- Entire Place
- Listings where you have the whole place to yourself.
- Private Room
- Listings where you have your own room but share some common spaces.
- Shared Room
- Listings where you'll share your room or your room may be a common space.
- Room Type
- Social Connections
- Employee host
- Instant Book
- Property Type
- Host Language
953 Rentals · Hillsdale
953 Rentals · Hillsdale
This impeccably kept, two bedroom glass cabin in the woods is the perfect Hudson Valley retreat. Nestled in the forest with lovely western views, this chic, warm and comfortable home is ideally located near Hudson NY, Great Barrington and Catamount. Learn More
Our glass cabin was a labor of love. Our goal, to live in the woods, protected from the elements as close to nature as possible. Modest, and peaceful, this home is the perfect Hudson Valley retreat and was design by Adam Rolston Architect, INC Architecture & Design PLLC (incorporatedny.com) The entire six acre lot is surrounded by woods and utterly private. The home is oriented toward a pretty southwesterly view of rolling farmland and is nestled into an acre of lush fern forest. Our drive...
Historic 1840s house with a modern vibe. Centrally located to all things Berkshires and the Hudson Valley. The sunny queen bedroom has a private attached bath. Stylish living rooms, gourmet kitchen and a relaxing porch for a perfect country retreat. Learn More
This second floor bedroom has a queen bed and a private attached bathroom. The view looks out back towards the barn. Downstairs has a large den with a 60" TV, a sunroom with a wood burning stove, the formal living room, the dining room and the kitchen with another wood burning stove. There is also a large front porch perfect some hanging out time. Out back is a large fenced in yard. There is a small dog on the property Guests have access to all of the public spaces in the house including ...
Our apartment was designed and constructed to reflect a country sophistication in a fully renovated circa 1845 property. Amenities include marble bathroom, efficiency kitchen, 2 BR, cable TV, internet access, all in the Taconic/Berkshire Mtn region. Learn More
We found a great circa 1845 house in the Berkshire/Taconic Mtn area and fully renovated the entire building creating retail shops and a sophisticated but casually comfortable 2 BR apt. saving many of the original building features. Couch in LR converts to queen size bed. Efficiency kitchen (convention microwave, induction cooktop, Mr. Coffee, all utensils, cookware, DW) with a W/D, marble bath, sleeps 4 , cable TV and internet. Bright and airy, full AC. Children friendly with tamper proof o...
This cabin is in a lovely, peaceful setting. Cozy and private, it has enough room for a big family gathering. The cabin has almost 10 acres of privacy and lots of outdoor space, but is very close to all of the Berkshires attractions. Learn More
This rustic, low-key and affordable cabin provides lots of space for a family gathering or a cozy weekend for two in the Berkshires. The house has been enjoyed by my family for four generations. Beds for ten (one queen, two twins and three bunk beds), two full bathrooms with showers (one tub) and a well-equipped kitchen. Laundry facilities in the basement. The house is well shaded by trees on all sides and stays cool in the summer (but also comes with fans). The front room has an open ...
A historic house with a modern vibe. A great base to explore all things Berkshires and Hudson Valley. Located in Hillsdale's Historic Hamlet, an easy drive to Great Barrington, Hudson, Tanglewood, theater festivals, museums, and outdoor activities. Learn More
This second floor room has a queen size bed. In the cooler months, the bed is fitted with a mattress warmer. Light pours though the three windows with views of majestic mature trees. A shared bathroom is down the hall. 1 night minimum except for stays including a Friday or Saturday night, which have a two night minimum. Guests have access to all the public areas of the house, including the living rooms, kitchen, porch and yard. Hillsdale is a sweet little village nestled in the Berkshire...
