Title: Windsor Apartment Rentals from CA $245 | Expedia.ca

  

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## Check prices for these dates

Next weekend

[Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6005427&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=APARTMENT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6005427&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=APARTMENT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=6005427&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=APARTMENT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6005427&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=APARTMENT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Windsor Apartments

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73730000/73729000/73728934/19f12f1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![WiFi, bed sheets](https://images.trvl-media.com/lodging/74000000/73730000/73729000/73728934/5912604c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/74000000/73730000/73729000/73728934/99fcbf69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/74000000/73730000/73729000/73728934/b5789346.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Rustic Apt in 18th c Berkshire Farmhouse

Lanesborough

9.6/10

Exceptional

(67)

"Great value, so much better than all the touristy motels in the area!"

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

Chris G.

CA $189

CA $290 total

includes taxes & fees

Oct 26 - Oct 27

[](https://www.expedia.ca/Lanesborough-Hotels-Cozy-Rustic-Apt-In-18th-C-Berkshire-Farmhouse.h73728934.Hotel-Information)

![Game room](https://images.trvl-media.com/lodging/95000000/95000000/94997100/94997038/6ec376ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/95000000/95000000/94997100/94997038/6106c112.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/95000000/95000000/94997100/94997038/642ec8d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hair dryer, towels, soap, shampoo](https://images.trvl-media.com/lodging/95000000/95000000/94997100/94997038/93fa936b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Park Street Penthouse Apartment

Adams

9.6/10

Exceptional

(13)

"Adams is a beautiful town and looks and feels like the appalachian trail! "

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

judy r.

CA $110

CA $274 total

includes taxes & fees

Oct 27 - Oct 28

[](https://www.expedia.ca/Adams-Hotels-Park-Street-Penthouse-Apartment.h94997038.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/102000000/101740000/101733900/101733845/dfd30b97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/102000000/101740000/101733900/101733845/49cd1317.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101740000/101733900/101733845/5c100665.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)

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

Williamstown

9.4/10

Exceptional

(9)

"Lovely property, in good shape. Close to many Williamstown attractions."

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

Scott M.

CA $168

CA $377 total

includes taxes & fees

Oct 26 - Oct 27

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

![Interior](https://images.trvl-media.com/lodging/102000000/101740000/101733900/101733841/8cd7c5a7.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)

![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

Williamstown

10/10

Exceptional

(6)

"Perfect setup for anyone visiting Williamstown."

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

Michael P.

CA $182

CA $387 total

includes taxes & fees

Oct 26 - Oct 27

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

![TV, DVD player](https://images.trvl-media.com/lodging/91000000/90190000/90182200/90182167/32688657.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/91000000/90190000/90182200/90182167/739b3363.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

Hancock

10/10

Exceptional

(8)

"Great location. Howie is very communicative. Wish we could have stayed longer. "

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

Una D.

CA $155

CA $339 total

includes taxes & fees

Oct 27 - Oct 28

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

![Indoor pool](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786767/960f4565.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786767/38cbcac5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786767/w1280h960x0y6-5bd9f8f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786767/w1333h900x16y0-26f07573.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Hancock

10/10

Exceptional

(3)

"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 $155

CA $339 total

includes taxes & fees

Oct 27 - Oct 28

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

![Exterior](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786765/3b948672.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786765/w992h667x8y0-e5344523.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786765/w1298h680x0y0-b31746a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786765/9bebc4e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

Hancock

9.4/10

Exceptional

(6)

"Great location. Very nice vacation. Would def go again. "

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

Elizabeth M.

CA $157

CA $342 total

includes taxes & fees

Oct 29 - Oct 30

[](https://www.expedia.ca/Hancock-Hotels-1st-FL-Mtn-View-Woodland-Suite-On-Jiminy-Sleeps-4-Ski-OnOff.h90786765.Hotel-Information)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/110000000/109420000/109415600/109415543/1b2bd489.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/110000000/109420000/109415600/109415543/0f4e686a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/110000000/109420000/109415600/109415543/30c487a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/110000000/109420000/109415600/109415543/a0995ab5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Whitingham

10/10

Exceptional

(2)

"as advertised."

