Airbnb your place

Holiday rentals in Town of Hillsdale

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Town of Hillsdale

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

1 of 1 pages1 / 1
Top guest favourite
The A-frame cabin features large windows that provide a view of the surrounding woods. In the foreground, a wooden hot tub is set on a deck, accompanied by a stylish firewood holder. Outdoor lights are visible, adding a warm ambiance to the evening scene.
Cabin in Saugerties
5 out of 5 average rating, 142 reviews

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!

Top guest favourite
Loft in Great Barrington
4.99 out of 5 average rating, 364 reviews

The Old Red Barn

Renovated studio in barn built circa 1830, centrally located to all activities in the Berkshires. Bright and sunny space with views of fields and spectacular sunsets. Open upstairs loft bedroom with pine floors, catherial ceiling, exposed beams, full kitchen , bathroom and washer and dryer. The Berkshires are beautiful in the fall , come stay ! 5 minute drive to town. Walk to the Green River , hike the trails. We provide all basic household supplies. We invite all to enjoy our old red barn.

Guest favourite
An A-frame cabin is nestled within a forested area, featuring a striking black exterior and a sloping roof with wooden accents. Tall grasses and shrubs surround the entrance, creating a natural backdrop. A gravel path leads to the cabin, framed by lush greenery.
Cabin in Saugerties
4.97 out of 5 average rating, 162 reviews

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.

Top guest favourite
A spacious great room features a stone fireplace amidst large windows, allowing natural light to fill the space. A wooden dining table is placed near a comfortable sectional sofa, creating an inviting area for relaxation and dining. The warm wood beams add a rustic touch.
Home in Staatsburg
4.99 out of 5 average rating, 131 reviews

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.

Guest favourite
An inviting bedroom is adorned with warm knotty pine walls and features a queen bed with decorative pillows. Two windows allow natural light to fill the space, with bedside lamps providing additional illumination. A cozy ottoman sits at the foot of the bed, complementing the rustic decor.
Cabin in Copake Lake
4.93 out of 5 average rating, 268 reviews

Cabin in Woods w/ Lake Access & *private* Hot Tub!

Don't miss your opportunity for a spring adventure at this cozy, secluded cabin with its own private hot tub and lake access! Welcome to Cabin on Hillside, a peaceful haven from the stresses of daily life. Situated in the charming town of Copake Lake, you get all the fun of a quaint lakeside community with the solitude of a wooded retreat. Whether you are looking for outdoor adventures, trips into town, or a peaceful homestay, this cabin provides it all! Come visit! Your oasis awaits!

Top guest favourite
Home in Lee
4.99 out of 5 average rating, 311 reviews

Berkshire Mountain retreat with Urban eco-luxuries

600 West Rd (an eco-friendly energy efficient home) serves as a haven of relaxation in the mountains, with all the comforts and conveniences of urban luxury. We are located in a prime location, directly in between Stockbridge, Lenox and Lee and only 15 minutes to Great Barrington. Whether you are here to ski, hike, hear the great musicians at Tanglewood, take in a play at Shakespeare & Co, or just relaxing our wood-fired hot tub- we hope you enjoy your stay and will visit us again.

Superhost
A living area is visible, featuring a sleek gray couch and a modern chair positioned near a stylish fireplace. Artwork is displayed on the wall, and natural light illuminates the space. A neutral rug adds texture to the polished floor, with a bedroom area partially seen in the background.
Flat in Copake Falls
4.9 out of 5 average rating, 367 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! Note: there is no TV.

Guest favourite
A spacious deck features two wooden lounge chairs and a small side table, surrounded by lush greenery. The railing provides unobstructed views of the wooded area, allowing natural light to create a serene atmosphere.
Cabin in Hillsdale
4.91 out of 5 average rating, 128 reviews

Secluded Mountain Getaway with Swimming Pond.

This is the perfect country getaway in a serene wooded setting yet close to town. Great for couples, solo adventurers, and families (with kids). A large deck and yard provide great views of the outdoors. This house is privately set but only a short walk to an inviting shared swim pond, meadow & trails. Area attractions include great hiking, skiing, restaurants, breweries, stores and markets. Near Great Barrington & Hudson and all the Berkshires and Hudson Valley have to offer.

