Title: Canaan Vacation Rentals from CA $175: Short-Term Rentals for 2026 | Expedia.ca

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Photo by Robin/Loving Life

# Canaan Vacation Rentals

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## Check prices for these dates

In two weeks

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=55619&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=55619&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=55619&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=55619&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Canaan vacation rentals

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73730000/73729000/73728934/c3b6bbdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/74000000/73730000/73729000/73728934/83729050.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/74000000/73730000/73729000/73728934/c3d91b95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/74000000/73730000/73729000/73728934/9c369939.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Lanesborough

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

9.6/10

Exceptional

(67)

"We had a lovely stay! The studio was comfortable, clean, and just what we needed. Our hosts were friendly and helpful!"

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

Janice L.

CA $186

CA $283 total

includes taxes & fees

Dec 17 - Dec 18

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

![Exterior](https://images.trvl-media.com/lodging/90000000/89720000/89714400/89714351/ec8e2057.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/edecce8c.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)

### Cabin in Hinsdale

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

9.8/10

Exceptional

(34)

"Great cottage - well appointed and very clean. No air conditioning so a bit warm when it’s hot out, but all in all a great stay"

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

Lindsey E.

CA $223

CA $575 total

includes taxes & fees

Dec 17 - Dec 18

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

![Interior](https://images.trvl-media.com/lodging/70000000/69790000/69787500/69787457/2a4ba750.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Hancock

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

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 $145

CA $321 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Hancock-Hotels-SKI-ONOFF-1BR-SUITE-1ST-FLR-SLEEPS-4-JIMINY-PEAK.h69787457.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/91000000/90790000/90786800/90786765/9bebc4e1.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)

![TV, DVD player, offices](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786765/fe1becd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Hancock

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

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 $145

CA $321 total

includes taxes & fees

Dec 17 - Dec 18

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/52bc41a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/c50e9e6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/caf5dd09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/dcb799f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Great Barrington

[](https://www.expedia.ca/Great-Barrington-Hotels-Home-In-Great-Barrington.h84672833.Hotel-Information)

9.8/10

Exceptional

(26)

"Enjoyed our stay!!!"

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

Fred W.

CA $215

CA $363 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Great-Barrington-Hotels-Home-In-Great-Barrington.h84672833.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/75000000/74320000/74312900/74312811/w1080h783x0y5-9ee375ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/75000000/74320000/74312900/74312811/w1075h806x0y5-6945b1ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/75000000/74320000/74312900/74312811/w1075h808x0y2-de6afae7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/75000000/74320000/74312900/74312811/c54967a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Hancock

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

10/10

Exceptional

(14)

"Clean, comfortable place with nice amenities. "

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

Mike H.

CA $222

CA $526 total

includes taxes & fees

Dec 17 - Dec 18

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

![Exterior](https://images.trvl-media.com/lodging/68000000/67640000/67635500/67635438/8a26cf53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/68000000/67640000/67635500/67635438/11a36f07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/68000000/67640000/67635500/67635438/184c6f2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/68000000/67640000/67635500/67635438/976ef973.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Hancock

[](https://www.expedia.ca/Hancock-Hotels-Spacious-3BR-3BA-Ski-OnOff-Jiminy-Mountain-Resort.h67635438.Hotel-Information)

9.8/10

Exceptional

(72)

"We had a wonderful stay, thank you! "

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

Gary L.

CA $364

CA $741 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Hancock-Hotels-Spacious-3BR-3BA-Ski-OnOff-Jiminy-Mountain-Resort.h67635438.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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76720000/76713300/76713290/78da5d01.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)

### Apartment in Hancock

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

9.6/10

Exceptional

(30)

"Great and clean property! Very easy to access and good parking too."

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

Todd A.

CA $218

CA $448 total

includes taxes & fees

Dec 17 - Dec 18

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

![Interior](https://images.trvl-media.com/lodging/91000000/90190000/90182200/90182167/805904c6.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)

### Apartment in Hancock

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

10/10

Exceptional

(8)

"We had a wonderful 3 day weekend! Perfect location for families."

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

Eric B.

