Vacation home rentals in Boys & Girls Club of the Berkshires Ice Rink

La Maison Hudson: Charming 1BR In Prime Location

Welcome to La Maison in Hudson! This charming three-story townhouse, just two blocks from vibrant Warren Street, is perfect for families, friends, or a romantic getaway. Apartment 2 offers 1 bedroom, 1 bath, and accommodates 2 guests. Enjoy cozy thrifted decor, a private balcony, convenient parking, and a fully equipped kitchen with a dining table for six. Warren St: 3-min walk Train station: 15-min walk Olana: 8-min drive Art OMI: 15-min drive Your ideal mix of convenience & culture awaits!

Lakefront Retreat | Kayaks, Paddle Board & Hot tub

Welcome to the newly renovated lakefront vacation house in the Catskills. It is perfect for family & friends looking for a getaway in the Hudson valley and Catskill mountains. Close to ski resorts like Hunter & Windham. This peaceful retreat is located in a beautiful lake community with a large waterfront backyard.  You will enjoy:  • Gathering around the fire pit by the waterfront with s’mores • Relaxing in the Hot Tub overlooking the lake • Wake up to the beautiful lake view from your bedroom

Mountain escape in Hunter/Tannersville

Nestled between Hunter and Tannersville, our cozy and clean house is minutes from Hunter Mountain. Enjoy skiing, snowboarding, hiking, and the nearby lakes. Tannersville has great restaurants, boutique stores, a park with pickleball courts and kayak rentals, a theater, a supermarket, and more. Our home has four spacious bedrooms, two bathrooms, a full kitchen, a deck, and a living area for entertaining. Enjoy ping-pong, the outdoor hot tub, or gather around the fire pit for a mountain bonfire!

Historic 1827 House | 2BR • AC • Downstairs Unit

Attending a wedding or event at Farm Road Estate? Do you need a pet-friendly walkable location? Stay at the 1827 House! We are located directly across the street—a quick walk to the venue. Located right next to the VT Adventure Challenge & 1846 Tavern! Perfect for vacationers, wedding guests, and traveling professionals, this beautifully renovated first-floor 2BR unit blends historic charm with modern comforts—including crisp AC!! Note: Historic front porch renovations in progress through July

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

The Perfect Catskills Escape for Families and Groups

Pine Hill House is a renovated 1870s boarding house with loads of old charm mixed in with new luxuries. Take a left from the house to find miles of hiking trails. Take a right and walk to town with its vibrant restaurant scene and a lively community center. Belleayre Beach and Belleayre ski area are both a 5-minute drive away, as are some of the Catskills' hottest restaurants, spas, and cider houses. Don't want to leave? Relax around the woodburning stove and soak in the clawfoot tub.

*Farmhouse Chic with Mountain and Lake Views*

Welcome to Bright Sparrow Farmhouse! Located on 8 acres of private land with greenery and a wetland lake, this home is the perfect spot to reconnect with nature and enjoy quality time with loved ones. Just mins from Windham and Hunter mountains. Enjoy skiing, hiking, biking, zip lining, water park, lakes, dining, and winery. Our home is a sustainable retreat, powered by solar energy and equipped with a backup battery system. This means you'll enjoy a comfortable and uninterrupted stay.

The Dahlia Villa within Westerhall Gardens

Reconnect with nature at this unforgettable escape. A gorgeous mature garden in a park like setting. Two queen bedrooms, great room, 75 inch TV. Radiant bathroom floor. Outdoor 45,000 gallon salt pool…that’s shared with other property (summer months - POOL IS FOR REGISTERED GUESTS ONLY - NO EXCEPTIONS) Decompress in our sauna. This a no smoking/vaping property. A sprawling 17plus acre estate. Dahlia Villa is a beautiful two bedroom completely independent unit on the estate.

Home in Great Barrington. Steps from downtown!

Central and Private! Just steps away from historic downtown Great Barrington. East Mt. Hiking trails are a quick walk away. Enjoy sunset views with friends and family, before you walk into town for a night out! Butternut Ski Area: 5-10 min drive(traffic depending) Tanglewood: 20-25 min This new home features all new appliances and furniture. Enjoy luxury, charm, and privacy while you rest easy at The Maple. 🫶 {STAND ALONE UNIT} Recent review*^ Bed- Not Broken.

COZY HOUSE *15min Windham *Stunning view*

Take a break and unwind at this peaceful home with the breathtaking view of Catskill Green County . It’s truly a place to get lost and find again , place where you will never tire of finding new adventures… Forget your worries in this specious and serene freshly renovated well maintained and clean vacation home. Perfect for a Family getaway or a weekend reunion with friends this mountain escape in prime location will guarantee you the truly unforgettable memories…..

Perfect Serene Waterfront All Season Retreat!

Enjoy everything the Berkshires has to offer from this beautiful, secluded, nicely renovated waterfront house set on two wooded acres of forested land. Explore the stream that runs through the property, or just sit on the large deck or down by the crystal clear lake and listen to the sounds of nature while feeling the warm sun on your face. Very private--just one near neighbor. The sunny house has 2 bedrooms, study with sofa bed, 2 full baths, full kitchen!

Riverfront rustic 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.