Large group vacation rentals in Pine Plains, NY

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 Park This well-appointed home provides a peaceful respite for couples or digital nomads looking to explore the Pine Plains area. Bedroom: Queen Bed INDOOR LIVING: Smart TVs w/ cable, dining table, office w/ desk, board games, ceiling fans KITCHEN: Fully equipped, stainless steel appliances, dishwasher, microwave, coffee maker, cooking basics, toaster, dishware & flatware, spices GENERAL: Free WiFi, linens & towels, central heating, window A/C units, complimentary toiletries, washer & dryer, walk-in shower, hair dryer, iron & ironing board, trash bags & paper towels SUITABILITY: Stairs required to access, bedroom & bathroom on top floor PARKING: Driveway (2 vehicles) -- THE LOCATION -- OUTDOOR RECREATION: Stissing Lake Park (0.7 miles), Stissing Mountain Fire Tower (1.5 miles), Thompson’s Pond Preserve (1.6 miles), Wilcox Memorial Park (7.4 miles), Stanford Recreation Park (9.3 miles), Harlem Valley Rail Trail (9.6 miles), Lake Taghkanic State Park (11.0 miles), Red Hook Country Club ( 11.1 miles), Hotchkiss School Golf Course (13.5 miles), Bash Bish Falls State Park (18.0 miles), Hudson River (18.0 miles), Poet’s Walk Park (18.0 miles), Ferncliff Forest (19.4 miles), Falling Waters Preserve (27.2 miles), Esopus Bend Nature Preserve (27.9 miles) AREA ATTRACTIONS: The Stissing Center (0.7 Miles), Mashomack Polo Club (2.2 Miles), Pine Plains Equestrian Center (2.8 miles), Weathersfield Estate & Gardens (8.4 miles), Harney & Sons Tea (9.5 miles), Trever Zoo at The Millbrook School (12.1 miles),Old Rhinebeck Aerodrome (13.1 miles), Four Brothers Pizza Drive-In Movie Theater (16.0 miles), Mirbeau Inn & Spa (16.0 miles), Montgomery Place Historic Estate (16.4 miles), Dutchess County Fairgrounds (16.7 miles), Samuel’s Sweet Shop (17.0 miles), Clermont State Historic Site (18.1 miles), Wilderstein Historic Site (19.8 miles), Hudson River Maritime Museum (25.8 miles), Catskill Mountain Railroad (27.9 miles) EAT & DRINK: Champetre (0.7 miles), The Stissing House (0.8 miles), Tower Pizza (0.8 miles), Lia's Mountain View Restaurant (0.9 miles), Spud Shack (0.9 miles), El Guacamole (0.9 miles), Cider Bros Roadhouse (8.3 miles), The Pond (10.0 miles), The Red Hook Diner (15.0 miles), The Beekman Arms (17.0 miles), Gaby’s (17.0 Miles), Buns Burgers (18.0 miles), VISIT NEARBY: The Millbrook School (12.1 miles), Hotchkiss School (13.5 miles), Bard College (15.8 miles), Tivoli (16.1 miles), Millbrook (16.6 miles), Rhinebeck (16.7 miles), Hudson (23.8 miles), Kingston (25.6 miles) AIRPORTS: Hudson Valley Regional Airport (35.4 miles), Bradley International Airport - Hartford (62.5 miles), Albany International Airport (69.4 miles) -- REST EASY WITH US -- Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: The property requires stairs to access Licence number: H22-064

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 nearby 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 bed and a modern glass-enclosed shower. Moving down the hall two guest bedrooms, one on either side of the hallway, include comfy queen beds, and they share the second full bathroom, which has also been renovated with modern fixtures, and includes a tub/shower. Then into the heart of the house where the A Frame style, with its soaring ceiling, becomes evident. The open plan space is flooded with natural light emanating from the west-facing wall of windows at the far end. Whitewashed with a light pickled wood floor, the ambience is bright and airy, while the contemporary Scandinavian style with personal flourishes makes the house feel like a home. The fireplace is a focal point, with built-in wood storage adding a rustic vibe to the otherwise almost beachy space. Cozy up on the sectional before a roaring fire and dive into movies or shows on numerous streaming services, or just powwow with your crew. There are lots of books, board games and puzzles for all ages. This is Lounge Central. Then there are those for whom time off means the luxury of preparing a feast. And this kitchen is wonderfully appointed and efficiently laid out, with loads of counter space, storage and culinary accoutrements. And best thing, it’s open to the living room, so the cook can remain part of the conversation. A wonderful long farmhouse table is the ideal final component in any good Upstate getaway, and this one fits the bill. Now there is nothing that says that adults won’t adore the twin bedroom upstairs, with its own TV and play space, but our younger guests will SO appreciate being separate from the adults in their own part of the house. There is a sprawling deck outside the living room and it looks out of a wide swath of level lawn with a newly installed 14-ft heated saltwater pool. Lounges, a barbecue and dining table make this a go-to spot in warmer months. Off near the edge of the woods a swing hangs from a great maple, and a firepit ringed with seating is where