27,207 properties available

Located in Red Hook, New York, United States. rural, serene + sophisticated space In the country, yet accessible to the Hudson River Valley's engaging towns. So many guests have a hard time leaving to go out and explore .... so beware! This is a great spot to never leave as well a launch pad....YOU can use our sweet-spot as the sleep & cook spot for outdoor sporty adventure or a the stay and lounge serene escape. Plenty of folks come to the Gallatin Farmstead barn to sit by the fireplace and write!The barn was reclaimed and reconfigured from a tumbledown but picturesque outbuilding. The interior was designed, built and furnished by the owners, who live in the farmhouse next door. (See photos for proximity). Lovely open spaces are seamlessly connected with smaller spaces ... which create nooks of privacy as well as places to gather. The barn accommodates five guests. There are two queen beds and one pull-out sofa. One queen and the sofa-bed are in the communal space. The other upstairs bedroom can be closed off. The down

Located in Pine Plains, New York, United States. Secluded and Spectacular Views The Silo Set on 700 acres of wooded Hudson Valley real estate, The Silo is reached by crossing a bridge over a flowing stream (part of the intricate Hudson River watershed system). Though the home and property feel secluded, they are within easy driving distance to some of the region’s most chic, lively towns, such as Rhinebeck and Hudson. Though The Silo has the feel of a converted antique barn, it is entirely new construction, steeped with delicious touches, from the rounded walls of the “silo” to the warm, wide-board flooring. The spacious rooms of this country home are flooded with light from soaring windows that face in all directions. A big, family-style eat-in kitchen promises lively gatherings for meal preparation, casual dining, conversation, and games as you enjoy the views and the cozy warmth of the antique wood burning stove on winter days. Also on the entrance floor is a majestic great room—living and dining space perfect for holidays, lazy a

Located in Copake, New York, United States. Secluded getaway: beach access, modern amenities, screened porch and projector Nestled in the heart of Robinson Pond's serene lake community, our home offers a picturesque retreat for those seeking tranquility and adventure. Modern Amenities: Our home is newly renovated, equipped with new appliances and a movie projector. The home also has brand new heating and cooling units to keep you comfortable through the seasons. Lake Access: For water enthusiasts, the house offers access to the pristine waters of Robinson Pond via two manicured beaches. If you're looking for more water fun you and your guests can take a short drive to Copake Lake or many other local state parks and lakes. Local Attractions: Venture into the charming nearby towns of Hillsdale, Hudson, and Great Barrington. We've outlined a expansive local guide. Columbia County has so much to offer. There are plenty of fine dining, distilleries/breweries, retails shopping and outdoor locations to explore during your stay.

Located in Millerton, California, United States. Modern Ranch Retreat in Hudson Valley Discover a contemporary and recently renovated retreat in the charming village of Millerton, NY. You can relax in this immaculate space with 3 comfortable bedrooms, an energizing sunroom, and fully equipped kitchen. The convenient location and close proximity to village main street means you can take a short walk into town for shopping, dining, a movie, or an enjoyable stroll. Centrally located near vibrant cities of NY+CT+MA. A fantastic place to recharge while you visit the Hudson Valley!Endless hiking and walking trails are available nearby. Multiple Ski resorts are located nearby. Butternut Ski (16 miles) or Catamount Ski (19 miles) or Mohawk Mountain Ski (18 miles). Located two hours from NYC, the Metro North line to Wassaic is a quick trip to this special get-away place.Convenient location to a number of schools including Hotchkiss, Indian Mountain School, Salisbury Boys School, Maplebrook. and Millbrook School

