Ferienunterkünfte in Hillsdale

Gorgeous Mountain Views Retreat: Family & Nature

Wake up to fog lifting off the Berkshires in Columbia Co. Step onto the deck, 6 private acres of mountainside below you, no neighbors, nothing but open sky. Meadow View Manor is a 4BR Hillsdale retreat with a fire pit. Perfect for families. Enjoy the deck, remodeled kitchen, fireplace, and game room with ping-pong. Sleeps 8. Hear nothing but wind and birds. 2hrs from Manhattan, 10min from Catamount, 15min to great golf, restaurant, bar & live music, 30min from Hudson & Great Barrington. Dogs ok.

Waterfront Retreat in a woodsy haven

Love to share our beautiful home with design and comfort for your enjoyment. Whether it’s with family or friends, you deserve the perfect destination for luxury, fun, and relaxing. Open space and cozy bedrooms welcome you to spend weekend or weeks long getaways. Visit Copake Lake for water activities and golfing. Stay during the winter to ski at Catamount Mountain Resort or Ski Butternut in Great Barrington. Enjoy restaurants and shopping options in the nearby areas. See manual for more info.

Perfect Apt near Berkshires, Hudson Valley

Enjoy a stylish, elegant experience at this centrally-located newly restored 2 bedroom apartment with 1.5 baths in a historic building built in 1881, placed on the National Register of Historic places in 2010. Unit is on the 2nd floor and has a private entrance. Step back in time and stay in Second-Empire mansard Victorian that retains beautiful original details/layout and help it's restoration. Perfect location where the Hudson Valley meets the Berkshires. I have 4 other listings available.

Cheerful 3-bedroom cottage with woodstove.

Relax with the whole family at this peaceful Berkshire getaway with easy access to all the area has to offer. A quick 20-minute drive to Butternut or Catamount ski hills, as well as downtown Great Barrington. Tanglewood and Jacob's Pillow are a half-hour's drive. Or stay at home and enjoy the peace and quiet of the surrounding woods, light a fire in the woodstove, cook in the large fully-equipped kitchen or head out back to barbecue on the large deck and play a game of badminton in the yard.

Modern Copake Falls Getaway - 8 Mins to Catamount

Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! Note: there is no TV.

Secluded Mountain Getaway with Swimming Pond.

This is the perfect country getaway in a serene wooded setting yet close to town. Great for couples, solo adventurers, and families (with kids). A large deck and yard provide great views of the outdoors. This house is privately set but only a short walk to an inviting shared swim pond, meadow & trails. Area attractions include great hiking, skiing, restaurants, breweries, stores and markets. Near Great Barrington & Hudson and all the Berkshires and Hudson Valley have to offer.

Historic 1850s "The Bell House" with Private Pool

Escape to the 1850s Bell House, a historic 5BR/4.5BA estate in Hillsdale NY, once home to the prominent Bell family. Set on 3.6 acres, this fully restored gem blends period charm with modern luxuries like central A/C, heating & WiFi. Enjoy a large private swimming pool, cozy patio & ample space for the whole family. Walk to town for dining, galleries, boutiques & farmers markets. Perfect for unforgettable family getaways in a timeless countryside setting.

Hilltop Barn - Views, Hot Tub, Plunge Pool, Sauna

A private hilltop oasis in nature. Newly renovated barn with some luxury amenities including sauna & outdoor firepit & movie theater screen & hot tub & stock tank pool on a 15-acre hilltop w/ views & privacy in Hudson Valley / Berkshires. Fully stocked for cooking & tons of games. Near great shops & restaurants in Hudson & Great Barrington. We can point you to the best people to book for private massages or yoga classes right at the house.

Quaint center of town Farmhouse

This farmouse sits in the center of Hillsdale ideally positioned between Hudson and The Berkshires. Just steps to fresh town, Cook & Larder and the Rail Trail, this well appointed house is the perfect country getaway. Culture, endless restaurants and adventure at your disposal with Catamount ski area is 3.5 miles down the road and Tanglewood just 22 miles. The house is newly renovated and perfectly appointed.

Beautiful cottage at the foot of the Birkshires

Come stay with us in our beautiful cozy cottage, on a small lot located in the heart of Copake Falls, walking distance to Taconic State Park. Enjoy great farm to table dining, ski the Berkshires (just under 10 minutes to Catamount Resort), hike to Bash Bish Falls, bike the Harlem Valley Rail Trail, and swim in the spring fed iron ore pit during the open season.

Cabin in the woods near Catamount Ski resort

Rustic and romantic Cabin in the wood next to a Waterfall. Surrounded by trees with a private Driveway. This is the perfect getaway for couples and groups up to 5 people. It is about 20 min from Catamount Ski resort.This is a very special magical place. let yourself be enchanted.

Meadowland Farmhouse — 5 minutes from town

Our house is located in the heart of the Berkshires, midway between NYC and Boston, this newly renovated modern rustic style home sits on three acres just five minutes from the town of Hillsdale, NY. Perfect for getaways all year round, and perfect for families of various sizes.