SPECIAL TWO DAY WEEKEND AVAILABLE 7/17-7/19!! for $600 Enjoy summer in this fabulous 1810 4 bedroom home. Use it as base to explore the Berkshires and Columbia County or just enjoy staying at home. Modern updates and Old World charm. Kids welcome. Learn More
Enjoy rural beauty in the Berkshires! Our 200 year old house is authentic, comfortable and family friendly. The house is 2 hours from NYC, 10 miles from Great Barrington and 20 miles from Hudson. The house has hammocks,swings, antiques, books and games, 5 fireplaces and a massage chair. 1 BR has a queen sized bed, one has a full size bed. There are two kid's BR’s; one with a brand new full sized bed and a full size futon and the other with a single bed. Great for a romantic weekend, a spa ...
A private setting in the woods located on the Green River. A perfect getaway for families where kids can run wild in the woods, play in the river, and relax around a fire. Less than 10 miles from restaurants, shopping and tons of trails for hiking! Learn More
Our property is located on a dead-end dirt road, so it is very quiet and private. Each house on the road is on a 5 or 7 acre parcels. Ideal for families and those looking for peaceful setting. Great Barrington is a 9 mile drive from the house. You will need a car.
The Candlestick Guest Room is one of three bedrooms available in my 1800 "Eyebrow" Colonial home. My home is located in bucolic Columbia County NY which is nestled between the Berkshires of MA and the beautiful Hudson River. Learn More
The "Candlestick Room" is located in a charming 1800 "eyebrow" colonial located in bucollic Columbia County, NY which is perfectly nestled between the Berkshires and the Hudson River. During your stay enjoy the tranquility of two secluded acres surrounded by wood and fields, with views of rolling hills and beautiful sunsets. The grounds include an in-ground swimming pool, pond, mature gardens and organic vegetable garden. The entire house is tastefully decorated with antiques and artwor...
Our large light-filled home is high on a hill in the Berkshires with stunning views all the way to the Catskills. Sits on 100 private acres with its own lake. Relish modern comfort in a secluded country setting. Learn More
Looking for the perfect spot for a getaway with family or friends? This spacious home in the Berkshires offers beauty, privacy and comfort. A long, densely wooded driveway opens to a private three acre lake and a lawn that sweeps up to a modern country house with a wraparound porch. Light pours in through glass doors that surround the open-concept first floor. You will enjoy the conviviality of a large, well-stocked kitchen that flows into a dining area with a farmhouse table that can accom...
Lovely, comfortable farmhouse 5 minutes to Catamount. Ski in the winter, hike, swim, bike in the summer. Close to Tanglewood and other fun cultural outlets. 20 minutes to Great Barrington, 30 to Hudson. Great restaurants nearby complete the picture. Learn More
This house is cozy and comfortable with a woodstove in the livingroom, all amenities in the kitchen and a clawfooted tub and separate shower in the bathroom. We love the country setting but we also like being near good food and having access to cultural outlets, Warren Street in Hudson, yoga in Great Barrington, Tanglewood and Jacob's pillow in the summer. The porch overlooking the garden is one of our favorite places to be in the summer. While the house can accommodate 6, we reserve that...
Farmhouse & barn nestled in the NY Berkshires, perfect for a couple escaping, or a family gathering. 1 mi from Catamount, 20 min from Gt Barrington & Hudson. 7 bedrooms, 5 acres (protected by 21 more) - fields, games, home theater, spa & more! Learn More
Built in 1818 and originally known as the Pixley-Foster General Store, our farmhouse has known only four owners in almost 200 years. Quirky and beautiful, you can emphasize quiet or fun, depending on your mood. The rooms are a mix of single, double and queen beds - with a few hidden trundles - that can comfortably handle up to 15 guests. The house is a product of every era - the downstairs has an early-19th century ruggedness, while the upstairs still maintains the charm of its past as a b...
Home on four acres, large deck, lots of privacy and just 2 miles from town center. Two queen bedrooms each with full bath. Separate study with half bath. Large eat-in kitchen. Large living and dining room. Easy access to charming Berkshire towns. Learn More
The house is decorated with pleasant colors and comfortable furnishings. Kitchen is fully equipped. Great views of gardens and wooded areas. If needed there is a pullout couch in the living room for additional sleeping space. The outdoor property is available for your use. You can take great walks on the road or on neighboring roads. The study/office is not available for your use. Otherwise you have the whole house and can access wifi, especially in kitchen and living room. There wi...
