Title: Great Barrington Vacation Rentals from CA $204: Short-Term Rentals for 2025 | Expedia.ca

 

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![Great Barrington which includes signage and night scenes](https://images.trvl-media.com/place/110336/4c3d827f-8ba1-4754-a7a1-6fe14b81f0f7.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Great Barrington Vacation Rentals

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## Check prices for these dates

In two weeks

[Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=110336&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=110336&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=110336&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=110336&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)

## Vacation Rentals in Great Barrington

![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)

![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

Great Barrington

9.8/10

Exceptional

(25)

"Enjoyed our stay!!!"

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

Fred W.

CA $221

CA $373 total

includes taxes & fees

Nov 19 - Nov 20

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

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

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

### Pet Friendly Riverfront Home in Great Barrington

Great Barrington

9.0/10

Wonderful

(4)

"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 $268

CA $397 total

includes taxes & fees

Nov 20 - Nov 21

[](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/121000000/120150000/120149100/120149051/772f14ec.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)

![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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/2cdfc6fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Great Barrington

10/10

Exceptional

(1)

"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 $798

CA $1,868 total

includes taxes & fees

Nov 20 - Nov 21

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

![Exterior](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/1bcf2f0b.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)

![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)

### Great Barrington Get Away

Great Barrington

9.4/10

Exceptional

(25)

"The host was very communicative and responsive during our arrival and check out. The listing and everything was as it said we were very pleased with both the location of the home and the actual home itself and the property walking distance to town truly cannot say enough. Thank you for Your hospitality. Our family is very grateful. "

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

Amy B.

CA $400

CA $727 total

includes taxes & fees

Nov 20 - Nov 21

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

![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107110000/107109200/107109194/220997f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/108000000/107110000/107109200/107109194/1ebb7045.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/108000000/107110000/107109200/107109194/6b0b575e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/108000000/107110000/107109200/107109194/dd672984.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Chatham

10/10

Exceptional

(3)

"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 $302

CA $506 total

includes taxes & fees

Nov 19 - Nov 20

[](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)

![Exterior](https://images.trvl-media.com/lodging/103000000/102810000/102806400/102806391/f7d742eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102810000/102806400/102806391/10a12328.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/103000000/102810000/102806400/102806391/c465f1b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Chatham

10/10

Exceptional

(6)

"Perfect blend of decore, comfort, and function. We went to Tanglewood which was only a half hour away. Came back to hot tub and fire pit. Beds here are soooo comfy! This is our 2nd time here and won’t be our last."

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

Melissa D.

CA $301

CA $504 total

includes taxes & fees

Nov 19 - Nov 20

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

![Indoor pool, outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/5c348ca4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/f251fc45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property - evening/night](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/eda478dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/f5477a61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Ponds at Foxhollow

Lenox

8.6/10

Excellent

(134)

"We were 4 adult friends sharing a 2-bedroom and enjoyed the size of the space and the location of the condo was under a 10 min drive to all the sights"

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

michelle

CA $195

CA $218 total

includes taxes & fees

Dec 5 - Dec 6

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

![Balcony](https://images.trvl-media.com/lodging/40000000/39670000/39665000/39664922/d78d1e6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![8. The Riverview Room](https://images.trvl-media.com/lodging/40000000/39670000/39665000/39664922/40f18d40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/40000000/39670000/39665000/39664922/4eca1141.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/40000000/39670000/39665000/39664922/5d3c366a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Micosta Leisure Inn

Hudson

9.2/10

Wonderful

(131)

"Clean, pet friendly , just an overall super nice place to stay "

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

Gail

CA $182

CA $204 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Hudson-Hotels-Micosta-Leisure-Inn.h39664922.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/121000000/120660000/120659000/120658954/b25675ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books, music library](https://images.trvl-media.com/lodging/121000000/120660000/120659000/120658954/b10644c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books, music library](https://images.trvl-media.com/lodging/121000000/120660000/120659000/120658954/7a00417e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120660000/120659000/120658954/a0bb237f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pet-Friendly Hudson Escape w/ Hot Tub

Stottville

CA $214

CA $452 total

includes taxes & fees

Nov 19 - Nov 20

[](https://www.expedia.ca/Hudson-Hotels-Pet-Friendly-Hudson-Escape-W-Hot-Tub.h120658954.Hotel-Information)

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

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

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

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/60000000/60000000/59995300/59995220/f501a761.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### All the comforts of home

Hudson

9.2/10

Wonderful

(28)

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

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

Marisa P.

