & fees

Mar 1 - Mar 2

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

![Exterior detail](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/f9227a2e.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)

![Exterior](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/079bb1c9.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 $248

CA $419 total

includes taxes & fees

Feb 23 - Feb 24

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

![Outdoor dining](https://images.trvl-media.com/lodging/46000000/45480000/45471500/45471406/f020a98b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/46000000/45480000/45471500/45471406/4c69da5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/46000000/45480000/45471500/45471406/0fb5f28d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/46000000/45480000/45471500/45471406/d0b6023a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### New Studio In Town, By the Water

[](https://www.expedia.ca/Williamstown-Hotels-New-Studio-In-Town.h45471406.Hotel-Information)

Williamstown

10/10

Exceptional

(10 reviews)

"Great location, we really enjoyed our stay! "

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

Lydia J.

CA $164

CA $368 total

includes taxes & fees

Feb 23 - Feb 24

[](https://www.expedia.ca/Williamstown-Hotels-New-Studio-In-Town.h45471406.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/84000000/83130000/83121200/83121139/110dcfc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/84000000/83130000/83121200/83121139/da7bcfa0_edited_f66a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83130000/83121200/83121139/795ea67b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/84000000/83130000/83121200/83121139/6000dad3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

[](https://www.expedia.ca/Hancock-Hotels-Gorgeous-Zen-Must-See-Suite-At-Jiminy-Country-Inn-Sleeps-4-Ski-OnOff-At-Mtn.h83121139.Hotel-Information)

Hancock

9.4/10

Exceptional

(16 reviews)

"Nice Place"

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

Tom C.

[](https://www.expedia.ca/Hancock-Hotels-Gorgeous-Zen-Must-See-Suite-At-Jiminy-Country-Inn-Sleeps-4-Ski-OnOff-At-Mtn.h83121139.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)

![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)

![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/2281e60c.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)

### 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

(12 reviews)

"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"

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

Matthew F.

CA $219

CA $540 total

includes taxes & fees

Feb 22 - Feb 23

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

![Pool](https://images.trvl-media.com/lodging/70000000/69540000/69537800/69537711/5a4b4d18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/70000000/69540000/69537800/69537711/ab502668_edited_0f54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/70000000/69540000/69537800/69537711/w1008h683x16y0-5d2c42d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/70000000/69540000/69537800/69537711/a470b34d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base

[](https://www.expedia.ca/Hancock-Hotels-Ski-OnOff-1BR-SUITE-SLEEPS-4-Best-Location-Jiminy.h69537711.Hotel-Information)

Hancock

9.6/10

Exceptional

(30 reviews)

"Was in town for my HS reunion and loved my stay! Great location and amenities and the condo itself is super cute."

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

Maura S.

CA $188

CA $378 total

includes taxes & fees

Feb 23 - Feb 24

[](https://www.expedia.ca/Hancock-Hotels-Ski-OnOff-1BR-SUITE-SLEEPS-4-Best-Location-Jiminy.h69537711.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/91000000/90190000/90182200/90182171/c3f6a1ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90190000/90182200/90182171/w1184h801x16y0-0381e8a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, DVD player, books](https://images.trvl-media.com/lodging/91000000/90190000/90182200/90182171/752486e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/91000000/90190000/90182200/90182171/14cd60b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn

[](https://www.expedia.ca/Hancock-Hotels-WOW-New-Ski-OnOff-Suite-By-Pool-Sleeps-4-Jiminy-Pk-Fully-Redone-Gorgeous-Inn.h90182171.Hotel-Information)

Hancock

8.8/10

Excellent

(15 reviews)

"We enjoyed our stay. We would definitely stay here again in the future."

