Title: Windsor Vacation Rentals from CA $231: Short-Term Rentals for 2026 | Expedia.ca

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## Check prices for these dates

In two weeks

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=6005427&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=6005427&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)

In three months

[Jun 26 - Jun 28](https://www.expedia.ca/Hotel-Search?regionId=6005427&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 24 - Jul 26](https://www.expedia.ca/Hotel-Search?regionId=6005427&startDate=2026-07-24&endDate=2026-07-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Windsor vacation rentals

![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/dba15cbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/807b3960.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/8425e45e.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/106000000/105240000/105230400/105230373/22ef1826.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

[](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

(14 reviews)

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

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

Matthew F.

CA $223

CA $548 total

includes taxes & fees

Apr 6 - Apr 7

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89720000/89714400/89714351/669a10ae.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)

### 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 $242

CA $606 total

includes taxes & fees

Apr 1 - Apr 2

[](https://www.expedia.ca/Hinsdale-Hotels-Beautiful-2-Bedroom-Loft-With-Hot-Tub-At-Lake-Ashmere.h89714351.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/83d3f833_edited_d758.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/a133e616.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/2e0581f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/0e4076ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

[](https://www.expedia.ca/Becket-Hotels-Dog-Friendly-A-Frame-In-The-Berkshires-Walk-To-Lake-With-Beach-Access.h115469906.Hotel-Information)

Sherwood Forest

10/10

Exceptional

(5 reviews)

"We loved it! Lots of local hiking trails and a wonderful relaxing place."

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

Sharon K.

CA $203

CA $523 total

includes taxes & fees

Apr 6 - Apr 7

[](https://www.expedia.ca/Becket-Hotels-Dog-Friendly-A-Frame-In-The-Berkshires-Walk-To-Lake-With-Beach-Access.h115469906.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/90000000/89510000/89505500/89505416/d4e277cc.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/90000000/89510000/89505500/89505416/3e8858f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/90000000/89510000/89505500/89505416/31ffedca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, toaster](https://images.trvl-media.com/lodging/90000000/89510000/89505500/89505416/604150ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Getaway Near Mass MoCA, Great Hiking, Scenic Views

[](https://www.expedia.ca/Stamford-Hotels-Getaway-Near-Mass-MoCA.h89505416.Hotel-Information)

Stamford

10/10

Exceptional

(29 reviews)

"We enjoyed our stay "

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

Lydia T.

CA $94

CA $198 total

includes taxes & fees

Apr 1 - Apr 2

[](https://www.expedia.ca/Stamford-Hotels-Getaway-Near-Mass-MoCA.h89505416.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039338/5bbd846e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039338/d791261d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039338/23c80aaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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

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

Shelburne Falls

CA $216

CA $415 total

includes taxes & fees

Apr 1 - Apr 2

[](https://www.expedia.ca/Shelburne-Falls-Hotels-Rose-Wisteria-4-Guests-2-Bedrooms-Fullqueen-Beds.h120039338.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 | 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/a965b40f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Bungalow | Living area](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/1e2d02da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Huttopia Berkshires 

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

Williamstown

9.4/10

Exceptional

(10 reviews)

"Healthy food too!"

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

GEORGINA

CA $234

CA $262 total

includes taxes & fees

Apr 2 - Apr 3

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

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101740000/101733900/101733841/5619200c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101740000/101733900/101733841/7239287a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Downtown | Waterfront | Walk to Shops

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

Williamstown

10/10

Exceptional

(7 reviews)

"Perfect setup for anyone visiting Williamstown."

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

Michael P.

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

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

![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)

![Lobby](https://images.trvl-media.com/lodging/99000000/98520000/98512800/98512708/c5fd4f84.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

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

Hancock

10/10

Exceptional

(6 reviews)

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

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

Carrie C.

CA $146

CA $324 total

includes taxes & fees

Apr 1 - Apr 2

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

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90190000/90182200/90182167/11079675.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/91000000/90190000/90182200/90182167/4483726a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, DVD player](https://images.trvl-media.com/lodging/91000000/90190000/90182200/90182167/53296390.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/91000000/90190000/90182200/90182167/ab2ba3ee.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

(12 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 $146

CA $323 total

includes taxes & fees

Apr 1 - Apr 2

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

![Exterior](https://images.trvl-media.com/lodging/101000000/100730000/100720400/100720354/eab00089.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/101000000/100730000/100720400/100720354/296ae5ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/101000000/100730000/100720400/100720354/516bcaba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100730000/100720400/100720354/3d81b129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 14mi to Mt. Snow! Arcade, Private Suite, King Bed!

