Town of Hillsdale, New York Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Town of Hillsdale, New York on RentalSaver.com!

Town of Hillsdale Rentals

From $306 per night (USD)
VRBO
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Escape to Serenity in the Heart of the Berkshires: A Modern Retreat Surrounded by Nature Immerse yourself in the awe-in ...
From $306 per night (USD)
VRBO
From $279 per night (USD)
Expedia
Charming, Quiet, River Front
Bedrooms:
2
Bathrooms:
3
Sleeps:
13
A cozy modern log cabin nestled in the hills of the Berkshires in a large wooded area with landscaped yard and fishpond. ...
From $279 per night (USD)
Expedia
From $160 per night (USD)
VRBO
Ideal location for summer and winter activities with plenty of outdoor space.
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Tory Hill cabin is located at seven minutes from the Taconic State Park in Copake Falls and four minutes from Catamount ...
From $160 per night (USD)
VRBO
From $612 per night (USD)
VRBO
Secluded Tranquility, Contemporary Comfort,upstate
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Summary: A true escape, this luminous home and verdant property inspires peace, ease, and comfort. Lovingly tended garde ...
From $612 per night (USD)
VRBO
From $267 per night (USD)
VRBO
Saltbox-style residence in the Berkshires
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Discover the allure of this enchanting Saltbox-style residence nestled in the picturesque town of Hillsdale, NY. With t ...
From $267 per night (USD)
VRBO
From $9540 per night (USD)
VRBO
The Brooks Buy Out, Wedding Groups Inquire Today!
Bedrooms:
24
Bathrooms:
26
Sleeps:
60
Summary: Hosting an event at Catamount or Taconic Ridge Farms? Direct your guests to The Brooks Motel, located directly ...
From $9540 per night (USD)
VRBO
From $200 per night (USD)
VRBO
Heart of Historic Hillsdale, NY, charming carriage house, Swiss Chalet-style
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Located in the heart of the Berkshires, equidistant from NYC and Boston, this newly equipped and renovated carriage hous ...
From $200 per night (USD)
VRBO
From $508 per night (USD)
VRBO
Silver Ridge: sweeping views in luxury chalet
Bedrooms:
5
Bathrooms:
5
Sleeps:
8
Summary: Silver Ridge is a perfectly-sited contemporary mountain lodge, perched high on the hills above Hillsdale, with ...
From $508 per night (USD)
VRBO
From $166 per night (USD)
VRBO
Country Karma -Quiet Wooded Getaway
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
You're considering renting a modern saltbox house, perched on a hilly wooded property, overlooking pristine Columbia Cou ...
From $166 per night (USD)
VRBO
$Beautiful, Unique Country House w\/Large Deck$
From $195 per night (USD)
VRBO
Beautiful, Unique Country House w\/Large Deck
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Charming and cozy 2 story, 1 bedroom country house, perfect for couples looking for the meditative beauty of an artist's ...
From $195 per night (USD)
VRBO
From $240 per night (USD)
VRBO
Quiet Guest House In The Green River Valley
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Located in the heart of the Berkshires, midway between NYC and Boston, this newly renovated Guest House is nestled on 10 ...
From $240 per night (USD)
VRBO
From $235 per night (USD)
VRBO
Secluded Country Getaway On 22 Magical Acres. Catamount ski resort 5 min away
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
The adventure awaits in the Berkshires. Escape the hustle and bustle of your everyday life and come chill in a renovated ...
From $235 per night (USD)
VRBO
From $200 per night (USD)
VRBO
Beautifully decorated & immaculate log chalet on 3 acres, winter views.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Private and secluded log cabin chalet is situated on three picturesque acres overlooking tall pines and forests with he ...
From $200 per night (USD)
VRBO
From $215 per night (USD)
VRBO
Two Rooms with En-Suite in Quiet Woodland
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Located in the heart of the Berkshires, midway between NYC and Boston, this newly renovated two bedroom apartment is nes ...
From $215 per night (USD)
VRBO
Click For Pricing
VRBO
Private Hillsdale Home With Views Of Catamount.
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Three bedroom three bathroom home located at the end of a country lane in hillsdale NY. 6.8 miles to catamount ski area ...
Click For Pricing
VRBO
From $610 per night (USD)
VRBO
Serene Hillsdale Cottage Amped with Tech and Wifi
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Escape the city and relax at our serene Hillsdale House, nestled alongside a picturesque creek and pond with acres of sh ...
From $610 per night (USD)
VRBO
From $958 per night (USD)
VRBO
Views of Catamount! Tanglewood, Skiing, Bash Bish Falls, Barn At Liberty Farms!