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

Scott

CA $188

CA $378 total

includes taxes & fees

Feb 23 - Feb 24

[](https://www.expedia.ca/Hancock-Hotels-WOW-New-Ski-OnOff-Suite-By-Pool-Sleeps-4-Jiminy-Pk-Fully-Redone-Gorgeous-Inn.h90182171.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/112000000/111670000/111663300/111663271/3e2af0e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/112000000/111670000/111663300/111663271/34492d26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Gift shop](https://images.trvl-media.com/lodging/112000000/111670000/111663300/111663271/87c90776.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/112000000/111670000/111663300/111663271/c1de7213.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

[](https://www.expedia.ca/Hancock-Hotels-2-BR-Condo-Mountain-Views-At-Jiminy-Peak-Sleeps-7.h111663271.Hotel-Information)

Hancock

7.4/10

Good

(12 reviews)

"Perfect spot for Mountain Adventures, property was well equipped with comfortable necessities. It was very clean and spacious for six people, 3 adults and 3 young boys. We would definitely stay again. "

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

PK N.

CA $188

CA $465 total

includes taxes & fees

Feb 23 - Feb 24

[](https://www.expedia.ca/Hancock-Hotels-2-BR-Condo-Mountain-Views-At-Jiminy-Peak-Sleeps-7.h111663271.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/77000000/76720000/76713300/76713290/a99d06d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/77000000/76720000/76713300/76713290/63833f21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/77000000/76720000/76713300/76713290/643b3865.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/77000000/76720000/76713300/76713290/w1008h683x16y0-093e3f17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

[](https://www.expedia.ca/Hancock-Hotels-Chic-2BR-Suite-On-Jiminy-Mtn-Sleeps-8-Gorgeous.h76713290.Hotel-Information)

Hancock

9.6/10

Exceptional

(34 reviews)

"Great and clean property! Very easy to access and good parking too."

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

Todd A.

[](https://www.expedia.ca/Hancock-Hotels-Chic-2BR-Suite-On-Jiminy-Mtn-Sleeps-8-Gorgeous.h76713290.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)

![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)

![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)

![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/61000000/60770000/60763800/60763766/w524h683x260y0-f1656d72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### North Getaway Cottage

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

Williamstown

9.2/10

Wonderful

(24 reviews)

"We stayed here on a beautiful fall weekend so that my son could tour William's college. It was perfect!"

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

Carole S.

CA $277

CA $614 total

includes taxes & fees

Feb 24 - Feb 25

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

![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/121000000/120310000/120304900/120304823/9af2b9a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/055ed8a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/cc4451e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Family Ski Getaway in the Berkshires

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

Great Barrington

9.0/10

Wonderful

(11 reviews)

"Close to a great bakery and near to a farm market and shopping mall. "

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

Cristine C.

CA $277

CA $430 total

includes taxes & fees

Mar 6 - Mar 7

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

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## 

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## Find vacation rentals that suit your style

Cabins

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Private vacation homes

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Cottages

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Aparthotels

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Chalets

[](https://www.expedia.ca/Hotel-Search?destination=The+Berkshires%2C+Massachusetts%2C+United+States+of+America&regionId=6047665&latLong=42.166802%2C-73.149597&adults=2&startDate=2026-05-21&d1=2026-05-21&endDate=2026-05-24&d2=2026-05-24&lodging=CHALET)

Apartments

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Condos

[](https://www.expedia.ca/Hotel-Search?destination=The+Berkshires%2C+Massachusetts%2C+United+States+of+America&regionId=6047665&latLong=42.166802%2C-73.149597&adults=2&startDate=2026-05-21&d1=2026-05-21&endDate=2026-05-24&d2=2026-05-24&lodging=CONDO)

Villas

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## Top The Berkshires Hotel Reviews

![Holiday Inn Express Hotel & Suites Great Barrington by IHG](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598_y.jpg)

### Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent

"Great location, amenities, pool and hot tub for the kids, friendly staff, comfortable room."

