27,207 properties available

Located in Pine Plains, New York, United States. Stylish Pine Plains Home Near Parks & Hiking! Small town charm meets modern convenience at this updated home in Pine Plains! With 1 bedroom, 1 bathroom, and a fully equipped kitchen, this vacation rental property provides everything you need for a hassle-free stay. During your stay, head to the Stissing Mountain Fire Tower for a hike with stunning views, or visit the waterfalls at Bash Bish Falls State Park. After a day spent outside, grab dinner at one of the local restaurants before heading back to get some work done in the home office.-- THE PROPERTY --Recently Renovated | Remote-Work Friendly | 18 Mi to Bash Bish Falls State ParkThis well-appointed home provides a peaceful respite for couples or digital nomads looking to explore the Pine Plains area.Bedroom: Queen BedINDOOR LIVING: Smart TVs w/ cable, dining table, office w/ desk, board games, ceiling fansKITCHEN: Fully equipped, stainless steel appliances, dishwasher, microwave, coffee maker, cooking basics, toaster, dishware & fl

Located in Copake, New York, United States. Waterfront Perfection! Weekly or weekends for 3 seasons and we prefer monthly or seasonal for the summer. Newer custom built home with expansive lawn and views of Upper Rhoda Lake/Pond. Gorgeous double height ceiling and wood-burning fireplace in Living Room, large renovated kitchen and wonderful indoor/outdoor porch with built in grill and fireplace. Extremely bright and airy throughout this home with skylights, and many corner room.. 3 full charming bedrooms and a den. And 3 full renovated bathrooms - one is a jack and jill bathroom. Magical screened in gazebo with fireplace located directly on the water. Lovely dock with boats. Some would call this home a heavenly retreat.

Located in Copake, New York, United States. Three-level dog-friendly home with a washer/dryer, central AC, yard, & patio Colonial ClassicOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Tucked away at the end of a private road, this charming, four-bedroom home offers seclusion and tranquility, making it the perfect escape from the hustle and bustle. For outdoor enthusiasts, hiking trails and picturesque lakes are just a stone's throw away, providing ample opportunities for exploration and adventure. Plus, the renowned Catamount Ski Resort is only eight miles from your door, offering winter sports enthusiasts a convenient and thrilling experience. Lake Taghkanic State Park is another great attraction located 18 miles away. For even more mountain and hiking adventures, the home is also at the base of the Berkshire Mountains in Massachusetts. Step inside to discover a comfortable living area with a wood-burning fireplace, perfect for chilly fall

Located in Pine Plains, New York, United States. Twin Island Lake House • Hot Tub Hudson Valley’s best kept secret. Built in 2018, perched on 4 acres. 3 bedrooms 2 full baths include master suite with private bathroom. Open concept kitchen/living room. A perfect getaway to relax and recharge in our year round 6 person hot tub. Amazing views and sunsets over the lake and mountains. Great hiking, fishing, kayaking, canoeing and bird watching. 16 miles to the center of Rhinebeck. Explore the local farms, restaurants, distilleries, wineries.

Located in Egremont, Mississippi, United States. 5 Minutes from Catamount Ski Area Cozy house conveniently located in a quiet area near the village of South Egremont. Fresh air, natures beauty all together close to Great Barrington and 2 ski resorts. This house is close to one of the most beautiful parts of the Appalachian Trail as it travels through the Berkshires. Nearby are beautiful lakes, mountain views and waterfalls. There are amazing country roads with spectacular colors in autumn.The house contains the basics and has a spacious modern kitchen. Relax in the cozy den or the rustic living room. Even with its convenient location, it is quiet, and has been known to have a variety of wildlife around the yard.

