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

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=6047665&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=6047665&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=6047665&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=6047665&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 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)

![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)

![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)

### Vacation Village in the Berkshires

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

Williamstown

8.8/10

Excellent

(2,231 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)

![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)

![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/a8f10f60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, open 8:00 AM to 10:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/3f592f94.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)

![Exterior](https://images.trvl-media.com/lodging/91000000/90190000/90182200/90182167/70501210.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)

![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)

![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)

### 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

CA $187

CA $376 total

includes taxes & fees

Feb 8 - Feb 9

[](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/46000000/45480000/45471500/45471406/f020a98b.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)

![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)

### 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 $367 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Williamstown-Hotels-New-Studio-In-Town.h45471406.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/114000000/113780000/113777300/113777287/65ba1b08.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)

![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)

### 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)

![Exterior](https://images.trvl-media.com/lodging/102000000/101430000/101424500/101424483/d4b659d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/102000000/101430000/101424500/101424483/c5ae2be8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, DVD player, books](https://images.trvl-media.com/lodging/102000000/101430000/101424500/101424483/6205c26e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Gift shop](https://images.trvl-media.com/lodging/102000000/101430000/101424500/101424483/5d6310f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor

[](https://www.expedia.ca/Hancock-Hotels-Deluxe-Mountain-Fox-Suite-Jiminy-Peak-Ski-On-Off-Fully-Redone-Decor.h101424483.Hotel-Information)

Hancock

10/10

Exceptional

(1 review)

"The one-bedroom aparment is spacious, very clean, nice and funtional furniture and a perfectly well equipped kitchen area. Our 2 grandchildren had a fun time. And the apartament is footsteps from the ski lifts - a real treat! I highly recommend it!Ps. And the owner is always at hand, very helpful, and concerned that all is perfect for the guest's stay."

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

Antonio S.

CA $187

CA $376 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Hancock-Hotels-Deluxe-Mountain-Fox-Suite-Jiminy-Peak-Ski-On-Off-Fully-Redone-Decor.h101424483.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/70000000/69790000/69787500/69787457/da03c730.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/70000000/69790000/69787500/69787457/a110f773.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/70000000/69790000/69787500/69787457/9abb62fb_edited_7b4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/70000000/69790000/69787500/69787457/80ab6b54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

[](https://www.expedia.ca/Hancock-Hotels-SKI-ONOFF-1BR-SUITE-1ST-FLR-SLEEPS-4-JIMINY-PEAK.h69787457.Hotel-Information)

Hancock

10/10

Exceptional

(23 reviews)

"This property is spacious, clean and well- appointed. I would stay here again!"

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

Amanda M.

CA $223

CA $423 total

includes taxes & fees

Feb 12 - Feb 13

[](https://www.expedia.ca/Hancock-Hotels-SKI-ONOFF-1BR-SUITE-1ST-FLR-SLEEPS-4-JIMINY-PEAK.h69787457.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)

![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)

![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)

![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.

CA $187

CA $377 total

includes taxes & fees

Feb 10 - Feb 11

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

![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)

![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)

### 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)

![Interior](https://images.trvl-media.com/lodging/75000000/74320000/74312900/74312811/w1075h808x0y2-de6afae7.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)

![Exterior](https://images.trvl-media.com/lodging/75000000/74320000/74312900/74312811/w1075h806x0y5-6945b1ad.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)

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

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

Hancock

10/10

Exceptional

(14 reviews)

"lovely place to stay"

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

Nancy P.

CA $220

CA $533 total

includes taxes & fees

Feb 8 - Feb 9

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

![TV, offices](https://images.trvl-media.com/lodging/102000000/101740000/101733900/101733845/c5241605.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)

![Gift shop](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786767/2e9623f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786767/a21be151.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786767/w1280h960x0y6-ac51750e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786767/w1333h900x16y0-bf275b9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

[](https://www.expedia.ca/Hancock-Hotels-Must-See-Jurassic-Dino-Suite-At-Jiminy-Country-Inn-Sleeps-4-Ski-OnOff-At-Mtn.h90786767.Hotel-Information)

Hancock

10/10

Exceptional

(3 reviews)

"We had a great stay! The kids absolutely loved the room. Great location and lots to do. Thanks again!!"

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

Jen B.

