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 $367 per night (USD)
VRBO
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
Bedrooms:
2
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 $367 per night (USD)
VRBO
From $203 per night (USD)
Expedia
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 $203 per night (USD)
Expedia
From $781 per night (USD)
VRBO
Saltbox-style residence in the Berkshires
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Discover the allure of this enchanting Saltbox-style residence nestled in the picturesque town of Hillsdale, NY. With t ...
From $781 per night (USD)
VRBO
From $232 per night (USD)
VRBO
magical cabin in the woods
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Our ‘Cabin in the Woods’ can be described in many different ways, but simply put it’s nothing short of MAGICAL. Tucked a ...
From $232 per night (USD)
VRBO
From $1254 per night (USD)
VRBO
Newly renovated private 3 bedroom house on a dead end road.13 acres & 360 views
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to your dream upstate country escape! This newly remodeled 3-bedroom, 3-bathroom home offers a perfect blend of ...
From $1254 per night (USD)
VRBO
From $204 per night (USD)
Expedia
Private Unit in shared 1830 Farmhouse
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to The Johnson Farmhouse, a delightful retreat steeped in charm and history, located in the heart of the picture ...
From $204 per night (USD)
Expedia
From $275 per night (USD)
VRBO
Sweet 2-bedroom apartment on horse farm in Hillsdale with WiFi and AC
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Nestled on our horse farm in Hillsdale, this delightful farm-stay has 2 cozy queen bedrooms and 2 full bathrooms with sh ...
From $275 per night (USD)
VRBO
$★Private Pool★ Spacious Historic 1850s \Bell House\ @ Hillsdale, NY Town Center$
From $641 per night (USD)
Expedia
★Private Pool★ Spacious Historic 1850s \"Bell House\" @ Hillsdale, NY Town Center
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Escape to the 1850s Bell House, a historic 5BR/4.5BA estate in Hillsdale NY, once home to the prominent Bell family. Set ...
From $641 per night (USD)
Expedia
$Restored Historic 1850s Barn \Carriage House\ Studio @ Hillsdale Town Center$
From $192 per night (USD)
VRBO
Restored Historic 1850s Barn \"Carriage House\" Studio @ Hillsdale Town Center
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Escape to the 1850s Carriage House - a charming 1-bedroom studio tucked inside a restored barn on a historic Hillsdale, ...
From $192 per night (USD)
VRBO
From $795 per night (USD)
VRBO
Hilltop: Panoramic Views w/ Pool near Catamount
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 $795 per night (USD)
VRBO
From $675 per night (USD)
VRBO
Silver Ridge: Hilltop Chalet w/ Sweeping Views
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Summary: Perched high on the hills above Hillsdale, Silver Ridge is a perfectly-sited contemporary mountain lodge offeri ...
From $675 per night (USD)
VRBO
From $6682 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 $6682 per night (USD)
VRBO
From $376 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 $376 per night (USD)
VRBO
From $185 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 $185 per night (USD)
VRBO
From $194 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 $194 per night (USD)
VRBO
From $663 per night (USD)
VRBO
Serene Hillsdale Cottage Amped with Tech and Wifi
Bedrooms:
2
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 $663 per night (USD)
VRBO
From $1085 per night (USD)
VRBO
Views of Catamount! Tanglewood, Skiing, Bash Bish Falls, Barn At Liberty Farms!
Bedrooms:
4
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 $1085 per night (USD)
VRBO
From $243 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 $243 per night (USD)
VRBO
From $238 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 $238 per night (USD)
VRBO
From $208 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 $208 per night (USD)
VRBO
From $376 per night (USD)
VRBO
3-bedroom house in fantastic Hillsdale with mountain views, WiFi, AC
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Discover this delightful 3-bedroom gem in Hillsdale. This lovely house features 1 king bed and 2 queen beds, perfect for ...
From $376 per night (USD)
VRBO
From $201 per night (USD)
Expedia
The Brooks Motel: Exceptional Suite
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Welcome to The Brooks Motel, this is a recently renovated motel located 2 minutes from Catamount, 15 mins from ...
From $201 per night (USD)
Expedia
From $183 per night (USD)
VRBO
Brooks Motel: Perfect Suite, Seasonal Waterviews
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Welcome to The Brooks Motel, this is a recently renovated motel located 2 minutes from Catamount, 15 mins from ...
From $183 per night (USD)
VRBO
From $201 per night (USD)
Expedia
The Brooks Motel: Exceptional Suite
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Welcome to The Brooks Motel, this is a recently renovated motel located 2 minutes from Catamount, 15 mins from ...
From $201 per night (USD)
Expedia
From $540 per night (USD)
VRBO
Dreamy 6 Bedroom House, Come Enjoy Hillsdale!
