Holiday rentals in North East

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.

Newly renovated cutie

Newly renovated apartment in private home. Pets may be allowed on a case by case basis. Please contact me to discuss. Ample parking off road. Quiet location. Centrally located. Hudson to the north (20 mins). Millerton (10 mins) to the East. Rhinebeck (20 mins)to the west. Poughkeepsie to the south. Summertime polo matches only 5 mins from the house. Town beach a couple mins away. Many dining options within minutes. The Stissing Center offering musical and theater options also within minutes.

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.

Luxury A-Frame Cabin in the Woods with Sauna

🔨 Heads up: We’re currently making improvements to the property and there’s a chance of construction activity nearby on weekdays between 8am–4pm for the next few months. Evenings, nights, and weekends are completely peaceful and unaffected. 🏡 Modern A-frame in the Catskills with woodland views. Cedar barrel sauna, outdoor shower, smokeless fire table, and wrap-around deck. Queen bedroom with forest views, outdoor fireplace, fast Wi-Fi. Minutes to trailheads, waterfalls, and farmers markets.

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

Romantic Sunset view, Peace n Quiet, 10 Mn to Silo

Luxurious private suite with stunning 60 mile Hudson River Valley sunset views! Horse country, ideal for horse and nature lovers and 200+bird species. Private entrance, kitchen, bathroom, HEPA filters, 500Mbps WiFi, 55” 4K TV. 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 risk. Stargaze & delight in fireflies! Relax on the deck with crisp mountain air. Near picturesque towns.

Charming Guest Suite in the Hudson Valley

Nestled in the heart of the Hudson Valley on a quiet country road, this house features a private, newly renovated space at the back of a unique house built in 1789. Surrounded by trees and nature, it makes for a perfect relaxed setting, with access to your own private deck and back yard. A short walk to enjoy Hunns Lake and close to the Buttercup Sanctuary, Stissing Mountain trails, Pine Plains and Millbrook villages. It’s the ideal retreat for a peaceful country getaway.

Hilltop Hideaway- fire pit, hot tub, mountain view

Escape to our cozy retreat, a perfect place to take in breathtaking sunsets and Catskill Mountain views. This tranquil getaway is ideal for those looking to unwind. Enjoy your morning coffee or evening glass of wine on the peaceful deck. Explore nearby quaint towns, scenic hiking trails, and local gems—just minutes from Millbrook Winery and so much more. Whether you're seeking adventure or simply a quiet place to recharge, this is the perfect spot to relax and take it all in.

bright serene + spacious barn @barn and bike

a bright serene space built by us on the property we live on. we are in - what we think - is the most beautiful region of the Hudson River Valley - surrounded by pastoral beauty and dramatic landscapes all around. 6 quaint towns are within 10-25 minutes drive. please read the entire description & rules before booking • beyond 2 guests, the rate adds 50$/night/per person • please add dogs (2 max. 50$/per dog) when booking (no cats) • we look forward to having you here!

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.

Breathtaking Views of Secluded Paradise

Nestled atop a sprawling pasture and surrounded by the rolling Catskills, Casa Lobato Farmhouse offers refined comfort and timeless charm. Spacious yet intimate, this elegant retreat is designed for effortless relaxation with elevated amenities. Take in sweeping views, unwind by the firepit beneath the stars, or hike to a cascading stream. As a certified “Healthy Home,” we proudly provide a stay that feels both indulgent and restorative.