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Cottage holiday rentals in Berkshire County
Find and book unique cottages on Airbnb
Top-rated cottage rentals in Berkshire County
Guests agree: these cottages are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for cottage rentals in Berkshire County
Cottage rentals with a hot tub
![](https://a0.muscache.com/im/pictures/miso/Hosting-740564898926259984/original/ea671844-fac3-47b8-b6f0-0f61eb9ba3bc.jpeg?im_w=720)
Cottage in Lanesborough
5 out of 5 average rating, 12 reviewsNorte Maison 2 beds 2 Baths Minutes to Jiminy Peak
![](https://a0.muscache.com/im/pictures/miso/Hosting-50097728/original/abf12b54-b14b-4d11-a821-dc962afdfee6.jpeg?im_w=720)
Cottage in Otis
4.97 out of 5 average rating, 32 reviewsBerkshire lakefront cabin with modern luxuries
![](https://a0.muscache.com/im/pictures/miso/Hosting-51506571/original/8d327e93-66f8-41b0-a287-5d6ad9b1ce4b.jpeg?im_w=720)
Cottage in Great Barrington
4.87 out of 5 average rating, 30 reviewsTHE GREAT ESCAPE BERKSHIRE SKI COTTAGE w/HOT TUB!
![](https://a0.muscache.com/im/pictures/20cfcd04-c9d5-4499-972e-c8e2e6f76fcc.jpg?im_w=720)
Cottage in Monterey
4.91 out of 5 average rating, 11 reviewsmountain refuge
![](https://a0.muscache.com/im/pictures/90824439-b517-4318-bd37-399b6932c144.jpg?im_w=720)
Cottage in Becket
4.63 out of 5 average rating, 155 reviewsA Magical Spot on Little Robin Lake
Pet-friendly cottage rentals
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Cottage in Williamstown
4.76 out of 5 average rating, 66 reviewsPet friendly, cozy, modest cape, two bedrooms
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Cottage in Great Barrington
4.9 out of 5 average rating, 49 reviewsCarriage house with Chef's Kitchen, close to town
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Cottage in Becket
4.77 out of 5 average rating, 145 reviewsPrivate Lake Cottage on 3 acres w/350 sq. ft. deck
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Cottage in Becket
5 out of 5 average rating, 18 reviewsCheerful 3+ bedroom cottage with lake views
![](https://a0.muscache.com/im/pictures/miso/Hosting-51835308/original/ff320a6b-fb5c-435a-8315-daf2b799f4e6.jpeg?im_w=720)
Cottage in Spencertown
5 out of 5 average rating, 31 reviewsRock Haven Cottage
![](https://a0.muscache.com/im/pictures/9591062a-54b0-46f3-83b2-5270a183afc9.jpg?im_w=720)
Cottage in New Lebanon
4.89 out of 5 average rating, 44 reviewsCozy Cottage in the Clouds With Mountain Views
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Cottage in Florida
4.8 out of 5 average rating, 114 reviewsPeaceful Mountain Cabin by Ski, Kayak, Museums +!
![](https://a0.muscache.com/im/pictures/96156284/8f3ef3ce_original.jpg?im_w=720)
Cottage in East Chatham
4.93 out of 5 average rating, 200 reviewsBeautifully Nestled Berkshires Home
Private cottage rentals
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Cottage in Lanesborough
5 out of 5 average rating, 7 reviewsPontoosuc Lakeshore
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Cottage in Becket
4.58 out of 5 average rating, 102 reviewsArtist Retreat in Lake Community
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Cottage in Pittsfield
4.8 out of 5 average rating, 92 reviewsThe Oliver Wendell Holmes Guesthouse @ Holmesdale
![](https://a0.muscache.com/im/pictures/prohost-api/Hosting-34674233/original/50ca2484-46e0-482d-84b3-50851f6f4258.jpeg?im_w=720)
Cottage in Hinsdale
5 out of 5 average rating, 20 reviewsPicturesque Cottage with Sunroom on Ashmere Lake!
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Cottage in West Stockbridge
4.97 out of 5 average rating, 32 reviewsTanglewood Cottage in the heart of the Berkshires
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Cottage in Otis
4.8 out of 5 average rating, 5 reviewsCozy Cottage in the Berkshires
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Cottage in Stockbridge
5 out of 5 average rating, 16 reviewsRustic Berkshires Cottage
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Cottage in New Marlborough
4.83 out of 5 average rating, 30 reviewsCountry Cottage near Great Barrington
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