Guest favourite
Tiny home in New Marlborough
4.94 out of 5 average rating, 181 reviews

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.

Top guest favourite
A spacious living area features a large, cushioned sectional sofa in a warm hue, complemented by a round coffee table. Natural light floods through tall windows, highlighting a minimalistic bookshelf and a stylish armchair in the corner, enhancing the room's cozy atmosphere.
Home in Hudson
4.98 out of 5 average rating, 120 reviews

Chic Hudson Farmhouse w/ Fireplace & Porch

1873 Stylish & cozy Hudson Farmhouse w/ a wood burning stove & the perfect porch. 14 minute drive to Warren St This 3 bedroom + office home has been lovingly updated while maintaining the original details of this historic property. Located on over an acre of land, on a quiet street, this peaceful retreat is the perfect escape to unwind and relax. With high ceilings, tons of oversized windows, and an open layout, this house feels both airy & bright.

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, 362 reviews

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

Blush at Art Park Homes is a romantic boutique tiny home getaway in Chatham, NY—just 2.5 hrs from NYC & Boston. 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
Barn in Hillsdale
4.97 out of 5 average rating, 178 reviews

Hilltop Barn - Views, Hot Tub, Plunge Pool, Sauna

A private hilltop oasis in nature. Newly renovated barn with some luxury amenities including sauna & outdoor firepit & movie theater screen & hot tub & stock tank pool on a 15-acre hilltop w/ views & privacy in Hudson Valley / Berkshires. Fully stocked for cooking & tons of games. Near great shops & restaurants in Hudson & Great Barrington. We can point you to the best people to book for private massages or yoga classes right at the house.

Popular amenities for Town of Hillsdale holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Town of Hillsdale

Top guest favourite
The exterior of a red barn-style structure is shown, surrounded by trees in a woodland setting. A large garage door faces the driveway, while a side window and a picnic table are visible. The gravel path leads up to the barn, emphasizing its rural ambiance.
Barn in Ancram
5 out of 5 average rating, 28 reviews

Serene Modern Barn near Hudson

Superhost
The red barn-style structure stands surrounded by lush greenery, with a well-maintained grassy lawn. Large trees create a natural canopy, providing shade and a serene atmosphere. A gravel pathway leads to the entrance, emphasizing the inviting outdoor setting.
Barn in Hillsdale
4.88 out of 5 average rating, 16 reviews

Historic 1850s Carriage House Studio @ Town Center

Guest favourite
A welcoming craftsman house is depicted, showcasing a covered front porch with a peaked roof. Colorful flowerbeds with various plants and herbs are seen surrounding the entrance. The lawn is well-maintained, featuring lush green grass under a bright blue sky.
Home in Hillsdale
4.89 out of 5 average rating, 18 reviews

Craftsman Cottage

Top guest favourite
Barn in Hillsdale
5 out of 5 average rating, 11 reviews

Blue Door Barn - Pond and Sweeping Views

Top guest favourite
Home in Catskill
5 out of 5 average rating, 8 reviews

Cozy stylish Cabin in the Woods

Top guest favourite
Home in East Jewett
5 out of 5 average rating, 11 reviews

Creekside Couple's Escape w/ Hot Tub Sauna & More!

Guest favourite
Two eco homes are situated in a tranquil forest setting, softly illuminated by warm exterior lights at dusk. Wooden decks extend from the homes, providing a connection to the surrounding green space. Trees frame the scene, enhancing the natural ambiance.
Cabin in Ancram
5 out of 5 average rating, 51 reviews

2bed farm stay as seen in Dezeen, architects cabin

Top guest favourite
An aerial view captures the serene landscape surrounding the home, showcasing a mix of trees transitioning into autumn colors. The house is situated on a green patch of land, with a winding path leading towards it, surrounded by the natural beauty of the countryside.
Home in Hillsdale
4.97 out of 5 average rating, 78 reviews

Gorgeous Mountain Views Retreat: Family & Nature

Frequently Asked Questions

  • What are the best places to stay in Hillsdale?

