Title: The Berkshires Vacation Rentals from CA $157: Short-Term Rentals for 2025 | 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)

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# The Berkshires Vacation Rentals

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## Check prices for these dates

In two weeks

[Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2025-11-21&endDate=2025-11-23&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Vacation Rentals in The Berkshires

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

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

![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)

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

### Vacation Village in the Berkshires

Williamstown

8.8/10

Excellent

(2126)

"Clean and great pool and hot tub facilities "

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

Alyce

CA $127

CA $157 total

includes taxes & fees

Nov 25 - Nov 26

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

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

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

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

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

### Jiminy Peak Mountain Resort

Hancock

8.2/10

Very good

(984)

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

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

Sandhya

CA $209

CA $234 total

includes taxes & fees

Nov 10 - Nov 11

[](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/bc7f49dc.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/fd380371.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Huttopia Berkshires

Williamstown

10/10

Exceptional

(7)

"Perfect place for a relaxing getaway! We loved everything! "

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

Cammie

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

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

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

![Property grounds](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/ebd04e74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

### The Ponds at Foxhollow

Lenox

8.6/10

Excellent

(132)

"Perfect location "

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

krystle

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

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

![Microwave, oven, stovetop, eco-friendly cleaning products](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/780d89c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

### Pet Friendly Riverfront Home in Great Barrington

Great Barrington

8.8/10

Excellent

(3)

"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 $269

CA $397 total

includes taxes & fees

Nov 17 - Nov 18

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

![Exterior detail](https://images.trvl-media.com/lodging/77000000/76010000/76003400/76003386/5bf808fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76010000/76003400/76003386/d7946d7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76010000/76003400/76003386/aa330ef5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/77000000/76010000/76003400/76003386/aa306e51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Kemble- Built by a US Secretary of State in Lenox

Lenox

10/10

Exceptional

(17)

"We booked this house as the venue for our wedding, and it was absolutely perfect! Every room was gorgeous, with elegant décor and plenty of space for our guests. Even the bathrooms were stunning, making every part of the home feel special. The kitchen had everything we needed to host our 50-person wedding, from all the utensils to the appliances, making meal prep and serving a breeze. The communication with the hosts was amazing—Daniel was quick to respond, incredibly helpful, and made sure...

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

Carrie S.

[](https://www.expedia.ca/Lenox-Hotels-The-Kemble-Built-By-A-US-Secretary-Of-State-In-Lenox.h76003386.Hotel-Information)

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

![Interior](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/c189cee9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

### Hancock Village Inn Near Jiminy Peak

Hancock

10/10

Exceptional

(15)

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

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

Jim O.

CA $841

CA $1,560 total

includes taxes & fees

Nov 18 - Nov 19

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91600000/91593500/91593496/02c7301e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91600000/91593500/91593496/a366bf74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/92000000/91600000/91593500/91593496/960bf7a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/92000000/91600000/91593500/91593496/e175fcb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Amore Estate - beautiful room with many places to explore and relax in.

Lenox

9.2/10

Wonderful

(32)

"Beautiful property with tons of space and fantastic for a group of friends or family"

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

Greg S.

[](https://www.expedia.ca/Lenox-Hotels-October-Mountain-Escape.h91593496.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/34000000/33940000/33932800/33932760/63595554.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33940000/33932800/33932760/62b3ce52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/34000000/33940000/33932800/33932760/eccd60b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/34000000/33940000/33932800/33932760/7d7a19ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Stockbridge

10/10

Exceptional

(132)

"Clean house, well appointed, great location, responsive owner"

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

sara m.

[](https://www.expedia.ca/West-Stockbridge-Hotels-Location-Location-Berkshire-Glamour.h33932760.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/31000000/30780000/30777100/30777071/afd0b229.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/31000000/30780000/30777100/30777071/f26456ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/31000000/30780000/30777100/30777071/0f6c9404.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/31000000/30780000/30777100/30777071/2598e461.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Peace and quiet on the lake

Sherwood Forest

9.6/10

Exceptional

(227)

"Property was very clean and had all amenities that we needed. It was perfect for a cozy winter getaway weekend. Would definitely stay there again! "

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

Anika J.

