Holiday rentals in Princetown

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Top-rated holiday rentals in Princetown

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

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Top guest favourite
A modern cottage is positioned amidst vibrant fall foliage. The exterior features a dark green facade with a black metal roof. A gravel pathway leads to a seating area with wooden chairs, surrounded by colorful leaves, creating a serene outdoor space.
Cabin in Middleburgh
4.94 out of 5 average rating, 104 reviews

Catskill Mountain Cabin: Valley Views/16 Skylights

Experience total serenity in this chic, solar-powered cabin. Nestled on a wooded hillside with stunning Catskill Mountain views, our tiny house features 16 skylights for world-class stargazing. You will have a cozy, perfect getaway to forget your busy life and reconnect with beautiful nature. Prime Location for Adventure: Skiing: 25 mins to Windham Mountain Hiking: 7 mins to Huyck Preserve; near 200 acres of state parks Culture: <30 mins to trendy Hudson & Catskill Shopping & restaurants

Top guest favourite
A serene pond reflects the surrounding landscape, featuring an expansive green lawn and a red barn with white trim. Nearby, white houses are nestled among trees under a partly cloudy sky. The calm water showcases patches of green algae, enhancing the natural setting.
Farm stay in Delanson
4.96 out of 5 average rating, 136 reviews

Misty Isle Acres

Our homestead, Misty Isle Acres, is our little imperfect oasis, nestled within the beautiful Helderberg hilltowns of Albany county. Our in-law apartment contains a bedroom, full bathroom, and living room with TV (inc. Netflix & Disney+), DVD player, and futon. There is an enclosed porch and deck, complete with tables, chairs, and grill. We also have a large pond and woods to explore. Please note, this is a working homestead; the grass isn't always mowed and sometimes there are animal smells.

Top guest favourite
A private hot tub is situated on the covered deck, emitting steam in the evening light. Warm illumination enhances the wood paneling, creating a serene atmosphere. A view of the landscape is visible in the background, accentuating the relaxing setting.
Place to stay in Amsterdam
4.99 out of 5 average rating, 176 reviews

Romantic 1840s Schoolhouse | Hot Tub Getaway

Sleep inside 185 years of history. This one-room schoolhouse was built in 1840, and has been completely renovated into a private retreat for two — original timbers and antique sliding doors preserved, modernized around a king bed, propane fireplace, private hot tub on the covered deck, and an oversized rain-shower for two. An hour from Saratoga, easy reach to Cobleskill, Howe Caverns, and the southern Adirondacks. Built for couples who want somewhere that doesn't feel like everywhere else.

Guest favourite
A well-appointed bedroom features a spacious bed with soft linens, accented by a decorative headboard. A cozy armchair and a small desk offer comfortable seating options. Natural light enters through a large window draped with light pink curtains, enhancing the relaxed atmosphere.
Home in Cropseyville
4.97 out of 5 average rating, 36 reviews

Grey House

Nestled in the beautiful hills of Grafton New York Greyhouse welcomes you. Grey house is a one story home that has been completely renovated with your comfort in mind. Adjacent to Greywacke Meadows. The 3 bedrooms are attractive and comfortable and sleep up-to six guests. Master bedroom has a private bathroom and a main bathroom is centrally located. Not wheelchair accessible at this time as there are stairs into the house. Multi level porches and a large patio with seating areas.

Top guest favourite
The yurt is illuminated by warm orange light from the windows, creating a welcoming contrast against the night sky. Tall trees surround the structure, while pathway lights guide the way. The soft glow enhances the tranquil outdoor setting under a starry backdrop.
Yurt in Pattersonville
4.99 out of 5 average rating, 1,000 reviews

Mariaville Goat Farm Yurt

A charming, stylish 20’ yurt in the woods on our small, off-the-grid goat farm! If you are looking to get away from it all (and still be close to SO much) - this is the place for you! Enjoy a nap in the hammock, s’mores around a campfire, a great night’s sleep under the stars, a freshly-made country breakfast - and goats! Take a walk in the woods...enjoy the artistic landscaping...try goat yoga! Or, experience some of the area’s AMAZING food, beverages, shopping, and attractions!