CA $149

CA $199 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Hudson-Hotels-All-The-Comforts-Of-Home.h59995220.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/w5278h3491x0y0-d48a63f5.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)

![Dining](https://images.trvl-media.com/lodging/115000000/114880000/114878300/114878238/e6df39fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Home in the Woods

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 $237

CA $451 total

includes taxes & fees

Nov 20 - Nov 21

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

![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)

![Exterior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/51a25809.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)

### Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Sherwood Forest

10/10

Exceptional

(4)

"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 $205

CA $530 total

includes taxes & fees

Nov 19 - Nov 20

[](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/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)

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

Russell

10/10

Exceptional

(143)

"Lovely old farmhouse with authentic yet comfortable furnishings. Would recommend!"

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

Jon O.

CA $216

CA $438 total

includes taxes & fees

Nov 19 - Nov 20

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

![Property grounds](https://images.trvl-media.com/lodging/60000000/59990000/59987600/59987529/41313771.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/60000000/59990000/59987600/59987529/97b8d9ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/60000000/59990000/59987600/59987529/90-e74888f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/60000000/59990000/59987600/59987529/90-d8c61953.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### All comforts of home

Hudson

9.8/10

Exceptional

(50)

"Loved the place and would love to come back. "

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

Georgine

CA $138

CA $185 total

includes taxes & fees

Nov 19 - Nov 20

[](https://www.expedia.ca/Hudson-Hotels-All-Comforts-Of-Home.h59987529.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/100000000/99410000/99407400/99407400/0791e99a.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)

![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)

![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

New Lebanon

CA $1,147

CA $2,306 total

includes taxes & fees

Nov 19 - Nov 20

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

![Property grounds](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/2278baae.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)

### Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

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 $225

CA $550 total

includes taxes & fees

Nov 20 - Nov 21

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

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

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

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

![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

Lebanon Springs

8.8/10

Excellent

(20)

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

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

Kaye S.

CA $192

CA $525 total

includes taxes & fees

Nov 19 - Nov 20

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

![Exterior](https://images.trvl-media.com/lodging/113000000/112620000/112619100/112619076/072199c3.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)

![Interior](https://images.trvl-media.com/lodging/113000000/112620000/112619100/112619076/fe676105.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 3-bedroom Cabin for nature lovers

Stephentown

7.0/10

Good

(2)

"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 $185

CA $408 total

includes taxes & fees

Nov 20 - Nov 21

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

![Dining](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/9fa6f837.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/eca50f2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/edf60411.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/565807cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Guesthouse Cabin vacation rentals in Berkshire County

Sheffield

10/10

Exceptional

(9)

"Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space. "

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

deborah d.

CA $576

CA $978 total

includes taxes & fees

Nov 20 - Nov 21

[](https://www.expedia.ca/Sheffield-Hotels-Guesthouse-Cabin-Vacation-Rentals-In-Berkshire-County.h99962392.Hotel-Information)

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## Top Great Barrington Hotel Reviews

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

10/10 Excellent

"Everything was amazing my bf did get a beer at the bar that was expired but everything else was amazing "

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

### Monument Mountain Motel

10/10 Excellent

"my go to spot when visiting area. owners care about their property and always clean. "

[](https://expedia.ca/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.Hotel-Information)

### The Yankee, Trademark Collection by Wyndham

10/10 Excellent

"Great stay!"

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

### Berkshire Mountain Lodge

10/10 Excellent

"The suites were large. Nice to have separate bedroom. Kitchen with all the basics. Perfect for a getaway "

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

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

10/10 Excellent

"The room was nice, but wish we would have asked for the lake view. The breakfast area was really nice and they had good food. The coffee machine was available 24/7 and it made a pretty good mocha! "

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

### Berkshires Untold

10/10 Excellent

"Enjoyed the Clubhouse before retiring in for the evening. Cozy, comfortable, and relaxing atmosphere."

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

### Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

10/10 Excellent

"Clean room, very courteous staff "

[](https://expedia.ca/Great-Barrington-Hotels-Fairfield-Inn-Suites-By-Marriott-Great-Barrington-LenoxBerkshires.h913175.Hotel-Information)

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

10/10 Excellent

"Early check in."

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

### Pet Friendly Riverfront Home in Great Barrington

10/10 Excellent

"Amazing cosy property. The berkshires are beautiful and Marisa was a great host. Thank you for having us!"

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

## Find out more about Great Barrington

**Everything you need to know about** **Great Barrington** **vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Great Barrington vacation rental for you. At Expedia, you can take your pick from [private vacation homes](https://www.expedia.ca/aa/PrivateVacationHomes), [apartments](https://www.expedia.ca/aa/Apartments), cottages, [cabins](https://www.expedia.ca/aa/Cabins), villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Great Barrington vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

**Great Barrington vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Great Barrington. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Great Barrington vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Great Barrington vacation rentals we have selected for you start as low as CA $204 per night. Entering your travel dates in the search wizard you might find even better deals!

