Title: The Berkshires Vacation Rentals from CA $132: 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)

![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

# The Berkshires Vacation Rentals

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## Check prices for these dates

Tonight

[Nov 21 - Nov 22](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2025-11-21&endDate=2025-11-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Nov 22 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2025-11-22&endDate=2025-11-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

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

Next weekend

[Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2025-11-28&endDate=2025-11-30&adults=2&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)

![Dining room](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/16150550.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)

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

### Condo in Williamstown

8.8/10

Excellent

(2138)

"Great place!"

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

Nicole

CA $104

CA $132 total

includes taxes & fees

Nov 23 - Nov 24

[](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)

![Exterior](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/9c53d20e.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)

### Condo resort in Hancock

8.2/10

Very good

(986)

"This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the property has great sandwiches and things needed for your stay."

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

Amy

CA $209

CA $234 total

includes taxes & fees

Nov 23 - Nov 24

[](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/114000000/113780000/113777300/113777287/4ac9d6f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Camping in 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

CA $266

CA $298 total

includes taxes & fees

Dec 14 - Dec 15

[](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)

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

### Condo resort in Lenox

8.6/10

Excellent

(134)

"We were 4 adult friends sharing a 2-bedroom and enjoyed the size of the space and the location of the condo was under a 10 min drive to all the sights"

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

michelle

CA $179

CA $200 total

includes taxes & fees

Dec 5 - Dec 6

[](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)

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

![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/59edf6fe.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)

### Vacation Home in Great Barrington

9.2/10

Wonderful

(5)

CA $284

CA $415 total

includes taxes & fees

Nov 23 - Nov 24

[](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)

![Lobby](https://images.trvl-media.com/lodging/77000000/76010000/76003400/76003386/aa306e51.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)

### Villa in Lenox

10/10

Exceptional

(17)

"Perfect house for our family reunion. Everything was perfect."

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

Michael C.

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

![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)

![Exterior](https://images.trvl-media.com/lodging/31000000/30780000/30777100/30777071/bc016b9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Sherwood Forest

9.6/10

Exceptional

(228)

"This property provides direct access to a lovely lake for kayaking and swimming. It is also a terrific location for Berkshire musts such as Jacob's Pillow and Tanglewood. The owner is quickly responsive to questions and directions for check in were easy to follow. The house has strong WiFi for any work days you have while traveling. Highly recommend and look forward to staying there again in the future! "

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

Leslie K.

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

![Property grounds](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/w1440h1084x0y1-9f76bc91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

### Vacation Home in Hancock

10/10

Exceptional

(15)

"Amazing Inn. Cozy and everything we needed. "

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

Price F.

CA $844

CA $1,566 total

includes taxes & fees

Dec 2 - Dec 3

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

![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)

![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)

### Vacation Home in Great Barrington

10/10

Exceptional

(28)

"Wonderful old house, very comfortable space for a large family gathering. The kitchen was well-equipped, and exceptionally clean. The host was communicative and responsive, although everything was so well-thought out on his part, we didn't have much need to talk to the hosts. Excellent location, less than five minutes to Great Barrington, and twenty to Tanglewood and Lenox. "

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

Johnathan B.

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

![Interior](https://images.trvl-media.com/lodging/34000000/33940000/33932800/33932760/7d7a19ab.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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33940000/33932800/33932760/35eff0e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Stockbridge

10/10

Exceptional

(133)

"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)

![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33500000/33492300/33492239/a5ddb496.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)

![Exterior](https://images.trvl-media.com/lodging/34000000/33500000/33492300/33492239/85b23873.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)

### Vacation Home in Pittsfield

9.8/10

Exceptional

(149)

"We had a fabulous stay at this lovely home in the Berkshires! The house was well equipped with everything needed to make our stay with our family so enjoyable. Great communication with the host in helping to resolve a small issue with loss of power on 2nd floor but was easily resolved."

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

Sarah A.

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109440000/109435000/109434975/f076ba69_edited_5004.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)

![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)

### Vacation Home in Hancock

9.0/10

Wonderful

(7)

"Kind and responsive host."

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

Javier

CA $452

CA $1,029 total

includes taxes & fees

Nov 23 - Nov 24

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

![Living area](https://images.trvl-media.com/lodging/92000000/91600000/91593500/91593496/b2d17216.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)

![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)

### Vacation Home in Lenox

9.2/10

Wonderful

(32)

"Beautiful property. The house and grounds, including a beautiful pool were amazing. Loved sitting on the porch and watching the birds.So much to do in the Berkshires, would definitely like to come back."

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

Jacquie S.

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

![Interior](https://images.trvl-media.com/lodging/28000000/27130000/27129600/27129515/1e626f4a.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)

![Dining](https://images.trvl-media.com/lodging/28000000/27130000/27129600/27129515/7d583158.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Sheffield

9.8/10

Exceptional

(93)

"The property was beautiful. Very spacious, inside and out. "

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

Michelle C.

