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Holiday rentals in Town of Hillsdale

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Top-rated holiday rentals in Town of Hillsdale

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

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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
4.99 out of 5 average rating, 158 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
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 Town of Hillsdale
4.98 out of 5 average rating, 83 reviews

Gorgeous Mountain Views Retreat: Family & Nature

Wake up to fog lifting off the Berkshires in Columbia Co. Step onto the deck, 6 private acres of mountainside below you, no neighbors, nothing but open sky. Meadow View Manor is a 4BR Hillsdale retreat with a fire pit. Perfect for families. Enjoy the deck, remodeled kitchen, fireplace, and game room with ping-pong. Sleeps 8. Hear nothing but wind and birds. 2hrs from Manhattan, 10min from Catamount, 15min to great golf, restaurant, bar & live music, 30min from Hudson & Great Barrington. Dogs ok.

Top guest favourite
Home in Copake Lake
5.0 out of 5 average rating, 16 reviews

Waterfront Retreat in a woodsy haven

Love to share our beautiful home with design and comfort for your enjoyment. Whether it’s with family or friends, you deserve the perfect destination for luxury, fun, and relaxing. Open space and cozy bedrooms welcome you to spend weekend or weeks long getaways. Visit Copake Lake for water activities and golfing. Stay during the winter to ski at Catamount Mountain Resort or Ski Butternut in Great Barrington. Enjoy restaurants and shopping options in the nearby areas. See manual for more info.

Guest favourite
A spacious kitchen is equipped with white cabinetry and a large wooden island, featuring bar seating. Natural light floods the room through multiple windows. A dining table for six complements the space, with a fruit bowl as a centerpiece.
Cottage in Sheffield
4.92 out of 5 average rating, 193 reviews

Cheerful 3-bedroom cottage with woodstove.

Relax with the whole family at this peaceful Berkshire getaway with easy access to all the area has to offer. A quick 20-minute drive to Butternut or Catamount ski hills, as well as downtown Great Barrington. Tanglewood and Jacob's Pillow are a half-hour's drive. Or stay at home and enjoy the peace and quiet of the surrounding woods, light a fire in the woodstove, cook in the large fully-equipped kitchen or head out back to barbecue on the large deck and play a game of badminton in the yard.

Top guest favourite
A serene bedroom features a spacious bed dressed in a light, textured coverlet. Two comfortable floral armchairs sit beside a dresser, complemented by a full-length mirror. Soft light filters through a window, illuminating the gentle pastel tones of the room.
Flat in Town of Hillsdale
4.96 out of 5 average rating, 102 reviews

Perfect Apt near Berkshires, Hudson Valley

Enjoy a stylish, elegant experience at this centrally-located newly restored 2 bedroom apartment with 1.5 baths in a historic building built in 1881, placed on the National Register of Historic places in 2010. Unit is on the 2nd floor and has a private entrance. Step back in time and stay in Second-Empire mansard Victorian that retains beautiful original details/layout and help it's restoration. Perfect location where the Hudson Valley meets the Berkshires. I have 4 other listings available.

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
4.89 out of 5 average rating, 371 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 Town of 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
Home in Town of Hillsdale
4.89 out of 5 average rating, 19 reviews

Historic 1850s "The Bell House" with Private Pool

Escape to the 1850s Bell House, a historic 5BR/4.5BA estate in Hillsdale NY, once home to the prominent Bell family. Set on 3.6 acres, this fully restored gem blends period charm with modern luxuries like central A/C, heating & WiFi. Enjoy a large private swimming pool, cozy patio & ample space for the whole family. Walk to town for dining, galleries, boutiques & farmers markets. Perfect for unforgettable family getaways in a timeless countryside setting.

Top guest favourite
Barn in Town of Hillsdale
4.97 out of 5 average rating, 185 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.

Superhost
Home in Town of Hillsdale
5.0 out of 5 average rating, 3 reviews

Quaint center of town Farmhouse

This farmouse sits in the center of Hillsdale ideally positioned between Hudson and The Berkshires. Just steps to fresh town, Cook & Larder and the Rail Trail, this well appointed house is the perfect country getaway. Culture, endless restaurants and adventure at your disposal with Catamount ski area is 3.5 miles down the road and Tanglewood just 22 miles. The house is newly renovated and perfectly appointed.

Top guest favourite
A charming cottage is nestled among lush greenery, featuring a large wooden deck that invites relaxation. Sunlight filters through trees, and the inviting front porch is accessible from the yard, offering a seamless transition between indoor and outdoor spaces.
Cottage in Copake Falls
4.92 out of 5 average rating, 407 reviews

Beautiful cottage at the foot of the Birkshires

Come stay with us in our beautiful cozy cottage, on a small lot located in the heart of Copake Falls, walking distance to Taconic State Park. Enjoy great farm to table dining, ski the Berkshires (just under 10 minutes to Catamount Resort), hike to Bash Bish Falls, bike the Harlem Valley Rail Trail, and swim in the spring fed iron ore pit during the open season.

Guest favourite
The living area features wooden beams and warm wooden flooring. A cozy gray sofa adorned with patterned cushions faces a small coffee table. A comfortable chair and a desk are included, with natural light streaming through multiple windows.
Cabin in Town of Hillsdale
4.88 out of 5 average rating, 189 reviews

Cabin in the woods near Catamount Ski resort

Rustic and romantic Cabin in the wood next to a Waterfall. Surrounded by trees with a private Driveway. This is the perfect getaway for couples and groups up to 5 people. It is about 20 min from Catamount Ski resort.This is a very special magical place. let yourself be enchanted.

Popular amenities for Town of Hillsdale holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Town of Hillsdale

Guest favourite
A bright living room features a modern design with a large wall mirror above a white-brick fireplace. A comfortable black sofa and a teal accent chair provide seating, while an area rug adds color. Tall windows illuminate the space, surrounded by subtle decor elements.
Home in Town of Hillsdale
4.97 out of 5 average rating, 37 reviews

Hillsdale Modern Retreat

Top guest favourite
An aerial view of the chalet-style home reveals a spacious wrap-around deck with multiple seating arrangements, illuminated by string lights. The landscaped grounds are surrounded by trees, featuring an outdoor fire pit nearby and a garden area visible in the background.
Chalet in Copake
4.99 out of 5 average rating, 76 reviews

Private upstate home nestled in the Hudson Valley

Guest favourite
The exterior of the house is showcased among lush greenery, featuring a light-colored facade and a welcoming wrap-around porch. Rocking chairs sit on the front porch, and a flag gently waves in the breeze. Surrounding gardens add color to the charming landscape.
Home in Town of Hillsdale
5.0 out of 5 average rating, 25 reviews

Meadowland Farmhouse — 5 minutes from town

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 Town of Hillsdale
4.91 out of 5 average rating, 22 reviews

Craftsman Cottage

Top guest favourite
A spacious open-plan living area is showcased, featuring large windows that invite natural light. A modern sectional sofa in warm tones is arranged around a low table. A dining area with a long table and dining chairs is visible in the background, enhancing the inviting atmosphere.
Home in Egremont
5.0 out of 5 average rating, 73 reviews

The Catamount Ski Haus with Pool & Hot Tub

Guest favourite
Home in Great Barrington
4.92 out of 5 average rating, 13 reviews

Pool & Hot Tub Escape • Hudson Valley-Berkshires

Guest favourite
Home in Town of Hillsdale
5.0 out of 5 average rating, 9 reviews

Lake Front House with Rustic and Charming Feel

Guest favourite
Barn in Town of Hillsdale
5.0 out of 5 average rating, 15 reviews

Blue Door Barn - Pond and Sweeping Views

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