[](https://www.expedia.ca/Becket-Hotels-Peace-And-Quiet-On-The-Lake.h30777071.Hotel-Information)

![A heated pool](https://images.trvl-media.com/lodging/110000000/109440000/109435000/109434975/18066543.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/110000000/109440000/109435000/109434975/dcf5df54_edited_d00b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/110000000/109440000/109435000/109434975/6658a41d_edited_267e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/110000000/109440000/109435000/109434975/e43d10e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Comfortable Berkshires retreat on mtn resort, SISO

Hancock

8.8/10

Excellent

(6)

"Family ski trip was made extremely enjoyable by staying at this property. Everything worked out as advertised"

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

Henry C.

CA $226

CA $759 total

includes taxes & fees

Nov 10 - Nov 11

[](https://www.expedia.ca/Hancock-Hotels-Comfortable-Berkshires-Retreat-On-Mtn-Resort.h109434975.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33500000/33492300/33492239/a5ddb496.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33500000/33492300/33492239/63cb703a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/34000000/33500000/33492300/33492239/89102e9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/34000000/33500000/33492300/33492239/7e362400.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Pittsfield

9.8/10

Exceptional

(149)

"You'll do some walking and stair climbing but otherwise was just what we needed and wanted! Owner was very accommodating when we had to bring the grandpup unexpectedly. Definitely recommend staying here."

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

Wendy Cameron L.

[](https://www.expedia.ca/Pittsfield-Hotels-Beautiful-8-Bedroom.h33492239.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/68000000/67260000/67255100/67255071/4b89dca4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/68000000/67260000/67255100/67255071/w1024h683x0y1-30c5b99d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, free WiFi](https://images.trvl-media.com/lodging/68000000/67260000/67255100/67255071/eb0a776d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/68000000/67260000/67255100/67255071/61b3f659.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Private Island - Largest Fresh Water Reservoir in Mass

Otis

8.6/10

Excellent

(9)

"The house’s position on the water, being further out than all other surrounding homes, makes for beautiful views of the lake and all it activities. The sunrises are beautiful. Unfortunately when you don’t have proper running water and a toilet that flushes without having to put water in the tank almost every time, the experience is less than ideal. The host warned us of the toilet about 15 min before we arrived and never had the kitchen sink fixed in the 5 days we stayed. That was rather...

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

Colleen W.

[](https://www.expedia.ca/Otis-Hotels-Private-Island-On-Largest-Fresh-Water-Reservoir-In-Mass-Ski-Boat-Included.h67255071.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/35000000/34350000/34341700/34341645/40ba9321.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Golf](https://images.trvl-media.com/lodging/35000000/34350000/34341700/34341645/w640h476x0y4-5c1b61d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/35000000/34350000/34341700/34341645/2e6a29c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/35000000/34350000/34341700/34341645/889170d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox

Hancock

9.8/10

Exceptional

(70)

"Nice house; good location near Jimney Peak and Mt. Greylock. Enjoyed my stay very much."

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

Ted S.

[](https://www.expedia.ca/Williamstown-Hotels-Huge-Beautiful-House-Fits-2-Families-16-Acres-Low-Rates-2-Min-From-Jiminy-Peak.h34341645.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/28000000/27130000/27129600/27129515/46c8a41a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/28000000/27130000/27129600/27129515/f9623fb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/28000000/27130000/27129600/27129515/1e626f4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/28000000/27130000/27129600/27129515/751b9826.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Antique Farmhouse Totally Restored

Sheffield

9.8/10

Exceptional

(93)

"Enjoyed the property, location and charming house that was well stocked with everything we needed."

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

Sharon S.

[](https://www.expedia.ca/Sheffield-Hotels-Antique-Farmhouse-Totally-Restored.h27129515.Hotel-Information)

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

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

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

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

### The Greylock Cabin

Florida

10/10

Exceptional

(4)

"We really enjoyed our stay at Greylock Cabin! It is clean, well maintained, and was very prepared for our arrival. Extra towels, bedding, and basic cookware were helpful for a comfortable getaway. It was easy to access the cabin and park. The host was very communicative and easy to reach throughout our stay. The outdoor space had a great view and was perfect to grill and unwind by the fire."

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

Robert G.