Bedrooms:
5
Bathrooms:
5
Sleeps:
14
This extremely private luxury home with Catamount Ski views and close to The Barn at Liberty Farms is situated on 33-acr ...
From $958 per night (USD)
VRBO
From $240 per night (USD)
Expedia
Restored 1810 Farmhouse in Hillsdale, NY
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enjoy our sensitively renovated 1810 farmhouse just minutes away from the best the Berkshires and Hudson Valley has to o ...
From $240 per night (USD)
Expedia
Click For Pricing
VRBO
Cozy Cottage by Berkshires, Hudson, Roe Jan Brew Co., Catamount & Taconic Ridge
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
A great location in the middle of it all! Not only is this adorable cottage walking distance to all that Hillsdale has t ...
Click For Pricing
VRBO
From $300 per night (USD)
VRBO
Private Contemporary Country Chalet
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Charming chalet situated on the top of a wooded mountainside, with a long, private driveway and 11 acres of woods with a ...
From $300 per night (USD)
VRBO
From $662 per night (USD)
VRBO
Modern, private, spacious vacation home, deck, mountain views, near Tanglewood
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Sunset views, huge deck, chef's kitchen, fireplace, high-speed WiFi. This home is fully-equipped for your comfort and re ...
From $662 per night (USD)
VRBO
From $515 per night (USD)
Expedia
Hudson Valley and The Berkshires getaway
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Summary: Welcome to the Hudson Valley getaway. Located in the heart of the Hudson Valley in Hillsdale NY, sits our 4 be ...
From $515 per night (USD)
Expedia
From $101 per night (USD)
VRBO
Hudson valley and The Berkshires Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Welcome to your luxury cottage escape. Located in the heart of the Hudson Valley in Hillsdale, NY sits a calm, ...
From $101 per night (USD)
VRBO
$Berkshire\/Hudson Valley Gather Family and Friends$
Click For Pricing
Expedia
Berkshire\/Hudson Valley Gather Family and Friends
Bedrooms:
4
Bathrooms:
5
Sleeps:
6
Country charm with a modern vibe. A perfect place to gather family and friends. Set in picturesque Hillsdale, close to e ...
Click For Pricing
Expedia
$Meadowland Farmhouse with Playful Attic & Beautiful Sunsets \n5 minutes from town$
From $335 per night (USD)
VRBO
Meadowland Farmhouse with Playful Attic & Beautiful Sunsets \n5 minutes from town
Bedrooms:
2
Bathrooms:
5
Sleeps:
8
Our cozy home is located in the heart of the Berkshires, midway between NYC and Boston. This newly renovated modern rust ...
From $335 per night (USD)
VRBO
From $421 per night (USD)
Expedia
Hudson & The Berkshires Upstate Hideaway
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Cozy, stylish, newly-renovated home, perfect for couples, groups, and families looking for a peaceful retreat that's clo ...
From $421 per night (USD)
Expedia
From $390 per night (USD)
VRBO
Perfect House In Hillsdale, Brings Friends & Fam
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
Summary: Welcome to this beautiful historical house! We've given this budget-friendly, vintage gem a refresher with 5 co ...
From $390 per night (USD)
VRBO
From $1700 per night (USD)
Expedia
4 bedroom house with a heated pool
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
Indulge in ultimate luxury living in the heart of Columbia County, New York! This magnificent and spacious (6000 sq ft) ...
From $1700 per night (USD)
Expedia
Click For Pricing
VRBO
Chef’s Kitchen, Fast Wi-Fi
Bedrooms:
4
Bathrooms:
5
Sleeps:
14
We are on 35 acres, on top of a mountain and the views of the Hudson Valley mountains are spectacular. Enjoy your first ...
Click For Pricing
VRBO
Click For Pricing
Expedia
It's All About the Mountain Views, Modern Farmhouse
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Separate private entrance of main house to a large, En Suite apartment in fully built out bottom floor. One bedroom with ...
Click For Pricing
Expedia
From $500 per night (USD)
VRBO
Art Studio House in Private Mountaintop Nature Preserve
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Art Studio House is situated at the end of a 1.5 mile woodland road and surrounded by an 150 acre private scenic mountai ...
From $500 per night (USD)
VRBO
Click For Pricing
Expedia
R&R in the treetops with lrg outdoor living space and all the comforts of home.
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Need to get away from the city for some rest and relaxation but stay connected? Stay in our rural, quiet getaway. Huge o ...
Click For Pricing
Expedia
Click For Pricing
VRBO
Historic Hillsdale House With Pool, Near Catamount Ski Area
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Come stay in this fabulous homey 1810 4 bedroom, 2 bathroom home in chic Hillsdale New York. The house is 2 miles from ...