Enjoy all Columbia County has to offer with this quiet country house as your base. Outside deck, open lawn and plenty of space to spread out. Just 25 minutes from the Berkshires or ever hip Hudson. Great restaurants in nearby Philmont. Relax! Learn More
This house is on a quiet plot of land surrounded by an open lawn and woods with a lot of birds. Sit quietly on the outdoor deck and deer, wild turkeys and rabbits will saunter by. The entire house is available for rent. Kid friendly bed room with books and some toys. I am available by phone at anytime throughout the stay if a guest needs advice on the house or the area. This country chalet on 14 verdant acres is centrally located between a nice selection of small villages with a lot ha...
Book now for ski season. Nestled between hip Hudson, NY and the heart of the Berkshires in Great Barrington, MA; perfect locale for a tranquil getaway with culture close by. 15 min drive to Catamount Ski Area and 25 min drive to Butternut. Learn More
Please note special minimum stays for holidays: for Christmas I will require booking Wed Dec 24-Sun Dec 28, and for Valentines Weekend I will require Fri-Sun minimum.
Secluded modern A frame style home at the top of the Toconic Hills. View to the west of the Catskill mnts. Close to Hudson and Great Berington. Bash Bish and Toconic State park. Boat rental at Copeck Lake. Gardens, fire pit. Screened in dining room! Learn More
Private but not desolate. House on 2 acres next to open private wooded land. We have a small grass lawn for badminton or croquet. Access to woods and sun! Decks and screened room. Easy to get there. Just 2 hours north of the city off the Toconic parkway. 3 bedrooms sleep 4 comfortably. Also an additional fold out couch in the ping pong room. We will not be there but have cell phones and help full neighbors if need be. Lots to do in Columbia county. Near tangle wood in NW Mass. Swimming i...
This idyllic property sits on a quaint little village of Hillsdale in Western Berkshires, just on the New York side of MA-NY border. Comfortably accommodates 8 in the main house (3 bedrooms and a sofa bed) and 2-4 more in optional extension room. Learn More
This house sits on a private road of fewer than 15 homes, about half of which are vacation/weekend properties. It's quiet without being lonely and the natural beauty is immense. The property was gut-renovated -- practically rebuilt -- by the owner through the 80s and 90s. It's a perfect getaway from a busy city life. Antiquing, art galleries, ski resorts, and the Tanglewood as well as a myriad of high-end dining options, real farm-to-table style. Check-in and Check-out Serene, clean, and...
This private 19th Century White Farmhouse of the New York State vernacular has multiple historic outbuildings and barns. A large grassy yard and meadow with views of conservation farmland and private wooded grounds. Learn More
Guests have private access to the front entrance and center hall, living room, upper floor bedrooms and master bathroom. Living room fireplace can be utilized with limited supervision by host residing downstairs. A small dog lives in the home but will not have access to private guest space. The formal dining room and kitchen are available between 7 and 11am and will serve complimentary breakfast of local and organic yogurt, fruit, granola, and sandwiches. Additional meals and kitchen acces...
SPECIAL INTRO RATE -$250/NIGHT (base rate) + $22.50/ADDITIONAL GUEST/NT when booked between 8/28 & 10/1! Spacious, relaxing, farm house, with beautiful views of the Berkshire mountains! Perfect getaway for friends and family. Accommodates 10 Learn More
NEW LISTING Available Starting 8/29 - SPECIAL INTRO RATE -$250/NIGHT (base rate) + $22.50/ADDITIONAL GUEST/NT when booked between 8/28 & 10/1!! Situated on 60 hillside acres, you will feel miles from civilization, but when the mood strikes, find yourself just 20 minutes to high-end restaurants and shopping in either Hudson, NY or Great Barrington, MA. Tastefully decorated, this newly renovated Colonial sits apart, on what was once New England's most renowned Arabian horse farms, now in ...
Book without waiting for your reservation to be accepted