**How to find incredible deals on Great Barrington rentals**

At Expedia, we put the best Great Barrington vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Great Barrington rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Great Barrington vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Great Barrington. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

## Explore a world of travel with Expedia

-   Trending destinations on Expedia.ca
-   All accommodation types in Great Barrington

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-   [Vacation Homes in Great Barrington](https://expedia.ca/Great-Barrington-Private-Vacation-Homes.d110336-aaPrivateVacationHomes.Travel-Guide-Accommodation)
-   [Cottages in Great Barrington](https://expedia.ca/Great-Barrington-Cottages.d110336-aaCottages.Travel-Guide-Accommodation)
-   [Apartments in Great Barrington](https://expedia.ca/Great-Barrington-Apartments.d110336-aaApartments.Travel-Guide-Accommodation)
-   [B&B in Great Barrington](https://expedia.ca/Great-Barrington-Bed-And-Breakfast.d110336-aaBedAndBreakfast.Travel-Guide-Accommodation)
-   [Farmstay in Great Barrington](https://expedia.ca/Great-Barrington-Agritourism.d110336-aaAgritourism.Travel-Guide-Accommodation)
-   [Cabin Rentals in Great Barrington](https://expedia.ca/Great-Barrington-Cabins.d110336-aaCabins.Travel-Guide-Accommodation)
-   [Motels in Great Barrington](https://expedia.ca/Great-Barrington-Motels.d110336-aaMotels.Travel-Guide-Accommodation)
-   [Guest Houses in Great Barrington](https://expedia.ca/Great-Barrington-Guest-Houses.d110336-aaGuestHouses.Travel-Guide-Accommodation)
-   [Condo Rentals in Great Barrington](https://expedia.ca/Great-Barrington-Condos.d110336-aaCondos.Travel-Guide-Accommodation)
-   [Inns in Great Barrington](https://expedia.ca/Great-Barrington-Inns.d110336-aaInns.Travel-Guide-Accommodation)
-   [Resorts in Great Barrington](https://expedia.ca/Great-Barrington-Resort-Hotels.d110336-aaResortHotels.Travel-Guide-Accommodation)
-   [Aparthotels in Great Barrington](https://expedia.ca/Great-Barrington-Apart-Hotels.d110336-aaApartHotels.Travel-Guide-Accommodation)
-   [Chalets in Great Barrington](https://expedia.ca/Great-Barrington-Chalets.d110336-aaChalets.Travel-Guide-Accommodation)
-   [Villas in Great Barrington](https://expedia.ca/Great-Barrington-Villas.d110336-aaVillas.Travel-Guide-Accommodation)
-   [Lodges in Great Barrington](https://expedia.ca/Great-Barrington-Lodges.d110336-aaLodges.Travel-Guide-Accommodation)
-   [Condo Resorts in Great Barrington](https://expedia.ca/Great-Barrington-Condominium-Resort.d110336-aaCondominiumResort.Travel-Guide-Accommodation)
-   [Country Houses in Great Barrington](https://expedia.ca/Great-Barrington-Country-House.d110336-aaCountryHouse.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find a vacation rental in Great Barrington?

> Yes, there are vacation rentals close to the most popular points of interest in Great Barrington, or you can select a secluded option if you're looking for relaxation. Visitors like the top-notch restaurants and live music in Great Barrington. Leave some time to check out the ski slopes and theater scene during your trip.

### What are some of the best vacation rentals in Great Barrington?

> [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): Visitors give good reviews to this Great Barrington vacation home rental, which is located on a river and has a fireplace, a garden, and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms in addition to a kitchen with a stovetop and a microwave. You and your friends and family can relax into your vacation with amenities like a selection of games.

### How many vacation rentals are there in Great Barrington?

> With 95 Expedia vacation rentals, you're sure to find just the right place for your Great Barrington stay.

### What can I see and do in Great Barrington?

> Cultural attractions include Mahaiwe Performing Arts Center and Art et Industrie, whereas Housatonic River Walk and Housatonic River are a couple of picturesque spots to enjoy the outdoors. Lake Mansfield Park and Ski Butternut are other places to visit while you're in town.

### What are vacation rentals like in Great Barrington?

> Vacation rentals are privately owned properties you can reserve for several days or more in Great Barrington. Vacation rentals offer extras such as patios, hot tubs, and fire pits so your stay will be comfortable. If you're concerned about a clean environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a great choice for a family getaway.

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Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

Scan the QR code with your device camera and download our app

![QR code to download the app](data:image/png;base64,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)