everyone loves to gather under the stars for stories, laughs and memories. Milan Hill is centrally-located to a number of fun towns. It’s an easy 13 minutes into buzzing Red Hook and to Rhinebeck, is 35 minutes from skiing at Catamount and is handy to Germantown and Tivoli. Milan Hill A-Frame is just over two hours from New York City, and you’ll definitely want a car to get there and to explore around the area. For winter visits, we strongly recommend a four wheel drive vehicle. Some roads are difficult to access in inclement weather, and the driveway is long and uphill. Metro-North Train to Poughkeepsie (30 mins) or Amtrak to Rhinecliff (15 mins) are also accessible. STR License No. H21-004 *Please note that the pool is available during the summer season only. Please inquire regarding opening and closing dates. * The pool is heated up to 75 degrees, complimentary. If you desire additional heating, there is a fee, please inquire for more information. There is a minimum of 2 nights charge for pool heating and the cost ranges from $200-$300 total for pool heating. **Dogs are welcome at the property (with an additional per-pet fee). Sorry, cats are not permitted. License number: H21-004

Prepare to be awed as you approach the Hammock Hill House, with its circular driveway, lush landscaping, and wrap-around porch. This expanded A-frame log-cabin provides an impressive presentation and a hint of the upscale features awaiting you. Situated on over 20 acres with an abundance of space over 3 floors, this home offers its guests the opportunity to shake off the stress of the city, find a comfortable space to relax in relative solitude, and enjoy the peace that being amongst nature always brings. Living Spaces We often hear about the “WOW” factor in particularly spectacular homes. When you walk into the Hammock Hill House, you’ll experience it first hand. Walk into the sun-dappled living room, with its soaring ceilings, two-story windows, and a floor-to-ceiling rock fireplace and that “WOW” factor comes to life. Sink into one of the two facing modern sofas or side chair, kick off your shoes, switch on the fireplace and find yourself both mesmerized and calmed by the dancing flames. Or maybe you’re ready to tackle the book you’ve saved for vacation from the comfort of the hanging egg-chair. Or even better, you just want to absorb your surroundings in one of the Acapulco chairs facing the endless view. Later, slip downstairs to the lounge for a game of pool, or darts, or even a board game, as you sip on your favorite drink. Then stream your favorite show or movie on the HDTV as you relax on the cozy sectional sofa. Cooking & Dining This gourmet kitchen will make even the pickiest of chefs proud. This generous space offers Wolf and Miele appliances in stainless steel, a beautifully tiled backsplash, abundant counter space for food prep and enough cabinets for all of your groceries. A Keurig coffee maker is provided with a selection of coffee pods. In keeping with the open concept theme, the dining room is adjacent to the kitchen, with an extended table that seats 8 comfortably. This space overlooks the deck, providing lovely natural light and views of the outdoor scenery. Sleeping Accommodations and Bathrooms The Hammock Hill House has 4 bedrooms and 3.5 baths, comfortably accommodating your group of up to 10. The spacious primary bedroom is located off the living room and features a king size bed, with dual nightstands and lamps, a full-length mirror and ceiling fan. The en-suite bath has a soaking tub and separate walk-in shower. Upstairs, the first guest room offers soaring ceilings with beam accents, a queen bed and two twins. The second guest room also offers soaring, beamed ceilings and a queen bed. The upstairs bath features a tiled walk-in shower and is fully stocked with towels and soaps . On the lower level, just off the lounge, is the last guest room with a king bed, dual nightstands and lamps. The lower level guest bath offers a tub/shower. Outdoor Amenities Imagine yourself sitting comfortably on the wrap-around deck, breathing in the sweet mountain air, as you smell your dinner cooking on the gas grill. Enjoy that meal al fresco, at the dining table for 6. Later, take in the night stars from the bubbling warmth of the hot tub on the deck. Or perhaps, you’d rather have a good old-fashioned campfire in the firepit, as you lounge on the Adirondack chairs, roasting marshmallows and telling ghost stories. Shane lives 5 minutes away. 12min drive into Rhinebeck where there are famed restaurants, shops, bakery, markets, and more. Even closer is Red Hook, with its own community charm. Enjoy hikes, historical sites, fairgrounds, and farm stands right in the local area. You must drive everywhere. There isn’t really uber or lyft. Schedule taxi’s in advance especially when arriving outside of normal work hours. We recommend a vehicle with all wheel drive during the winter. The home is on a hill with a gravel driveway.