Located in Pine Plains, New York, United States. Swim, kayak, hike, fish, ski and enjoy the countryside in this rustic cabin Revamped and Ready! Get cozy at Stissing Lake Guest Cabin, just 90 miles from NYC. Nestled in the Hudson Valley, this rustic 2-bed, 2-bath retreat sits on an 11 acre estate by serene Stissing Lake now boasts a fresh look. 🏊‍♂️ Dive into the lake, kayak, and savor small-town charm.🚗 Explore nearby adventures: antiquing, horseback riding, golf, skiing, ziplining, and more.Pick from two inviting bedrooms: The sunny yellow room has twin beds and a soothing clawfoot tub. The blue bedroom, with two cozy double beds and en-suite bathroom, is your haven for a tranquil, uninterrupted night’s sleep — heads up no window – perfect for those who cherish their privacy and peaceful darkness.Located a stroll away from the lake, our cabin is available for year-round rentals, ideal for companies seeking monthly stays for temporary workers.$5.5k/month for the full experience or hit us up for shorter escapes. Embrace the cabin lif

Located in Hillsdale, Georgia, United States. Restored 1810 Farmhouse in Hillsdale, NY Enjoy our sensitively renovated 1810 farmhouse just minutes away from the best the Berkshires and Hudson Valley has to offer. Catamount Ski Mountain and Terrain Park is 5 minutes away and Ski Butternut is 20. The center of Hillsdale is also 5 minutes away with a grocery store, wine merchant, and other cute local shops. Great Barrington is about a 15 minute drive and Hudson about 20 minutes with many great restaurants, shopping. Don't forget Tanglewood is close by as well! There are amazing hiking paths like Bash Bish Falls within 10 minutes. If you are a cyclist - there are incredible country roads and epic climbing in every direction too!A generous dining table is the perfect spot to gather around for a family meal or enjoy your morning coffee while watching for deer and wild turkeys. The large windowed family room has a wood burning stove and TV and looks right out onto the tree ridge and is a favorite place to watch the snow fall or autumn le

Located in Pine Plains, New York, United States. Lakefront Home in Hudson Valley Dutchess County, Pine Plains, New York Located on a peninsula in Pine Plains, New York. Enjoy the lakefront view from all angles by relaxing on the deck or lounging by the fireplace. A five minute walk down the street introduces a recreational area for activities of all sorts, such as baseball, and basketball. Swimming at the Pine Plains Beach which is down the road from the property. The beautiful town of Rhinebeck is 15 miles away, providing amazing restaurants, specialty shops, antique shops, The Center for Performing Arts, and much more. If you enjoy skiing, you can hit the slopes in 40 minutes. Try our local wineries or see a polo match. Attend one of the many seasonal festivals throughout the year. A popular amongst our renters is the Sheep Festival. Kids and adults will love the Dutchess County fair that is in town every August. If you are a hiker, there are plenty of trails located by the property. If any questions arise, please feel free to con

Located in Millerton, California, United States. Pet-Friendly Millerton Home, Walk to Downtown Fall in love with Millerton’s small-town charm when you stay at this chic 3-bedroom, 2-bathroom vacation rental! Complete with a fully equipped country kitchen, a dog bath for your furry friends, and family-friendly amenities, this charming abode has everything you'll need for an effortless stay. Take a short stroll downtown to peruse the shops and galleries, then explore the Taconic Trails, shred the slopes of the Catamount Mountain Resort, or let the kids splash around in Rudd Pond.-- THE PROPERTY --WFH Friendly | Dog Bath w/ Dryer | 12 Mi to Metro North Rail to NYC (Wassaic Train Station) | Fall Leaf Peeping | Near Boarding SchoolsBedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen Bed | Additional Sleeping: Pack ‘n PlaySTEP OUTSIDE: Seasonal outdoor shower, ping-pong table, fire pit, charcoal grill, patio furniture, picnic table, cornholeINDOOR LIVING: 5 Smart TVs, cable TV (living room), drum set, dining table, desk workspace

