Holiday rentals in Millerton

The Red Country Cottage

Perfect getaway in this countryside cottage nestled in nature but walking distance to town center. Spend some relaxing time watching the creak run by, walk or bike (provided/bring own) on the 26mi flat scenic Harlem Valley Rail Trail from the cottage. Enjoy the evening sitting by the fire/comfortable patio. Visit the 60’s themed movie theater and restaurant walking distance, near by brewery/winery/cafe/restaurants, wedding venues, Lime Rock Racing, skiing. Direct train to Wassaic from MetroNorth

Amenia Main St Cozy Studio

Cozy studio in well maintained house from 1900. 150 sq ft with full size bed. Unit is comfortable for one, tight for two. Right in small town of Amenia. Front porch with seats/table. Walking to food, shops, drive-in movie theatre, and rail trail. Trail is 1/4 mile from house, paved and only allows walking/biking. On trail: Arts village Wassaic (3 miles south) Millerton (8 miles north). Train to NYC is 2.5m south. Tons in area: wineries, distillery, lakes, hiking, theatre & quaint towns.

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!

Charming Mountain House

Tastefully updated 1860's farmhouse on 5 rewilded acres, less than 2 hours from New York City. Quiet and private with great energy. Nestled in a mountain hollow near world class food, bike paths, swimming, skiing, horse farms, the Appalachian Trail, this home is ideally located for exploring the Hudson Vally, from the Catskills to the Berkshires. Artesian spring water, on-demand hot water, fast Wi-FI, solar power, birds and nature all around. Lots of nature. Accessible via Metro North (Wassaic).

Peaceful Farmhouse w/ Views + Rail Trail Access

Relax in this charming 3BR farmhouse with mountain views, a sunny reading room, and direct access to the Harlem Valley Rail Trail. With-in an hour to Lime Rock Race Track, skiing, snow boarding, sledding, Sharon playhouse, and excellent restaurants in CT, MA and NY. Just a mile from downtown Millerton, this family-friendly retreat features a kids’ playroom, remote work desk w/ external monitor, full kitchen, open yard, and pet-friendly vibe. Perfect for couples, families, or work-from-retreats.

Boulder Tree House

Boulder Tree House 🌲🌲🌲 SMOKE FREE • ALLERGY FREE Rates Include a 15.5% AirBB Service Fee Early Check In & Late Check Out Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for an exciting, romantic, unique experience but can accommodate a 3rd person.

Luxe Cabin Oasis: 40 acres with stream-ideal for 2

Escape to a charming, contemporary cabin nestled above a babbling stream. Perfect for couples seeking a tranquil retreat, our cozy haven offers endless relaxation and outdoor adventures. Nestled on 40 acres of lush fields and woods. Take walks along the stream to the ruins of a former mill from the 1700’s or collect eggs from our chickens. The cabin is steps away from the Hudson Valley rail trail so you can leave your car behind and take a short walk to Millerton for coffee, movies or food.

The Upstate A - Modern Luxury in the Hudson Valley

The Upstate A is a 3-bedroom + sleeping loft, 2.5-bathroom A-frame set on a quiet cul-de-sac in the heart of the Hudson Valley. Built in 1968 and fully renovated in 2020–2021, the home blends cozy cabin character with modern comforts for a relaxed yet elevated stay immersed in nature. You'll find great hiking in the summer, vibrant fall foliage, peaceful snowy winters, fresh upstate air year-round, and serenity all day and night. See for yourself: check us out on IG @upstate_aframe

Mountain SkyLoft. Fast WiFi, Peace n Quiet!

Atop Silver Mountain, outdoor living in the private forest overlooking the Hudson Valley. Enjoy nature with 200+ bird species, yoga, meditation, or quiet reading in the fresh, crisp mountain air Fast WiFi, a 60” HD TV and wood burning fire stove. Unwind on a huge deck with cushioned chaise lounges for stargazing and Bar BQ. During the Fall, Winter and Spring seasons it is cold , snowy , icy, frozen ground. You agree that you are on the property at your own r

Bedroom Forest View I Sauna I Fire-pit I Trails

Escape to a secluded custom built tiny house nestled amongst old pines and the Umpachene River. Inside, rustic charm meets modern comfort with 2 lux queen-sized beds, a well-equipped kitchen and bathroom, a massive bedroom forest view and a private sauna. Outside the home you can find a cozy fire-pit, trails that lead down to the river, and a dining table for all your meals. Go out for a day of hiking and exploring, and come back to unwind to sounds of nature.

The Studio

Millerton, NY is a weekender's dream! Enjoy a peaceful stay in our newly renovated studio, fully furnished with a queen bed and private entrance. You're just a short walk from everything the village has to offer—from breakfast at Oakhurst Diner and coffee at Irving Farm to shopping at Westerlind, browsing Oblong Books, or catching a film at The Moviehouse. We also offer simple, transparent pricing with no cleaning fee. Perfect for a relaxing Hudson Valley getaway.

Gorgeous Modern New Ranch near Rail Trail!

Brand new top to bottom high end renovation on a stylish home just a mile from the quaint town of Millerton on 3 acres with tremendous views of the rolling hills of the Hudson Valley. Immaculate home boasts all the comforts and amenities to fully relax and absorb the landscapes. The Harlem Valley Rail Trail is a few hundred yards away. Walk or bike into town. Walk up the hillside 50 yards to capture unbelievable views. A truly stunning home and area.