"The Barn at Doodletown" is a thrilling 1863 post-and-beam barn turned extraordinary home on 11 private acres. Inside, enjoy a chef’s kitchen, open living spaces, wood burning stove, and serene bedrooms with plenty of space. Surrounded by nature and close to Hudson, The Berkshires and Rhinebeck, this unique escape is just 2 hrs from NYC & under 3 hrs from Boston. "The Barn at Doodletown" is a captivating 1863 post-and-beam barn turned extraordinary Upstate abode, nestled on 11 private acres along a picturesque road in Ancram, New York. This remarkable property seamlessly marries the rustic charm of yesteryears with modern luxury, promising an exhilarating escape in the heart of nature. This captivating retreat spans a sprawling 4100 square feet across three levels, each offering its own personality and surprise touches. The adventure begins on the first level, where a smart open kitchen awaits. The fully equipped kitchen, complete with a Wolf stove, a Bosch 4-burner induction cooktop, wine cooler, and not one, but two dishwashers, is a culinary haven. A delightful family dining room, a charming bedroom, and a full bath beckon you, with seamless access to the private backyard - your gateway to nature’s embrace. Ascending to the second level, the dramatic space transforms into a formal dining room and lavish living area. Here, a plush couch sits cozily by the wood-burning stove, setting the scene for unforgettable gatherings. To the rear, discover an additional workspace and lounge area, complete with a smart TV, making this level a versatile hub for both relaxation and productivity. The third level, hosts three restful bedrooms and two full bathrooms. On one end is the primary, with a King bed and en-suite bathroom. Bridges span to each wing, adding an extra layer of intrigue to your stay. On the other side are two additional guest bedrooms with Queen beds and a shared full bath. Each bedroom is a peaceful sanctuary, and the bathrooms are designed to ensure your ultimate comfort. "The Barn at Doodletown" is not just a dwelling; it’s an outdoor playground. With 11 acres of pristine land at your disposal, you’re invited to explore, relax, and reconnect with nature. The 690-acre Doodletown Wildlife Management Area is your neighbor, offering endless opportunities for hiking, wildlife-watching, and immersion in the great outdoors. Perched on one of the most breathtaking roads in Columbia County, this home is just 25-minutes from Hudson, a vibrant town with an Amtrak station, providing effortless access to this bucolic haven. The Barn at Doodletown is about two hours from New York City and under 3 hours from Boston. You’ll definitely want a car to get there and around the area. In the winter, we recommend a car with four-wheel drive that can handle the snow and gravel roads.

Escape to Doodletown Cabin, a remarkable 4 bed/ 3 bath log country cabin, just 2 hrs from NYC & under 3 hrs from Boston! Featuring stunning interiors and outdoor amenities amidst the Catskills and Berkshire Mountains. Enjoy a year-round getaway with a floor-to-ceiling fireplace, stone patio with dining table and grill with beautiful pond views, a swimmable and fishable pond with paddle boat, garden firepit and hiking trails. Nearby towns: Hudson (25 mins), Rhinebeck (30 mins) On entering you the home, you are on the upper level greeted by a charming seating area and wooded balcony that overlooks the stunning living room. Immediately, floor-to-ceiling picture windows that adorn the front wall capture your gaze with stunning outdoor views. As you make your way down the stairs, exposed oak beams, slate floors, and a grand floor-to-ceiling stone fireplace create an atmosphere of warmth and sophistication, inviting you to unwind and soak in the natural beauty. The large front doors of the living space open directly onto a beautiful stone patio where a charming dining table awaits, offering a picturesque setting for al fresco meals. Fire up the large grill and savor the flavors of outdoor dining against the backdrop of breathtaking views, creating unforgettable moments under the open sky. An entertainer’s delight, the kitchen is equipped with professional Viking appliances: stove, refrigerator and oven where chefs and bakers alike will feel right at home. Boasting slate-tiled floor and a handcrafted oak dining table seating 8, this space is perfect for gathering with loved ones and creating lasting memories. Retreat in comfort in four spacious bedrooms, thoughtfully designed to ensure a restful night’s sleep and a rejuvenating stay. Three bedrooms feature full ensuite bathrooms ensuring privacy and convenience for your guests. The Master Bedroom on the main level offers a plush King bed, serene pond views, and ensuite bathroom. Bedroom 2, also on the main level, has a cozy Full bed with ensuite bathroom. On the second level, Bedroom 3 has Queen bed and ensuite bathroom, and Bedroom 4, is ideal for families with three Twin beds and scenic views. The cabin has a baby gate at the top of the stairs, a pack and play in the twin bedroom closet, and a highchair in the laundry room. As the sun sets, gather around the inviting fire pit and enjoy the warmth of crackling flames, creating the perfect ambiance for cozy evenings under the stars. For the adventurous souls, a network of marked hiking trails meanders through the picturesque landscape, beckoning you to explore and discover hidden treasures at every turn. Take the paddleboat for a row across the shimmering pond, where you can also enjoy swimming and fishing, or simply sunbathe while taking in the serene natural surroundings. The pond is approximately 1.5-2 acres in size and is stocked with bass, crappie, and catfish. Experience the magic of every season at Doodletown Cabin! Whether you crave cozy