CA $145

CA $321 total

includes taxes & fees

Dec 17 - Dec 18

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

![TV, DVD player, books](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786767/b31564d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786767/f74a2d8d.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)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786767/56cd6111.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Hancock

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

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 $145

CA $321 total

includes taxes & fees

Dec 17 - Dec 18

[](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/1000000/920000/911400/911313/cf8c8830.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)

![Exterior](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/662f1ebe.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)

### Condo resort in Hancock

[](https://www.expedia.ca/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information)

8.2/10

Very good

(987)

"nice and clean, good customer service, but the room is smell. "

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

Huang

CA $260

CA $291 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/60000000/60000000/59995300/59995220/4b325a19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/60000000/60000000/59995300/59995220/90-b25e9082.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/60000000/60000000/59995300/59995220/90-00a818b8.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/60000000/60000000/59995300/59995220/f501a761.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Hudson

[](https://www.expedia.ca/Hudson-Hotels-All-The-Comforts-Of-Home.h59995220.Hotel-Information)

9.2/10

Wonderful

(28)

"Really liked staying at Steven’s place! The hot tub was a great touch. Stayed in Unit 1 - it’s small but perfect for what we needed it for! "

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

Marisa P.

CA $146

CA $195 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Hudson-Hotels-All-The-Comforts-Of-Home.h59995220.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/fbef3554.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/65181381.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/f0ba5959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/1df26d5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Lebanon Springs

[](https://www.expedia.ca/New-Lebanon-Hotels-Historic-Berkshires-Home-Near-Tanglewood.h84357520.Hotel-Information)

8.8/10

Excellent

(20)

"It was great - just what we were looking for. "

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

Kaye S.

CA $186

CA $509 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/New-Lebanon-Hotels-Historic-Berkshires-Home-Near-Tanglewood.h84357520.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/33000000/32810000/32807400/32807378/e3e0e9fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/33000000/32810000/32807400/32807378/8e812ffc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/33000000/32810000/32807400/32807378/d9fe6b36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/33000000/32810000/32807400/32807378/52f8efbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Valatie

[](https://www.expedia.ca/Albany-Hotels-Escape-To-Lakefront-Leisurehudson.h32807378.Hotel-Information)

10/10

Exceptional

(59)

"Great spot on the lake. Super quiet and relaxing."

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

vincent m.

CA $372

CA $728 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Albany-Hotels-Escape-To-Lakefront-Leisurehudson.h32807378.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/6339dfc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/ac2c5f84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/3bd0d6d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/a7e5baab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Housatonic

[](https://www.expedia.ca/Housatonic-Hotels-Sweet-Cozy-Victorian-In-Housatonic-Close-To-Everything.h102018223.Hotel-Information)

10/10

Exceptional

(3)

"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."

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

Cheryl F.

CA $186

CA $334 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Housatonic-Hotels-Sweet-Cozy-Victorian-In-Housatonic-Close-To-Everything.h102018223.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/665b8282.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, computer monitors](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/af920cc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/f26544ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/99d3f85f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Sheffield

[](https://www.expedia.ca/Sheffield-Hotels-Cheerful-3-Bedroom-Cottage-With-Woodstove.h75599864.Hotel-Information)

10/10

Exceptional

(41)

"The property was centrally located for skiing, and was a comfortable stay."

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

Kelly R.

CA $326

CA $692 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Sheffield-Hotels-Cheerful-3-Bedroom-Cottage-With-Woodstove.h75599864.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)

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

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

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

### Vacation Home in Great Barrington

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

9.4/10

Exceptional

(6)

CA $279

CA $410 total

includes taxes & fees

Dec 17 - Dec 18

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

![Indoor pool](https://images.trvl-media.com/lodging/79000000/78540000/78537700/78537603/b5482417.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/79000000/78540000/78537700/78537603/w1333h900x16y0-4045c8c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/79000000/78540000/78537700/78537603/9e312028.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/79000000/78540000/78537700/78537603/w905h678x0y5-7353a588.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Hancock

[](https://www.expedia.ca/Hancock-Hotels-Disney-Magic-At-Jiminy-Must-See-Gorgeous-Sleeps-4.h78537603.Hotel-Information)

9.8/10

Exceptional

(18)

"We enjoyed our stay in this adorable Disney Themed condo. The attention to detail in the theming was fantastic and the condo was perfect for our February Vacation ski trip."

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

Allison V.