[](https://www.expedia.ca/Whitingham-Hotels-14mi-To-Mt-Snow-Arcade.h100720354.Hotel-Information)

Whitingham

10/10

Exceptional

(14 reviews)

"Extended family of 10 stayed 6 nights and all had a great stay. Beds were comfortable, house was very clean with everything you need to enjoy yourself and was in good repair. "

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

Jacklyn D.

CA $276

CA $705 total

includes taxes & fees

Apr 6 - Apr 7

[](https://www.expedia.ca/Whitingham-Hotels-14mi-To-Mt-Snow-Arcade.h100720354.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)

![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)

![Property grounds](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786767/a21be151.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

(5 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 $146

CA $323 total

includes taxes & fees

Apr 1 - Apr 2

[](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/100000000/99250000/99243600/99243554/8de4c71d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/43b40eb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/00cc85e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/06261f5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Near Tanglewood: Historic Summer Retreat

[](https://www.expedia.ca/New-Lebanon-Hotels-Near-Tanglewood-Historic-Summer-Retreat.h99243554.Hotel-Information)

New Lebanon

9.4/10

Exceptional

(26 reviews)

"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."

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

Paul S.

CA $170

CA $492 total

includes taxes & fees

Apr 1 - Apr 2

[](https://www.expedia.ca/New-Lebanon-Hotels-Near-Tanglewood-Historic-Summer-Retreat.h99243554.Hotel-Information)

![Gift shop](https://images.trvl-media.com/lodging/97000000/96840000/96837300/96837232/2b285fa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/97000000/96840000/96837300/96837232/78a1069e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/97000000/96840000/96837300/96837232/d4a1d841.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/97000000/96840000/96837300/96837232/w1333h900x16y0-00a84624.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

[](https://www.expedia.ca/Hancock-Hotels-Gorgeous-Mountain-View-Suite-Ski-OnOff-At-Jiminy-Fully-Redone-Decor.h96837232.Hotel-Information)

Hancock

10/10

Exceptional

(3 reviews)

"Stayed one night at one of my favorite ski spots. Will be back again!"

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

Neil J.

CA $146

CA $323 total

includes taxes & fees

Apr 1 - Apr 2

[](https://www.expedia.ca/Hancock-Hotels-Gorgeous-Mountain-View-Suite-Ski-OnOff-At-Jiminy-Fully-Redone-Decor.h96837232.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/122000000/121910000/121902900/121902882/2f78aa12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/122000000/121910000/121902900/121902882/08591748.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/122000000/121910000/121902900/121902882/20e7ddaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121910000/121902900/121902882/09a3de30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charlemont Chalet - A 15 Acre Private Retreat

[](https://www.expedia.ca/Charlemont-Hotels-Charlemont-Chalet-Where-The-Mountains-Meet-Luxury.h121902882.Hotel-Information)

Charlemont

CA $292

CA $683 total

includes taxes & fees

Apr 1 - Apr 2

[](https://www.expedia.ca/Charlemont-Hotels-Charlemont-Chalet-Where-The-Mountains-Meet-Luxury.h121902882.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/65000000/64430000/64428500/64428459/a7eb284a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/65000000/64430000/64428500/64428459/2435c38a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/65000000/64430000/64428500/64428459/2788df34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/65000000/64430000/64428500/64428459/cc0a8ffe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Stephentown

8.4/10

Very good

(12 reviews)

"Great location and property. thank you"

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

Christine P.