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

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

![Dining](https://images.trvl-media.com/lodging/112000000/111670000/111663300/111663271/a111c8ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111670000/111663300/111663271/d1c43c74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/112000000/111670000/111663300/111663271/7e1d3e97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Hancock

8.0/10

Very good

(8)

"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 $202

CA $485 total

includes taxes & fees

Nov 24 - Nov 25

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

![Interior](https://images.trvl-media.com/lodging/95000000/94910000/94905400/94905364/c212bf26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/95000000/94910000/94905400/94905364/0bd314dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/95000000/94910000/94905400/94905364/36e5f192.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/95000000/94910000/94905400/94905364/85bd5591.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in New Marlborough

9.6/10

Exceptional

(17)

"Lovely cottage. Great for 2 couples. Lots of privacy for each but comfy gathering spots for dining and relaxing. Host was very responsive to questions. Great stay!"

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

Lisa T.

[](https://www.expedia.ca/Great-Barrington-Hotels-Pine-View-Cottage.h94905364.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)

![Children's area](https://images.trvl-media.com/lodging/35000000/34350000/34341700/34341645/820f3267.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)

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

### Vacation Home in Hancock

9.8/10

Exceptional

(70)

"Great stay at a comfortable house with three generations of our family. Debbie was very responsive to several questions we had. The house was perfectly situated for day trips in the area. Thanks much!"

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

Wayne G.

[](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/121000000/120150000/120149100/120149051/772f14ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/61aeb8a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/b2f15e32.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)

### Vacation Home in 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 $1,866 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Great-Barrington-Hotels-Berkshires-Best-Large-Deck-With-Hotub.h120149051.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)

![Exterior](https://images.trvl-media.com/lodging/120000000/119140000/119137900/119137863/f2b309c8.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)

### Vacation Home in Florida

10/10

Exceptional

(4)

"Wonderful view, peaceful quiet area, cosy cabin."

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

Anonymous traveller

CA $365

CA $610 total

includes taxes & fees

Dec 14 - Dec 15

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

![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)

![Outdoor dining](https://images.trvl-media.com/lodging/68000000/67260000/67255100/67255071/e427035e.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)

### Cottage in Otis

8.6/10

Excellent

(9)

"We had a great time. The owner Bill was a great host."

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

Drew D.

[](https://www.expedia.ca/Otis-Hotels-Private-Island-On-Largest-Fresh-Water-Reservoir-In-Mass-Ski-Boat-Included.h67255071.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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## Find vacation rentals that suit your style

Cabins

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Private vacation homes

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Cottages

[](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=2026-02-19&d1=2026-02-19&endDate=2026-02-22&d2=2026-02-22&lodging=COTTAGE)

Apartments

[](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=2026-02-19&d1=2026-02-19&endDate=2026-02-22&d2=2026-02-22&lodging=APARTMENT)

Aparthotels

[](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=2026-02-19&d1=2026-02-19&endDate=2026-02-22&d2=2026-02-22&lodging=APART_HOTEL)

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=2026-02-19&d1=2026-02-19&endDate=2026-02-22&d2=2026-02-22&lodging=CONDO)

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=2026-02-19&d1=2026-02-19&endDate=2026-02-22&d2=2026-02-22&lodging=CHALET)

Villas

[](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=2026-02-19&d1=2026-02-19&endDate=2026-02-22&d2=2026-02-22&lodging=VILLA)

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## Top The Berkshires Hotel Reviews

![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

"Everything was amazing my bf did get a beer at the bar that was expired but everything else was amazing "

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

"Just stayed overnight, literally there 12 hours, so was not able to take advantage of any of the amenities, but would definitely come back for a longer stay!"

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

![Monument Mountain Motel](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/fa93cb94_y.jpg)

### Monument Mountain Motel

10/10 Excellent

"my go to spot when visiting area. owners care about their property and always clean. "

[](https://expedia.ca/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.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

"Great stay!"

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

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

### Berkshire Mountain Lodge

10/10 Excellent

"The suites were large. Nice to have separate bedroom. Kitchen with all the basics. Perfect for a getaway "

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

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

### Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent

"Clean, pleasant staff and good breakfast. "

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

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

### The Williams Inn

10/10 Excellent

"Did not eat breakfast"

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

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

### Berkshires Untold

10/10 Excellent

"Enjoyed the Clubhouse before retiring in for the evening. Cozy, comfortable, and relaxing atmosphere."

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

"Beautiful historic hotel. Loved the heated outdoor pool for an early morning swim. Good early morning coffee and delicious breakfast too. And they upgraded me to a suite! Couldn't be happier with my stay. "

[](https://expedia.ca/North-Adams-Hotels-The-Porches-Inn.h7662392.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)
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-   [Visit Martha's Vineyard](https://expedia.ca/Marthas-Vineyard.dx6047691)
-   [Visit Hyannis Port](https://expedia.ca/Hyannis-Port.dx183332)
-   [Visit Nantucket Island](https://expedia.ca/Nantucket-Island.dx6047676)

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