Title: Sandisfield Vacation Home Rentals from CA $319: Search Top Private Vacation Homes for Rent | Expedia.ca

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![Berkshire Mountains in Autumn, Deerfield, Massachusetts](https://images.trvl-media.com/place/6005416/6595cd42-1d01-4e5f-9aef-a684aa8e9639.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Sandisfield Vacation Rentals

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## Check prices for these dates

Next weekend

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6005416&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6005416&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=6005416&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6005416&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Sandisfield vacation homes

![Exterior detail](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/3db87cef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/e729bc4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/1e32801e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/1c3ab355.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### CT Gate House Goshen CT, Gate House Goshen CT

[](https://www.expedia.ca/Goshen-Hotels-Gate-House-Goshen-CT.h106031055.Hotel-Information)

Goshen

9.8/10

Exceptional

(7)

"The property was great and the house was huge even for all 12 of us "

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

Ryan L.

CA $130

CA $871 total

includes taxes & fees

Dec 16 - Dec 17

[](https://www.expedia.ca/Goshen-Hotels-Gate-House-Goshen-CT.h106031055.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/115000000/114880000/114878300/114878238/abcd3f54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/115000000/114880000/114878300/114878238/5ffcffb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/115000000/114880000/114878300/114878238/138b1f2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/115000000/114880000/114878300/114878238/w5278h3491x0y0-d48a63f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Home in the Woods

[](https://www.expedia.ca/Westfield-Hotels-Home-In-The-Woods.h114878238.Hotel-Information)

Russell

10/10

Exceptional

(3)

"We really enjoyed our stay at the Home in the Woods. We stayed for 1 night on the way to Amherst for a graduation. The home is very cozy and clean. Jessica was easy to communicate with and the check-in/check out process was simple. Highly recommend!"

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

Travis H.

CA $234

CA $443 total

includes taxes & fees

Dec 12 - Dec 13

[](https://www.expedia.ca/Westfield-Hotels-Home-In-The-Woods.h114878238.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)

![Exterior](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/e0f691bb.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)

### 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)

"Enjoyed our stay!!!"

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

Fred W.

CA $181

CA $319 total

includes taxes & fees

Dec 15 - Dec 16

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

![Outdoor dining](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/ecdea449.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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)

![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/162d61f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/4bbc4f9b.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)

"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 $201

CA $516 total

includes taxes & fees

Dec 22 - Dec 23

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

![Property grounds](https://images.trvl-media.com/lodging/114000000/113210000/113200800/113200740/045435f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/114000000/113210000/113200800/113200740/058c7fd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books, stereo](https://images.trvl-media.com/lodging/114000000/113210000/113200800/113200740/8a868c6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/114000000/113210000/113200800/113200740/be1e6f28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

[](https://www.expedia.ca/East-Granby-Hotels-The-Olde-Tobacco-Barn-East-Granby-Close-To-Airport.h113200740.Hotel-Information)

East Granby

8.6/10

Excellent

(4)

"Great Stay at the Olde Tobacco Barn. Was here for a work trip, and the place was perfect for our needs. House is set back really nicely and private. Host was super responsive and easy to deal with. Overall 5/5 stay. Thank you!"

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

Sgt W.

CA $207

CA $601 total

includes taxes & fees

Dec 16 - Dec 17

[](https://www.expedia.ca/East-Granby-Hotels-The-Olde-Tobacco-Barn-East-Granby-Close-To-Airport.h113200740.Hotel-Information)

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

![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)

![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/347359ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/c04d3199.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)

"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 $222

CA $543 total

includes taxes & fees

Dec 15 - Dec 16

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

![Smart TV, fireplace](https://images.trvl-media.com/lodging/108000000/107970000/107960200/107960143/2df5cbed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/108000000/107970000/107960200/107960143/c79da4f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/108000000/107970000/107960200/107960143/81d94858.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107970000/107960200/107960143/affcc370.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sun Filled Lake House Living

[](https://www.expedia.ca/Avon-Hotels-Sun-Filled-Lake-House-Living.h107960143.Hotel-Information)

Avon

6.0/10

(3)

"Enjoyed my stayConvenient location for restaurants, shopping etcHome was clean and neat and in a nice quiet neighborhood Good value"

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

Joseph C.