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

Joshua G.

CA $485

CA $879 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Whitingham-Hotels-Amazing-34-Foot-High-Shipping-Container-Home-In-Whitingham-On-Sadawga-Lake.h109415543.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/74000000/73420000/73412800/73412761/ed9e2bb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/74000000/73420000/73412800/73412761/70cf70fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/74000000/73420000/73412800/73412761/857f23fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73420000/73412800/73412761/22df2f50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bright Boho Apt in 18th c Berkshire Farmhouse

Lanesborough

9.0/10

Wonderful

(22)

"Really enjoyed our stay"

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

Thomas H.

CA $203

CA $308 total

includes taxes & fees

Oct 26 - Oct 27

[](https://www.expedia.ca/Lanesborough-Hotels-Bright-Boho-Apt-In-18th-C-Berkshire-Farmhouse.h73412761.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/46000000/45480000/45471500/45471406/696406e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/46000000/45480000/45471500/45471406/26298240.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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/d0b6023a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### New Studio In Town, By the Water

Williamstown

10/10

Exceptional

(8)

"Great location, we really enjoyed our stay! "

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

Lydia J.

CA $168

CA $360 total

includes taxes & fees

Oct 26 - Oct 27

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

![Exterior](https://images.trvl-media.com/lodging/84000000/83130000/83121200/83121139/c7d54926.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/84000000/83130000/83121200/83121139/5621347f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/84000000/83130000/83121200/83121139/a66f938e_edited_9d39.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/84000000/83130000/83121200/83121139/1dc2230f.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

Hancock

9.4/10

Exceptional

(16)

"We absolutely enjoyed this pleasant apartment. Its within the walking distance from the ski lifts which was perfect for all of us including 5 year old kid. "

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

Janja

CA $155

CA $339 total

includes taxes & fees

Oct 27 - Oct 28

[](https://www.expedia.ca/Hancock-Hotels-Gorgeous-Zen-Suite-Sleeps-4-Ski-On-Off-Jiminy-Mtn-Must-See-Luxury.h83121139.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/70000000/69790000/69787500/69787457/9c846f70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/70000000/69790000/69787500/69787457/w1008h683x16y0-72a8567d.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)

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

Hancock

10/10

Exceptional

(23)

"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 $155

CA $339 total

includes taxes & fees

Oct 27 - Oct 28

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100960000/100959100/100959022/2bbc5f71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/101000000/100960000/100959100/100959022/20953855.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/101000000/100960000/100959100/100959022/6e198ab2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/101000000/100960000/100959100/100959022/2d7f6c54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Berkshires Apartment at the Stephentown Hotel

Stephentown

10/10

Exceptional

(3)

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

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

Matt E.

CA $150

CA $307 total

includes taxes & fees

Nov 10 - Nov 11

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/65000000/64430000/64428500/64428459/6fee80cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, stereo](https://images.trvl-media.com/lodging/65000000/64430000/64428500/64428459/c57e6700.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/65000000/64430000/64428500/64428459/982e0d52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/65000000/64430000/64428500/64428459/18b2a505.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2 Bed Berkshire Apt minutes to Jiminy Peak Ski

Stephentown

8.4/10

Very good

(12)

"The apartment is cozy, clean, and perfect for visiting Jiminy Peak."

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

William G.

CA $191

CA $377 total

includes taxes & fees

Oct 26 - Oct 27

[](https://www.expedia.ca/Stephentown-Hotels-2-Bed-Berkshire-Apt-Minutes-To-Jiminy-Peak-Ski.h64428459.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/77000000/76720000/76713300/76713290/949e9107.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/77000000/76720000/76713300/76713290/97765f2f_edited_8669.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

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

Hancock

9.6/10

Exceptional

(30)

"We really enjoyed our stay it was a very nice place for a family."

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

Shmaya G.

