House holiday rentals in Millbrook

The Wheelhaus—Restored Home in Hamlet of Amenia

Open a bottle of wine and stretch out on the blue sectional sofa in the sunny living room. The fun and stylish decor is a modern interpretation of the area’s agricultural roots, with wood floors and exposed-brick accents in the loft bedroom. Two laptop friendly work spaces available and high speed WiFi. Reach out with any special requests! Check out our other properties nearby! Hitchbrook in Sharon, CT Thimble House in Millbrook, NY Social: @amenia.union Guests will have access to the entire home and yard. Happy to help enhance your experience and address any concerns if they arise! Walk to restaurants and cafes in the center of town, and catch a new release at the drive-in movie theater. Explore the vineyards and go hiking and biking in the local area. Explore further afield from Metro North train station, only minutes away. Parking available at the house. Close (3 miles) to Metro North Railroad. Easy access (.25 miles) to the Harlem Valley Rail trail, a walking and bike path. Walking distance to restaurants in the town of Amenia.

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.

Woodstock Historic Artist Estate - The Pond House

Awaken to an idyllic lake view through a timber-framed glass facade. Acclaimed social realist painter Reginald Marsh's family estate is known to be unique for Woodstock with its ball shaped junipers, a pond that brackets the house, expansive lawns, a gathering of birches and 100 year old cone shaped cedar trees. In short walking distance to the center of Woodstock the secluded setting with a private waterfall bordering a public preserve as well as the attention to architectural detail is unique.

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

Mindful Escape: Theater, Trails, Wood Stove

Exhale and recharge in this luxurious space at the foot of the Shawangunk Mountains. This gem features an open-concept kitchen and living room, perfect for connecting with nature. Enjoy the high-end Foster Leather Sofa, cozy movie nights on a 120" projector screen, and a wood-burning stove for chilly evenings. Every detail, from fresh linens to a meaningful library, is thoughtfully curated. Discover hidden messages throughout the house, inviting you to explore and unwind in this serene retreat.

Serene Waterfront Mill House, Stroll to Village

Sweet 1840 mill house on the water, nature-filled back deck yet 5 mins walk to antiquing & excellent Millbrook restaurants. Make this your base as you explore the beautiful Hudson Valley. Or relax out back & enjoy the birds & stream. Farmhouse antique shabby chic decor with king tempurepedic bed in large second floor master BR, two BRs with twin trundle beds, 1 bathroom upstairs & 1 down, A/C, ceiling fan, cozy woodstove, wifi with smart tv, eat-in kitchen, coffee/tea, plenty of free parking.

Boulder Tree House

Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE 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 a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.

HEAVEN ON EARTH - Hudson Riverfront Home

Voted one of the Most Romantic AirBnB's Near NYC (Time Out NY). Location, Location, Location! Smiths Point-is definition-Riverfront. Panoramic stunning views of the Hudson AND private river access yr round. Enjoy your private sauna & steam shower inside & hot tub on covered lower deck. Kayaks/SUP/Fishing Poles provided. Enjoy brunch, dinner or high tea on the Gazebo suspended over the Hudson with a private chef. Explore Hudson, Woodstock....also only 30 mins to Hunter/Skiing/Snowboarding!

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

Rustic Swedish Barn/Featured in Airbnb Magazine

Enjoy expansive views of the Catskill Mountains from this renovated but rustic Scandinavian barn. Featured in many magazines and catalogues, including AirBnB Magazine. Walk the property, with its big open field, an organic orchard, walking paths, and flower gardens. A large private pond is swimmable (after heavy rains it does get muddy). The Barn has central heat and air conditioning. A full bathroom features an antique bathtub. Enjoy dining inside, or outdoor grilling and dining.

Hillside Views in Hudson Valley

Escape to this modern, cozy retreat where nature surrounds you. Fall asleep to owls, crickets, and frogs. Just 2 mins from Rosendale and a short drive to Kingston, New Paltz, and Stone Ridge, with restaurants and trails nearby. Enjoy a gas fireplace, a reading nook with treetop views, and a large deck that feels like you’re in the trees. The private outdoor space includes a fire pit, all on a serene 3-acre lot offering total peace and quiet. Your perfect Hudson Valley escape awaits!

The Farmhouse

Enjoy staying at our charming Farmhouse in the heart of our working dairy farm. Our farm sits on some of the most beautiful hills in Cornwall with the famous Gateway to Cornwall view where you can see our dairy cows grazing in the grandeur of nature. Come say hello to the cows in the barn during milking or watch the herd cross the road evoking sites you might expect to see in small European farming villages. You'll likely see us on our tractors bringing hay and water to our cows!