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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

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!

ValueLocationQuiet

4.99 out of 5 average rating, 159 reviews
Top guest favourite
Cabin in East Nassau

Fall Foliage Luxury Cabin & View Autumn Adventures

Welcome to our mountain retreat, nestled in the heart of nature and brought to you by Den Outdoors. 25 mins to Tanglewood, 35 mins to Jacobs Pillow, 15 mins to Jiminy Peak, 30 mins to The Clark, MASS MoCA, and the Berkshire region. 10 mins to a swimmable lake. 2.5 hrs from NYC and from Boston. Come experience all Autumn has to offer! Stunning views, no visible neighbors, Goodland wood fired hot tub, Breeo Fire pit, large Webber Grill, radiant floor, EV charging, and the MOST STUNNING view!

LocationFamilyHot tub

4.97 out of 5 average rating, 110 reviews
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

Gorgeous Mountain Views Retreat: Family & Nature

Escape to Meadow View Manor, a 4BR modern-rustic Hillsdale retreat set on 6 private mountainside acres near the Berkshires. Wake to fog lifting over the hills, then gather around the brick fireplace, cook in the remodeled kitchen, play ping-pong, or enjoy the expansive deck and fire pit. Sleeps 8 and welcomes dogs. With no nearby neighbors, hear only birds and wind. Just 2 hrs from Manhattan, 10 min to Catamount, 15 min to golf, dining and live music, and 30 min to Hudson or Great Barrington.

ValueFamilyAmenities

4.98 out of 5 average rating, 83 reviews
Top guest favourite
A dining area is set with a large table surrounded by colorful chairs. Plates, glasses, and utensils are arranged for a meal. Large windows provide views of the landscape, allowing natural light to fill the space, while soft curtains frame the glass.
Home in Copake

Cheerful Home with Stunning Views

The house is located in Copake, NY. 25 minutes from Hudson, NY & Great Barrington, MA&Sharon, CT. 10 min. from Bash Bish fall&Catamount Ski. Fully furnished. Full kitchen include top-of-the-line stainless steel KitchenAid fridge; sleek cooktop, double oven, microwave; white quartz countertop; and Kohler sink—Harwood floors throughout, with neutral color palette. The primary bathroom has a spa-style bathtub. Two guest bathrooms have showers. This house is spacious, serene, and stylish.

LocationValueSleep quality

5.0 out of 5 average rating, 31 reviews
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

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.

ValueLocationBack garden

4.88 out of 5 average rating, 375 reviews
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

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.

LocationValueGetting around

4.91 out of 5 average rating, 129 reviews
Top guest favourite
A spacious bedroom features a wooden four-poster bed adorned with green and white pillows. A dining table with two chairs sits in one corner. Soft lighting is provided by a lamp and two hanging chandeliers, creating a calm ambiance.
Flat in Town of Hillsdale

Serene Suite: Hudson & Berkshires, Walk to Brewery

No cleaning fee and no chores! A peaceful, highly rated private suite in the heart of historic Hillsdale, where the Hudson Valley meets the Berkshires. Walk to shops, restaurants, a brewery, cooking school, grocery, wine and liquor store. Minutes to Hilltown, the Harlem Valley Rail Trail, scenic hikes, and beautiful drives, with galleries, antiques, live music, and cultural gems nearby. A serene, perfectly located home base for spring dining, exploring, and unwinding.

ValueLocationAccuracy

4.98 out of 5 average rating, 264 reviews
Guest favourite
Home in Town of Hillsdale

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.

LocationFamilyNearby

4.9 out of 5 average rating, 21 reviews
Top guest favourite
Barn in Town of Hillsdale

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.

ValueFamilyBack garden

4.97 out of 5 average rating, 185 reviews
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

Hillsdale Modern Retreat

Perfect Summer Escape in the Hudson Valley | Mid-Century Retreat w/ Fire Pit close to The Berkshires Welcome to Modern Hillsdale retreat, your serene and stylish retreat nestled in the heart of the Hudson Valley. Whether you're looking for a peaceful weekend escape, a creative work-from-home getaway, or a longer stay immersed in nature, this beautifully renovated mid-century modern home has everything you need—and more.

LocationFamilyGrill

4.97 out of 5 average rating, 37 reviews
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

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.

LocationFamilyOutdoor spaces

4.92 out of 5 average rating, 410 reviews
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

Meadowland Farmhouse — 5 minutes from town

Our house is located in the heart of the Berkshires, midway between NYC and Boston, this newly renovated modern rustic style home sits on three acres just five minutes from the town of Hillsdale, NY. Perfect for getaways all year round, and perfect for families of various sizes.

FamilyValueAmenities

5.0 out of 5 average rating, 25 reviews

Popular amenities for Town of Hillsdale holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Town of Hillsdale

Superhost
Home in Town of Hillsdale

Quaint center of town Farmhouse

FamilyLocationSleep quality

5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Copake Lake

Waterfront Retreat in a woodsy haven

ValueFamilyKitchen

5.0 out of 5 average rating, 17 reviews
Top guest favourite
Cabin in Town of Taghkanic

Rest. Reset. Reconnect. Upstate.

FamilyLocationAccuracy

4.96 out of 5 average rating, 48 reviews
Guest favourite
The modern kitchen features a central island with seating for four, complemented by sleek black cabinetry and a white countertop. Large windows provide ample natural light, overlooking the outdoor scenery. A round wooden dining table with four chairs is positioned nearby.
Chalet in Town of Hillsdale

Hudson Valley and The Berkshires Getaway

FamilyLocationView

4.91 out of 5 average rating, 56 reviews
Guest favourite
Home in Great Barrington

Farmhouse Retreat • Hot Tub • Fireplace • Ski

FamilyLocationCleanliness

4.93 out of 5 average rating, 15 reviews
Superhost
An outdoor pool is framed by a spacious patio, with lounge chairs positioned alongside. The contemporary home features expansive windows and a screened porch, set against a backdrop of clear skies and lush greenery.
Home in Town of Hillsdale

Hilltop: Panoramic Views w/ Pool near Catamount

LocationValueAccess

4.88 out of 5 average rating, 50 reviews
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

Private upstate home nestled in the Hudson Valley

FamilyValueCleanliness

4.99 out of 5 average rating, 77 reviews
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 Town of Ancram

2bed farm stay as seen in Dezeen, architects cabin

LocationFamilyQuiet

4.98 out of 5 average rating, 59 reviews

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