CA $225

CA $459 total

includes taxes & fees

Oct 29 - Oct 30

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

![Living area](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039338/e86ed09e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Rose wisteria 4 guests 2 bedrooms-full+queen beds

Shelburne Falls

CA $192

CA $370 total

includes taxes & fees

Oct 30 - Oct 31

[](https://www.expedia.ca/Shelburne-Falls-Hotels-Rose-Wisteria-4-Guests-2-Bedrooms-Fullqueen-Beds.h120039338.Hotel-Information)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/88000000/87820000/87818800/87818778/w1276h853x4y0-72ff2a65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/88000000/87820000/87818800/87818778/9722e51d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/88000000/87820000/87818800/87818778/82bd0b83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/88000000/87820000/87818800/87818778/832c9210.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming Apt in 18th c Berkshire Farmhouse

Lanesborough

9.4/10

Exceptional

(39)

"It’s a nice comfortable apartment with a good kitchen. We were traveling to see a concert and some art at Mass MOCA. Patrick is a friendly and welcoming host."

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

Roy

CA $189

CA $290 total

includes taxes & fees

Oct 26 - Oct 27

[](https://www.expedia.ca/Lanesborough-Hotels-Charming-Apt-In-18th-C-Berkshire-Farmhouse.h87818778.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/99000000/98520000/98512800/98512708/250d56fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

![Interior](https://images.trvl-media.com/lodging/99000000/98520000/98512800/98512708/639a239f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/99000000/98520000/98512800/98512708/0ac89dfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Hancock

10/10

Exceptional

(4)

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

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

Carrie C.

CA $155

CA $339 total

includes taxes & fees

Oct 27 - Oct 28

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

"Clean room"

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

"An amazing service the staff is very friendly and helpful, it’s a nice location and a great place "

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

"Check in was easy. Room was clean and well-stocked. Lay out for the double room was great. Pool was well-maintained. Game room was added benefit. Very nice stay."

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

"This motel is an original from the 50's or 60's. I would not say it has been renovated, it has been updated and merticusly maintained over the years. The ambience is truly retro. In an instant I recognized this is a loved family owned property."

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

![Hotel Downstreet, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/10000/3000/2943/73bb1216_y.jpg)

### Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent

"Good value. A good place."

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

![The Black Swan Lee - Lenox, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/30000/20500/20447/588051f1_y.jpg)

### The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"Our room was clean as a pin and we loved the option of daily maid service. Love that there’s a closet with adequate hangers, extra blanket, clock, and the shampoo, body wash dispensers in the shower. Towels were big and fluffy. LOVE the heat lamp in the bathroom!"

[](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information)

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

### Berkshire Mountain Lodge

10/10 Excellent

"Clean room "

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

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

### Berkshires Untold

10/10 Excellent

"Had a lovely stay at the Berkshires Untold! We checked in late and the staff reached out to confirm our arrival time and accommodated us without issue. The lobby was absolutely gorgeous and this renovated motel was very well done. We didn’t get to enjoy the fire pits outside but they looked cozy. We also did not have any food or beverage. The room was perfect for two of us, had all the basic amenities and was charming. Overall had a very pleasant stay! "

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

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

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

10/10 Excellent

"All was very good at this hotel, our room was modernized and updated. The people at the front desk as well as all the employees were all well trained and pleasant . Pittsfield is in the middle of The Berkshires and so it was a great location to see what we wanted to see. "

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

## Find out more about Windsor

## Windsor Apartments information

| Number of reviews | 88 |
| --- | --- |
| Accommodation | 106 Apartments |
| Lowest Price | CA $245 |
| Highest Price | CA $879 |

## Frequently asked questions

### What's it like to stay at an apartment in Windsor?

> You might not have many choices centrally in Windsor, but Expedia can help you find lodging options in the area with similar amenities to an apartment. When you search for a place to stay on Expedia, you can filter by amenities you might find in an apartment like a kitchen. You can even filter by similar properties such as condos, vacation homes, or cottages.

### Are you thinking about an apartment for your stay?

> An apartment features a kitchen for convenient meals, and usually is more spacious than a traditional hotel room. Apartments are a good option for couples who want to live like locals, and also for families who want the conveniences of home.