CA $83

CA $336 total

includes taxes & fees

Jan 6 - Jan 7, 2026

[](https://www.expedia.ca/Avon-Hotels-Sun-Filled-Lake-House-Living.h107960143.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)

![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)

![Exterior](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/333900eb.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)

### Sweet Cozy Victorian in Housatonic. Close to everything. 

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

Housatonic

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 15 - Dec 16

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

### Perfect House In Hillsdale, Brings Friends & Fam

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

Hillsdale

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 $258

CA $717 total

includes taxes & fees

Dec 12 - Dec 13

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/52000000/51690000/51685500/51685419/1bc1a012.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/52000000/51690000/51685500/51685419/w1026h680x0y3-1207c37a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/52000000/51690000/51685500/51685419/cd7d0c00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/52000000/51690000/51685500/51685419/4f70f9c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

[](https://www.expedia.ca/Canton-Hotels-Gorgeous-River-Views-On-Rails-To-Trails-And-Just-Steps-To-Quaint-Collinsville.h51685419.Hotel-Information)

Collinsville

10/10

Exceptional

(61)

"Fabulous location. I can honestly say cleanest VRBO we’ve ever stayed!!"

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

Jeanmarie G.

CA $399

CA $675 total

includes taxes & fees

Dec 16 - Dec 17

[](https://www.expedia.ca/Canton-Hotels-Gorgeous-River-Views-On-Rails-To-Trails-And-Just-Steps-To-Quaint-Collinsville.h51685419.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)

![Dining](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/8f9296e7.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)

### Cheerful 3-bedroom cottage with woodstove

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

Sheffield

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 $272

CA $625 total

includes taxes & fees

Dec 15 - Dec 16

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

![Property grounds](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/7377fc19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/0e82b119.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/508c5b2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/af5c0679.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Big farmhouse in the foothills of the Berkshires

[](https://www.expedia.ca/Russell-Hotels-Big-Farmhouse-In-The-Foothills-Of-The-Berkshires.h19107245.Hotel-Information)

Russell

10/10

Exceptional

(143)

"Perfect spot for a family celebration!"

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

Kerry P.

CA $276

CA $494 total

includes taxes & fees

Dec 16 - Dec 17

[](https://www.expedia.ca/Russell-Hotels-Big-Farmhouse-In-The-Foothills-Of-The-Berkshires.h19107245.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)

![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/59edf6fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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)

### Pet Friendly Riverfront Home in Great Barrington

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

Great Barrington

9.4/10

Exceptional

(6)

CA $280

CA $412 total

includes taxes & fees

Dec 15 - Dec 16

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/505c31c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/53261c35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/1bcf2f0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player, books, stereo](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/8d87241a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Great Barrington Get Away

[](https://www.expedia.ca/Great-Barrington-Hotels-Great-Barrington-Get-Away.h29615546.Hotel-Information)

Great Barrington

9.4/10

Exceptional

(25)

"We stayed here for Memorial Day weekend and had a wonderful trip. Close to the downtown shops, and all the supplies a family needs staying in a home. Thanks for the great stay!"

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

Elizabeth G.

CA $393

CA $712 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Great-Barrington-Hotels-Great-Barrington-Get-Away.h29615546.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/1993f238.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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/145ce996.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/w2439h1242x124y0-c2be86b7.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

(29)

"Great stay in a well appointed house close to trails, Stockbridge center, and a quick car trip to Lenox, Great Barrington, Tanglewood, Jacobs Pillow, and Shakespeare & Co. we enjoyed the morning walks, coffee at the Lost Lamb, drinks at the Red Lion Inn, dance at Jacob’s Pillow, music at Tanglewood, ice cream at High Lawn Farm, and just that Berkshire vibe! "

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

Phillip F.

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99880000/99871300/99871289/9b2ca530.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/100000000/99880000/99871300/99871289/3b701cd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books, stereo](https://images.trvl-media.com/lodging/100000000/99880000/99871300/99871289/74e75f2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/100000000/99880000/99871300/99871289/62d8f4dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern Ranch Retreat in Hudson Valley

[](https://www.expedia.ca/Millerton-Hotels-Modern-Ranch-Retreat-In-Hudson-Valley.h99871289.Hotel-Information)

Millerton

10/10

Exceptional

(4)

"Great communication and a fantastic property! The setting is quiet and short walk to downtown Millerton. The Harlem Valley Rail Trail Line is just down the road which offers excellent opportunities for adventures!"

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

Scott E.