Click For Pricing
VRBO
From $350 per night (USD)
VRBO
Farm House Getaway on 200 acre horse farm
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Escape the hustle and bustle of daily life, and find yourself transformed, in a place of total relaxation and peacefulne ...
From $350 per night (USD)
VRBO
Click For Pricing
VRBO
Quiet Country road getaway
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Old farmhouse with 4 bedrooms and dining room, 2 living rooms, patio, lawns, paths and trails, woods and cornfield, tota ...
Click For Pricing
VRBO
From $350 per night (USD)
VRBO
Lg Beautiful Country Home in Scenic Upstate NY!
Bedrooms:
4
Bathrooms:
5
Sleeps:
11
Large traditional country home with amazing scenery, nestled between the Berkshire and Catskill Mountains. 5 Bedrooms wi ...
From $350 per night (USD)
VRBO
From $1333 per night (USD)
VRBO
Hilltop: Spectacular vista, true luxury with pool.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: With 360-degree views of the Catskill and Berkshire Mountains from the highest point in Hillsdale, Hilltop is a ...
From $1333 per night (USD)
VRBO
From $154 per night (USD)
VRBO
Serene Hudson Valley Farmhouse
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
*PLEASE READ full details below before booking* Renovated 1900 farmhouse on 3-acres of land with views & privacy. We ha ...
From $154 per night (USD)
VRBO
From $690 per night (USD)
VRBO
Hillsdale Mountain View Estate by Evergreen Home
Bedrooms:
5
Bathrooms:
7
Sleeps:
12
A beautiful estate on a hill overlooking the Hawthorne Valley, with mountain views. Nestled between Hudson, NY and Grea ...
From $690 per night (USD)
VRBO
Click For Pricing
Expedia
Mountain Views at Fern Hill House
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: A beautiful estate on a hill overlooking the Hawthorne Valley, with mountain views. Nestled between Hudson, NY ...
Click For Pricing
Expedia
From $225 per night (USD)
VRBO
Hudson Valley: Spacious and Kid Friendly Retreat Near Everything!
Bedrooms:
2
Bathrooms:
2
Sleeps:
10
Come enjoy this 2 bedroom, 2 bath home surrounded by forest and acres of protected land. Sleeps up to 6 people and is lo ...
From $225 per night (USD)
VRBO
From $867 per night (USD)
Expedia
Beautiful Berkshire Farm House on 160+ Acres
Bedrooms:
5
Bathrooms:
7
Sleeps:
16
This is a unique property located on more than 1000 feet of the Green River. Over a hundred and sixty acres of beautiful ...
From $867 per night (USD)
Expedia
From $839 per night (USD)
VRBO
Escape the City! Incredible Hillside Country House. Sleeps 11.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Charming four-season country home on three beautifully landscaped acres, only two hours from NYC. The house is geared to ...
From $839 per night (USD)
VRBO
From $200 per night (USD)
VRBO
Modern Rustic Artist's Getaway
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
I spent a lifetime living and working as a professional fashion photographer in Paris, Milan and New York. My visual se ...
From $200 per night (USD)
VRBO
From $710 per night (USD)
VRBO
Private Estate, Heated YEARROUND Outdoor Pool
Bedrooms:
5
Bathrooms:
7
Sleeps:
17
Summary: Awaiting your next trip in our former horse farm turned luxury vacation rental, recently upgraded and re-furnis ...
From $710 per night (USD)
VRBO
From $243 per night (USD)
VRBO
NEW! Clean & Cozy Hillsdale Cabin, minutes to Catamount, Tanglewood
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Relax in the country at this idyllic Berkshires post and beam close to skiing at Butternut and Catamount. Twenty minutes ...
From $243 per night (USD)
VRBO
From $366 per night (USD)
VRBO
Farmhouse with views nestled among nature reserve
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This preserved 18th century farmhouse is situated on a picturesque 24 acre estate boasting southerly views of rolling hi ...
From $366 per night (USD)
VRBO
From $950 per night (USD)
VRBO
Hudson Valley GetAway: Great for Skiing, family holidays and summers by the pool
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
This home has breathtaking views stretching all the way to the Catskills. A lovely pool welcomes in the summer and the ...
From $950 per night (USD)
VRBO
From $450 per night (USD)
VRBO
Beautifully Restored, Secluded Farmhouse
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
Tucked away on private lane and bordering hundreds of acres of preserved land, this tastefully renovated 1840 farmhouse ...
From $450 per night (USD)
VRBO
From $1200 per night (USD)
VRBO
Hudson Hilltop Retreat
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Welcome to a “Four Season Adventure Seeking” property located on six pristine hilltop acres with rolling meadows, 15 min ...