### What's a favorite apartment for a stay in Windsor?

> Here are some of the top apartments in the area to choose from: [Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton](https://www.expedia.ca/Dalton-Hotels-Bright.h107876022.Hotel-Information): Located in Dalton, 5.7 mi/9.2 km from the heart of Windsor. Includes free WiFi, separate dining areas, and Smart TVs. Access to onsite laundry facilities is available on site. [FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!](https://www.expedia.ca/Pownal-Hotels-FARM-TO-TABLE-Eating.h33998602.Hotel-Information): Located 21.6 mi/34.8 km away in Pownal. A private pool, free WiFi, and private patios are included. Onsite laundry facilities and an outdoor pool are on site. [Elegant 19th Century New England Newly Renovated 1BR Vacation Rental](https://www.expedia.ca/Lee-Hotels-Elegant-19th-Century-New-England-Newly-Renovated-1BR-Vacation-Rental.h19992324.Hotel-Information): Located in Lee, 17.4 mi/28 km away. Includes private patios and fireplaces. Access to onsite laundry facilities is available on site. [Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4](https://www.expedia.ca/Hancock-Hotels-Luxury-Jiminy-Ski-On-Off-Village-Ctr-Condo-Sleeps4.h119236971.Hotel-Information): Located 12.9 mi/20.7 km away in Hancock. Amenities include fireplaces. A fitness center and a hot tub are on site. [Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous](https://www.expedia.ca/Hancock-Hotels-Chic-2BR-Suite-On-Jiminy-Mtn-Sleeps-8-Gorgeous.h76713290.Hotel-Information): Located in Hancock, 12.8 mi/20.7 km from Windsor. Includes fireplaces and sofa beds. A fitness center and onsite laundry facilities are on site.

### What can I expect from the weather during my trip to Windsor?

> Weather is only one factor, but it can really affect your travel plans, especially when you are planning a longer stay in Windsor. The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Windsor are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

### What should I see and do in Windsor?

> While exploring the area, visit family-friendly sights like Berkshire Museum, or get outside and enjoy nature at Mount Greylock State Reservation Visitor Center. In the larger area, you'll find Mount Greylock and Barrington Stage Company.

### What's the best way to get to and around Windsor?

> Knowing a bit about the transportation options can save you time when you get to your destination. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 13.8 mi (22.2 km) away from the city center. Otherwise, you can search for flights to Westfield, MA (BAF-Barnes Municipal), which is 28.9 mi (46.5 km) away. If you'd like to venture out around the area, you may want a rental car for your journey.

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-   [Washington Hotels](https://www.expedia.ca/Washington-Hotels.d553248634998690770.Travel-Guide-Hotels)
-   [Boutique Hotels in Worthington](https://www.expedia.ca/Worthington-Hotels-Boutique-Hotel.0-0-d6005428-tBoutiqueHotel.Travel-Guide-Filter-Hotels)
-   [Worthington Hotels](https://www.expedia.ca/Worthington-Hotels.d6005428.Travel-Guide-Hotels)

-   [Flights to Savoy Mountain State Forest](https://www.expedia.ca/Cheap-Flights-To-Savoy-Mountain-State-Forest.d6339858.Travel-Guide-Flights)
-   [Flights from Adams](https://www.expedia.ca/lp/flights/6005393/flights-from-adams)
-   [Flights from Plainfield](https://www.expedia.ca/lp/flights/6005414/flights-from-plainfield)

-   [Adams Vacations](https://www.expedia.ca/Adams.d6005393.Destination-Travel-Guides)
-   [Florida Vacations](https://www.expedia.ca/Florida.d553248634999031091.Destination-Travel-Guides)

-   [Dalton Vacation Rentals](https://www.expedia.ca/Dalton-Vacation-Rentals.d6911.Travel-Guide-VacationRentals)
-   [Florida Vacation Rentals](https://www.expedia.ca/Florida-Vacation-Rentals.d553248634999031091.Travel-Guide-VacationRentals)

-   [Book Apartments in Windsor on Expedia.com](https://www.expedia.com/Windsor-Apartments.d6005427-aaApartments.Travel-Guide-Accommodation)