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Compare 117 Cottages in Great Barrington with updated reviews, rates, and availability.

Private Island - Largest Fresh Water Reservoir in Mass....

9.0 out of 10, Wonderful, (7)
"From beginning to end, could not have dreamed of a better island getaway, in the Berkshire’s none-the -less. Bill was a wonderful host. Very friendly, responsive and helpful. Super welcoming. The home was simple, quaint, and super cozy. Perfect for a nice long relaxing weekend for both the dogs and people. The views from the sun room were lovely. The deck/patio area had a beautiful view of the water. The fire pit was a nice perk in the evening. Surrounded by water, the place felt so private....
Private Island - Largest Fresh Water Reservoir in Mass....

Two Bedroom Cottage Close To Town

9.4 out of 10, Exceptional, (19)
"We enjoyed three nights at the cottage. It's beautifully decorated, comfortable, warm and welcoming - a perfect home base for nearby hikes and exploring the area. The large yard was perfect for playing soccer with our child. Renters note: we also had a fabulous meal at nearby restaurant Fern. "
Two Bedroom Cottage Close To Town

East Otis Vacation Rental w/ Private Deck & BBQ!

9.6 out of 10, Exceptional, (7)
"Wally and Donna were very hospitable! We loved this cottage and its location to everything we wanted to do. The neighborhood was tranquil and beautiful. Such a great place!"
East Otis Vacation Rental w/ Private Deck & BBQ!

Idillic summer getaway in Litchfield Hills, CT.

10.0 out of 10, Exceptional, (13)
"The place was as described and very comfortable. We enjoyed our stay!"
Idillic summer getaway in Litchfield Hills, CT.

Family-Friendly Richmond Cottage w/ Private Yard

2.0 star property
10.0 out of 10, Exceptional, (4)
"Comfortable. Homey. Very well stocked, especially the kitchen. Plenty of room and light. Thank you for our visit. "
Family-Friendly Richmond Cottage w/ Private Yard

Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

9.2 out of 10, Wonderful, (11)
"A short getaway with family. "
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

Cozy Berkshire cottage with fireplace.

10.0 out of 10, Exceptional, (24)
"Very good! Enjoyed every moment once we got the thermostat set to the right temp for us. Clean and cozy!"
Cozy Berkshire cottage with fireplace.

Welcome to the Red Bridge Cottage!

10.0 out of 10, Exceptional, (1)
"Good experience. Love the front porch"
Welcome to the Red Bridge Cottage!

West Cornwall Cabin ~ 4 Mi to Covered Bridge!

3.0 star property
West Cornwall Cabin ~ 4 Mi to Covered Bridge!

The Blue Elm - A Historic Berkshire Cottage

10.0 out of 10, Exceptional, (7)
"Housing is just as beautiful as the pictures show and the residential neighborhood is quiet, conveniently situated. Hosts are very responsive. We really enjoyed our stay!! "
The price is SAR 750
SAR 1,538 total
includes taxes & fees
12 Mar - 13 Mar
The Blue Elm - A Historic Berkshire Cottage

Quiet rustic cottage with shared lake access

10.0 out of 10, Exceptional, (103)
"I am originally from Western Mass, and was looking for a quiet get away for my fiancé and I for my birthday weekend. This more than fit the bill, we had many romantic nights in front of the fire (big y or tractor supply good for indoor wood). The cabin was delightful, quaint. And it was so quiet this time of year with no one else around us, which was just what I was looking for. Our hosts were great, made everything very easy for check in and check out and were easily valve through the App....
Quiet rustic cottage with shared lake access

4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!

2.0 star property
10.0 out of 10, Exceptional, (1)
"This property was exactly as advertised and was in a safe and private location. The hosts perfectly accommodated our stay and we cannot be more thankful to them for a fully-functional house that was suitable for the adults and children. It was truly a pleasure to stay at this home."
4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!

Beachwood Cottage

10.0 out of 10, Exceptional, (3)
"We had a great week at this cottage and Daryl was a responsive and helpful host. Our kids are already asking to return next year."
Beachwood Cottage

The Cottage at Highland Lake, year-round, waterfront with a boat dock

10.0 out of 10, Exceptional, (4)
"Jeanne was wonderful to work with and very responsive when we booked our last minute get away. Location is ideal - we brought our kayaks and very easy launching area. Would definitely not hesitate to come back to the same spot. Thanks for sharing your home with us. "
The Cottage at Highland Lake, year-round, waterfront with a boat dock

Private Lake Cottage on 3 acres w/350 sq. ft. deck

Private Lake Cottage on 3 acres w/350 sq. ft. deck

Peaceful Goshen Cottage w/ Screened Porch & Views!

