Holiday rentals with a patio in Boys & Girls Club of the Berkshires Ice Rink

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

Escape to Falls Road – a private mid-century country home nestled on the edge of 20 acres of preserved woodlands. Our home has been thoughtfully updated, featuring an array of resort quality amenities as well as a wood-burning fireplace, soaking tub, outdoor shower, projector & a 4ft deep cedar hot tub to unwind in. The yard includes a stock tank plunge pool, deck, grill, and fire pit. Located just over 2 hours from NYC/Boston and only 8 miles from Hudson center. Minutes to hiking, golf, & more!

Timberwall Ranger Station | Your Upstate Base Camp

The Timberwall Ranger Station is the perfect home base for your peaceful upstate escape. Located minutes from Woodstock, Saugerties, and Kingston, this breathtaking hand-built cabin is close to all the Catskills and Hudson River Valley have to offer. The cabin is a restful place year-round: for enjoying spring birdsong at breakfast; swaying away an afternoon in a breezy summer hammock; starry skies and luscious wines around an autumn campfire; a cozy winter morning amidst freshly fallen snow.

Cozy Hilltown Cottage

Enjoy a peaceful stay in this cozy, creative space. Set on 10 acres of gardens and woods, this cottage is perfectly located to explore Western Massachusetts - with places like MASS MoCA, Shelburne Falls, Tanglewood and Northampton all within a 30min to 1 hour drive. Upstairs is a queen bed and full bath, while downstairs features a functional kitchen, work desk, grand windows, and a living space with full sleeper sofa. We live in the main house on property but respect your privacy-see photos!

Stylish Shales Brook Cottage-Cozy up to happiness

Bright & inviting! Welcome to our charming cottage, a stylish 2-bedroom, 2-bath retreat by Shales Brook. Relax on cool evenings beside the vintage Malm wood-burning stove. Enjoy modern comforts with central air, a screened-in porch, and a deck overlooking the tranquil waters of Shales Brook. The soothing sounds of the brook enhance your stay.. Located near fabulous Berkshire attractions, fantastic hikes, 15 minutes to the town of Lee, minutes to Jacob‘s pillow and 20 minutes to Tanglewood,!

Boulder Tree House

Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.

Luxury A-Frame Cabin in the Woods with Sauna

Modern, glass‑fronted A‑frame perched in the Catskills, offering sweeping mountain vistas. Relax in the private cedar barrel sauna & refreshing outdoor shower, gather round the smokeless propane fire-table, or fire up the propane grill for al‑fresco dinners. A stylish bedroom with woodland views, luxe linens, fast Wi‑Fi, and a cozy electric fireplace blend comfort with design. Minutes to trailheads, waterfalls & farmers markets - ideal for couples seeking a serene and restorative escape.

Sweet Victorian in Housatonic

Fresh and simple living in a three bedroom family friendly duplex. Experience the Berkshires while staying in a newly renovated Victorian house in Housatonic. Tasteful clean furniture, organic new sheets, pillows and duvets. Lovely clean kitchen that is fully equipped to host dinners. Situated up on a hill in Housatonic this three bedroom is conveniently located to to Great Barrington, Lake Mansfield, Stockbridge, Butternut, Catamount, Tanglewood, Kripalu and Monument Mountain.

King Bed |Wi-Fi| 2m to Ski Resort

Remodeled Mid-Century Motel, that sits in the heart of the Berkshires. Located in Great Barrington, MA. Just steps from fantastic restaurants, eateries, shops, etc. A very short drive to Butternut Ski Resort. * 1.5 miles to Downtown * 1.3 miles to Mahaiwe Performing Arts Center * 44 miles to Albany International Airport *4.5 miles to Great Barrington Airport KEY FEATURES: *MCM Design * Plush King Sized Bed w/ high end Centium Satin Linens *High Speed Internet *58" TV w/ Hulu + Live

The Upstate A - Modern Luxury in the Hudson Valley

The Upstate A is a 3 bedroom + sleeping loft, 2.5 bathroom A-frame set on a quiet cul-de-sac in the heart of the Hudson Valley. Built in 1968, it was fully renovated in 2020-2021. Staying here you’ll experience a cozy yet modern vibe, immersed in nature but with all the accoutrements of an upscale stay. You'll find great hiking in the summer, skiing in the winter, fresh upstate air year-round and serenity all day and night. See for yourself: check us out on IG @upstate_aframe

Boutique TINY home+private HOT TUB-walk to Main St

Love month at Art Park. Romance is built in—no add-ons needed: Roses-Prosecco-Robes-Slippers. Boutique-luxe tiny home with private hot tub, firepit, and dreamy loft lounge. Plush queen bed, full kitchen, and curated charm throughout. A peaceful oasis just 2 mins from Chatham’s Main Street lined with restaurants, brewery, shops & theater. The perfect upstate NY getaway for couples—hike, visit galleries, stroll to dinner, or unwind in your own private spa oasis at @artparkhomes.

3-bedroom Berkshire bungalow on 2.5 peaceful acres

Modern farmhouse bungalow with private bridge and brook! Offering privacy as well as nearby nightlife, set upon 2.5 acres of beautiful Berkshire landscape but only 7 minutes to downtown Great Barrington and a short drive to Catamount and Butternut ski area. Mountains, waterfalls, countless hikes and bike routes, farmers' markets, coffee shops, breweries, Shakespeare and Co, Tanglewood, and world-class restaurants all come together in this quintessential New England community.

Contemporary Cabin in Catskill Mountains

Our luxurious cabin is more than just an Airbnb; it's a personal sanctuary designed with your comfort and tranquility in mind. Nestled on 1.5 acres of Catskill Mountain beauty, this idyllic retreat offers everything you need for a relaxing getaway or extended stay. Enjoy the modern amenities, cozy furnishings, and breathtaking views that make our cabin a truly special place. View more pictures at @the_reve_cabin Ready to escape the ordinary? Book your stay today.