Great Barrington cottages

We found 42 cottages — enter your dates for availability

Find spaces that suit your style

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    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

Are there any cottage rentals in Great Barrington?
Opt for one of our 42 cottage rentals in Great Barrington and get set to enjoy the comfort, charm and unique experiences that come with this type of property. Town of Copake, Canann Village Historic District and North Canaan are among the city's most sought-after neighbourhoods.
How much does it cost to stay in a cottage rental in Great Barrington?
Where you stay, what time of year you travel and the length of your trip will influence the price of a cottage rental in Great Barrington. Key in your travel dates on Bookabach to compare your options and then lock in one that's right for you.
When is the best time to rent a cottage in Great Barrington?
With temperatures ranging from -8ºC to -2ºC, January is when the majority of visitors book a cottage rental in Great Barrington. Since it's the busiest month, it's wise to secure your stay well in advance. Alternatively, consider the off-season for a quieter The Berkshires escape.
Where can I rent a Great Barrington holiday cottage with great views?
Bookabach makes it simple to find the impressive views you're looking for in your stay. Just use our "Location" filter to narrow down the kind of area you prefer to be in, and the views you like to immerse yourself in, while searching cottage rentals in Great Barrington.
Does Great Barrington have any lakeside cottages?
Wake up to lovely scenery every morning and fall asleep to the sweet sounds of nature at night in one of Bookabach's lakeside cottage rentals. Add some outdoor fun in the daytime and you'll have the perfect holiday by the water. To find out if there are any lakeside cottages in Great Barrington, use our "Location" filter and then click on "Lake."
What are the top things to do in Great Barrington?
It's easy to see why families love Great Barrington, with cool attractions like Tanglewood Music Centre, National Shrine of the Divine Mercy and Norman Rockwell Museum to explore. Check out this destination's best sights together and then return to the cosy comforts of your cottage rental.
Why should I book my holiday cottage with Bookabach?
Bookabach provides customer support from the moment you book until the end of your trip, so every aspect of your holiday is worry-free. Plus we think our cottage rentals are something special — think amenity-packed stays ideal for families and rustic options perfect for an escape for two. Book with Bookabach and you can also take advantage of flexible cancellation policies and other benefits like payment and deposit protection.
Holiday Rental options in Great Barrington
Oceanfront holiday rentals in Great Barrington
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Family-friendly holiday rentals in Great Barrington
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Holiday rentals with spa pool in Great Barrington
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Ski holiday rentals in Great Barrington
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Lake holiday rentals in Great Barrington
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Monthly rentals in Great Barrington
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Pet-friendly holiday rentals in Great Barrington
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Mountain holiday rentals in Great Barrington
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Beach holiday rentals in Great Barrington
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Holiday rentals with pool in Great Barrington
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