winter nights by the fireplace or the vibrant beauty of spring by the pond, our remarkable log cabin offers endless adventures. From summer picnics to fall hikes, there’s something for everyone to enjoy! Doodletown Cabin is part of a two home property on 100 acres. Guests enjoy access to the Log Cabin, garden firepit & games barn. The Main House, tennis, pickleball, bocce, pool, and pool house are not accessible to guests that rent the Cabin only. The pond and gardens are shared spaces for both Main House and Cabin guests. Please note that if you’ve only rented the Cabin only, the Main House may accommodate other guests during your stay, though the expansive property provides privacy for everyone. If you wish to include the Main House and its amenities in your rental, please inquire for availability and rates. Doodletown Cabin is just 2 hours from New York City and under 3 hours from Boston. You’ll definitely want a car to get there and around the area. In the winter, we recommend a car with four-wheel drive that can handle the snow and gravel roads

Discover unparalleled elegance at Doodletown Lodge, a stunning house on a 100 acre estate, just 2 hrs from NYC & under 3 hrs from Boston! This spectacular property boasts 5 bedrooms, 4 full/2 half bathrooms. Inspired by the grandeur of Adirondack camps, this house offers a truly impressive estate leaving nothing to be missed, complete with a heated pool with a built in hot tub, pond, tennis and pickleball courts, and hiking trails. Nearby towns: Hudson (25 mins), Rhinebeck (30 mins) Step into elegance through the stately port cochere, where broad double doors unveil an impressive living space. Here, a magnificent 25-foot central stone fireplace and tall vaulted ceilings create a dramatic and welcoming atmosphere. A front wall of picture windows offers panoramic views of the estate’s rolling hills and meadows. The open plan design of the main floor creates an easy flow between the spacious living room, indoor dining area, kitchen and deck. Sink into comfy couches while watching TV beside the grand fireplace, and enjoy dining for 10 on the elegant indoor dining table. Large doors open onto the elevated deck, with multiple seating areas, covered al fresco dining, a firepit lounge area, a large grill, and breathtaking views from every angle. The gourmet chef’s kitchen is a masterpiece, equipped with top-of-the-line Viking appliances, granite countertops and a large kitchen island with eat-in dining. Another door from the kitchen opens directly to the outdoor dining area for effortless indoor-outdoor entertaining. A dedicated office space on the main level ensures productive work can be done and a half bathroom adds convenience for guests. The master suite on the main level is its own private oasis with a king bed, large windows and glass doors that open onto the deck. The en-suite bathroom features a whirlpool tub and his-and-her sinks, for the ultimate rejuvenating experience. The main house has a crib, a gate at the top of the stairs and a booster seat. Descending to the lower level, you’ll discover a spacious entertainment room featuring a cozy stone fireplace, oversized couches, and a flat-screen TV—perfect for enjoying a movie or a friendly game night. Large doors open directly onto the property’s gardens, offering delightful views of the surrounding landscape. On this level, 3 ensuite bedrooms await with restful accommodations. Bedroom 2 offers another king bed, Bedroom 3 has two single beds, and Bedroom 4, a queen bed. The fifth bedroom is ideal for children with two bunk beds(twin over full and twin over twin) and an additional half bathroom completes this level. Stepping outside, the estate transforms into an outdoor paradise. Recreational facilities abound, with on-property tennis, pickleball and basketball courts providing endless opportunities for sports enthusiasts or casual play. The heated in-ground pool and infinity hot tub offer relaxation with a view, nestled behind a grand wall of pines for ultimate privacy. For a serene experience, take a row on the shimmering pond in the paddleboat, enjoy a swim or casting a line for fishing the tranquil waters. The pond is approximately 1.5-2 acres in size and is stocked with bass, crappie, and catfish. Bluetooth speakers throughout the home and over the deck create the perfect ambiance, elevating your stay with high-quality sound that flows seamlessly through each room and outdoor space, enhancing every moment. Doodletown Lodge is more than just a home; it is an experience, offering elegant interiors and an abundance of onsite amenities, all surrounded by wildlife, lush gardens, and pristine landscapes. We invite those who appreciate the finer side of country life to indulge in the delights of this one-of-a-kind estate! Guests enjoy private access to the Main House, tennis and pickleball courts, pool with hot tub, and pool house. The Log Cabin, garden firepit and entertainment barn are not accessible to guests that rent the Main House only. The pond and gardens are shared spaces for both Main House and Cabin guests. Please note that if you’ve only rented the Main House, the Log Cabin may accommodate other guests during your stay, though the expansive property provides privacy for everyone. If you wish to include the Cabin in your rental, please inquire for availability and rates. Doodletown Lodge is just 2 hours from New York City and under 3 hours from Boston. You’ll definitely want a car to get there and around the area. In the winter, we recommend a car with four-wheel drive that can handle the snow and gravel roads. * Please note that the pool and hot tub are available during the summer season only. Please inquire regarding opening and closing dates. * The playground is available for guests in both houses.