CA $178

CA $360 total

includes taxes & fees

Apr 6 - Apr 7

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

![Interior](https://images.trvl-media.com/lodging/113000000/112620000/112619100/112619076/e67896be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/113000000/112620000/112619100/112619076/26d4c402.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112620000/112619100/112619076/3f3d1749.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/113000000/112620000/112619100/112619076/3d396b42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 3-bedroom Cabin for nature lovers

[](https://www.expedia.ca/Stephentown-Hotels-Charming-3-Bedroom-Cabin-For-Nature-Lovers.h112619076.Hotel-Information)

Stephentown

6.8/10

(3 reviews)

"It’s a duplex, half of an old farm house. The bedrooms are all up a steep staircase to the second floor. The only bathroom is on the main floor with the kitchen and LR. It was clean but had a mild old house smell. It’s out in the country with a great view from the enclosed porch and the open deck. The kitchen was well stocked with appliances and everything worked. It needs more seating and lights in the LR. "

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

Bill B.

CA $183

CA $407 total

includes taxes & fees

Apr 2 - Apr 3

[](https://www.expedia.ca/Stephentown-Hotels-Charming-3-Bedroom-Cabin-For-Nature-Lovers.h112619076.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/93000000/92060000/92050600/92050515/79e104d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/93000000/92060000/92050600/92050515/ed6f8836.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, printers](https://images.trvl-media.com/lodging/93000000/92060000/92050600/92050515/a233230f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![6 bedrooms, desk, travel crib, WiFi](https://images.trvl-media.com/lodging/93000000/92060000/92050600/92050515/fc7d25b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Valley View Post & Beam Villa!

[](https://www.expedia.ca/South-Deerfield-Hotels-Cozy-Valley-View-Post-Beam-Villa.h92050515.Hotel-Information)

Whately

10/10

Exceptional

(8 reviews)

"Thanks for a great stay"

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

Andrea M.

CA $695

CA $883 total

includes taxes & fees

Apr 1 - Apr 2

[](https://www.expedia.ca/South-Deerfield-Hotels-Cozy-Valley-View-Post-Beam-Villa.h92050515.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/61000000/60770000/60763800/60763766/w907h683x58y0-59aad182.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/61000000/60770000/60763800/60763766/w507h683x259y0-1d5f8c7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/61000000/60770000/60763800/60763766/w510h683x258y0-04b5e846.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

### North Getaway Cottage

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

Williamstown

9.2/10

Wonderful

(24 reviews)

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

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

Carole S.

CA $281

CA $623 total

includes taxes & fees

Apr 6 - Apr 7

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

![Exterior](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/db44d375.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)

![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 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

(2,318 reviews)

"Clean rooms, and very friendly staff"

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

Amr

CA $145

CA $177 total

includes taxes & fees

Apr 14 - Apr 15

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/38000000/37820000/37817200/37817199/c077bee3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/38000000/37820000/37817200/37817199/1ae2e1b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/38000000/37820000/37817200/37817199/b4b598c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/38000000/37820000/37817200/37817199/212e023d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious 5BR w/ Hot Tub & Games

[](https://www.expedia.ca/Colrain-Hotels-10-Guests-5-BR.h37817199.Hotel-Information)

Colrain

9.8/10

Exceptional

(48 reviews)

"Great house for family gatherings "

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

John Paul B.

CA $395

CA $904 total

includes taxes & fees

Apr 1 - Apr 2

[](https://www.expedia.ca/Colrain-Hotels-10-Guests-5-BR.h37817199.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=2026-04-14&endDate=2026-04-15&regionId=6005427&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Aparthotels

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Cabins

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Villas

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Condos

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Private vacation homes

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Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America&regionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&lodging=COTTAGE)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America&regionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&lodging=CHALET)

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## Top Windsor Hotel Reviews

![The Porches Inn at Mass MoCA](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/66dde072_y.jpg)

### The Porches Inn at Mass MoCA

8/10 Good

"We very much enjoyed our night at theThe Porches Inn. Check-in was easy, the room was spacious, clean and comfortable. The shower was the best rainfall shower I have ever had and we even had a claw foot bathtub! The only drawback to our room was proximity to the main entrance door of the building which could hear opening and closing. We would have liked to use the exterior hot tub but it was not available due to pool renovations. We were able to enjoy the sauna and shower as an alternative. The breakfast was ample for a "continental buffet". Lastly, the free car charging was a life saver! I hope I have the opportunity to visit again."

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

![Berkshires Untold](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/3d64e1fb_y.jpg)

### Berkshires Untold

10/10 Excellent

"Easy check-in, secure and clean"

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

![The Black Swan Lee - Lenox, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/bca96d17_y.jpg)

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

10/10 Excellent

"Breakfast is excellent, quiet place is peaceful you can relax really well it has an Indian cuisine restaurant inside also a bar the restaurant is excellent all you request they will do it as long that they have it they will do everything is excellent to this In. Friendly staff."