Guest favourite
The A-frame cabin is framed by vibrant autumn foliage, featuring warm lighting that highlights its contemporary exterior design. A spacious wooden deck is furnished with seating and a dining area, overlooking a manicured lawn. The surrounding trees display a palette of orange and yellow leaves.
Cabin in Stamford
4.97 out of 5 average rating, 324 reviews

The A-Frame at Harvest Moon Acres

Escape to this cozy, pet friendly Aframe tucked in the mountains - perfect for a peaceful getaway surrounded by nature with fireplace and mountain views in Stamford, NY, where the beauty of the Catskill Mountains surrounds you. Whether you’re sipping coffee by the fire, exploring nearby trails, or unwinding under the stars, the cabin is designed for comfort, relaxation and a little adventure Close to scenic hiking trails and nature spots. Short drive to local coffee shop and cafe.

Guest favourite
Cabin in Middleburgh
5 out of 5 average rating, 16 reviews

Catskills Cabin w/Private SAUNA-Perfect NYC Escape

Escape to our cozy Catskills cabin, a peaceful retreat on 11 private acres. Wake up to birdsong, unwind by the fireplace, and enjoy the perfect blend of rustic charm and modern comfort in a fully stocked home. This spacious one-bedroom cabin features two king beds, a fireplace, a fully equipped kitchen and a sauna to unwind and recharge. A short drive brings you to Hudson Valley’s fine-dining scene with craft cocktails, breweries, and nearby skiing and winter adventures.

Guest favourite
Cabin in Gloversville
5 out of 5 average rating, 16 reviews

Camp Karahkwa- Private Hot Tub & Lake Access

Beautiful, newly built cabin on quiet road perfect for your summer getaway. Your ideal home base for all the outdoor adventures that upstate NY has to offer. Shared lake access just 1/4 mile away. Unwind in your private hot tub under the stars after a day of adventure or cozy up by the pellet stove playing games or watching movies with loved ones. All basic cookware, utensils, soaps, clean linens & towels, and more provided for your convenience. Just bring your luggage!

Top guest favourite
A modern cabin exterior is set against a backdrop of colorful autumn foliage. The structure features large glass doors and windows, allowing natural light to flow inside. A spacious lawn is visible, complemented by seating arrangements on the patio, inviting relaxation in nature.
Cabin in Round Top
4.99 out of 5 average rating, 166 reviews

Contemporary Cabin in Catskill Mountains

Our luxurious cabin is more than just an Airbnb; it's a personal sanctuary designed with your comfort and tranquility in mind. Nestled on 1.5 acres of Catskill Mountain beauty, this idyllic retreat offers everything you need for a relaxing getaway or extended stay. Enjoy the modern amenities, cozy furnishings, and breathtaking views that make our cabin a truly special place. View more pictures at @the_reve_cabin Ready to escape the ordinary? Book your stay today.

Guest favourite
A geodesic dome is situated amidst expansive green pastures, surrounded by rolling hills and trees. The outdoor dining area with lounge chairs and a firepit can be seen adjacent to the dome, offering a scenic view of the countryside.
Dome in Cobleskill
4.95 out of 5 average rating, 128 reviews

Dome on Agroforestry Farm w/ Mountain View & Ponds

Welcome to The Dome on Long Future Farms! Our unique lodging is designed to provide a relaxing experience for 2-4 guests, with a focus on minimizing our environmental impact and supporting local ecological farming. (There are currently NO animals on the farm, as this is primarily a nut tree farm.) Our dome offers a breathtaking view of our 171-acre agroforestry land, hills and ponds, allowing you to truly connect with the natural beauty of the region.

Top guest favourite
The yurt is softly illuminated at night by string lights, creating a warm glow around the outdoor deck. Surrounded by trees and greenery, the structure offers a serene, secluded ambiance, highlighting a welcoming retreat among nature.
Cabin in Amsterdam
5 out of 5 average rating, 45 reviews

Hillside Cabin-Yurt

Discover a charming yurt-shaped house perched on a quiet hill with beautiful pond views. Inside is an open concept studio with a comfy king bed, two futons, a full kitchen, and bathroom. The large deck with dining area is perfect for meals outdoors, and the fire pit invites cozy evenings under the stars. Secluded and hidden from the road, this peaceful retreat offers a magical blend of comfort and nature’s beauty.

Guest favourite
Cabin in Berne
5 out of 5 average rating, 10 reviews

Log Cabin w/ Mountain Views + Large Deck

Escape to this peaceful 2-bedroom log cabin in the Helderbergs, where mountain views, a large deck, and cozy cabin charm make it easy to unwind. Sip coffee outside, grill dinner under the open sky, and relax by the pellet stove after a day exploring Thacher Park, Howe Caverns, Altamont, and nearby hiking trails. Perfect for couples, friends, or small families looking for a quiet upstate getaway.

Popular amenities for Princetown holiday rentals