Located in Sheffield, Montana, United States. Spectacular 88-acre Berkshires Retreat w/ Tennis Court - Family Friendly Enjoy your vacation in a beautiful historic house located in the heart of the Berkshires. Located two and a quarter hours north of New York City, this circa-1770s center chimney colonial will charm and delight your family and guests. The rarest of New England homes, with historic bones and bright contemporary additions, August Moon sits on 88 acres of private and peaceful land in the heart of the Berkshires with mountain views from various parts of the property. Just steps away from beautiful hiking trails, it features a perfect blend of new and old, urbane and rustic, and with an eternal quality that is felt throughout the home and the vast property. Enjoy western views of Mount Race and Mount Everett from the grounds, or explore the walking trail through the woods. The trailhead to Racebrook Falls can be accessed by walking down the dirt road where the house is located.With 3100 sq. ft of wood floors and coz

Located in Copake Falls, New York, United States. Luxurious & Modern 3 BR 1.5 Bath Log Cabin Have fun with the whole family at this stylish cabin close to activities, food & natural beauty. Located just outside Taconic State Park & the Harlem River Rail Trail, it's a short walk to hiking, Bash Bish Falls, swimming, a playground & several local businesses (tavern, deli, bike shop). Several ski areas nearby, starting with one less than 10 minutes away. After your outdoor adventures, enjoy the beverage of your choice on one of the porches or the many areas set up for spending time together.Catamount ski area 10 minsGreat Barrington 20 minsJiminy Peak Mountain Resort 45 minsHudson & much more nearby

Located in Red Hook, New York, United States. Milan Hill A-Frame - Heated Pool near Rhinebeck Summary:Milan Hill A-Frame is a charming A-Frame style home in the heart of the Hudson Valley, 10 minutes from Rhinebeck and Red Hook, and just 2 hours from NYC. Set on a 6+ private acres, with tree top views , the house has 4 bedrooms and 2 full baths. Amenities include a heated saltwater pool, a fireplace, firepit & access to the best hiking and dining in the region!The whole family will enjoy the many stylish spaces to relax, indoor and out, and the ease to explore great local businesses nearbyThe Space:The anticipation mounts as one cruises the country roads heading for Milan Hill. Well-maintained old farmhouses and pastoral vistas line the route until turning up the long private driveway where the muted red house eventually comes into view. It’s not immediately evident that the house is an A Frame. The tall gabled section has a perpendicular addition that accommodates a gracious foyer, as well as the master suite, which features king

Located in Red Hook, New York, United States. Firebrook - a peaceful retreat near Rhinebeck Our home is perfectly situated for outdoor adventures during the day and cozy evenings by the fire. Perched on a hill, we have spectacular views from almost every room in the house. There are four bedrooms and three full baths. The master bedroom is set up for kids with twin beds and shelves of games and books; the other three bedrooms have queen sized beds. The common spaces are ideal for relaxing and entertaining. We have 2 living rooms, one with a wood burning stove for chilly nights or rainy days. A fully-equipped kitchen is perfect for cooking with family and friends and you can easily host 10+ people at the dining room table. On warm days, hang out or eat dinner on the large deck or patio. We're a 10-20 minute drive to Red Hook, Rhinebeck, Omega Institute, and Bard College, countless other small towns with restaurants, breweries, hikes and antiquing. Our property is on a hill making for spectacular sledding in winter (sleds provided!)

Located in Egremont, Mississippi, United States. Luxury Berkshire Estate: Proximity to all the best the Berkshires has to offer! "Words can't describe the incredible experience our family had during the holiday season at this magnificent property.""The house radiates warmth and coziness, making it the ideal setting for our holiday gathering."This 20+ acre estate features a 5 bedroom haven and four full and two half bathrooms. There are two additional rooms featuring sleeper sofas to accommodate your entire group comfortably. Great for larger families, with an abundance of space to spread out. There are three separate living rooms, each equipped with its own TV and plush furniture.There is a spacious and fully equipped gourmet kitchen, perfect for family cooking, entertainment, and bonding. It has Subzero/Wolf appliances and offers breathtaking mountain views. Don't forget to check our freezer, where locally made SOCO ice cream is stocked as our gift to you.The main living/gathering room has been completely redesigned, featuring comfo