CA $332

CA $569 total

includes taxes & fees

Nov 11 - Nov 12

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

![Property grounds](https://images.trvl-media.com/lodging/117000000/116600000/116593900/116593874/22f66f00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116600000/116593900/116593874/ab36cb2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/117000000/116600000/116593900/116593874/f9dd0939.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/117000000/116600000/116593900/116593874/589cb0f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Tranquil Lakeside Escape in the Berkshires

Lenox

10/10

Exceptional

(1)

"perfect location to go everywhere in the Berkshires"

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

Edward G.

[](https://www.expedia.ca/Lenox-Hotels-Tranquil-Lakeside-Escape-In-The-Berkshires.h116593874.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/70000000/69740000/69737600/69737532/f418f910.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/70000000/69740000/69737600/69737532/866c485c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/70000000/69740000/69737600/69737532/31d32156.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/70000000/69740000/69737600/69737532/7d7c96e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

Great Barrington

10/10

Exceptional

(53)

"Great house for a large group. Lots of seating areas indoors and outdoors to accommodate kids and adults. House was very clean and kitchen was well stocked for cooking. We loved that the bedrooms were nicely separated for privacy, particularly the bunk rooms and nearby game room. Great for the late nighters in the bunch!Beautiful property and less than 10 mins to town."

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

Carol R.

[](https://www.expedia.ca/Great-Barrington-Hotels-The-Great-Escape-Ski-Cottage-WHOT-TUB-Great-Barrington.h69737532.Hotel-Information)

![Smart TV, fireplace, DVD player](https://images.trvl-media.com/lodging/79000000/78710000/78701100/78701034/be941bed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![7 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/79000000/78710000/78701100/78701034/9e7f1a99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, DVD player](https://images.trvl-media.com/lodging/79000000/78710000/78701100/78701034/d795e81b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78710000/78701100/78701034/13f97fa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Great Barrington

10/10

Exceptional

(28)

"We had a wonderful time with family and friends. The location was great and it was helpful for everyone to have their own bathroom. Kitchen was well stocked and toys for kids was a bonus."

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

Erin B.

[](https://www.expedia.ca/Great-Barrington-Hotels-Minutes-From-Ski-Butternut.h78701034.Hotel-Information)

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

![Dining](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/7c5dd880.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, printers](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/69c2e8f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Great Barrington

10/10

Exceptional

(1)

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

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

Roberta

CA $795

CA $1,865 total

includes taxes & fees

Nov 10 - Nov 11

[](https://www.expedia.ca/Great-Barrington-Hotels-Berkshires-Best-Large-Deck-With-Hotub.h120149051.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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## Top The Berkshires Hotel Reviews

![Hampton Inn & Suites Berkshires-Lenox](//images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/59f14822_y.jpg)

### Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent

"Breakfast was awesome"

[](https://expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information)

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

### The Williams Inn

10/10 Excellent

"This is the quintessential new england inn. Comfortable, well appointed, clean, and inviting. The proximity to Williams could not be better. We will stay here the next time we are at MassMOCA for an event. The restaurant serves excellent food and has the equivalent friendly service."

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

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

### The Yankee, Trademark Collection by Wyndham

10/10 Excellent

"Staff…great Room…great We enjoy it here and stay annually "

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

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

### Quality Inn

10/10 Excellent

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

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

![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](//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

"Place was great!"

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

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

### The Red Lion Inn

10/10 Excellent

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

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

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

### Vacation Village in the Berkshires

10/10 Excellent

"Yes, spotless room, courteous staff"

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

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

### Berkshire Mountain Lodge

10/10 Excellent

"Everything was so perfect for a weekend to just get away and decompress, the staff were great, the room was awesome. "

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

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

### Hotel On North

10/10 Excellent

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

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

## Find out more about The Berkshires

**Everything you need to know about** **The Berkshires** **vacation rentals**

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

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

**The Berkshires vacation rentals: An excellent choice for every season**

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

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A The Berkshires vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of The Berkshires vacation rentals we have selected for you start as low as CA $157 per night. Entering your travel dates in the search wizard you might find even better deals!

**How to find incredible deals on The Berkshires rentals**

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

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

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

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Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

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

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