- Haddock Cotter Chic Farmhouse and Barn w PoolOld Chatham
- Pet-Friendly Cottage in a Working Farm near Hudson, New YorkCatskill
- Copake Lakes Hidden TreasureCopake10.0
- NEW 6-Bedroom Retreat Book Your Summer GetawayLebanon Springs
- Shaker Mill Inn9.1West Stockbridge
- Pondfront Gem Minutes from Hudson’s Best Shops Cafes The Stillwater HouseHudson
- Walk to Dtwn Hudson Cozy Upstate ApartmentHudson5.0
- Berkshire Vacation Rentals 1900s Factory Turned Modern Berkshires RetreatGreat Barrington
- Farmhouse Retreat, Outdoor Dining, Fire-Pit, Fast Wifi, Golf and 3-Acre PrivacyValatie
- Cozy Berkshires Stay, Mins from Ski SlopesLebanon Springs
- Unique Vacation Rental on a Working Farm near Hudson, New YorkCatskill
- Secluded w Deck Views Hot Tub Ping Pong Hudson in the Berks by AvantStayEast Chatham
- Riverfront Hudson Valley Gem with Beach Access!Athens
- Stylish Camping Tents Set on an Organic Farm in Hudson Valley, New York StateGhent
- 1 Mi to Vineyard Serene Berkshires Country EscapeRichmond
- Secluded Cottage Rental with a Heated Pool in Red Hook for Family Getaways in New York StateMount Ross
- Riverfront Cabin with Beautiful Views of Housatonic River in Great Barrington, Massachusetts
- Charm at the foot of the BerkshiresHillsdale8.0
- Beautiful House in the Woods, Huge Yard, Hot TubGreat Barrington
- Private Island on Twin Island Lake, Pine Plains, NYPine Plains
- Gray Owl Lodge- A Serene Lakefront Retreat on Sleepy Hollow Lake near Hudson NYAthens
- Nautical Nest Hudson8.9Hudson
- Pleasant Valley Motel West Stockbridge5.5West Stockbridge
- Wm. Farmer and SonsHudson9.0
- Lxry Est HeatedPool Hottb ViewsCopake
- Secluded Cabin with Gorgeous Views near Stockbridge in the Berkshires of Massachusetts
- Prospect BerkshiresNorth Egremont9.8
- Romantic Glamping Getaway in a Pet Friendly Caravan, Ideal to Explore Hudson Valley
- Stay Near Ski Berkshires, Mid-Week & Promo Deals!10.0
- Beautifully Designed 4BR Home Heated Pool HotTubValatie10.0
- Buttonball InnSouth Egremont
- Pet-Friendly Vacation Rental on a Working Farm near Hudson, New YorkCatskill
- 6 Mi to Tanglewood Peaceful Berkshire Apt!Richmond
- Lxry Est HeatedPool Hottb ViewsCopake
- 9 Mi to Dtwn Hudson Pet-Friendly Home with PoolCraryville
- Gorgeous Getaway Suite in a Converted Barn near Hudson, New YorkCatskill
- 8 Mi to Tanglewood and Butternut Ski Spacious Home!8.0
- 4 Mi to Great Barrington Berkshires Retreat!Sheffield
- 4 Mi to Dtwn Catskill Mtn-View HomeCatskill
- Inn at Silver Maple Farm9.4East Chatham
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