A large stone church with a tall bell tower and arched windows.

Holiday Homes in Great Barrington

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Great Barrington holiday homes

Coffee/tea maker, fridge, microwave, oven

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.6 out of 10, Exceptional, (34 reviews)
"Adorable guest home in Great Barrington! Light and bright. Perfect space for our family of 4. Well equipped kitchen and easy walk to downtown and groceries at the co-op. Would definitely stay here again!"
United States
Julie J.
The price is AU$624
includes taxes & fees
9 Aug - 10 Aug
Home in Great Barrington
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.4 out of 10, Exceptional, (19 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is AU$513
includes taxes & fees
10 Aug - 11 Aug
Cozy Riverside Berkshires Retreat
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, (6 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$1,867
includes taxes & fees
23 July - 24 July
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
TV, fireplace, stereo

Great Barrington, Cabin Sleeps 14, Walk To Town

Great Barrington, Cabin Sleeps 14, Walk To Town
Great Barrington
9.6 out of 10, Exceptional, (50 reviews)
"The host was wonderful and the place was amazing!"
United States
James M.
The price is AU$3,349
includes taxes & fees
2 Aug - 3 Aug
Great Barrington, Cabin Sleeps 14, Walk To Town
TV, fireplace, DVD player, books

Hudson Valley Multi-Unit Escape: Secluded + Scenic

Hudson Valley Multi-Unit Escape: Secluded + Scenic
Claverack
The price is AU$1,415
includes taxes & fees
23 July - 24 July
Hudson Valley Multi-Unit Escape: Secluded + Scenic
Outdoor dining

Berkshires Mountain Retreat w Panoramic Views, 5 Decks, Hot Tub, near Tanglewood

Berkshires Mountain Retreat w Panoramic Views, 5 Decks, Hot Tub, near Tanglewood
New Lebanon
The price is AU$1,156
includes taxes & fees
21 July - 22 July
Berkshires Mountain Retreat w Panoramic Views, 5 Decks, Hot Tub, near Tanglewood
Smart TV

stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.0 out of 10, Wonderful, (2 reviews)
"Property was just as described, clean and well equipped. Had excellent communication with the host. Would highly recommend staying here."
United States
Donna K.
The price is AU$595
includes taxes & fees
21 July - 22 July
stylish Berkshires Retreat
Interior

Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (7 reviews)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
The price is AU$722
includes taxes & fees
2 Aug - 3 Aug
Sweet Cozy Victorian in Housatonic. Close to everything.
Property grounds

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (34 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is AU$205
includes taxes & fees
26 July - 27 July
All the comforts of home
TV

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
United States
Samantha G.
The price is AU$988
includes taxes & fees
22 July - 23 July
Treetop Hideaway in Tyringham
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 AU$607
includes taxes & fees
28 July - 29 July
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Interior

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is AU$483
includes taxes & fees
23 July - 24 July
Real Estate: Therapy - Lake, Laundry, Love it
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 AU$605
includes taxes & fees
28 July - 29 July
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Exterior

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (39 reviews)
"Charming house in a wonderful setting in the Berkshires. "
United States
Mark Cristen J.
The price is AU$1,501
includes taxes & fees
22 July - 23 July
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
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
9.8 out of 10, Exceptional, (9 reviews)
"Mark was very accommodating and always available immediately if I had a question. The place was very clean and comfortable. Perfect location. We would love to come back in the summer when we can use the fire pit and the creek in the back. "
United States
Jessica V.
The price is AU$532
includes taxes & fees
28 July - 29 July
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
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, (148 reviews)
"Great location"
United States
Will G.
The price is AU$506
includes taxes & fees
26 July - 27 July
Big farmhouse in the foothills of the Berkshires
TV, fireplace, DVD player, books

Mtn-View Retreat in Huson Valley: Great for Groups

Mtn-View Retreat in Huson Valley: Great for Groups
Claverack
9.6 out of 10, Exceptional, (14 reviews)
"Beautiful rental - spacious, beautiful views, and gorgeous home!"
United States
Samantha A.
The price is AU$1,084
includes taxes & fees
23 July - 24 July
Mtn-View Retreat in Huson Valley: Great for Groups
2 bedrooms, free WiFi, bed sheets

Peaceful and cozy 1 bed 1 bath in quaint Winchester

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
The price is AU$293
includes taxes & fees
26 July - 27 July
Peaceful and cozy 1 bed 1 bath in quaint Winchester
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, (3 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$796
includes taxes & fees
21 July - 22 July
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
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, (95 reviews)
"Great location, quiet and beautiful. Loved the trails, picturesque drives between small towns and cozy accommodations. "
United States
Chad J.
The price is AU$855
includes taxes & fees
25 July - 26 July
Lakefront Summer Stunner in New England Just 2 Hours From NYC
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Great Barrington Hotel Reviews

Monument Mountain Motel

Monument Mountain Motel

10/10 Excellent
"Well situated in the Berkshires and kind staff."
Helen 1-night trip
Posted 2 hours ago
Monument Mountain Motel

Find out more about Great Barrington

Great Barrington Holiday Homes information

Number of reviews
476
Accommodation
547 Holiday Homes
Lowest Price
AU$205
Highest Price
AU$3,349