Holiday Homes in The Berkshires

Private new house on 10 acres of pristine nature

Brand new home! Bring friends and family to this private and stylish place. House provides everything you need for a comfortable and peaceful stay. Fully equipped kitchen, inviting living spaces, large front and back yards with many exploring trails and a pond a few steps away from the house. Close to many 5 star restaurants, wineries, galleries and shops. Hiking, swimming, boating, skiing just to mention a few outdoor activities Close by: Kent School Mohawk Ski Area Lake Waramug High Watch

Modern/Private Five ★ /Hotel quality stay/1 BR Apt

Enjoy the comfort and tranquility of this modern apt. A lovely space to relax after a busy day. This clean and bright apt offers a tranquil residential vibe alongside quick, easy access to the Torrington downtown areas, restaurants, stores and bars. It features an open-concept layout, a neutral color scheme, wood surfaces, tasteful furnishings and decor. Designed comfortably for your stay offering WiFi, Netflix, laundry, queen bed, well equipped kitchen, and clean fresh white bed sheets.

☆Mulberry Guest House☆Private☆Walk to village

The Mulberry Guesthouse is a garden apartment with a romantic living room fireplace, cozy den, sunroom, and two bedrooms -- all fully furnished and equipped for easy living while you’re in town. Private outdoor space includes dining table, propane grill, and fire pit. The beauty of our location is the quiet, wooded setting that feels away-from-it-all, but is also walkable to the cafes, shops, and restaurants of downtown New Paltz. Local walking and biking trails are just 2 blocks away.

Unique BellEayre River retreat

#2024-STR-AO-85 As seen in Chronogram magazine Chronogram/docs/chronogram-april-2023 High ceilings, Rough cut beams, All new HVAC and Hearthstone soapstone wood burning stove. Take it easy at this tranquil getaway while you see and hear only the water flow with wrap around 4 season river right off deck. Close to scenic hiking, skiing, river tubing, and great restaurants along "Rapid Water"- The Algonquin Nation word for "Shandaken". Dogs welcome (Up to 2), sorry no cats.

Great top fl near cnter with sunroom and a view cc

Experience comfort and convenience in this Hudson apartment, perfect for solo travelers, couples, or small families. Enjoy the cozy ambiance of this space, complete with a fully equipped kitchen, and organic washing and cleaning products. You'll find comfortable sleeping arrangements, as well as Smart TV and board/card games for your entertainment. Unwind on your private patio. Whether you're here for business or leisure, don't miss out on this spacious, bright, peaceful space.

Riverfront, cozy farmhouse near Rhinebeck

This historic Clinton Hollow house was built by Isaac Fraleigh in the late 1700's and overlooks the waterfalls of Wappingers Creek. The house has the architectural details of an antique colonial and the open, spacious feel of a modern contemporary. The great room with its big fireplace has different vibes and seating areas and is just perfect for family and friends gathering. The Petanque field in the garden add a fun convivial activity.

Private, modern carriage house. Great for couples.

Newly built in 2022, our charming, modern carriage house is tucked away within a small courtyard garden on a quiet residential street in the heart of Beacon NY. Guests will enjoy an efficient, elegantly designed and furnished interior with views of the Mount Beacon ridgeline from this comfy and private abode. The owners are long-time Airbnb hosts who work hard to ensure their guests have a peaceful, relaxing stay.

Explore the Berkshires from this charming home.

The whole group will enjoy easy access to everything from this centrally located place. Ski Bousquet, Butternut, or Jiminy Peak. Visit charming towns of Great Barrington, Lee, Stockbridge, Lenox, Adams, N. Adams and Williamsburg. All within a short drive. Soak up some culture by visiting Clark Museum, Mass Moca, or the Rockwell Museum, or listen to some great live music at Tanglewood during the summers.

UNIQUE and GORGEOUS historic loft style rental

Beautifully bright third floor loft style space with private entry available for your enjoyment. Basic kitchen, laundry, and bath are located on the second floor. Due to the stairs in this unique space, it would be ideal for a single traveler or couple looking for a getaway. Walkable to historic Woodbury, minutes to amazing land trust hiking trails in Roxbury, and only 1.5 hours from NY City.