Holiday Homes in The Berkshires
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Top-rated Holiday Homes in The Berkshires
Guests agree: These holiday homes 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 The Berkshires holiday homes
Family-Friendly holiday homes
Holiday home in Halcott
4.51 out of 5 average rating, 179 reviewsA Frame in the Mountains with Hot tub + Fast Net
Holiday home in Cairo
4.65 out of 5 average rating, 23 reviewsChalet on the Hill
Holiday home in Hudson
4.82 out of 5 average rating, 102 reviewsGreat top fl near cnter with sunroom and a view cc
Holiday home in Hudson
4.82 out of 5 average rating, 71 reviews2 blocks to Warren ST with an office and a yard cb
Holiday home in Hudson
4.76 out of 5 average rating, 63 reviews2 blocks to Warren ST with Backyard,& Parking
Holiday home in Hudson
4.86 out of 5 average rating, 95 reviews3 block to Warren ST with a Yard and parking ga
Holiday home in Hudson
4.94 out of 5 average rating, 85 reviews2BRT 3 blocks to Warren ST
Holiday home in Hudson
4.91 out of 5 average rating, 87 reviews2 blocks to Warren ST w/ a yard and parking
Holiday home rentals with a patio
Holiday home in Beacon
5 out of 5 average rating, 53 reviewsPrivate, modern carriage house. Great for couples.
Holiday home in Salt Point
4.88 out of 5 average rating, 41 reviewsRiverfront, cozy farmhouse near Rhinebeck
Holiday home in East Hampton
5 out of 5 average rating, 29 reviewsFamily Friendly Lake House Lake Pocotopaug Sunsets
Holiday home in Putnam Valley
4.91 out of 5 average rating, 23 reviewsHudson Valley Glass-sided Lakehouse
Holiday home in Town of Rockingham
4.96 out of 5 average rating, 55 reviewsCozy studio at Leslie's Tavern in Rockingham
Holiday home in Litchfield County
4.93 out of 5 average rating, 14 reviewsPacer's Pasture
Holiday home in Windham
4.93 out of 5 average rating, 61 reviews*Farmhouse Chic with Mountain and Lake Views*
Holiday home in Ulster Park
4.9 out of 5 average rating, 20 reviewsWeeping Willow Hideaway on the Lake Studio Suite
Holiday home rentals with a washing machine and dryer
Holiday home in Becket
4.95 out of 5 average rating, 43 reviewsPerfect Serene Waterfront All Season Retreat!
Holiday home in Otis
5 out of 5 average rating, 11 reviewsSunny oasis in the woods in Otis
Holiday home in Brewster
4.94 out of 5 average rating, 53 reviewsScandi Peaceful Oasis, Private Pool, Hottub!
Holiday home in Athens
4.92 out of 5 average rating, 78 reviewsLakefront Retreat | Kayaks, Paddle Board & Hot tub
Holiday home in Hadley
5 out of 5 average rating, 19 reviewsEntire House-Sacandaga Lakeview Home on Rosebloom
Holiday home in Dover
4.87 out of 5 average rating, 23 reviewsWalk to Mount Snow, Cozy, Clean and Comfortable
Holiday home in Napanoch
4.86 out of 5 average rating, 22 reviewsThe Swallow's Nest Catskills with pool & firepit
Holiday home in Gardiner
5 out of 5 average rating, 21 reviewsCountry oasis on 75 acres with pond and hiking
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