CA $422

CA $758 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Millerton-Hotels-Modern-Ranch-Retreat-In-Hudson-Valley.h99871289.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/123000000/122840000/122835900/122835857/f5b911c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/123000000/122840000/122835900/122835857/6f1f9830.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/123000000/122840000/122835900/122835857/w1512h1050x0y79-c667dc04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122840000/122835900/122835857/w1255h1510x0y6-72057f34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Litchfield Retreat, Wineries, Foliage & Skiing

[](https://www.expedia.ca/Torrington-Hotels-Litchfield-Retreat.h122835857.Hotel-Information)

Torrington

CA $320

CA $497 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Torrington-Hotels-Litchfield-Retreat.h122835857.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/124000000/123030000/123028900/123028859/e6a8de71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/124000000/123030000/123028900/123028859/07647859.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/124000000/123030000/123028900/123028859/9f6d0429.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/124000000/123030000/123028900/123028859/4ac89d04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills

[](https://www.expedia.ca/Goshen-Hotels-Sequoia-House-Charming-Goshen-Getaway-Quiet-Retreat-In-Litchfield-Hills.h123028859.Hotel-Information)

Goshen

CA $344

CA $723 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Goshen-Hotels-Sequoia-House-Charming-Goshen-Getaway-Quiet-Retreat-In-Litchfield-Hills.h123028859.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/772f14ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

![TV, fireplace, printers](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/69c2e8f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/b2f15e32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

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

Great Barrington

10/10

Exceptional

(2)

"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"

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

Roberta

CA $781

CA $1,832 total

includes taxes & fees

Dec 21 - Dec 22

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

![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/58b0972d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/d06b32cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/636f9a34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/fb68a83f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious 5-bedroom house in charming Lee with WiFi

[](https://www.expedia.ca/Lee-Hotels-Spacious-5-Bedroom-House-In-Charming-Lee-With-WiFi.h117382215.Hotel-Information)

Lee

8.0/10

Very good

(1)

"House was large, clean, and comfortable. "

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

John Z.

CA $530

CA $1,022 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Lee-Hotels-Spacious-5-Bedroom-House-In-Charming-Lee-With-WiFi.h117382215.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=2025-12-25&endDate=2025-12-26&regionId=6005416&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Apartments

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Private vacation homes

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Villas

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Cottages

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Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Sandisfield%2C+Massachusetts%2C+United+States+of+America&regionId=6005416&latLong=42.112591%2C-73.143166&adults=2&startDate=2026-03-10&d1=2026-03-10&endDate=2026-03-13&d2=2026-03-13&lodging=CABIN)

Chalets

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## Top Sandisfield Hotel Reviews

![Simsbury Inn](https://images.trvl-media.com/lodging/1000000/20000/16800/16756/ceb52ab8_y.jpg)

### Simsbury Inn

10/10 Excellent

"The personnel was very helpful & accomodating, both at the front desk & upstairs restaurant. I appreciated that they set out two rooms as adjoining even before I asked. "

[](https://expedia.ca/Weatogue-Hotels-Simsbury-Inn.h16756.Hotel-Information)

![Holiday Inn Express Hotel & Suites Great Barrington by IHG](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598_y.jpg)

### Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent

"Great hospitality "

[](https://expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.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

"Excellent stay, nice, clean 2 bedroom Villa, staff excellent, amenities excellent, great location would definitely stay again "

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

"Comfortable, quiet, clean, great breakfast "

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

"It was all well cared for."

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

![Days Inn by Wyndham Torrington](https://images.trvl-media.com/lodging/1000000/50000/50000/49932/c8b8e6a2_y.jpg)

### Days Inn by Wyndham Torrington

10/10 Excellent

"Clean comfortable room,great parking and local shopping "

[](https://expedia.ca/Torrington-Hotels-Days-Inn-By-Wyndham-Torrington.h49932.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 am a cross country traveling nurse. The Berkshire Mountain Lodge was perfect for my needs. A fully functioning well appointed kitchen. Spacious living quarters with excellent views. The best water pressure on a shower that I have ever known. Fantastic after a long day of work or out hiking the many nature trails here. And the bed was so perfectly firm and cozy that I drifted effortlessly to sleep. The grounds, the amenities and the coordinated activities to bring you together in community made me feel included. Definitely a place I will continue to return to for many years."

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

"The room was spacious and clean, the jetted tub was a nice treat, and the breakfast was fresh. "

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

![The Ponds at Foxhollow](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/5c348ca4_y.jpg)

### The Ponds at Foxhollow

10/10 Excellent

"There was a coffee machine but no filters nor beans. I wish they had been provided."

[](https://expedia.ca/Lenox-Hotels-The-Ponds-At-Foxhollow-By-Capital-Vacations.h18109961.Hotel-Information)

## Find out more about Sandisfield

## Sandisfield Vacation Homes information

| Number of reviews | 362                |
| ----------------- | ------------------ |
| Accommodation     | 384 Vacation Homes |
| Lowest Price      | CA $319            |
| Highest Price     | CA $1,832          |

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