Located in Sheffield, Montana, United States. Guesthouse Cabin vacation rentals in Berkshire County Undermountain Lodge offers an escape to a serene cabin, nestled between pristine natural spring lakes with panoramic mountain views, it comfortably accommodates up to 12 guests. Beyond the 6th guest, there's a $135 per person fee. Couples enjoy special discounts, inquire for details. Whether with family or friends, find solace in this tranquil retreat from everyday life. Book now for an unforgettable escape.Undermountain Lodge boasts four inviting bedrooms, comfortably accommodating up to 12 guests. Spread across three levels, it offers two bathrooms, a spacious living room, a charming dining room, and a well-appointed kitchen. The property also features an expansive deck and a covered porch, surrounded by abundant outdoor space.Here's a detailed breakdown of the bedrooms:Bedroom #1 (Upstairs): This room features two queen beds and showcases rustic log and shiplap walls, providing a cozy and rustic atmosphere.Bedroom #2 (Main Floor)

Located in Copake Falls, New York, United States. Superb Views -- Sunsets, Mountains, Valley Summer 2024 overview: September, available 9/13 to 9/22 October, available starting 10/21 thru mid-NovemberMinimum rental period is 5 days.Enjoy the best of each season from this exceptional mountain view home with a heated swimming pool, tennis/pickleball court, and room for your entire family. House is fully A/C. Nestled on 10 acres with sweeping panorama of the distant mountains and valley! High ceilings, large windows, and oak wood detailing make every room bright and airy. Enjoy the modern kitchen, wrap-around deck, and outside eating. During the summers, enjoy all meals outside on the deck, with a large awning for shade. Unforgettable evening sunsets.Swimming pool is 20 yards long, ideal for laps and for children; it can be heated, if needed, making it delightful starting in June and continuing past Labor Day (depending on weather). Sliding glass doors on upper and lower levels. Tennis/pickleball court and large lawn area avail

Located in Copake, New York, United States. Beautiful Waterfront Home in the Foothills of the Berkshires Introducing an exquisite 6-bedroom family retreat nestled on 6 acres of pristine landscape with exclusive waterfront access. Discover abundant space both indoors and outdoors, featuring cozy living areas complete with a spacious TV lounge and a delightful wrap-around porch, including a screened-in section for uninterrupted relaxation.Experience the epitome of year-round comfort and leisure in this idyllic abode. Bask in the warmth of sunlit days by the inviting pool, indulge in serene kayak on the lake, or read a book on the porch. Embrace the changing seasons with vibrant fall foliage, hand-pick your own fruits, and leisurely wander through the charming nearby Berkshire towns. When winter arrives, venture to local mountains for exhilarating skiing or tubing adventures.Families with children will delight in the plethora of entertainment options, from playground adventures on the jungle gym to lively rounds of board games and

Located in Millerton, California, United States. Mountain View Farmhouse, pool/hot tub, fire pit, 4 seasons porch, game room Welcome to the Irondale Manor, an 1870s farmhouse with modern touches. While only half a mile from Millerton's Main St, one of America's coolest small towns, the house sits on over 7 acres with gorgeous views of the Berkshires. The house is great for staying in with a cozy living room, game room, and year round porch built for curling up with a book and a cup of tea (Check out the Harney & Son's flagship location around the corner). There is a hot tub, and fire pit and an above ground pool open in the summer months. But, if you're looking to explore other small towns, Millerton is centrally located and is roughly 30 minutes from Rhinebeck and Millbrook, Great Barrington, Stockbridge, and Lakeville. Not to mention nearby Catamount Ski resort, multiple golf courses including Copake Country Club, and hiking trails including the Rail Trail that is accessible right in Millerton. We look forward to hosting you! Plea

Located in Hillsdale, Georgia, United States. Secluded Country Getaway On 22 Magical Acres. Catamount ski resort 5 min away The adventure awaits in the Berkshires. Escape the hustle and bustle of your everyday life and come chill in a renovated grist mill on 22 acres. This getaway is located .5 miles from Catamount and 4 to Butternut. The property has a 10 Ft pound, waterfall and a babbling brook that can be viewed from every window. Enjoy the lush views and walking trails on the property. There are 4 fire pits on the property. I try to keep logs by the fire pit but if there has been rain and it is wet, Stewart’s sells packs of wood in an easy to carry pack. I have fire starters, long lighters and the colorful burn sticks.You can choose the Hudson food and art scene or the Great Barrington/Egremont Massachusetts food, antique shopping and hiking scene. Tanglewood is only 14 miles away. The home is decorated with Piet Boon furniture and other unique pieces. There is a full kitchen for your own culinary experience or you can call