Welcome to Doodletown Lodge & Cabin, an extraordinary 100-acre estate just 2 hrs from NYC and under 3 hrs from Boston! This expansive estate features 2 beautiful dwellings offering 9 bedrooms for up to 21 guests and an abundance of indoor & outdoor amenities. Enjoy breathtaking views of rolling hills, grand stone fireplaces, a pool with built in hot tub, tennis & pickleball courts, hiking trails, a pond and more. Truly a one-of-a-kind upstate escape! Nearby towns: Hudson (25 mins), Rhinebeck (30 mins) <strong>Main House</strong> Step into elegance through the stately port cochere, where broad double doors unveil an impressive living space. Here, a magnificent 25-foot central stone fireplace and tall vaulted ceilings create a dramatic and welcoming atmosphere. A front wall of picture windows offers panoramic views of the estate’s rolling hills and meadows. The open-plan design of the main floor creates an easy flow between the spacious living room, indoor dining area, kitchen, and deck. Sink into comfy couches while watching TV beside the grand fireplace, and enjoy dining for 10 on the elegant indoor dining table. Large doors open onto the elevated deck, with multiple seating areas, covered al fresco dining, a firepit lounge area, a large grill, and breathtaking views from every angle. The gourmet chef’s kitchen is a masterpiece, equipped with top-of-the-line Viking appliances, granite countertops, and a large kitchen island with eat-in dining. Another door from the kitchen opens directly to the outdoor dining area for effortless indoor-outdoor entertaining. A dedicated office space on the main level ensures productive work can be done and a half bathroom adds convenience for guests. The master suite on the main level is its own private oasis with a king bed, large windows, and glass doors that open onto the deck. The en-suite bathroom features a whirlpool tub and his-and-her sinks, for the ultimate rejuvenating experience. The main house has a crib, a gate at the top of the stairs and a booster seat. The cabin has a baby gate at the top of the stairs, a pack and play in the twin bedroom closet, and a highchair in the laundry room. Descending to the lower level, you’ll discover a spacious entertainment room featuring a cozy stone fireplace, oversized couches, and a flat-screen TV—perfect for enjoying a movie or a friendly game night. Large doors open directly onto the property’s gardens, offering delightful views of the surrounding landscape. On this level, 3 ensuite bedrooms await with restful accommodations. Bedroom 2 offers another king bed, Bedroom 3 has two single beds, and Bedroom 4, a queen bed. The fifth bedroom is ideal for children with two bunk beds (twin over full and twin over twin) and an additional half bathroom completes this level. Bluetooth speakers throughout the home and over the deck create the perfect ambiance, elevating your stay with high-quality sound that flows seamlessly through each room and outdoor space, enhancing every moment. <strong>Log Cabin</strong> On entering the Log Cabin, you are greeted by a charming seating area and wooded balcony that overlooks the warm and inviting living room. Immediately, floor-to-ceiling picture windows that adorn the front wall capture your gaze with stunning outdoor views. As you make your way down the stairs, exposed oak beams, slate floors, and a grand floor-to-ceiling stone fireplace create an atmosphere of warmth and sophistication, inviting you to unwind and soak in the natural beauty. The large front doors of the living space open directly onto a beautiful pondside stone patio where a charming dining table awaits, offering a picturesque setting for al fresco meals. Fire up the large grill and savor the flavors of outdoor dining against the backdrop of breathtaking views, creating unforgettable moments under the open sky. An entertainer’s delight, the kitchen is equipped with professional Viking appliances: stove, refrigerator, and oven where chefs and bakers alike will feel right at home. Boasting a slate-tiled floor and a handcrafted oak dining table seating 8, this space is perfect for gathering with loved ones and creating lasting memories. Retreat in comfort in four spacious bedrooms, thoughtfully designed to ensure a restful night’s sleep and a rejuvenating stay. Three bedrooms feature full ensuite bathrooms ensuring privacy and convenience for your guests. The Master Bedroom on the main level offers a plush King bed, serene pond views, and an ensuite bathroom. Bedroom 2, also on the main level, has a cozy Full bed with an ensuite bathroom. On the second level, Bedroom 3 has a Queen bed and an ensuite bathroom, and Bedroom 4 is ideal for families with three Twin beds and scenic views. <strong>Outdoor Amenities</strong> Stepping outside, the estate transforms into an outdoor paradise, offering a wealth of recreational facilities and serene experiences. Engage in friendly competition on the tennis, pickleball and basketball courts. Unwind in the heated in-ground pool and infinity hot tub, both nestled behind a grand wall of pines for ultimate privacy. Take a peaceful row on the shimmering pond in the paddleboat, enjoy a swim, or cast a line for fishing in the tranquil waters. Explore groomed hiking trails that wind through the estate’s natural beauty, revealing hidden treasures at every turn. As the sun sets, gather around the inviting fire pit, enjoying the warmth of crackling flames and creating the perfect ambiance for cozy evenings under the stars. This outdoor haven ensures every moment is filled with relaxation, adventure, and unforgettable memories. <strong>Doodletown Lodge & Cabin</strong> epitomizes elegance, comfort, and natural beauty in an extraordinary estate. Featuring elegant interiors, state-of-the-art amenities, and a wealth of outdoor activities, it’s perfect for large groups, retreats, and memorable gatherings. Nestled among lush gardens and pristine landscapes, this property offers an ideal backdrop for relaxation, adventure, and entertainment in every season. Discover the essence of country living and immerse yourself in the countless pleasures of this exceptional estate. Doodletown Lodge - Main House & Cabin is just 2 hours from New York City and under 3 hours from Boston. You’ll definitely want a car to get there and around the area. In the winter, we recommend a car with four-wheel drive that can handle the snow and gravel roads. * Please note that the pool and hot tub are available during the summer season only. Please inquire regarding opening and closing dates. * The playground is available for guests in both houses.