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

"OK, the hotel needs updating, but the staff was so friendly and helpful it didn't even matter. We parked our car, walked everywhere, 2 min to the Colonial theater! Insider tip, if you buy a breakfast tix from the front desk it's less $ than paying at the restaurant. "

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

![Hotel On North](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/ef3ce5c5_y.jpg)

### Hotel On North

10/10 Excellent

"Very clean room, friendly staff, and a feeling of being in a “fancy” hotel while still being within budget. The location was great - I enjoyed walking around and felt safe after dark. Easy walking distance from the Colonial Theater. "

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

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

### The Yankee, Trademark Collection by Wyndham

10/10 Excellent

"Room was comfortable and quiet. Staff accommodated a request to change rooms after check-in as we discovered there was someone next door who was constantly on the phone speaking loudly in a voice that carried on something business related. Relocating us was very appreciated."

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

![Red Roof Inn PLUS+ South Deerfield – Amherst](https://images.trvl-media.com/lodging/1000000/790000/789000/788985/5f761ce4_y.jpg)

### Red Roof Inn PLUS+ South Deerfield – Amherst

8/10 Good

"Nice and quiet I stayed 2 weeks only had issue with housekeeping once with cleaning completely, they have certain days they clean weekly stays. I informed front desk and it was handled "

[](https://expedia.ca/South-Deerfield-Hotels-Red-Roof-Inn-PLUS-South-Deerfield-Amherst.h788985.Hotel-Information)

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

### The Williams Inn

10/10 Excellent

"The hotel is a great, upscale business hotel with friendly staff and a great restaurant."

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

![Best Western Plus Berkshire Hills Inn & Suites](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/0e628046_y.jpg)

### Best Western Plus Berkshire Hills Inn & Suites

8/10 Good

"Staff was very accommodating. Room was ok but toilet didn’t flush without the water constantly running. Shower gel, shampoo & condition bottles were all empty in the shower. Had to call for new ones. "

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

## Find out more about Windsor

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 Windsor. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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

- [Vacation Homes in Windsor ](https://expedia.ca/Windsor-Private-Vacation-Homes.d6005427-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Apartments in Windsor ](https://expedia.ca/Windsor-Apartments.d6005427-aaApartments.Travel-Guide-Accommodation)
- [Cottages in Windsor ](https://expedia.ca/Windsor-Cottages.d6005427-aaCottages.Travel-Guide-Accommodation)
- [B&B in Windsor ](https://expedia.ca/Windsor-Bed-And-Breakfast.d6005427-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Condo Rentals in Windsor ](https://expedia.ca/Windsor-Condos.d6005427-aaCondos.Travel-Guide-Accommodation)
- [Resorts in Windsor ](https://expedia.ca/Windsor-Resort-Hotels.d6005427-aaResortHotels.Travel-Guide-Accommodation)
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- [Motels in Windsor ](https://expedia.ca/Windsor-Motels.d6005427-aaMotels.Travel-Guide-Accommodation)
- [Cabin Rentals in Windsor ](https://expedia.ca/Windsor-Cabins.d6005427-aaCabins.Travel-Guide-Accommodation)
- [Guest Houses in Windsor ](https://expedia.ca/Windsor-Guest-Houses.d6005427-aaGuestHouses.Travel-Guide-Accommodation)
- [Chalets in Windsor ](https://expedia.ca/Windsor-Chalets.d6005427-aaChalets.Travel-Guide-Accommodation)
- [Inns in Windsor ](https://expedia.ca/Windsor-Inns.d6005427-aaInns.Travel-Guide-Accommodation)
- [Lodges in Windsor ](https://expedia.ca/Windsor-Lodges.d6005427-aaLodges.Travel-Guide-Accommodation)
- [Aparthotels in Windsor ](https://expedia.ca/Windsor-Apart-Hotels.d6005427-aaApartHotels.Travel-Guide-Accommodation)
- [Villas in Windsor ](https://expedia.ca/Windsor-Villas.d6005427-aaVillas.Travel-Guide-Accommodation)
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