9.0 out of 10, Wonderful, (29)
"Enjoyed our stay very much. The accommodations suited our needs. Appreciated the cleanliness of the property and the ease of checking in/out."
Peaceful Goshen Cottage w/ Screened Porch & Views!

Lake Views & Dock Access - Pittsfield Cottage!

10.0 out of 10, Exceptional, (1)
"This house was more than we could ask for it’s right on the water and has everything you could possibly forget handy! A all around, great place to enjoy nature and spend time with family and friends. Super straightforward didn’t need to ask the host any questions Will be booking here again! "
Lake Views & Dock Access - Pittsfield Cottage!

1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge

10.0 out of 10, Exceptional, (1)
"Stayed for 3 nights over Presidents Day weekend, and we loved the spot! Recently refreshed with a new kitchen, floors and fixtures, it’s still felt warm and inviting. The electric fire / heater in the living room was well used, and we cooked our meals with the new appliances and well equipped kitchen. Proximity to Great Barrington, Stockbridge, Lenox, Lee, and all of the outdoor adventures (and shopping/restaurants) worked out perfectly, even given the snowy/ice weather. Plenty of space for the...
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge

Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks

10.0 out of 10, Exceptional, (3)
"Nestled among luxe lakefront properties, this tidy cabin was perfectly suited to relaxing in kayaks and family dinners. Near Great Barrington and lovely hikes. Exceeded all expectations for a last minute getaway."
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks

Fun Getaway Lakehouse in the Hudson Valley

10.0 out of 10, Exceptional, (15)
"Can't say enough about this place. It looked like it was just recently built or renovated, and was very very clean. The place was warm, inviting, and very comfortable for my family of 5. Leticia is amazing, very very responsive and understanding. If you are staying in the area (the lake, skiing, etc.) I would highly recommend this place. We will definitely look to book this place again the next time we go skiing at Catamount."
Fun Getaway Lakehouse in the Hudson Valley
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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Other property types in Great Barrington

Private Estate, Heated Yearround Outdoor Pool

9.8 out of 10, Exceptional, (17)
"The home was beautiful and it was a gorgeous property too. It had all the right amenities in the kitchen. "
Private Estate, Heated Yearround Outdoor Pool

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

10.0 out of 10, Exceptional, (45)
"We had an amazing long ski weekend at the Great Escape Ski Cottage. The listing is very accurate. Great communication with Shay. The house was immaculate upon arrival. The layout of the house was perfect for our family (6 adults and 4 children aged 4-9). One beautiful Master Bedroom on the first floor. Two of the other equally beautiful bedrooms are on the second floor. The linens were hotel quality! The "Kid's Quarters" was located off of the kitchen/laundry room. A playroom with multiple games...
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

7.2 out of 10, Good, (43)
"The property was great overall. I was not impressed with finding cobwebs around furniture, or with the hair in the shower and the toothpaste on the sink, mirror mirrorandbehind behind"
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
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.

Frequently asked questions

How much do cottages in Great Barrington cost?
Prices for cottages in Great Barrington range between SAR 750 and SAR 750 per night. Whatever your budget, you’re sure to find the perfect place to immerse yourself in nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Great Barrington?
Make use of your vacation days and pick from 117 cottages in Great Barrington. Picturing a place where you can immerse yourself in nature? Expedia will help you find your ideal retreat in a few simple clicks.
Why book your cottage in Great Barrington with Expedia?
Reserving a cottage in Great Barrington is as simple as working out your travel dates and choosing your ideal place for a getaway in the outdoors. From chic retreats to low-cost stays and cottages that come with amenities like a kitchenette, Expedia has something for all traveler styles. As for the best deals around? We’ve have them as well!
How can I find cheap cottages in Great Barrington?
Expedia can help you look for cheap cottages in Great Barrington. To discover a superb stay in a few quick keystrokes, use our convenient filter tool to refine your search results by amenities, star rating and budget.