Holiday Homes in Great Barrington

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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Great Barrington holiday homes

Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.2 out of 10, Wonderful, (14 reviews)
"Great location and nice size house for a family of 5. We had a couple hiccups but the host responded quickly and handled things promptly. "
United States
Jennifer L.
The price is €268
includes taxes & fees
8 Jun - 9 Jun
Cozy Riverside Berkshires Retreat
Fridge, microwave, oven, stovetop

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 €300
includes taxes & fees
14 Jun - 15 Jun
Home in Great Barrington
3 bedrooms, iron/ironing board, WiFi, bed sheets

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 €450
includes taxes & fees
4 Jun - 5 Jun
Cozy. Clean. Free bagel shop. 3 Fireplaces.
TV, fireplace, printers

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 €1,131
includes taxes & fees
2 Jun - 3 Jun
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Property grounds

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 €125
includes taxes & fees
2 Jun - 3 Jun
All the comforts of home
Outdoor spa tub

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 €335
includes taxes & fees
2 Jun - 3 Jun
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Exterior

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 €379
includes taxes & fees
2 Jun - 3 Jun
Near Tanglewood: Historic Summer Retreat
Interior

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 €322
includes taxes & fees
2 Jun - 3 Jun
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Outdoor dining

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is €243
includes taxes & fees
7 Jun - 8 Jun
Real Estate: Therapy - Lake, Laundry, Love it
Outdoor dining

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 €249
includes taxes & fees
2 Jun - 3 Jun
Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.
Pool

Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson

Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson
Hudson
10.0 out of 10, Exceptional, (6 reviews)
"Our host was fantastic! She allowed us to check in early and check out late. The house was cozy and perfect for my girls weekend! "
United States
Kim W.
The price is €440
includes taxes & fees
2 Jun - 3 Jun
Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson
TV, fireplace, books

NEW: Chic Modern Barn Style Home in Fun Area

NEW: Chic Modern Barn Style Home in Fun Area
Pine Plains
The price is €581
includes taxes & fees
2 Jun - 3 Jun
NEW: Chic Modern Barn Style Home in Fun Area
TV

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 €494
includes taxes & fees
2 Jun - 3 Jun
Treetop Hideaway in Tyringham
Fridge, microwave, stovetop, dishwasher

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 €473
includes taxes & fees
2 Jun - 3 Jun
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Property grounds

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 €291
includes taxes & fees
4 Jun - 5 Jun
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Property grounds

Lakefront Summer Stunner in New England Just 2 Hours From NYC

Lakefront Summer Stunner in New England Just 2 Hours From NYC
Sharon
10.0 out of 10, Exceptional, (91 reviews)
"What a lovely place. The view across the lake even with the snow was stunning. Hosts very responsive when i had questions. Would highly recommend!"
United States
Jessica W.
Lakefront Summer Stunner in New England Just 2 Hours From NYC
Interior

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries
Lebanon Springs
9.0 out of 10, Wonderful, (21 reviews)
"Comfy beds, clean, great big deck with a view. "
United States
Corinne T.
The price is €406
includes taxes & fees
9 Jun - 10 Jun
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Property grounds

Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (146 reviews)
"The house is absolutely charming and cozy. It was very clean as well. "
United States
Amanda C.
The price is €312
includes taxes & fees
4 Jun - 5 Jun
Big farmhouse in the foothills of the Berkshires
Property grounds

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (43 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is €429
includes taxes & fees
2 Jun - 3 Jun
Cheerful 3-bedroom cottage with woodstove
Exterior detail

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 €441
includes taxes & fees
4 Jun - 5 Jun
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
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

Berkshires Untold

Berkshires Untold

4/10 Poor
"From the time we showed up and told that they had no reservation for us, when we paid in full for a king suite, until we left, this experience was frustrating and full of problems. All king suites were sold out, including the one we paid for! We were told we would receive a 50% credit back to our credit card and we have yet to see that. The coffee was either unavailable/self serve or pretty bad. We experienced all of these. The check in person was somewhat helpful but was limited as to what we/they could do to remedy the whole situation. Communications from the upper management have gone unanswered The room we were given instead was very small, no amenities as stated in our reservation, etc I could go on with the sub par remedies, lack of communication and any follow through. Ingress and egress from this hotel is extremely difficult and dangerous, coming from the main four lane highway with no lights. The whole experience was Not pleasant at all on a trip that was a milestone for us. We will not be returning"
AW 2-night trip
Posted 11 hours ago
Berkshires Untold

Find out more about Great Barrington

Great Barrington Holiday Homes information

Number of reviews
439
Accommodation
534 Holiday Homes
Lowest Price
€125
Highest Price
€1,131