Located in Salisbury, Vermont, United States. Luxurious, modernist barn in peaceful northwestern Connecticut - private swim! OPEN for Memorial Day! Our Connecticut retreat is equidistant from NYC and Boston and sits on 23 wooded acres with a serene, utterly private swimming lake down a forest path. Newly built in 2012, it has 3+ bedrooms, 3.5 baths, office with queen pullout bed, den with smart TV, fireplace, modern art & beautiful furnishings including mid-century modern standouts. Near Hotchkiss and Salisbury School, the Appalachian Trail, Millerton, Hudson, Great Barrington, Music Mountain, Jacob's Pillow & Tanglewood and easy day trip to MassMOCA. We prefer all-season bookings but please feel free to ask about your dates as well as about long-term discounts.

Located in Egremont, Mississippi, United States. Baldwin Hill Retreat Guest House In one of the most sought after destinations in New England, located just outside Great Barrington near the top of Baldwin Hill where the mountains ring your view in every direction, our private, spacious and inviting apartment with views of the surrounding trees out every window will be your new favorite Berkshires destination! The apartment was created in 2022 on the second story of our beautiful red barn. Everything is new! Plenty of parking right in front welcomes you to the gated courtyard that serves as your entrance. Up the stairs you will find three bedrooms, one with a king bed, one with a queen bed, and one with a double (full) bed. There is a full bath with walk-in shower and full-sized laundry equipment. The kitchen is large and fully equipped for any cooking needs you may have. It has a large gas range, dishwasher, large fridge and a separate ice maker, as well as microwave, coffee maker and toaster. Go one way from the kitchen and you'll

Located in Pine Plains, New York, United States. The Library Retreat: 3 Building Estate w/Pool+Pond Summary:Discover "The Library Retreat," a captivating multi-farmhouse in Pine Plains, just 2 hours from NYC. Set on a vast 67-acre estate, this rural haven is perfect for families and friend groupsThe mid-19th-century farmhouse, guesthouse, and loft offer 6 bedrooms plus 1 children's bedroom/ 5.5 bathrooms, a private pool, outdoor shower, fireplaces, multiple kitchens, and outdoor terraces with pond and meadow views.Explore Hudson Valley towns like Millbrook and Rhinebeck, both under 30 mins away.The Space:Discover an unparalleled retreat in the heart of the Hudson Valley, where a sprawling 67-acre estate unfolds to reveal a home accommodation designed for large groups of families and friends. Comprising three distinct buildings, each exuding its own charm and character, this property seamlessly blends historic allure with modern amenities amidst expansive natural beauty.The Grey House, a mid-19th century farmhouse, boasts two inviting

Located in Egremont, Mississippi, United States. Beautiful, Contemporary Home on 6 Private Acres; Summer 2022 Rental A warm, comfortable, contemporary home with large glass windows, a large deck, beautiful gardens, gourmet kitchen, hot tub, 6 acres of privacy, gardens and beautiful open views.Our home is located 125 miles from New York City and 125 miles from Boston (exit 1 or 2 on the Turnpike). REALLY! Keywords: Beautiful, Private, Comfortable, Spacious, Country, Views, Fireplace, Gourmet Kitchen, Sunny, Warm, Easy Access to Activities, Hiking, Tanglewood, Great Barrington, Berkshires

Located in Milan, Washington, United States. A Perfect Retreat Organic Farmstead On 90 Acres Pro Kitchen 1800's House We are a working Organic cow and pig farm with an in ground swimming pool (closed Sept 17th). Our barn and stable are used for raising pigs and cows. Please be careful not to touch white electric fencing or animals. The house was built in the 1880's, a charming white farmhouse, recently renovated with central A/C, professional kitchen with 60 inch wolf stove, double ovens, and sub zero in eat-in kitchen. Outdoor Dining areas on back porch and poolside. 3 equal sized upstairs bedrooms, 2 queen beds and 1 king, share 2 full bathrooms, one upstairs one downstairs. The upstairs bathroom has been renovated this year. We added a soaking tub and a steam shower. Music and large flat screen TV in the living room. We can stream from Netflix, Amazon and Hulu and watch DVD's from our library. We are not connected to cable service (happily). Very comfortable beds and bedding will be provided.Dining Room has a la