Located in Clinton Corners, New York, United States. Stylish Farmhouse with heated pool - 35 acres Drive down a small, quiet one-lane road to this stylishly renovated 1890's farmhouse. Enjoy 35 private acres with gardens, walking trails, 2 ponds and even entertain in the historic barn. The house has everything for a luxurious get- away...heated gunite pool, year round hot tub, rolling grassy lawns with not another house in site. Close to Rhinebeck, Millbrook and the Omega Institute, you can spend your days wandering the gorgeous Hudson Valley but you probably won't want to leave the house!

Located in Hillsdale, Georgia, United States. Underhill Cottage About this spaceCharming 1948 light filled cottage, recently gut renovated. It has two, cozy, queen guest bedrooms and a twin daybed. There are two, new, full bathrooms with vintage details. The wood burning fireplace adds that perfect touch for your country getaway.The spaceIn addition to the living room, there’s a south facing sun room where you can have coffee, and a large rev room in the basement to watch tv, put together a jigsaw puzzle or work at your laptop.Guest accessGuests have access to the entire house.

Located in Pine Plains, New York, United States. A Country Lodge Straight Out of the Pages of a Great Novel The Lodge Imagine a country lodge straight out of the pages of a great novel. Rustic chic combines with modern amenities in The Lodge, where vaulted ceilings, hunting trophies, and glowing wood floors convey warmth, luxury, and a sense of rural history. The outdoorsy visitor will feel at home amidst the elk heads and bear skins, and anyone fond of elegant country life will savor the beauty of The Lodge. Set on 700 acres of woods, farmland patchwork, and meadows, with views to the mountains, The Lodge puts its guests within easy distance of skiing, hiking, and fishing, as well as museums, historic sites, and fine restaurants. The Hudson Valley boasts one of the longest fall foliage seasons in the country. The autumn colors paint the entire valley with rich warmth from September deep into October. When the winter snows fall across the landscape, take out your snowshoes and experience the drifting silence of the woods under its w

Located in Copake Falls, New York, United States. Spectacular Private Hilltop Contemporary Estate (Pool/Catamount/Bash Bish Fall) This fully renovated contemporary estate has it all to make it your place to escape all year round. Sitting on 11 private acres abutting the Taconic State Park giving you access to over 6,000 acres from your own backyard. The 4,400 sqft house has an open floor plan ideal for entertainment with two sitting areas (each with its own fire place), a formal dining area which seats 10 people next to a large kitchen with Viking appliances and a granite countertop island. There are three bedrooms and three bathrooms on the main floor and an additional three bedrooms and two bathrooms on the second floor. The 6th bedroom is furnished as an office but can accommodate temporary beds. The Master bedroom not only has the best views in the house but a spectacular en-suite Master bathroom with a stand-alone extra-large tub, separate shower room and bidet.Enjoy the views of your own heated private pool and the mountai

Located in Red Hook, New York, United States. Blissful 1848 Farmhouse, vegetable garden, swim pond, screen porch Wonderful restored 1848 farmhouse with swimming, canoeing, fishing & ice-skating pond in an idyllic, 11-acre setting. Four bedrooms, four baths, huge chef's kitchen with Vulcan restaurant stove, organic vegetable garden from which you are welcome to harvest during the summer bounty, screen porch, wood-burning fireplace, swing, sports field, tree house,, diving dock on the pond. Located in Dutchess County, an hour and a half's drive from the George Washington Bridge. A great getaway for families with kids, groups of friends, writing groups or reading groups — anyone looking for a quiet retreat at any season of the year — the 3,000+ square foot house easily sleeps 10, and can accommodate up to 12 on daybeds and a comfortable queen sleeper. It is particularly perfect for groups who like to cook and eat large meals together.The house is on a back road used by only a few cars each day. It has four bedrooms, two with queen-

