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 tiny home features a private hot tub on the deck, illuminated by soft LED lights. The structure is surrounded by natural wood paneling, with doors leading into the cozy interior, where warm light spills out, creating an inviting ambiance.
Tiny home in Chatham
4.99 out of 5 average rating, 373 reviews

Boutique TINY home+private HOT TUB-walk to Main St

Sept. SPECIAL(Mon-Thurs): Includes Prosecco, s’mores kit, firepit supplies. Blush is a romantic boutique tiny home getaway in Chatham, NY—just 2.5 hrs from NYC. Enjoy a private hot tub, firepit, dreamy loft lounge, plush queen bed, full kitchen & curated luxe design throughout. Tucked into a peaceful private oasis, yet only a 2-min walk to Main St. restaurants, brewery, shops & theater. Perfect for couples seeking a unique Hudson Valley getaway near hiking, galleries, great dining. @artparkhomes

Top guest favourite
The kitchen features modern appliances, including a stainless-steel refrigerator and gas range. A central island with seating complements the space, accented by brick walls and decorative elements. Windows provide natural light, illuminating the geometric patterned floor and creating an inviting cooking environment.
Home in Schenectady
4.99 out of 5 average rating, 137 reviews

Historic Home, Downtown Schenectady

Located in the heart of the Historic Stockade District, this gorgeous home offers charm mixed with beautiful modern finishes. The moment you walk in the door, you'll feel the comfort and welcome offering a relaxing abode and make this your escape and enjoy a zen oasis. Enjoy reading the many books offered in the library loft area on the second floor, or take a rejuvenating bath in the jacuzzi tub, if you're looking to recharge, enjoy the outdoors in this private courtyard with the zen garden.

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, 108 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 charming treehouse is nestled among lush green foliage, featuring a rustic wooden exterior and a wraparound deck. Sunlight filters through the trees, creating a serene atmosphere that invites relaxation and connection with nature.
Treehouse in Argyle
4.99 out of 5 average rating, 130 reviews

Out On a Limb • A Magical Treehouse Experience

Welcome to Out on a Limb, our magical treehouse nestled in the serene woods of upstate New York. This cozy, charming hideaway offers a peaceful & romantic escape, perfect for couples or solo travelers looking to connect with nature. Surrounded by towering trees, the treehouse provides a unique experience year round—from relaxing in the hot-tub on a snowy night, to stargazing by the campfire. The treehouse is always stocked with waffle mix & homemade frozen cookies. We can’t wait to host you!

Top guest favourite
A cozy living area features two gray sofas adorned with patterned cushions, surrounded by warm light from a floor lamp. A wooden coffee table is placed in the center, holding a decorative tray and flowers. A small bar area with two stools is visible in the background.
Home in Schenectady
4.99 out of 5 average rating, 90 reviews

Schenectady Home, Perfect for your business needs.

Beautiful, safe and quite neighborhood. Newly remodeled home with everything you need. Office area with extremely fast internet and Wifi for your business/entertainment needs! Centrally located to all local businesses, colleges, hospitals and a downtown casino! Everything is 5-10 minute drive. Shopping plazas and supermarkets are around the corner. Beautiful Central park is minutes down the road and offers multiple walking/hiking paths. Wonderful restaurants/breweries and pubs minutes away.

Top guest favourite
Place to stay in Amsterdam
4.99 out of 5 average rating, 182 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 — Features a beautiful mixture of original and modernize atmosphere, with 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
The cottage is set against a backdrop of rolling hills, with a serene pond reflecting the landscape. Lush green lawn is bordered by trees showing autumn hues. A wrap-around porch offers an inviting space to enjoy the surrounding natural beauty.
Cabin in Middleburgh
4.88 out of 5 average rating, 348 reviews

Thyme Cottage-Summer Getaway

Our cottage is located in an idyllic mountain setting surrounded by spectacular & breathtaking views. The 7 acre property boasts a serene pond stocked with koi, carp & gold fish that can be viewed from the wrap-around porch. It is conveniently located within close proximity to numerous options for dining and activities such as boating, fishing, hiking, & antiquing at local shops and flea markets. Thyme Cottage is perfect for couples, solo adventurers or anyone looking for tranquility.

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, 1011 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, explore our nature trails, 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!

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, 178 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
4.94 out of 5 average rating, 144 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.

Guest favourite
Guest house in Schenectady
4.85 out of 5 average rating, 34 reviews

Private Princetown retreat

Princetown retreat- Your secluded and centrally located escape in Schenectady. We boast ✅ newly renovated private space. ✅Central Air ✅Roku TV ✅Complimentary , Tea and water. ✅ private patio with fire pit ✅ microwave ✅ complimentary kurig coffee Minutes to Rivers Casino , Proctors Theatre and Union College. 11min to Albany Airport Approx 25min to Saratoga Race way This modern gem awaits your presence

Top guest favourite
An open-concept living area is viewed from above, showcasing natural wood beams and high vaulted ceilings. The space is furnished with a green sofa and a wooden coffee table, complemented by large windows that provide panoramic views of the surrounding landscape.
Home in Schoharie
4.96 out of 5 average rating, 114 reviews

Mountainside Retreat Upstate New York

Retreat to this 3 bedroom 2.5 bath home that spreads out across 5 acres. The natural exposed warm wood beams with high vaulted ceilings finished with lustrous metals will give you all the feels. Take in all of natures beauty with the homes oversized windows that overlook the valley and mountains or step out back on the expansive deck and take in some of the most stunning sunsets/views in central New York.

Popular amenities for Princetown holiday rentals