Title: Southfield Vacation Home Rentals from CA $366: Search Top Private Vacation Homes for Rent | Expedia.ca

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## Check prices for these dates

In two weeks

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=6339785&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 two months

[Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=6339785&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=6339785&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 19 - Jun 21](https://www.expedia.ca/Hotel-Search?regionId=6339785&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Southfield vacation homes

![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/106000000/105240000/105230400/105230373/2281e60c.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

9.8/10

Exceptional

(13 reviews)

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

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

Matthew F.

CA $244

CA $570 total

includes taxes & fees

Mar 23 - Mar 24

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

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

![4 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/bf37a122.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/68707c00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106040000/106031100/106031055/979641d4.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

9.4/10

Exceptional

(9 reviews)

"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 $145

CA $892 total

includes taxes & fees

Feb 25 - Feb 26

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

![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)

![Living area](https://images.trvl-media.com/lodging/123000000/122840000/122835900/122835857/w1504h1042x0y3-2d812057.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)

### Litchfield Retreat, Wineries, Foliage & Skiing

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

Torrington

CA $357

CA $549 total

includes taxes & fees

Feb 28 - Mar 1

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

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

![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/055ed8a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/cc4451e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, stovetop, electric kettle](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/52345b94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Family Ski Getaway in the Berkshires

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

Great Barrington

9.0/10

Wonderful

(11 reviews)

"Close to a great bakery and near to a farm market and shopping mall. "

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

Cristine C.

CA $277

CA $430 total

includes taxes & fees

Feb 26 - Feb 27

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

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

![Property grounds](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/9046d578.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

(34 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 $409

CA $890 total

includes taxes & fees

Feb 26 - Feb 27

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

![Interior](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/0f27818f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/2350af4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/f63afa55.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 reviews)

"Perfect spot for a family celebration!"

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

Kerry P.

CA $246

CA $469 total

includes taxes & fees

Mar 4 - Mar 5

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

![Exterior](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/6137aab0.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)

![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)

### Home in Great Barrington

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

Great Barrington

9.8/10

Exceptional

(27 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 $221

CA $367 total

includes taxes & fees

Mar 2 - Mar 3

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

![TV, fireplace, printers](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/4d94597a.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)

![Exterior](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/772f14ec.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

(3 reviews)

"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 $775

CA $1,816 total

includes taxes & fees

Feb 25 - Feb 26

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

![Exterior detail](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/4ce0af29.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/ab946d75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/3e6e58ca.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

(42 reviews)

"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 $325

CA $691 total

includes taxes & fees

Mar 8 - Mar 9

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

10/10

Exceptional

(1 review)

"Without a doubt, we will be back! Your home was so beautiful, warm and comfortable. Our host was so helpful and friendly. We can't thank you enough for providing such a wonderful experience to our trip. "

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

Linda D.

CA $363

CA $820 total

includes taxes & fees

Feb 25 - Feb 26

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

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/399488d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/c34ecca5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/8b16599a.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 reviews)

"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 $185

CA $366 total

includes taxes & fees

Feb 25 - Feb 26

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

9.6/10

Exceptional

(4 reviews)

"Very charming, comfortable, and clean. It was in a great location and only minutes away from a lot of sightseeing locations. House management was very accommodating and friendly. I would stay here again."

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

Paulo I.

CA $246

CA $627 total

includes taxes & fees

Feb 25 - Feb 26

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

![Dining](https://images.trvl-media.com/lodging/119000000/118470000/118467400/118467341/60ca61c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/119000000/118470000/118467400/118467341/99099166.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/119000000/118470000/118467400/118467341/6dacf3a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/119000000/118470000/118467400/118467341/ac949794.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Whispering Estate Guest House - Countryside Getaway

[](https://www.expedia.ca/Goshen-Hotels-Whispering-Estate-Guest-House-A-Romantic-Countryside-Getaway.h118467341.Hotel-Information)

Goshen

10/10

Exceptional

(5 reviews)

"Beautiful property and great location. A true retreat. "

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

Andrea B.

CA $739

CA $1,220 total

includes taxes & fees

Feb 27 - Feb 28

[](https://www.expedia.ca/Goshen-Hotels-Whispering-Estate-Guest-House-A-Romantic-Countryside-Getaway.h118467341.Hotel-Information)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120050000/120045500/120045407/4f2c31bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/121000000/120050000/120045500/120045407/6873f6f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120050000/120045500/120045407/803c069e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/121000000/120050000/120045500/120045407/b9e06e08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy. Clean. Free bagel shop. 3 Fireplaces.

[](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Clean-Free-Bagel-Shop-3-Fireplaces.h120045407.Hotel-Information)

Great Barrington

10/10

Exceptional

(1 review)

"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"

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

Mary R.

CA $466

CA $802 total

includes taxes & fees

Feb 25 - Feb 26

[](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Clean-Free-Bagel-Shop-3-Fireplaces.h120045407.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/121000000/120280000/120275400/120275326/528fbc22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/121000000/120280000/120275400/120275326/1c2ae12d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/121000000/120280000/120275400/120275326/a296b140.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120280000/120275400/120275326/d9eeb6ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Secluded Sophistication in the Berkshires - 49 Acres of Quiet Luxury in Becket.

