Holiday rentals in Town of Milan

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Top-rated holiday rentals in Town of Milan

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite

A charming cabin is set against a backdrop of trees, featuring a blue exterior and a sloped metal roof. Reflections of the cabin are visible in the calm surface of a nearby pond. A small deck with steps descends into the water, enhancing the outdoor scenery.

Home in Rhinebeck

4.98 out of 5 average rating, 131 reviews

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.

FamilyLocationBack garden

Top guest favourite

The A-frame cabin features large windows that provide a view of the surrounding woods. In the foreground, a wooden hot tub is set on a deck, accompanied by a stylish firewood holder. Outdoor lights are visible, adding a warm ambiance to the evening scene.

Cabin in Saugerties

4.99 out of 5 average rating, 158 reviews

Luxury Catskills A-Frame Cabin | Hot Tub & Sauna

Nestled in the serene woods of Saugerties, NY, this luxurious A-frame cabin offers modern comfort and natural beauty. Just 10 mins from Woodstock and 2 hrs from NYC, NJ. it sits on a private 2-acre lot. Easy Access. Featuring premium queen Casper mattresses, a Breville espresso machine, a 4K projector, a firepit, grill, a cedar wood-fired hot tub & Sauna. Dog friendly! A cozy & stylish retreat near hiking, skiing, and top dining spots in the Catskills. Visit our ig ‘highwoodsaframe’ for more!

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Top guest favourite

A modern cabin features a peaked roof and large glass windows, set amidst lush greenery. A heated pool is visible in the yard, surrounded by comfortable lounge chairs, inviting relaxation in a tranquil outdoor setting.

Cabin in Red Hook

4.96 out of 5 average rating, 397 reviews

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.

FamilyLocationComfort

Top guest favourite

The exterior of the farmhouse is presented, showcasing its Romantic Carpenter Gothic style. A trellised porch is visible, surrounded by lush greenery and trees. A fieldstone wall frames the front yard, adding character to the historic property.

Home in Red Hook

4.98 out of 5 average rating, 102 reviews

The Cat's Meow Farmhouse Red Hook Rhinebeck

CATS Welcome! DOGS MUST BE APPROVED UPON REQUEST! Not for those allergic to cats. An 18th-century Carpenter Gothic style farmhouse c.1840 style with a trellised porch overlooking fields. Sleeps six in 3 bdrms. The house combines modern utilities (2 full baths, WIFI, smart TVs, washer/dryer, & full kitchen) antique furniture & two 18th-century stone fireplaces . Rural, yet only 1.6 mi. to village with many eateries, 2.8 to grocery store. 8.5 to Rhinebeck, 6 to Bard, and 2 to Aerodrome.

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Top guest favourite

The exterior view of the guest house is framed by a large tree, showcasing the red brick barn-style structure. Outdoor seating areas are visible, along with a shaded patio featuring a red umbrella. The surrounding lawn is well-kept, leading to fenced paddocks in the background.

Farm stay in Red Hook

4.98 out of 5 average rating, 178 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.

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Top guest favourite

The historic colonial farmhouse is flanked by lush greenery and flowering plants. A stone pathway leads to the inviting covered porch, where deep green columns support the upper deck. The metal roof glistens under the bright blue sky scattered with fluffy clouds, creating a peaceful country scene.

Home in Rhinebeck

5.0 out of 5 average rating, 32 reviews

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).

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Guest favourite

A serene stream cascades over smooth rocks, surrounded by a wooded area filled with autumn leaves. A wooden bench sits nearby, offering a tranquil spot to enjoy the peaceful atmosphere. The gentle flow of water reflects the greenery of the trees.

Home in Rhinebeck

4.95 out of 5 average rating, 304 reviews

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

LocationValueKitchen

Top guest favourite

A spacious dining area features a large wooden table surrounded by six comfortable chairs. Natural light streams in through two large windows, illuminating a centerpiece of fresh flowers. Reclaimed wood rafters and polished wooden floors contribute to a warm yet modern ambiance.

Home in Red Hook

4.94 out of 5 average rating, 70 reviews

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.

FamilyLocationRiver

Top guest favourite

Cabin in Red Hook

5.0 out of 5 average rating, 17 reviews

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.

FamilyLocationOutdoor spaces

Top guest favourite

The exterior of a charming cottage is seen, featuring a front porch with two black chairs and potted plants. Stone steps lead up to the entrance, flanked by shrubs and trees, creating a serene setting within the landscaped grounds.

Cottage in Rhinebeck

4.93 out of 5 average rating, 196 reviews

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.

FamilyValueIndoor spaces

Guest favourite

A charming white house is set amidst lush greenery. A stone walkway leads to a welcoming front porch, where a centered dark door complements the light exterior. Tall trees surround the property, providing shade and a sense of tranquility.

Home in Rhinebeck

4.93 out of 5 average rating, 61 reviews

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.

FamilyValueCleanliness

Guest favourite

A modern house is surrounded by trees with colorful autumn leaves. The exterior features a wraparound deck, and snow lightly covers the ground and plants. Clear blue skies enhance the peaceful outdoor setting, creating a serene atmosphere.

Home in Rhinebeck

4.91 out of 5 average rating, 267 reviews

Rhinebeck Home with an amazing outdoor space+H/tub

Primary bedroom has a king size bed, bathroom, flat/smart TV. Second bedroom has a queen size bed, both bedrooms with AC units window, TV/den has a CB2 modern sofa that extends into a queen size bed. Our house comfortably sleeps 5, with a fireplace, 2 baths, spacious outdoor deck that has screen doors to open or close with a hot tub and bbq. 8 Minutes to historic Rhinebeck, 12 minutes to Red Hook. Bard College, CIA & Omega Institute within reach!

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