Located in Ancramdale, New York, United States. Family-Friendly Home in a Private Lake It's our family weekend home, a place that has been exclusively enjoyed by our immediate family. We're excited to extend a warm welcome to other families who can appreciate the space, nature, and amenities our home has to offer.Nestled in a private lake community shared by only a handful of families, our home offers a unique opportunity to experience lake activities, hiking, skiing, and more.The spaceThe house is perfectly suited for relaxation, entertaining kids, and working from home as needed.Featuring 2 bedrooms, 2 living rooms, and a fully equipped kitchen with an dining area. You'll find one full bathroom with dual sinks, along with an outdoor shower, as well as a convenient half bath located in the basement area. Lake is 5 min walk from home and its community is very realx and chill. The basement offers versatility, serving as either a functional office space complete with WiFi and an external monitor, or as an engaging entertainment area f

Located in Pine Plains, New York, United States. Twin Island Lake Private Island Escape from it all on your own private island. A once in a lifetime experience to reconnect with nature. 10x12 canvas Safari style tent with queen size bed. Amazing 360* views over the lake and mountains. Outdoor kitchen, Weber grill. Fire pit, perfect for star gazing. Outdoor camping shower and loo. Truly off grid in the heart of the Hudson Valley. On the mainland property where you will be parking, at the dock a square back canoe awaits your arrival, with continuous use throughout your stay. Unique outdoor accommodations on a 1/4 acre private island. The entire property is solely yours to enjoy. Our campsite is off-the-grid which means there is no access to electricity, wifi, or modern plumbing. During your stay you will be provided with a canoe and 2 kayaks Phone service is excellent150 watt battery operated inverter to charge your electronics Solar and battery lighting Small cooler Upon check in, guests will be provided with all linens and 2.5 g

Located in Copake Falls, New York, United States. Summer rental 4Br - Big views + Pond, 10 acres bwtn Hudson and Great Barrington In the foothills of the Berkshire Mountains on a quiet country road halfway between Great Barrington (15Min) and Hudson (20min), this charming, newly renovated 4br house sits high on 10 breezy, bucolic acres and features great views of the Catskills. Bright, clean modern aesthetic & open floor plan. Accommodates up to 10 guests. With Bash Bish Falls State Park and amazing hiking and swimming a 2 minute drive, this is ideal for Boston and New York families looking for a big splash of summer fun!

Located in Great Barrington, Massachusetts, United States. Peaceful Compound Perfect for Groups 12 Minutes from Great Barrington! 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, sits a secluded estate with three separate homes in which to spread out! First there is the three bedroom Yellow House with heated pool, hot tub, sauna, wood firepit, extensive gardens, and pickleball court. Yellow House has a master bedroom suite located on the first floor with adjustable queen bed with an expansive two-room bath with walk-in shower and beautiful soaking tub surrounded by marble-- and your hot tub and sauna are right outside via your private door. This room is equipped with its own Asko washer and dryer. Upstairs, find two bedrooms (one with adjustable King bed and one with two Twins) and a large living room full of windows overlooking the forest. Living room has extra large flat screen TV and a gas fireplace, along wi

Located in Pine Plains, New York, United States. Elegant 6,000 Sq' 30 Acre Estate - Spectacular Views! Private 6,000 sq' home & 30 acre compound. Perfect family retreat. Sleeps 12+. Main House - 5 BR, 5 1/2 bath, gourmet kitchen (48" Sub-Zero + Wolf) , 2 huge stone fireplaces, 12 seat dining table, wide plank floors, cathedral ceilings, french doors leading to patio w/ sweeping views of Stissing Mountain. Master suite - cathedral ceilings, 4 poster king bed, flat screen TV and french doors to balcony with sweeping views of Stissing Mtn. Master bathroom has walk-in 7' slate walls & steam shower, clawfoot tub & double sink. Bedrooms - Master has King Bed, Guest Suite has queen bed, 2 BRs have Queen Beds, 1 BR has trundle bed. Guest/Pool Cottage has Queen Bed on mezzanine level.Pool/Guest Cottage - 20' Cathedral ceiling, loft bedroom. Full kitchen & bath. Bluestone floor. French doors leading to 45' gunite pool, teak seating & outdoor table, Har-tru tennis court, full gym with Peloton Bike & Tred, Elliptical, Pilates, Infrared sa