CA $145

CA $321 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Hancock-Hotels-Disney-Magic-At-Jiminy-Must-See-Gorgeous-Sleeps-4.h78537603.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95670000/95669000/95668997/17e920ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/96000000/95670000/95669000/95668997/788e1637.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, travel crib, WiFi](https://images.trvl-media.com/lodging/96000000/95670000/95669000/95668997/44b79f2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/96000000/95670000/95669000/95668997/e067dc85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Stephentown

[](https://www.expedia.ca/Stephentown-Hotels-2-Bed-Berkshire-Getaway-Stephentown-Hotel.h95668997.Hotel-Information)

10/10

Exceptional

(5)

"This place is amazing! It is so clean and updated with lots of amenities! Lots of arcade games in the apartment thatthe whole family enjoyed! It's a quick trip to jimney peak to ski it's just down the road. Great restaurants nearby. Definitely recommend this place."

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

elizabeth r.

CA $243

CA $441 total

includes taxes & fees

Dec 30 - Dec 31

[](https://www.expedia.ca/Stephentown-Hotels-2-Bed-Berkshire-Getaway-Stephentown-Hotel.h95668997.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/101000000/100060000/100053100/100053078/ffa8b349.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/101000000/100060000/100053100/100053078/f9a0c9d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100060000/100053100/100053078/db74a893.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/101000000/100060000/100053100/100053078/59725e4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Hillsdale

[](https://www.expedia.ca/Hillsdale-Hotels-Perfect-House-In-Hillsdale.h100053078.Hotel-Information)

8.4/10

Very good

(5)

"As a group of 10 friends, this house was everything we could have wanted. 5 bedrooms, a very large living room, and a dining table to fit all of us at once. Very close to Catamount, Hy’s Fried, Roe Jan brewery and more. Very clean for such an old house. "

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

Stefanie K.

CA $256

CA $733 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Hillsdale-Hotels-Perfect-House-In-Hillsdale.h100053078.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=2025-12-30&endDate=2025-12-31&regionId=55619&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Canaan%2C+New+York%2C+United+States+of+America&regionId=55619&latLong=42.411659%2C-73.447174&adults=2&startDate=2026-03-16&d1=2026-03-16&endDate=2026-03-19&d2=2026-03-19&lodging=COTTAGE)

Private vacation homes

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Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Canaan%2C+New+York%2C+United+States+of+America&regionId=55619&latLong=42.411659%2C-73.447174&adults=2&startDate=2026-03-16&d1=2026-03-16&endDate=2026-03-19&d2=2026-03-19&lodging=APART_HOTEL)

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Canaan%2C+New+York%2C+United+States+of+America&regionId=55619&latLong=42.411659%2C-73.447174&adults=2&startDate=2026-03-16&d1=2026-03-16&endDate=2026-03-19&d2=2026-03-19&lodging=CABIN)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Canaan%2C+New+York%2C+United+States+of+America&regionId=55619&latLong=42.411659%2C-73.447174&adults=2&startDate=2026-03-16&d1=2026-03-16&endDate=2026-03-19&d2=2026-03-19&lodging=APARTMENT)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Canaan%2C+New+York%2C+United+States+of+America&regionId=55619&latLong=42.411659%2C-73.447174&adults=2&startDate=2026-03-16&d1=2026-03-16&endDate=2026-03-19&d2=2026-03-19&lodging=VILLA)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Canaan%2C+New+York%2C+United+States+of+America&regionId=55619&latLong=42.411659%2C-73.447174&adults=2&startDate=2026-03-16&d1=2026-03-16&endDate=2026-03-19&d2=2026-03-19&lodging=CONDO)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Canaan%2C+New+York%2C+United+States+of+America&regionId=55619&latLong=42.411659%2C-73.447174&adults=2&startDate=2026-03-16&d1=2026-03-16&endDate=2026-03-19&d2=2026-03-19&lodging=CHALET)

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## Top Canaan Hotel Reviews

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

### The Yankee, Trademark Collection by Wyndham

10/10 Excellent

"This is a wonderful place to stay. The breakfast is delicious. The pool and hot tub are delightful. The staff are like family. "

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

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

"Very clean. Nice amenities. Had everything you needed. "