Welcome to Valley View, a unique 5 bed/4.5 bath home with stunning interiors and exceptional outdoor amenities, just 2.5 hrs from Boston and NYC. At its heart is a masterfully restored 1850s post and beam post office, preserved in full and paired with a significant modern build that brings the whole property into the present. Set on nearly 40 private acres with panoramic views, the home features a saltwater pool and deck, gym, outdoor dining, firepit, and a serene pond. Nearby towns: Hudson (30 mins), Great Barrington (30 mins) Valley View is a 5-bedroom, 4.5-bathroom property that tells two stories at once. The original structure, a fully outfitted suite dating to the 1850s, was built as a post office and general store, its post-and-beam bones intact and beautifully preserved. The new wing is a substantial modern home in its own right, designed to complement the historic suite while bringing light, space, and contemporary living to the forefront. Together, they create something genuinely uncommon. Set on nearly 40 acres of idyllic countryside, Valley View offers expansive panoramic pastoral views, a large serene pond, and mature trees that create a private and tranquil retreat. The new wing opens with a bright mudroom that leads into an expansive open-plan living, dining, and kitchen space. A glass window wall and fully retractable doors flood the interior with natural light and open directly onto the covered outdoor dining area, lounge, and saltwater pool deck beyond. Inside, a large sectional and wood-burning fireplace anchor the living area, while the dining table and fully equipped kitchen handle the rest. The historic cottage houses a study stocked with books and a desk for remote work, along with a guest bedroom featuring a king bed, original wood beams, natural wood floors, a sitting area, and private garden access. Upstairs, a lofted bedroom with a queen bed and full bathroom showcases the original structure at its finest. The primary suite, on the main level of the new wing, offers a king bed and large picture windows framing the rolling countryside. On the lower level, two additional guest bedrooms each have king beds and en suite bathrooms, alongside a TV room/den and a fully equipped gym. The home is climate-controlled throughout by a newly installed geothermal system, energy-efficient and designed for year-round comfort. Outside, nearly 40 acres of private land surround the property, with a saltwater pool as the centerpiece of the deck. A covered terrace and shaded lounge area are ideal for al fresco dining, while the firepit under the pergola is the spot to be after sundown. A serene pond and panoramic pastoral views complete the picture. At Valley View, the historic and the contemporary sit side by side, complemented by exceptional outdoor amenities and natural surroundings, for a stay that is genuinely hard to find elsewhere. Valley View is approximately 2.5 hours from Boston & New York City. You’ll definitely want a car to get enjoy the region. In the winter, we recommend a car with four-wheel drive that can handle the snow and gravel roads. There is plenty of parking on the premises. * Please note that the pool is available during the summer season only. Please inquire regarding opening and closing dates. * The pool is heated up to 75 degrees, complimentary. If you desire additional heating, there is a fee, please inquire for more information. There is a minimum of 2 nights charge for pool heating and the cost ranges from $200-$300 total for pool heating.

Navywood is a cozy retreat in the heart of the Hudson Valley, located 2 hours from NYC. Set on 3 private acres surrounded by woodland and meadows with walking trails and a small pond. The cabin has 3 bedrooms and 2 full baths. The house features a propane stove, firepit, and access to the best towns and parks in the region. Taghkanic State Park is under 10 minutes away. If you’re interested in town exploring, Red Hook (10 mins) Tivoli (15 minutes), Rhinebeck and Hudson (20 minutes) are quick and pretty drives! Navywood is your contemporary escape in the heart of the Hudson Valley. Elizaville, a hamlet of Livingston, lies just over the line separating Dutchess and Columbia Counties. This peaceful retreat with a minimalist flair will set you in the center of some of the best attractions the region has to offer. The home is set back on a long and winding driveway. As you enter the property, you’ll find a spacious three-acre lot with a mix of mature trees, an open meadow, and a small pond, fed by a trickling stream. Take some time to wander the paths around the pond and through the woods. Inside, the open-concept common spaces make Navywood a fantastic place to gather with family and friends. The home is tastefully renovated with light hardwood floors on both levels that set the tone for a motif of wood accents throughout. This bright and airy feel lends a welcoming tone to the shared spaces on the main floor: a dining table which accommodates six guests, and a comfy couch and seating looking out at the new deck (with BBQ grill) that spans the length of the home. The well-appointed kitchen has a gas range, and marble countertops and comes stocked with essential cookware and modern appliances, including all the basics you’d need for preparing a feast. Rounding out the main level are two bedrooms, both with queen-size beds, and each with individual temperature controls. These two guest rooms are separated by a renovated full bath with tub/shower and new marble floors. Downstairs, you’ll find a cozy entertainment room with a propane fireplace. Set the tone for an intimate night in as you sit by the fire, or gather with the family on the couch and tune into a favorite movie on the smart TV. The queen bedroom on this floor completes the sleeping arrangements for six guests at Navywood, and sports a desk with a monitor with an adapter for those who just have to sign on to work (but try not to.) This first floor also features a full bath with a walk-in shower and laundry facilities. An EV charger is available for guest use, with instructions provided in the guidebook. If you’re looking to explore the region, Elizaville is centrally located for visiting some of the most charming towns in the region. Shop boutiques in Rhinebeck, antiques in Hudson, peruse historic Bard College in Tivoli, or enjoy the serenity of Lake Taghkanic State Park. Navywood is two hours from New York City, and while you’ll definitely want a car to get enjoy the region. In the winter, we recommend a car with four-wheel drive that can handle the snow and gravel roads. There is plenty of parking on the premises. A/C: There is one mini-split A/C unit located in the main room on the second floor. Ceiling fans are available in all bedrooms, and portable fans are provided for additional cooling during exceptionally hot weather.