Located in Pine Plains, New York, United States. Hudson Valley - Picardy Farm: The Barn The bright and cozy Barn has just been renovated and is part of the Picardy Farm, surrounded by an idyllic pastoral setting with unobstructed views. It consists of 3 charming bedrooms, a huge living room, an updated bathroom and a full-size kitchen. All of it will be used exclusivly by you. Swimming lake, hiking, riding, fishing, organic farm food, all close by. On-site chef, yoga, meditation and massage resources can be recommended to complete your relaxation experience.The bright and cozy Barn has just been renovated and is part of the Picardy Farm, surrounded by an idyllic pastoral setting with unobstructed views. It consists of 3 charming bedrooms, a huge living room, an updated bathroom and a full-size kitchen. All of it will be used exclusivly by you. Swimming lake, hiking, riding, fishing, organic farm food, all close by. On-site chef, yoga, meditation and massage resources can be recommended to complete your relaxation experience.The B

Located in Pine Plains, New York, United States. The Blue House - St. Peter Hill Summit 3 Bedroom modern house including 2.5 Bathrooms with open living space. This house impresses with its warm, modern and stylish furnishings. Absolute seclusion, privacy and relaxation are guaranteed here. Your perfect, personal, intimate, serene retreat space - yoga teachers, meditation teachers, masseur’s, vegan and or organic chef upon request.You enter the house and go directly to the open, spacious living area with a fireplace and the open kitchen. Smaller and larger groups can be cooked in the fully equipped kitchen. The kitchen is a place of wellbeing and a place of communication in one.The stairs lead to the bedrooms. Also, you will find 2 full bathrooms and one smaller bathroom as well. If you want to be creative or productive, there is also a workspace including a desk.The interior features warm natural tones and wood, which integrate perfectly into the beautiful landscape. Both from the terrace and from the wide balcony you have a wonder

Located in Pine Plains, New York, United States. Hudson Valley- Picardy Farm: The Main House This 19th-century Greek revival home is full of history and character and possesses a surprisingly extensive interior. The home is an impressive 4 bedroom property with 3 full baths 1 powder room. Bedroom 1 is a King Size bed with an en suite bathroom. Bedroom 2 is a Queen size bedroom with en suite bathroom. Bedroom 3 and 4 are queen size bedrooms with a shared hallway bathroom.Accommodates up to 8 guests. Please no events and no pets.A wide center hall opens into a light filled living room with fireplace. French doors and two huge bay windows let the outdoors in. Another bright living and dining space with wide open vistas offers views over the rolling hills. The large country kitchen features everything needed to serve easily a group of 20 guests or even prepare and cook meals together in a larger group.The former home of Artie Shaw and Ava Gardner. The Picardy Farm - 10 acres plus the adjacent 33 acres allow an endless view over the ancie

Located in Red Hook, New York, United States. Cozy Cottage Retreat on Little Wappinger Creek with Spring Fed Swimming Pond Originally a homestead from the1800's this cottage on the Little Wappinger Creek is a charmer a mile from the Taconic Parkway. Just 15 minutes from both Red Hook and Rhinebeck our cottage was recently re-imagined by an interior designer and has all the coziness of a welcomed retreat and is a perfect outpost to explore the Hudson Valley. Our home has 2 bedrooms, one full and one 1/2 bath, a full eat-in kitchen with dining table and breakfast bar as well as a deck to enjoy the pristine nature and abundant wildlife. Whether your up visiting Bard College, taking in a weekend retreat at Omega Institute or just exploring the region the Creek Cottage is your home away from home.The Space You'll find comfy throws and pillow, memory foam beds, a wood burning stove and an outdoor fire pit with plenty of split wood and kindling. The kitchen has been updated with a modern stove and refrigerator and enough kitchenware to m