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

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

### The Red Lion Inn

10/10 Excellent

"We had a very nice experience staying at the Red Lion Inn. Our room was upgraded when checking in which was a nice surprise. The hotel was beautifully decorated for the season. We loved the cozy feel of the fireplace in the lobby especially on such a cold day. "

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

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

### Quality Inn

10/10 Excellent

"The rooms were very clean and well kept. The beds were very comfortable. The breakfast: There was no cereal or variety of breads like bagels. Yogurts were great. I do give them the benefit of the doubt on this because it was an off week, in between holidays. It was very quiet. Staff was wonderful. We will definitely be back. "

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

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

### Berkshires Untold

10/10 Excellent

"Lovely little elegant hotel. Beautiful well appointed rooms. Comfortable bed. Reasonably price. Great find. "

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

![Hampton Inn & Suites Albany-East Greenbush](https://images.trvl-media.com/lodging/16000000/15730000/15725300/15725242/24123a32_y.jpg)

### Hampton Inn & Suites Albany-East Greenbush

10/10 Excellent

"Pet friendly with good space for dog walking. Property was very clean, maybe a newly built Hampton Inn. Check in was easy, friendly and efficient. The room was spacious and much appreciated well lit."

[](https://expedia.ca/Albany-Hotels-Hampton-Inn-Suites-Albany-East-Greenbush.h15725242.Hotel-Information)

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

### Berkshire Mountain Lodge

10/10 Excellent

"Nice room"

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

![The Black Swan Lee - Lenox, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9_y.jpg)

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

10/10 Excellent

"Really quiet, peaceful stay and beautiful spot for the money. Front desk staff so nice. No elevator to second floor so keep in mind if have accessibility issues/wheelchair user. Great view and gluten free menu options. Would stay again if in area. Was just passing through on way to medical appointment. "

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

![Comfort Inn & Suites East Greenbush - Albany](https://images.trvl-media.com/lodging/2000000/1060000/1052400/1052319/ea181a79_y.jpg)

### Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent

"Clean and perfect."

[](https://expedia.ca/Albany-Hotels-Comfort-Inn-Suites-East-Greenbush-Albany.h1052319.Hotel-Information)

## Find out more about Canaan

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 Canaan. 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 Canaan ](https://expedia.ca/Canaan-Private-Vacation-Homes.d55619-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cottages in Canaan ](https://expedia.ca/Canaan-Cottages.d55619-aaCottages.Travel-Guide-Accommodation)
- [Apartments in Canaan ](https://expedia.ca/Canaan-Apartments.d55619-aaApartments.Travel-Guide-Accommodation)
- [Condo Rentals in Canaan ](https://expedia.ca/Canaan-Condos.d55619-aaCondos.Travel-Guide-Accommodation)
- [B&B in Canaan ](https://expedia.ca/Canaan-Bed-And-Breakfast.d55619-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Cabin Rentals in Canaan ](https://expedia.ca/Canaan-Cabins.d55619-aaCabins.Travel-Guide-Accommodation)
- [Resorts in Canaan ](https://expedia.ca/Canaan-Resort-Hotels.d55619-aaResortHotels.Travel-Guide-Accommodation)
- [Farmstay in Canaan ](https://expedia.ca/Canaan-Agritourism.d55619-aaAgritourism.Travel-Guide-Accommodation)
- [Motels in Canaan ](https://expedia.ca/Canaan-Motels.d55619-aaMotels.Travel-Guide-Accommodation)
- [Guest Houses in Canaan ](https://expedia.ca/Canaan-Guest-Houses.d55619-aaGuestHouses.Travel-Guide-Accommodation)
- [Chalets in Canaan ](https://expedia.ca/Canaan-Chalets.d55619-aaChalets.Travel-Guide-Accommodation)
- [Aparthotels in Canaan ](https://expedia.ca/Canaan-Apart-Hotels.d55619-aaApartHotels.Travel-Guide-Accommodation)
- [Inns in Canaan ](https://expedia.ca/Canaan-Inns.d55619-aaInns.Travel-Guide-Accommodation)
- [Villas in Canaan ](https://expedia.ca/Canaan-Villas.d55619-aaVillas.Travel-Guide-Accommodation)
- [RV Parks in Canaan ](https://expedia.ca/Canaan-RV-Parks.d55619-aaRVParks.Travel-Guide-Accommodation)
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## Frequently asked questions

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