Title: Stockbridge Vacation Rentals from CA $177: Short-Term Rentals for 2026 | Expedia.ca

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![Autumn reflection while walking in the vicinity of Norman Rockwell Museum, Stockbridge. #LivingtheDream #Stockbridge #NewEngland #Reflection #Autumn #Walking](https://images.trvl-media.com/place/162575/c9de4f96-7bf3-4163-b4b9-feb67c2d801a.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Adnan Kakazai

# Stockbridge Vacation Rentals

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## Check prices for these dates

In two weeks

[Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=162575&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=162575&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=162575&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=162575&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Stockbridge vacation rentals

![Exterior](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/w2439h1242x124y0-c2be86b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/b7940a62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/b86b4635.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/d970b68c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Walk into town, soak up sun on enclosed porch & steps away from nature trails!

[](https://www.expedia.ca/Stockbridge-Hotels-Walk-Into-Town.h77128037.Hotel-Information)

Stockbridge

10/10

Exceptional

(32 reviews)

"A college friends' retreat was fantastic, in part due to the location, cleanliness and amenities in this 3 bedroom house. Furniture was comfortable and kitchen was stocked with everything we needed. "

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

cathy c.

CA $416

CA $894 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Stockbridge-Hotels-Walk-Into-Town.h77128037.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](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/4ac9d6f4.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

10/10

Exceptional

(7 reviews)

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

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

Cammie

CA $266

CA $297 total

includes taxes & fees

Jan 13 - Jan 14

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

![Dining](https://images.trvl-media.com/lodging/108000000/107110000/107109200/107109194/aba54efe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/108000000/107110000/107109200/107109194/324c211f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107110000/107109200/107109194/4fcbd214.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107110000/107109200/107109194/504a6d5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sugar Shack - 300 square feet of pure sweetness.

[](https://www.expedia.ca/Chatham-Hotels-Sugar-Shack-300-Square-Feet-Of-Pure-Sweetness.h107109194.Hotel-Information)

Chatham

10/10

Exceptional

(3 reviews)

"By far one of my favorite rentals. Everything was perfect and the details were amazing. Not only do I highly recommend, I amSURE I will be returning soon. "

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

Sue G.

CA $299

CA $502 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Chatham-Hotels-Sugar-Shack-300-Square-Feet-Of-Pure-Sweetness.h107109194.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/103000000/102810000/102806400/102806391/143defff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102810000/102806400/102806391/dd92adc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102810000/102806400/102806391/21a1823e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102810000/102806400/102806391/9af8184a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### BLUSH: Boutique TINY home\*private spa\*walk to town

[](https://www.expedia.ca/Chatham-Hotels-BLUSH-Boutique-TINY-Home-W-Private-Spa-Walk-To-New-Yorks-Cutest-Village.h102806391.Hotel-Information)

Chatham

10/10

Exceptional

(6 reviews)

"We loved this property. All the bells and whistles as far as amenities go for a Vrbo! Great location and place to unwind, unplug ,and reconnect!"

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

scott B.

CA $299

CA $502 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Chatham-Hotels-BLUSH-Boutique-TINY-Home-W-Private-Spa-Walk-To-New-Yorks-Cutest-Village.h102806391.Hotel-Information)

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

![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/9e460e0a.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)

![Exterior](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/f5d5819a.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

(2,204 reviews)

"I great place to stay!!"

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

Maricel

CA $145

CA $177 total

includes taxes & fees

Jan 13 - Jan 14

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

![Exterior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/a0f802bf.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/116000000/115470000/115470000/115469906/0e4076ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

[](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

Jan 13 - Jan 14

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

![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/106000000/105240000/105230400/105230373/4e64ac0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/af01e53f.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/106000000/105240000/105230400/105230373/8c55822c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

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

Sherwood Forest

9.6/10

Exceptional

(10 reviews)

"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."

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

James D.

CA $223

CA $549 total

includes taxes & fees

Jan 13 - Jan 14

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

![Outdoor dining](https://images.trvl-media.com/lodging/83000000/82470000/82464100/82464081/161b78a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/83000000/82470000/82464100/82464081/cdc0837e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/83000000/82470000/82464100/82464081/f1ca888d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/83000000/82470000/82464100/82464081/dbb06288.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Little Longbow Lakefront Chalet

[](https://www.expedia.ca/Becket-Hotels-Little-Longbow-Lakefront-Chalet.h82464081.Hotel-Information)

Becket

9.8/10

Exceptional

(21 reviews)

"Absolutely perfect quiet get away to relax and recharge will be back! "

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

Dana V.

