Cottage vacation rentals in Berkshire County
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Top-rated cottage rentals in Berkshire County
Guests agree: these cottages are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Berkshire County cottage rentals
Cottage rentals with a hot tub
Cottage in Lanesborough
5 out of 5 average rating, 14 reviewsNorte Maison 2 beds 2 Baths Minutes to Jiminy Peak
Cottage in Monterey
4.69 out of 5 average rating, 13 reviewsmountain refuge
Cottage in Great Barrington
4.85 out of 5 average rating, 33 reviewsTHE GREAT ESCAPE BERKSHIRE SKI COTTAGE w/HOT TUB!
Cottage in Becket
4.65 out of 5 average rating, 164 reviewsA Magical Spot on Little Robin Lake
Cottage in Otis
4.98 out of 5 average rating, 42 reviewsBerkshire lakefront cabin with modern luxuries
Pet-friendly cottage rentals
Cottage in Hillsdale
4.85 out of 5 average rating, 67 reviewsSecluded Country Getaway on 22 acres
Cottage in Canaan
4.9 out of 5 average rating, 133 reviewsPlan your Berkshires by the lake
Cottage in Becket
5 out of 5 average rating, 25 reviewsCheerful 3+ bedroom cottage with lake views
Cottage in Austerlitz
4.92 out of 5 average rating, 74 reviewsHarvey Mountain Lodge by State Forest
Cottage in Hancock
4.85 out of 5 average rating, 74 reviewsBerkshire Cottage Queen Bd-Jiminy Peak 3 mi
Cottage in Becket
4.77 out of 5 average rating, 156 reviewsTranquil Lake Cottage on 3 Acres with Large Deck
Cottage in Williamstown
4.74 out of 5 average rating, 73 reviewsPet friendly, cozy, modest cape, two bedrooms
Cottage in Monterey
4.94 out of 5 average rating, 16 reviewsNew! Fully renovated private cottage
Private cottage rentals
Cottage in Pittsfield
4.84 out of 5 average rating, 77 reviewsBerkshire Lakeview Tranquility
Cottage in West Stockbridge
4.97 out of 5 average rating, 34 reviewsTanglewood Cottage in the heart of the Berkshires
Cottage in Lenox
4.98 out of 5 average rating, 59 reviewsThe Jaynes House ~ Cozy Lenox Retreat
Cottage in Lanesborough
5 out of 5 average rating, 25 reviewsLakefront Cottage Jiminy Ice Fishing Berkshire
Cottage in New Marlborough
4.91 out of 5 average rating, 34 reviewsSki, Fish, Swim, Hike Berkshires Cottage in woods
Cottage in Becket
4.57 out of 5 average rating, 104 reviewsArtist Retreat in Lake Community
Cottage in Pittsfield
4.79 out of 5 average rating, 95 reviewsThe Oliver Wendell Holmes Guesthouse @ Holmesdale
Cottage in Austerlitz
4.9 out of 5 average rating, 10 reviewsCozy Berkshire Cottage
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