[](https://www.expedia.ca/Becket-Hotels-Secluded-Sophistication-In-The-Berkshires-49-Acres-Of-Quiet-Luxury-In-Becket.h120275326.Hotel-Information)

Becket

10/10

Exceptional

(1 review)

"Beautiful home, attentive host. Location is as peaceful as can be. "

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

Rick M.

CA $471

CA $860 total

includes taxes & fees

Feb 25 - Feb 26

[](https://www.expedia.ca/Becket-Hotels-Secluded-Sophistication-In-The-Berkshires-49-Acres-Of-Quiet-Luxury-In-Becket.h120275326.Hotel-Information)

![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)

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/64f95c5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/87b97def.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

(26 reviews)

"Nice large kitchen and yard, walking distance to downtown, friendly neighborhood- we enjoyed our stay! "

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

Deb W.

CA $390

CA $714 total

includes taxes & fees

Mar 1 - Mar 2

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/8b34823f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/b9c0be0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, table tennis](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/17bd9585.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/9510eac9.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

8.8/10

Excellent

(3 reviews)

"House was clean and made our Thanksgiving great with it's size and amenities. "

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

Khalil S.

CA $650

CA $1,179 total

includes taxes & fees

Mar 16 - Mar 17

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34910000/34909900/34909812/c91d8041.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/35000000/34910000/34909900/34909812/335992a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/35000000/34910000/34909900/34909812/0c61e6f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/35000000/34910000/34909900/34909812/bb73a401.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

###  A Country Lodge Straight Out of the Pages of a Great Novel

[](https://www.expedia.ca/Pine-Plains-Hotels-A-Country-Lodge-Straight-Out-Of-The-Pages-Of-A-Great-Novel.h34909812.Hotel-Information)

Pine Plains

10/10

Exceptional

(13 reviews)

"Our group of parents and riders had a great stay during the Millbrook Horse Trials in July. Clean facility, ample room, responsive host. Would stay again."

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

Hessie S.

CA $1,219

CA $2,014 total

includes taxes & fees

Feb 25 - Feb 26

[](https://www.expedia.ca/Pine-Plains-Hotels-A-Country-Lodge-Straight-Out-Of-The-Pages-Of-A-Great-Novel.h34909812.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-03-10&endDate=2026-03-11&regionId=6339785&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## Find vacation rentals that suit your style

Aparthotels

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Apartments

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Condos

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Cottages

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Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Southfield%2C+Massachusetts%2C+United+States+of+America&regionId=6339785&latLong=42.10148%2C-73.232889&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=VACATION_HOME)

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Southfield%2C+Massachusetts%2C+United+States+of+America&regionId=6339785&latLong=42.10148%2C-73.232889&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=CABIN)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Southfield%2C+Massachusetts%2C+United+States+of+America&regionId=6339785&latLong=42.10148%2C-73.232889&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=CHALET)

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## Top Southfield 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

"Affordable price, clean bedroom and close to everything. "

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

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

### Quality Inn

10/10 Excellent

"Clean, breakfast was a nice option before heading to Butternut mountain nearby "

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

![Prospect Berkshires](https://images.trvl-media.com/lodging/117000000/116740000/116739800/116739795/b42c4262_y.jpg)

### Prospect Berkshires

10/10 Excellent

"The cabins are brand new, the property is gorgeous, restaurant features local and quality product and the staff is very responsive via text message. The lakeside sauna is private and easy to reserve. Great place!"

[](https://expedia.ca/Great-Barrington-Hotels-Prospect-Berkshires.h116739795.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 location, amenities, pool and hot tub for the kids, friendly staff, comfortable room."

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

"great customer service"

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

![Quality Inn](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/1d74d3f4_y.jpg)

### Quality Inn

10/10 Excellent

"Great "

[](https://expedia.ca/Lee-Hotels-Quality-Inn.h459706.Hotel-Information)

![Element Lenox Berkshires](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/c0933de7_y.jpg)

### Element Lenox Berkshires

10/10 Excellent

"Really nice hotel with incredibly accommodating staff"

[](https://expedia.ca/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information)

![Interlaken Inn & Resort](https://images.trvl-media.com/lodging/20000000/19680000/19679700/19679605/dbbfdf3a_y.jpg)

### Interlaken Inn & Resort

10/10 Excellent

"The restaurant, food and wait staff were fab!!! "

[](https://expedia.ca/Torrington-Hotels-Interlaken-Inn-Resort.h19679605.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

"Super clean spacious room! "

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

## Find out more about Southfield

## Southfield Vacation Homes information

| Number of reviews | 321                |
| ----------------- | ------------------ |
| Accommodation     | 368 Vacation Homes |
| Lowest Price      | CA $366            |
| Highest Price     | CA $2,014          |

## Explore a world of travel with Expedia

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