CA $407

CA $709 total

includes taxes & fees

Jan 16 - Jan 17

[](https://www.expedia.ca/Becket-Hotels-Little-Longbow-Lakefront-Chalet.h82464081.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/90000000/89720000/89714400/89714351/7d4bb1aa.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)

![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)

### 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

(35 reviews)

"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 $232

CA $591 total

includes taxes & fees

Jan 13 - Jan 14

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

![Pool](https://images.trvl-media.com/lodging/125000000/124020000/124014400/124014382/ec2d4d77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/125000000/124020000/124014400/124014382/0789534a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/125000000/124020000/124014400/124014382/cbafac8b_edited_20ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/125000000/124020000/124014400/124014382/w1008h683x16y0-6785a02b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

[](https://www.expedia.ca/Hancock-Hotels-Mountain-Getaway-Suite-Ski-OnOff-Jiminy-Peak-Fully-Redone-Decor.h124014382.Hotel-Information)

Hancock

10/10

Exceptional

(1 review)

"The host communicated everything and ensured we had all the necessary information for our arrival. The room was super clean and everything was new. Really enjoyed our stay and had plenty of room and closets for storage. Would definitely stay again and truly a premiere host!! Angelica "

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

Jeffrey R.

CA $191

CA $384 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Hancock-Hotels-Mountain-Getaway-Suite-Ski-OnOff-Jiminy-Peak-Fully-Redone-Decor.h124014382.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)

![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)

![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)

### Home in Great Barrington

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

Great Barrington

9.8/10

Exceptional

(26 reviews)

"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "

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

Cameron M.

CA $210

CA $358 total

includes taxes & fees

Jan 25 - Jan 26

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

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/23a17279.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/6d1211ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Historic Berkshires Home Near Tanglewood, Trails & Wineries

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

Lebanon Springs

8.8/10

Excellent

(20 reviews)

"Great stay in the Berkshires for a wedding. Amanda was very accommodating and communicative. "

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

Wendy D.

CA $188

CA $517 total

includes taxes & fees

Jan 13 - Jan 14

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

![Outdoor pool, open 8:00 AM to 10:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/3f592f94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/71df138f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Jiminy Peak Mountain Resort

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

Hancock

8.2/10

Very good

(989 reviews)

"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 $305

CA $340 total

includes taxes & fees

Jan 13 - Jan 14

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

![Beach](https://images.trvl-media.com/lodging/101000000/100960000/100959100/100959022/9c2c97d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/101000000/100960000/100959100/100959022/0bb2009d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/101000000/100960000/100959100/100959022/ea4a2ad0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100960000/100959100/100959022/917cabfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Berkshires Apartment at the Stephentown Hotel

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

Stephentown

10/10

Exceptional

(3 reviews)

"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 $186

CA $358 total

includes taxes & fees

Jan 13 - Jan 14

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

![Smart TV, books](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/cd1323be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/621adf1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/25e02c23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/412632db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sun Filled Lenox Retreat - Minutes to Tanglewood!

[](https://www.expedia.ca/Sun-Filled-Lenox-Retreat-Minutes-To-Tanglewood.h109590815.Hotel-Information)

Lee

9.4/10

Exceptional

(3 reviews)

"The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay."

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

Sarah D.

CA $250

CA $640 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Sun-Filled-Lenox-Retreat-Minutes-To-Tanglewood.h109590815.Hotel-Information)

![TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/100000000/99410000/99407400/99407400/caa0ad88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![15 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99410000/99407400/99407400/ca2ed981.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/100000000/99410000/99407400/99407400/856cedc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/100000000/99410000/99407400/99407400/2cd54c4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Berkshires farm, 30+ guests, 50 acres

[](https://www.expedia.ca/New-Lebanon-Hotels-Berkshires-Farm.h99407400.Hotel-Information)

New Lebanon

10/10

Exceptional

(1 review)

CA $1,414

CA $2,600 total

includes taxes & fees

Feb 4 - Feb 5

[](https://www.expedia.ca/New-Lebanon-Hotels-Berkshires-Farm.h99407400.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)

