Holiday rentals in Town of Milan

Slate Cabin - Stylish Country Escape x Rhinebeck

This designer cabin blends natural materials and modern finishes. — sophisticated & cozy. Gaze at (or swim in!) the stunning spring-fed pond steps from the house. Lounge on the deck or enjoy coffee in the sunroom. The interiors feature three bedrooms, two full bathrooms, living room with chic and cozy furniture and wood burning fireplace, and fully appointed kitchen that's a joy to cook in. Entertain your family & friends at the table for 10 and continue out to the grounds, beverage in hand.

Bee Kind Cottage

Forget your worries in this serene Modern Farm House. Bee Kind Cottage is on the same property as our small private apiary & home. Enjoy a cup of coffee or breakfast on the covered deck. Grill dinner, enjoy cocktails, play lawn games or sit by the fire pit on the stone patio. Lake Taghkanic State Park-9.3 miles, Wilcox Park (36 hole disc golf course) 1.9 miles, Rhinebeck Village- 8.4 miles, Historic FDR house/Mills/Vanderbilt Mansions- 15 miles, wineries/distilleries/breweries 1.9 to 9.3 miles

Private Estate w/Pool, Hot Tub+Sauna nr Rhinebeck

Perched at the top of a hill on 20 private acres, this upscale, modern log home serves as an ideal home base to discover the picturesque Hudson Valley. The Hammock Hill House offers guests upscale features such as heated gunite pool, Sonos speakers, and a gourmet kitchen complete with Wolf and Miele appliances. A lower level lounge promises hours of fun with a full-size pool table, darts, and classic board games. Either the hot tub or the firepit are a perfect end to a busy day of exploration.

Modern Upstate Cabin, near Rhinebeck NY

[ 🏊🏽‍♂️ Heated pool is open end of May - end of October. During the winter months we recommend soaking in our giant freestanding tub, which easily fits 2 humans.] Welcome to Maitopia - our modern, dog-friendly, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub, a floating fireplace and a heated pool in the summer. Plus, a fenced in yard for your pup to roam! Please note: Because of bad experiences we don’t accept bookings from guests without reviews.

Sackett & Van Dam Guest House @ Little 9 Farm 1706

Named one of "The 10 Best Remote AirBnBs for an Escape From Reality" according to the author of 'Leave the World Behind' First Floor Open Space includes a fully equipped Kitchen (Viking Range, Dishwasher, Washer, Dryer, FridgeFreezer, Caesartone Counters), a Dining Room for 8 and a Living Room with Decorative Fireplace, Smart TV & Cable Second floor has 2 Bedrooms: One with a King bed overlooking the paddocks One with 2 Queen beds and a Desk overlooking the pool One bathroom with shower.

All-Season Rhinebeck Modernized Colonial Retreat

Welcome to Blue Bird Farm, minutes from Rhinebeck! Nestled on a quiet road, our historic home features a master suite with a luxurious soaking tub, 2 cozy bedrooms, and a gourmet kitchen. Relax by the fire, unwind in the expansive yard, enjoy games in the renovated barn, or swim in Round Lake. Experience the perfect blend of nature and modern comfort, ideal for any season. Explore nearby Hudson Valley attractions like Dutchess County Fair, Omega, Bard, Vassar, & the Culinary Institute (CIA).

End summer on 120 acres, Hot Tub, River & Firepit

Spend the last days of summer hiking wooded trails, exploring the river, relaxing in the hot tub, and around the fire pit under the stars. Just 15 minutes from Red Hook, you'll feel completely secluded while staying close to the area's best restaurants, farms, wineries, and shops. Designed for families and groups, the home comfortably sleeps up to 9 with three private bedrooms plus a fun bunk room for kids. Unwind by the fireplace or watch a movie in the oversized TV room with a 65" 4K TV.

3Br Hilltop Ranch on 130acre farm w/ falls & creek

Newly renovated ranch house on a private hill top of an 130 acre magical property with stunning eastern views and overlooking a historic farm. Explore the hiking trails, dip in the wading pools of 90ft waterfall's upper cascades, bike to town or simply relax on the hammock while taking in views of the rolling hills. Escape to a beautifully designed private retreat, complete with a gourmet kitchen, cozy fireplaces, and comfortable bedrooms with quiet workspaces- learn more at cascadafarm

Stagecoach House on 99 acre nature preserve

**Now offering 1pm check-in and 1pm check-out** Bright, clean newly refreshed farmhouse on 99-acre organic farm and nature preserve. The home has five bedrooms, three full bathrooms and an exceptionally well-stocked kitchen for dinners of up to ten guests. Pristine trails offer year-round nature including woods, wetlands and abundant wildlife. This quiet and peaceful valley is located a few minutes off the Taconic Parkway and under 15 minutes to the towns of Rhinebeck & Red Hook.

Luxury Scandi Lakeside Cabin with Woodfired Sauna

Our Scandi cabin offers a serene retreat with stunning lakeside views that create a tranquil atmosphere. The wood-burning sauna invites ultimate relaxation, while the peaceful design focuses on simplicity and comfort. Surrounded by a breathtaking landscape, the cabin connects you with nature, making it the perfect escape to unwind, recharge, and enjoy the beauty of both the interior and the natural surroundings. A truly peaceful haven for those seeking calm and rejuvenation.

Intimate Cottage on Private Estate

Bulls Head Cottage is a thoughtfully-designed retreat nestled within a 2.5 acre estate 5 minutes from Omega Institute and 10 minutes from the charming Village of Rhinebeck. The 720 square foot guest cottage is a relaxing place for up to 2 guests, offering cozy indoor and outdoor space including an office overlooking the property's pond. Enjoy quick access to hiking, shopping, fine dining and more. Under 2 hours from New York City by car or train. Pets not typically allowed.

Lush Retreat Near Rhinebeck

Welcome to our charming retreat near Rhinebeck! This spacious home offers a perfect blend of relaxation and productivity, boasting ample space to unwind and a dedicated work area for your convenience. Enjoy the expansive backyard, perfect for outdoor activities or simply basking in nature's tranquility. The home offers 3 bedrooms and 1.5 baths. The home is a short drive from the charming town of Rhinebeck, where you can find great restaurants and shopping.