[](https://expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information)

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

### Berkshire Mountain Lodge

10/10 Excellent

"Yes great stay"

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

"Room was clean, amenities were clean as well. Staff extremely courteous, kind and friendly. It was our 2nd stay and we'll be back again. "

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

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

### Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent

"It was a solid experience at the Best western, staff was super nice, the room was spacious and clean, the breakfast was delicious and the location is superb. Overall it was a great experience and will definitely stay there again "

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

"Room was great.. Staff was wonderful . "

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

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

### The Williams Inn

10/10 Excellent

"Beautiful inn, wonderful staff."

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

"Super clean spacious room! "

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

![The Porches Inn at Mass MoCA](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/dcf42e0d_y.jpg)

### The Porches Inn at Mass MoCA

10/10 Excellent

"Pleasant staff, comfortable room (with porch), winter swimming and sauna, excellent breakfast-great location when visiting MassMoca."

[](https://expedia.ca/North-Adams-Hotels-The-Porches-Inn.h7662392.Hotel-Information)

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

### Quality Inn

10/10 Excellent

"Clean room, great location"

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

## Find out more about The Berkshires

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 The Berkshires. 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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- [Québec Vacation Rentals ](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals)

- [Vacation Homes in The Berkshires ](https://expedia.ca/The-Berkshires-Private-Vacation-Homes.d6047665-aaPrivateVacationHomes.Travel-Guide-Accommodation)
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- [Cottages in The Berkshires ](https://expedia.ca/The-Berkshires-Cottages.d6047665-aaCottages.Travel-Guide-Accommodation)
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- [Farmstay in The Berkshires ](https://expedia.ca/The-Berkshires-Agritourism.d6047665-aaAgritourism.Travel-Guide-Accommodation)
- [Cabin Rentals in The Berkshires ](https://expedia.ca/The-Berkshires-Cabins.d6047665-aaCabins.Travel-Guide-Accommodation)
- [Guest Houses in The Berkshires ](https://expedia.ca/The-Berkshires-Guest-Houses.d6047665-aaGuestHouses.Travel-Guide-Accommodation)
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- [Villas in The Berkshires ](https://expedia.ca/The-Berkshires-Villas.d6047665-aaVillas.Travel-Guide-Accommodation)
- [RV Parks in The Berkshires ](https://expedia.ca/The-Berkshires-RV-Parks.d6047665-aaRVParks.Travel-Guide-Accommodation)
- [Country Houses in The Berkshires ](https://expedia.ca/The-Berkshires-Country-House.d6047665-aaCountryHouse.Travel-Guide-Accommodation)
- [Castles in The Berkshires ](https://expedia.ca/The-Berkshires-Castles.d6047665-aaCastles.Travel-Guide-Accommodation)