This beautifully renovated 4 bedroom, 3.5 bathroom cape-style home offers the perfect Hudson Valley getaway—just 2.5 hrs from NYC! Commanding views of the majestic Catskill Mountains greet you from the front of the property, while a tranquil woodland paradise unfolds behind. Unwind by the sparkling pool, gather around the crackling firepit, or fire up the BBQ for an evening of laughter and good food. Enjoy nearby towns: Hudson (20 mins), Tivoli (25 mins) and, Rhinebeck (30 mins) As you enter the home, the first floor’s airy and open-plan design welcomes you and invites you to unwind and relax. Large windows showcase beautiful views from every room. The living room features a plush sofa, flat screen TV, and a cozy fireplace for chilly evenings, perfect for relaxing or entertaining. The modern kitchen is fully equipped with appliances and everything you need to whip up delicious meals. Enjoy dining inside or easily move through the sliding doors to the large screened-in patio, perfect for outdoor dining and relaxation. This property sits on over 6 acres of peaceful woodlands, ensuring a tranquil and serene atmosphere during your stay. With a refreshing pool, a warm firepit, a BBQ grill and breathtaking views, this home beckons you to unwind and reconnect with the beauty of the outdoors, offering a respite from the hectic pace of everyday life. Four beautifully appointed bedrooms offer restful accommodations for every guest. Three bedrooms have queen beds and the fourth, a charming children’s bunk room with two twin bunks. The primary suite has an ensuite bathroom with double vanity sinks and standing shower. Two guest bathrooms offer tub and shower combos ensure comfort and space for everyone. There is also a pack ’n play available if you’re traveling with a little one. And adding to the convenience, there’s a powder room on the first floor, along with a washer and dryer for any laundry needs. This home is designed to make the most of its beautiful surroundings, with large windows offering awe-inspiring views and beautiful outdoor spaces and amenities. Situated in serene woodlands, this charming cape-style retreat provides a quintessential countryside escape, promising serenity, seclusion, and outdoor revelry amidst the natural beauty of the Catskills. Sugar Mountain House is just 2.5 hours from New York City, and you’ll definitely want a car to get enjoy the region. In the winter, we recommend a car with four-wheel drive that can handle the snow and gravel roads. There is plenty of parking on the premises. *Please note that the heated pool is available during the summer season only. Please inquire regarding opening and closing dates. License number: 172.-1-62.200

Nestled at the end of a serene private road, our cozy four-bedroom home offers the perfect retreat to relax, recharge, and reconnect with nature. Whether you're dreaming of peaceful seclusion or thrilling outdoor adventures, this hidden haven has it all! You'll love warming up in the sauna after a day of outdoor adventure. -- THE PROPERTY -- Inside, you'll find a warm and inviting space, thoughtfully designed for comfort. Cozy up by the crackling wood-burning fireplace on chilly evenings or stay cool with central air during the warmer months. The chef's kitchen, complete with modern appliances, is ready to inspire unforgettable meals and memories. For the little ones, a dedicated kids‚ area with toys and games ensures hours of fun and entertainment, making this home perfect for family stays. Don't forget your furry family members‚ our home is dog-friendly, so your four-legged companions are welcome to join the adventure! Outside, gather around the cozy fire pit, complete with comfy Adirondack chairs and a peaceful view that's perfect for stargazing. For a little extra excitement, challenge your group to a lively game of Ping-Pong in the basement, fire up the gas grill for an alfresco feast, or simply unwind amidst the serene surroundings. With a streaming-ready TV, your own washer/dryer, and a guest-accessible garage, everything is designed to make your stay seamless and stress-free. Whether you're seeking romance, adventure, or cherished moments with loved ones, this forest hideaway promises an enchanting escape and memories to last a lifetime! -- THE LOCATION -- Step outside and explore hiking trails, pristine lakes, and the majestic Berkshire Mountains, all just minutes away. Winter sports lovers will delight in being only a 12-minute drive from Catamount Ski Resort, while Bash Bish Falls is also just 12 minutes away. For more outdoor fun, Lake Taghkanic State Park is a scenic 25-minute drive. Families will adore the private playground, just a 5-minute walk through a dreamy pine forest. -- REST EASY WITH US -- Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - Pet friendly w/ $200 fee (+ fees & taxes) max 2 pets of no more than 50 lbs each - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in

Step into The Rye House, a captivating hillside oasis with 4 bedrooms and 2.5 baths, where every detail is designed to delight and highlight the natural beauty around you. Located just off Copake Lake, this property offers sweeping vistas of the rolling hillside—just 2.5 hrs from NYC! Outdoors, enjoy a pool, built-in hot tub, outdoor dining & lounging by the firepit, and an elevated deck. Inside, well designed interiors invite you to unwind while picture windows frame scenic views. Nearby Towns: Copake (10 mins), Hudson (25 mins), Great Barrington (30 mins) As you enter the home, you are immediately embraced by the stunning vistas through glass windows and doors that open to the elevated deck. To the left, the open-plan living spaces are awash in natural light, thanks to grand picture windows that showcase the mesmerizing views. The living area is anchored by a generously sized sectional sofa that faces the beautiful views and is warmed by a charming wood-burning stove. Glass doors effortlessly