    Hillsdale has inviting stays in historic homes, countryside retreats, and options with views of rolling landscapes. Many travelers enjoy neighborhoods near the village center or peaceful rural areas.

  • What are the best things to do in Hillsdale with kids?

    Families can explore local parks, go hiking on gentle trails, or visit nearby farms that sometimes have seasonal activities. The area also has picnic spots and nature centers often suggested for young visitors.

  • What are some of the best things to do in Hillsdale?

    Explore Taconic State Park’s wooded paths, visit farm stands for local produce, or browse artisan shops around the village. Outdoor activities and cultural sites are frequently suggested by guests.

  • How is the weather in Hillsdale?

    Hillsdale has cold winters with snow and temperatures ranging from 16–35°F (-9–1°C), while summers feel mild to warm, with afternoons reaching 82°F (28°C) in July. Rainfall is spread throughout the year, and autumn brings crisp air and colorful leaves.

  • When is the best time to visit Hillsdale?

    Late spring through early autumn is often recommended for mild weather, outdoor activities, and vibrant scenery. Fall is popular for leaf-peeping as the area’s forests shift to autumn colors.

  • What are the best places to visit in Hillsdale?

    Frequently suggested spots include Taconic State Park for hiking and scenic views, and the town’s historic district, where visitors can explore local shops and galleries. Farm markets are also a favorite for fresh regional produce.

  • What are some hiking trails in Hillsdale?

    Taconic State Park has several woodland trails suited for different abilities, and the Harlem Valley Rail Trail draws those who enjoy walking or cycling along a paved route. Expect peaceful forest settings and seasonal wildflowers.

  • What are some family activities we can do in Hillsdale?

    Families can visit local farms, explore park playgrounds, or join guided nature walks. Seasonal activities, such as berry picking and wildlife observation, are often enjoyed by visitors of all ages.

  • What are some of the best day trip ideas from Hillsdale?

    Explore neighboring towns known for antique shops, visit local museums, or spend the day at parks with mountain views. Wineries and art galleries around the region are also frequently suggested for excursions.

  • Are there any pet friendly accommodations available in Hillsdale?

    Hillsdale has a variety of pet-friendly vacation rentals, particularly in rural areas and near trails. Parks and open green spaces make it easy to travel with pets.

  • What are some local tips for visiting Hillsdale?

    Pack layers, as weather can change quickly, and bring sturdy footwear for exploring trails and farms. Many local shops and eateries highlight ingredients grown nearby, so consider sampling seasonal specialties.

  • What is Hillsdale known for?

    Hillsdale is known for its rural landscapes, farming heritage, and access to outdoor recreation in the Taconic Mountains. The area has a history of small-scale agriculture and a creative community culture.

  • What are the best hidden gems to explore in Hillsdale?

    Look for tranquil woodland trails, small galleries featuring local artists, and lesser-known farm stands. Some visitors enjoy historic architecture in quieter parts of the village.

  • What are the best foods to try in Hillsdale?

    Freshly baked breads, cheeses from local dairies, and orchard-grown apples are frequently suggested. Farm-to-table eateries and seasonal jams showcase the region’s agricultural roots.

  • What should I bring for a trip to Hillsdale?

    Bring layers for variable weather, comfortable walking shoes for nature trails, and a reusable water bottle. In cooler months, pack warm outerwear, as evenings can be chilly even in spring and fall.

  • What is the nightlife in Hillsdale like?

    Hillsdale’s nightlife centers on relaxed venues, including local bars, farm-to-glass establishments, and occasional live music events. Evenings tend toward a laid-back, community-focused atmosphere.

  • What are the most popular events or festivals in Hillsdale?

    Annual summer fairs, autumn harvest festivals, and community concerts in the park are frequently suggested. Seasonal farmers markets feature local products and sometimes live entertainment.

  • Are there family friendly vacation rentals in Hillsdale?

    Hillsdale has many family-friendly stays, including homes with large yards, farmhouse-style rentals, and places near parks. Outdoor spaces and flexible layouts can suit guests of all ages.

Destinations to explore