Located in Millerton, California, United States. Modern Barn secluded in nature with Views for as far as the eye can see. Newly rennovated coutry house perched on a hill with views for miles. Conveniently located, to Sharon, Wassaic train station, and the village of Millerton. Open floor plan flows from living room to kitchen to screened in porch. Property captures breath-taking views from every room 365 days a year. Enjoy your mornings under the pergola with a cup of coffee, followed by days reading in the screened in porch and evenings by the outside fire pit.

Located in Taghkanic, New York, United States. Chalet on 20 acres with beautiful views from every room. Large family home with room for everyone. Spectacular views, private estate high on a hill. Very kid friendly, crib, stroller and toys available. Bring your sleds or use ours. Large living room with beautiful fireplace. A week together you will enjoy!

Located in Stanfordville, Pennsylvania, United States. Stunning Country Home This lovely and gracious 5 Bedroom Greek Revival house is located adjacent to Mashomack Preserve in the Stissing Mt Valley. The home, complete with Pool house with full kitchen and Ping Pong house - has been meticulously restored and is turn key. Beautifully appointed throughout with original plaster walls, 5 fireplaces, central air, generator, new kitchen and baths. There is a 20 x 50 gorgeous pool with pool house featuring full kitchen and bath; dining pagoda and 20 x 30 workout studio. All with impeccable taste and surrounded by exquisite perennial gardens and a pond. Monthly rentals only.

Located in Pine Plains, New York, United States. Hudson Valley - Picardy Farm: Entire Estate This 19th century Greek revival home is full of history and character, and possesses a surprisingly extensive interior. A wide center hall opens to a light filled living room with wet-bar and fireplace. French doors and two huge bay windows let the outdoors in. The home is impressive 10 bedroom property with 6 full baths and 2 powder rooms. Can comfortably accommodate 20 guests.Please no events and no pets.Realign in nature, with likeminded guests The 19th century Greek revival home is full of history and character, and possesses a surprisingly extensive interior. A wide center hall opens to a light filled living room with wet-bar and fireplace. French doors and two huge bay windows let the outdoors in. Another living and dining space is lined with bookshelves and has another of the home's 5 fireplaces. The large country kitchen features 2 deep farm style sinks, a 6 burner professional stove, and spacious pantry. This room opens onto an infor

Located in Pine Plains, New York, United States. Hudson Valley - Picardy Farm: The Garden House This impressive Bright and Sunny 3 Bedroom and 2.5 bath home is comfortable and quiet. With 2 queen bedrooms, 2 single beds,2 full bathrooms, and a powder room, plenty of space for you and your guests. There is a full kitchen, dishwasher, washer/dryer and tons of space to explore the great outdoors. Each bedroom has a window air conditioner. Accommodates 6 guests comfortably. Please no events and no pets.The Picardy Farm - 10 acres plus the adjacent 33 acres allow an endless view over ancient indian land. It is located in the Hudson Valley, 2 hours north of Manhattan. On the property are curving stone walls, white picket fences, old growth hardwoods, stream with a wooden bridge and perennial gardens.Other buildings, like the old schoolhouse, which is being transformed into a dedicated Meditation & Yoga room can be used upon request.Your perfect, personal, intimate, serene retreat space. Starting from 2021 we offer personal chef - yoga & m

Located in Copake, New York, United States. Pondmodern: Renovated Midcentury Ranch Our family-friendly house is the perfect spot to explore everything between the Berkshires and the Hudson River. We are part of a lake association known as Taconic Shores on Robinson Pond, a true mid-century resort development established in 1957. Less than a 5 min. walk to our private beach, you can enjoy swimming, picnics, boating, and fishing. Grab our little red wagon and head out for a beach day. For the colder months, we are a 15 min. drive to Catamount for excellent skiing.