### Expedia's Latest Trends

Hotels

- [Oceanfront Hotels in Cape Cod](https://expedia.ca/Cape-Cod-Hotels-Oceanfront-Hotels.0-0-d180061-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
- [All Inclusive Resorts and Hotels in Cape Cod](https://expedia.ca/Cape-Cod-Hotels-All-Inclusive-Hotel.0-0-d180061-tAllInclusiveHotel.Travel-Guide-Filter-Hotels)
- [Hotels in Martha's Vineyard](https://expedia.ca/Marthas-Vineyard-Hotels.d6047691.Travel-Guide-Hotels)
- [Marriott Hotels & Resorts Hotels in Martha's Vineyard](https://expedia.ca/Marthas-Vineyard-Hotels-Marriott-Hotels-Resorts.0-0-d6047691--bMarriottHotelsResorts.Travel-Guide-Filter-Hotels)
- [Family Hotels in Cape Cod](https://expedia.ca/Cape-Cod-Hotels-Family-Hotel.0-0-d180061-tFamilyHotel.Travel-Guide-Filter-Hotels)
- [Pet-friendly Hotels in Cape Cod](https://expedia.ca/Cape-Cod-Hotels-Pet-Friendly-Hotel.0-0-d180061-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
- [Spa Hotels in Western Massachusetts](https://expedia.ca/Western-Massachusetts-Hotels-Spa-Hotel.0-0-d6234063-tSpaHotel.Travel-Guide-Filter-Hotels)
- [Hotels with Kitchenettes in Central Massachusetts](https://expedia.ca/Central-Massachusetts-Hotels-Hotels-With-Kitchenettes.0-0-d6047670-tHotelswithKitchenettes.Travel-Guide-Filter-Hotels)
- [Adults Only Resorts & Hotels in Martha's Vineyard](https://expedia.ca/Marthas-Vineyard-Hotels-Adults-Only-Resorts.0-0-d6047691-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels)
- [Hotels in Cape Cod](https://expedia.ca/Cape-Cod-Hotels.d180061.Travel-Guide-Hotels)
- [Pet-friendly Hotels in Plum Island](https://expedia.ca/Plum-Island-Hotels-Pet-Friendly-Hotel.0-0-d553248635083907278-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
- [Hotels with Free Breakfast in Central Massachusetts](https://expedia.ca/Central-Massachusetts-Hotels-Hotels-With-Free-Breakfast.0-0-d6047670-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels)
- [Cheap Hotels in Cape Cod](https://expedia.ca/Cape-Cod-Hotels-Cheap-Hotels.0-0-d180061-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Hotels with Free Breakfast in Western Massachusetts](https://expedia.ca/Western-Massachusetts-Hotels-Hotels-With-Free-Breakfast.0-0-d6234063-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels)
- [Boutique Hotels in Western Massachusetts](https://expedia.ca/Western-Massachusetts-Hotels-Boutique-Hotel.0-0-d6234063-tBoutiqueHotel.Travel-Guide-Filter-Hotels)
- [Beach Hotel in Cape Cod](https://expedia.ca/Cape-Cod-Hotels-Beach-Hotel.0-0-d180061-tBeachHotel.Travel-Guide-Filter-Hotels)

Flights

- [Cheap Flights to Martha's Vineyard](https://expedia.ca/Cheap-Flights-To-Marthas-Vineyard.d6047691.Travel-Guide-Flights)
- [Cheap Flights to Nantucket Island](https://expedia.ca/Cheap-Flights-To-Nantucket-Island.d6047676.Travel-Guide-Flights)
- [Cheap Flights to Cape Cod](https://expedia.ca/Cheap-Flights-To-Cape-Cod.d180061.Travel-Guide-Flights)

Cars

- [Owners Car Rentals In Western Massachusetts](https://expedia.ca/Owners-Car-Rentals-In-Western-Massachusetts.d6234063-c1066.Car-Rental-Guide-Suppliers)
- [Alamo Rent A Car Car Rentals In Marthas Vineyard](https://expedia.ca/Alamo-Rent-A-Car-Car-Rentals-In-Marthas-Vineyard.d6047691-c6.Car-Rental-Guide-Suppliers)

Activities

- [Things to do in Nantucket Island](https://expedia.ca/Things-To-Do-In-Nantucket-Island.d6047676.Travel-Guide-Activities)
- [Things to do in Cape Cod](https://expedia.ca/Things-To-Do-In-Cape-Cod.d180061.Travel-Guide-Activities)

Packages

- [Cape Cod Vacations](https://expedia.ca/Cape-Cod.d180061.Destination-Travel-Guides)
- [Martha's Vineyard Vacations](https://expedia.ca/Marthas-Vineyard.d6047691.Destination-Travel-Guides)

Vacation Rentals

- [Cape Cod Vacation Rentals](https://expedia.ca/Cape-Cod-Vacation-Rentals.d180061.Travel-Guide-VacationRentals)

General

- [Visit Plum Island](https://expedia.ca/Plum-Island.dx553248635083907278)
- [Visit Cape Cod](https://expedia.ca/Cape-Cod.dx180061)
- [Visit Martha's Vineyard](https://expedia.ca/Marthas-Vineyard.dx6047691)
- [Visit Nantucket Island](https://expedia.ca/Nantucket-Island.dx6047676)

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