![Interior](https://images.trvl-media.com/lodging/113000000/112620000/112619100/112619076/fe676105.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)

### Charming 3-bedroom Cabin for nature lovers

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

Stephentown

7.0/10

Good

(2 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 $216

CA $445 total

includes taxes & fees

Jan 26 - Jan 27

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

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122170000/122165500/122165421/c0b1b1ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122170000/122165500/122165421/c1a3192b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122170000/122165500/122165421/0800588d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122170000/122165500/122165421/4cd10809.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

[](https://www.expedia.ca/Stephentown-Hotels-8-Mi-To-Jiminy-Peak-Resort-Mtn-View-Home-W-Deck.h122165421.Hotel-Information)

Stephentown

CA $273

CA $770 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Stephentown-Hotels-8-Mi-To-Jiminy-Peak-Resort-Mtn-View-Home-W-Deck.h122165421.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)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/6b5af50f.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

9.6/10

Exceptional

(24 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 $167

CA $489 total

includes taxes & fees

Jan 13 - Jan 14

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

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90190000/90182200/90182167/27b1a758.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90190000/90182200/90182167/w1333h900x16y0-62588f79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/91000000/90190000/90182200/90182167/9ec4188c.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

(8 reviews)

"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 $191

CA $384 total

includes taxes & fees

Jan 13 - Jan 14

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

![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

"Perfectly Clean. Great Service. Beautiful Place!"

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

![Holiday Inn Express & Suites Pittsfield - Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/6a7ad915_y.jpg)

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

10/10 Excellent

"Extraordinary"

[](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.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 good "

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

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

### Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent

"Very clean, modern hotel. Would definitely stay here again. "

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

"Absolutely fabulous!"

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

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

### Berkshire Mountain Lodge

10/10 Excellent

"I've stayed here several times over the past two years. A real gem of a location, especially if you are staying several nights. "

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

"Everyone that works here is so nice! I’ve stayed here twice and had such a nice time. Thank youN"

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

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

### Berkshires Untold

10/10 Excellent

"Delicious sundae! Cozy fire!"

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

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

### Hotel On North

10/10 Excellent

"Great staff, room was huge and comfortable. "

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

## Find out more about Stockbridge

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 Stockbridge. 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 Stockbridge ](https://expedia.ca/Stockbridge-Private-Vacation-Homes.d162575-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cottages in Stockbridge ](https://expedia.ca/Stockbridge-Cottages.d162575-aaCottages.Travel-Guide-Accommodation)
- [Apartments in Stockbridge ](https://expedia.ca/Stockbridge-Apartments.d162575-aaApartments.Travel-Guide-Accommodation)
- [Condo Rentals in Stockbridge ](https://expedia.ca/Stockbridge-Condos.d162575-aaCondos.Travel-Guide-Accommodation)
- [B&B in Stockbridge ](https://expedia.ca/Stockbridge-Bed-And-Breakfast.d162575-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Resorts in Stockbridge ](https://expedia.ca/Stockbridge-Resort-Hotels.d162575-aaResortHotels.Travel-Guide-Accommodation)
- [Cabin Rentals in Stockbridge ](https://expedia.ca/Stockbridge-Cabins.d162575-aaCabins.Travel-Guide-Accommodation)
- [Farmstay in Stockbridge ](https://expedia.ca/Stockbridge-Agritourism.d162575-aaAgritourism.Travel-Guide-Accommodation)
- [Motels in Stockbridge ](https://expedia.ca/Stockbridge-Motels.d162575-aaMotels.Travel-Guide-Accommodation)
- [Guest Houses in Stockbridge ](https://expedia.ca/Stockbridge-Guest-Houses.d162575-aaGuestHouses.Travel-Guide-Accommodation)
- [Aparthotels in Stockbridge ](https://expedia.ca/Stockbridge-Apart-Hotels.d162575-aaApartHotels.Travel-Guide-Accommodation)
- [Inns in Stockbridge ](https://expedia.ca/Stockbridge-Inns.d162575-aaInns.Travel-Guide-Accommodation)
- [Chalets in Stockbridge ](https://expedia.ca/Stockbridge-Chalets.d162575-aaChalets.Travel-Guide-Accommodation)
- [Lodges in Stockbridge ](https://expedia.ca/Stockbridge-Lodges.d162575-aaLodges.Travel-Guide-Accommodation)
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## Frequently asked questions

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