Holiday Homes in Great Barrington

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Our top choices for Great Barrington holiday homes

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.2 out of 10, Wonderful, (14 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is AU$438
includes taxes & fees
8 June - 9 June
Cozy Riverside Berkshires Retreat

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (31 reviews)
"Everything was as advertised!"
United States
Jessica S.
The price is AU$498
includes taxes & fees
14 June - 15 June
Home in Great Barrington

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 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
Mary R.
The price is AU$728
includes taxes & fees
17 June - 18 June
Cozy. Clean. Free bagel shop. 3 Fireplaces.

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

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (5 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
Roberta
The price is AU$1,809
includes taxes & fees
4 June - 5 June
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (32 reviews)
"The location was just what we were looking for, the cabin was cozy and clean, and the host was so helpful and welcoming!"
United States
Olivia C.
The price is AU$200
includes taxes & fees
7 June - 8 June
All the comforts of home

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AU$521
includes taxes & fees
4 June - 5 June
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (15 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is AU$540
includes taxes & fees
8 June - 9 June
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
The price is AU$540
includes taxes & fees
9 June - 10 June
stylish Berkshires Retreat

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.4 out of 10, Exceptional, (26 reviews)
"Very clean, fully stocked kitchen,great location "
United States
Karen H.
The price is AU$540
includes taxes & fees
7 June - 8 June
Near Tanglewood: Historic Summer Retreat

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

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.4 out of 10, Exceptional, (3 reviews)
"excellent communication with property manager."
United States
Nancy H.
The price is AU$787
includes taxes & fees
4 June - 5 June
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is AU$407
includes taxes & fees
7 June - 8 June
Real Estate: Therapy - Lake, Laundry, Love it

NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet

NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet
New Lebanon
8.0 out of 10, Very good, (1 review)
"This location is great as an overnight trip. It’s centralized between ski resorts, restaurants near Pittsfield, MA and local NY. "
United States
Luz A.
The price is AU$562
includes taxes & fees
5 June - 6 June
NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.6 out of 10, Exceptional, (5 reviews)
"Mark was very communicative and helpful, answering all questions quickly and accurately"
United States
Jim S.
The price is AU$477
includes taxes & fees
7 June - 8 June
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Larkspire I Sleepy Hollow Lake I Beach & Firepit

Larkspire I Sleepy Hollow Lake I Beach & Firepit
Athens
The price is AU$777
includes taxes & fees
8 June - 9 June
Larkspire I Sleepy Hollow Lake I Beach & Firepit

rural, serene + sophisticated space

rural, serene + sophisticated space
Red Hook
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful property with unique accommodations in the Hudson Valley"
United States
BRIAN PATRICK M.
The price is AU$554
includes taxes & fees
17 June - 18 June
rural, serene + sophisticated space

Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.

Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.
Hudson’
The price is AU$427
includes taxes & fees
9 June - 10 June
Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.

Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (147 reviews)
"The house is absolutely charming and cozy. It was very clean as well. "
United States
Amanda C.
The price is AU$507
includes taxes & fees
4 June - 5 June
Big farmhouse in the foothills of the Berkshires

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is AU$815
includes taxes & fees
9 June - 10 June
Treetop Hideaway in Tyringham

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Old Chatham
10.0 out of 10, Exceptional, (2 reviews)
"We enjoyed our stay at this property. The hot tub was great and the home was immaculate!"
United States
Terri E.
The price is AU$722
includes taxes & fees
4 June - 5 June
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]

Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]
Hudson
10.0 out of 10, Exceptional, (7 reviews)
"Nice house, decorations well done… communications with host were answered very quickly!"
United States
Brittaney O.
The price is AU$921
includes taxes & fees
22 June - 23 June
Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]
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 Great Barrington Hotel Reviews

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Great Barrington Holiday Homes information

Number of reviews
9,726
Accommodation
534 Holiday Homes
Lowest Price
AU$120
Highest Price
AU$1,744