CA $187

CA $377 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Hancock-Hotels-Must-See-Jurassic-Dino-Suite-At-Jiminy-Country-Inn-Sleeps-4-Ski-OnOff-At-Mtn.h90786767.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)

![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)

![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 $251

CA $464 total

includes taxes & fees

Feb 16 - Feb 17

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

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

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

![TV, offices](https://images.trvl-media.com/lodging/102000000/101740000/101733900/101733841/c3b9e910.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 $395 total

includes taxes & fees

Feb 18 - Feb 19

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

![Pool](https://images.trvl-media.com/lodging/125000000/124020000/124014400/124014382/ec2d4d77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/125000000/124020000/124014400/124014382/5f67b57c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/125000000/124020000/124014400/124014382/0789534a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/125000000/124020000/124014400/124014382/w1008h683x16y0-6785a02b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

[](https://www.expedia.ca/Hancock-Hotels-Mountain-Getaway-Suite-Ski-OnOff-Jiminy-Peak-Fully-Redone-Decor.h124014382.Hotel-Information)

Hancock

10/10

Exceptional

(2 reviews)

"The host communicated everything and ensured we had all the necessary information for our arrival. The room was super clean and everything was new. Really enjoyed our stay and had plenty of room and closets for storage. Would definitely stay again and truly a premiere host!! Angelica "

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

Jeffrey R.

CA $187

CA $377 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/Hancock-Hotels-Mountain-Getaway-Suite-Ski-OnOff-Jiminy-Peak-Fully-Redone-Decor.h124014382.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)

![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)

![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)

### 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)

![Outdoor dining](https://images.trvl-media.com/lodging/112000000/111670000/111663300/111663271/3e2af0e3.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)

![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)

### 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 $187

CA $464 total

includes taxes & fees

Feb 9 - Feb 10

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

![Living area](https://images.trvl-media.com/lodging/123000000/122140000/122136900/122136838/c64df1b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/123000000/122140000/122136900/122136838/12dc02ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/123000000/122140000/122136900/122136838/4b9dab09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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)

### Penthouse Apartment on Park Street

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

Adams

9.6/10

Exceptional

(14 reviews)

"Clean property, easy check in, and the owner was super communicative. "

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

Amanda W.

CA $198

CA $380 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Adams-Hotels-Penthouse-Apartment-On-Park-Street.h122136838.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/90000000/89720000/89714400/89714351/4fb8018b.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)

![Smart TV](https://images.trvl-media.com/lodging/90000000/89720000/89714400/89714351/7d4bb1aa.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)

![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)

![TV](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/3bbdf637.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)

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=6047665&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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Private vacation homes

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Apartments

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Chalets

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Condos

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Aparthotels

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Villas

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## Top The Berkshires Hotel Reviews

![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

"The staff is very helpful, and always willing to assist with any inquiries. The room was definitely clean and well-stocked throughout our entire stay."

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

"Spacious 2 bed 2 bath!"

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

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

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

10/10 Excellent

"Rooms were clean and spacious. Our room had 2 queen beds and they easily accommodated 2 of us and our late teen children. It's only 20 minutes from Jiminy Peak skiing area. There are several breakfast and food places nearby. "

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

![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)

![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 clean room. Staff great. Breakfast and selection great! "

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

"The great people!!!"

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

## 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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- [Vacation Homes in The Berkshires ](https://expedia.ca/The-Berkshires-Private-Vacation-Homes.d6047665-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Apartments in The Berkshires ](https://expedia.ca/The-Berkshires-Apartments.d6047665-aaApartments.Travel-Guide-Accommodation)
- [Cottages in The Berkshires ](https://expedia.ca/The-Berkshires-Cottages.d6047665-aaCottages.Travel-Guide-Accommodation)
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- [Inns in The Berkshires ](https://expedia.ca/The-Berkshires-Inns.d6047665-aaInns.Travel-Guide-Accommodation)
- [Aparthotels in The Berkshires ](https://expedia.ca/The-Berkshires-Apart-Hotels.d6047665-aaApartHotels.Travel-Guide-Accommodation)
- [Chalets in The Berkshires ](https://expedia.ca/The-Berkshires-Chalets.d6047665-aaChalets.Travel-Guide-Accommodation)
- [Lodges in The Berkshires ](https://expedia.ca/The-Berkshires-Lodges.d6047665-aaLodges.Travel-Guide-Accommodation)
- [Condo Resorts in The Berkshires ](https://expedia.ca/The-Berkshires-Condominium-Resort.d6047665-aaCondominiumResort.Travel-Guide-Accommodation)
- [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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