From $1200 per night (USD)
VRBO
From $310 per night (USD)
VRBO
Beautiful, Contemporary Home on 6 Private Acres; Summer 2022 Rental
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
A warm, comfortable, contemporary home with large glass windows, a large deck, beautiful gardens, gourmet kitchen, hot t ...
From $310 per night (USD)
VRBO
From $191 per night (USD)
VRBO
Quiet Renovated Barn
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Renovated barn sits just over the state line from the Berkshires, nestled on ten acres of the rolling hills of glorious ...
From $191 per night (USD)
VRBO
From $152 per night (USD)
VRBO
Newly renovated home - cozy 2 bedroom
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Whole house newly renovated. 2 bedroom with small additional bedroom, one bath, spacious living areas. All new applianc ...
From $152 per night (USD)
VRBO
From $238 per night (USD)
Expedia
Spacious secluded ranch yet close to Great Barrington, Lenox, & Hudson, NY.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This three-bedroom ranch on 6.5 acres provides all the comforts of home in a secluded bucolic setting. Relax in the gra ...
From $238 per night (USD)
Expedia
From $449 per night (USD)
VRBO
Luxury Barn Retreat . Year-Round Paradise. OVER 100 5 STAR REVIEWS!!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Absolutely everyone that has been here loves the setting. Read the >100 5 Star reviews first…. This is a beautiful pa ...
From $449 per night (USD)
VRBO
$Family friendly. In nature & all things Berkshire. Equidistant Hudson\/GtBarr,MA$
From $152 per night (USD)
VRBO
Family friendly. In nature & all things Berkshire. Equidistant Hudson\/GtBarr,MA
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
1791 farmhouse/cottage located just 3 miles East of the Taconic. A diamond in the rough. Peaceful farmland setting. S ...
From $152 per night (USD)
VRBO
From $1000 per night (USD)
VRBO
19th Century Farm House on 300 Acre Farm
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Sitting on a pastoral 300 acres of active farmland, the Old Ox Farmhouse is a quiet retreat nestled in the heart of the ...
From $1000 per night (USD)
VRBO
From $299 per night (USD)
Expedia
Underhill Cottage
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
About this space Charming 1948 light filled cottage, recently gut renovated. It has two, cozy, queen guest bedrooms and ...
From $299 per night (USD)
Expedia
From $205 per night (USD)
VRBO
Berkshire Mountain Cottage: in the Heart of the Berkshires
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Berkshire Mountain Cottage is a warm and cozy hideaway located in the Berkshire hills. Its located between North Egremon ...
From $205 per night (USD)
VRBO
From $449 per night (USD)
Expedia
Catamount, Zip Line, Private Setting, Book Now!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: Expertly renovated four bedroom house with views of Catamount, post and beam wood ceilings and a lovely centerp ...
From $449 per night (USD)
Expedia
From $500 per night (USD)
VRBO
Peaceful Retreat Compound 10 Minutes to Great Barrington!
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
In one of the most sought after destinations in New England, located just outside Great Barrington near the top of Baldw ...
From $500 per night (USD)
VRBO
From $813 per night (USD)
Expedia
Stunning 6-BR Country Home 10-min to Catamount
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
Summary: Escape to the highlands of the Berkshires on this peaceful, 4-acre lot 10-min to skiing at Catamount and 10-min ...
From $813 per night (USD)
Expedia
From $769 per night (USD)
VRBO
Chester by AvantStay | Amazing Views, Secluded Home, A True City Escape!
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Welcome to Chester! Fall head over heels in love with this gorgeous country home in the tranquil town of Austerlitz, NY. ...
From $769 per night (USD)
VRBO
From $750 per night (USD)
VRBO
Hudson Valley Escape
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
Awaken to clean air and beautiful forest sounds. Only 30 minutes outside of the quaint, artistic town of Hudson, NY. En ...
From $750 per night (USD)
VRBO
From $270 per night (USD)
VRBO
Family&Dog Friendly--40 Acres In Berkshires-minutes from Tanglewood & Skiing
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Enjoy the country in this sun drenched 4 bedroom, 3 full bathroom quiet home on 40 private acres with stunning views and ...
From $270 per night (USD)
VRBO
From $423 per night (USD)
VRBO
Austerlitz , New York, Columbia County
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Rustic country home with all amenities, spectacular mountain views , large pool with deck, wonderful terraces, and is su ...
From $423 per night (USD)
VRBO
From $695 per night (USD)
VRBO
Escape the City! Incredible Hillside Country House. Sleeps 11.
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Charming four-season country home on three beautifully landscaped acres, only two hours from NYC. The house is geared to ...
From $695 per night (USD)
VRBO

Search Your Destination Now!

Town of Hillsdale Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 67 Rentals