merge the indoor space with the elevated deck, allowing you to enjoy the beautiful surroundings. Adjacent to the living area, a sleek, contemporary kitchen awaits, complete with a large island featuring eat-in seating, top-of-the-line appliances, and everything you need to whip up delicious meals in style. An adjacent dining table is framed by more breathtaking views. Behind the kitchen, a perfect TV room/office space awaits. A plush sofa, a flat-screen TV, and a convenient desk setup with large doors that open directly to the deck and the pool area, seamlessly blends work and leisure. On the opposite side of the home, discover two inviting bedrooms, a guest bedroom with a Queen-size bed, plus a convenient powder room. The primary suite is a sanctuary of relaxation, featuring a comfy king bed, large picture windows, and doors leading to the elevated deck or property gardens. The ensuite bathroom offers a rejuvenating experience, complete with a soaking tub, a standing shower, double vanity sinks, and a walk-in closet. Across the hall, a charming nursery with a sleeper sofa, crib, and rocking chair is thoughtfully designed for families with little ones. Downstairs, two additional guest bedrooms offer comfort and privacy, with one Queen and another King sized bed, one with sliding doors that open directly onto the gardens. A full bathroom provides convenient access for both bedrooms. Outside, the magic truly unfolds. Enjoy alfresco dining, grilling, and lounging by the firepit, all while taking in the spectacular views of the rolling hillside. The pool area, with its sun loungers and attached spa pool, is the perfect spot to bask in the beauty of your surroundings. The Rye House offers an enchanting blend of astounding beauty, design and natural splendor, ensuring an unforgettable country escape. The Rye House is about 2.5 hours from New York City, and you’ll definitely want a car to get there and around the area. In the winter, we recommend a car with four-wheel drive that can handle the snow and gravel roads. *Please note that the pool is available during the summer season only. Please inquire regarding opening and closing dates. * The pool is heated up to 75 degrees, complimentary. If you desire additional heating, there is a fee, please inquire for more information. There is a minimum of 2 nights charge for pool heating and the cost ranges from $200-$300 total for pool heating. Crib: A full-sized crib is available, please inquire in advance of your arrival to have it set up for your stay.

Lakeville Lodge is a 3 bed, 2.5 bath retreat just 2.5 hrs from NYC and 3 hours from Boston, located in a quiet neighborhood just a short drive to Lake Wononscopomuc. This light filled, luxurious post and beam barn style home features a pool and hot tub for year round relaxation, an indoor basketball net, and a lovely outdoor living area. Nearby towns: Lakeville (5mins), Sharon (15mins), Canaan (15mins), Kent (30mins), Litchfield (35mins) Experience rustic craftsmanship at Lakeville Lodge, a secluded retreat with pool and hot tub set on generous acreage offering true peace and privacy. The post and beam barn style home features warm wood flooring, layered brick-and-timber textures, and expansive windows that allow natural light to flood the living spaces. The open concept living room welcomes you with cathedral ceilings, an impressive floor-to-ceiling brick chimney and a classic wood-burning stove that sits ready for cozy evenings. The seating area features plush, contemporary sofas and soft accent chairs arranged around a stylish round wooden coffee table with oversized windows that wrap the room in natural light and provide serene views of lush trees and open sky. Toss a few baskets on the unique soft play basketball hoop that takes advantage of the double height ceilings. The living area flows into a beautifully appointed dining and kitchen space featuring a long solid-wood dining table ideal for group meals or game nights, with a sliding door leading to the outdoor living room just beyond. The kitchen is crafted with natural wood cabinetry offering ample counter space for cooking and entertaining and a wall of windows with gorgeous views while you cook or socialize. A laundry room is available for guest use just off the kitchen. The primary bedroom, located on the main floor, offers a king size bed, laptop friendly workspace and an en-suite bathroom with a walk-in shower. Upstairs, the light-filled loft hosts a TV lounge with a comfortable sectional couch. and a wide selection of games for your group to enjoy. There are two additional guest rooms on this floor each with king size beds. These guest rooms share a bathroom with a shower/tub combo. The outdoor spaces of this home are top tier, with a spacious dining and lounging patio area with a grill and seating areas for meals or relaxation, and a charming fire pit lounge area complete with Adirondack-style chairs arranged on a stone patio. The pool with stone surround and hot tub offer relaxing retreats no matter the season, surrounded by lush lawn. The surrounding woodlands enhance the sense of seclusion, and the quiet neighborhood location is conveniently just outside of the charming town of Lakeville, known for Lake Wononscopomuc, Connecticut’s deepest lake. Lakeville Lodge is a year round retreat and a base for exploration of the beautiful surrounding Litchfield County towns, or a place to unplug and stay put. With ample room for your group, pool, hot tub and outdoor lounging, this is a fantastic location to book your next getaway. Lakeville Lodge is just 2.5 hours from New York City. The main access routes are the NY-22 S, I-684 S, Taconic State Pkwy and I-87 S. We strongly recommend a 4x4 or a car with four-wheel drive, especially in winter, to handle snow and gravel roads. Guests are not permitted to park in the garage. A/C: There are two split units: one in the living room and one in the primary bedroom.