Bedrooms:
3
Bathrooms:
6
Sleeps:
14
Summary: Welcome to this beautiful historical house! We've given this budget-friendly, vintage gem a refresher with 6 co ...
From $540 per night (USD)
VRBO
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Expedia
Apple Blossom Cottage by Evergreen Home
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
A newly renovated, thoughtfully designed mid-century retreat featuring a gourmet kitchen, high-end décor, 4K home theate ...
Click For Pricing
Expedia
From $1562 per night (USD)
VRBO
Hillsdale Escape with Pool, Firepit, Hot Tub, Game Room
Bedrooms:
4
Bathrooms:
7
Sleeps:
14
Escape to this beautifully restored 7BR farmhouse nestled in the rolling hills of Hillsdale. Just minutes from Catamount ...
From $1562 per night (USD)
VRBO
From $522 per night (USD)
VRBO
Beautifully eclectic Round House in the woods near Catamount
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Beautifully eclectic round house surrounded by 8 acres woods and a Waterfall with Private Driveway. This house is one of ...
From $522 per night (USD)
VRBO
From $346 per night (USD)
VRBO
Charming 3-bedroom house with AC, WiFi in quaint Hillsdale
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Get a taste of the Upstate life snug in the foothills of the Berkshires. In the quaint village of Hillsdale you are 10 m ...
From $346 per night (USD)
VRBO
From $826 per night (USD)
VRBO
Wolf Hill Acres: A Charming & Modern Country Home
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Escape to Wolf Hill Acres, a modern country home set on 20 peaceful acres in the Hudson Valley. This 5-bedroom home is ...
From $826 per night (USD)
VRBO
From $414 per night (USD)
VRBO
Hudson Valley and The Berkshires getaway
Bedrooms:
6
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 $414 per night (USD)
VRBO
From $310 per night (USD)
Expedia
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 $310 per night (USD)
Expedia
From $367 per night (USD)
VRBO
Private Contemporary Country Chalet
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Charming chalet situated on the top of a wooded mountainside, with a long, private driveway and 11 acres of woods with a ...
From $367 per night (USD)
VRBO
From $695 per night (USD)
VRBO
Modern, private, spacious vacation home, deck, mountain views, 5 mi to Catamount
Bedrooms:
4
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 $695 per night (USD)
VRBO
Click For Pricing
VRBO
R&R in the treetops with lrg outdoor living space and all the comforts of home.
Bedrooms:
2
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
VRBO
From $270 per night (USD)
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 ...
From $270 per night (USD)
Expedia
From $540 per night (USD)
VRBO
Art Studio House in Private Mountaintop Nature Preserve
Bedrooms:
2
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 $540 per night (USD)
VRBO
From $1128 per night (USD)
Expedia
Chef’s Kitchen, Fast Wi-Fi
Bedrooms:
3
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 ...
From $1128 per night (USD)
Expedia
From $507 per night (USD)
VRBO
Hudson & The Berkshires Upstate Hideaway
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Cozy, stylish, newly-renovated home, perfect for couples, groups, and families looking for a peaceful retreat that's clo ...
From $507 per night (USD)
VRBO
$Meadowland Farmhouse with Beautiful Sunsets \n5 minutes from town$
From $416 per night (USD)
Expedia
Meadowland Farmhouse with 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 $416 per night (USD)
Expedia
From $381 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 $381 per night (USD)
VRBO
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
From $1736 per night (USD)
VRBO
Hillside Spa Retreat / Pool • Sauna • Theater
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Wander Hillsdale Springs is a stunning secluded luxury home perfect for relaxation and entertainment. It features a spar ...
From $1736 per night (USD)
VRBO
$Mountain View: Airy + Secluded w\/Panoramic Views$
From $628 per night (USD)
VRBO
Mountain View: Airy + Secluded w\/Panoramic Views
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Summary: Welcome to Mountain View, a beautifully appointed 3-bed, 2.5-bath home perched on the mountainside—just 2.5 hrs ...
From $628 per night (USD)
VRBO
From $432 per night (USD)
VRBO
Farm House Getaway on 200 acre horse farm!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Escape the hustle and bustle of daily life, and find yourself transformed in a place of total relaxation and peacefulnes ...
From $432 per night (USD)
VRBO
Click For Pricing
Expedia
Hollywood Hills in the Berkshires
Bedrooms:
2
Bathrooms:
4
Sleeps:
5
Glamorous modern hilltop living. After a day laying by the pool, enjoy a bottle of wine by the fireplace, take a soak i ...
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Expedia
From $284 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 $284 per night (USD)
VRBO
From $416 per night (USD)
VRBO
Hillsdale home with Stunning Views. Dog friendly!
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
The views from this home are unique. The property is perched on a small hill looks out on conservancy land, as well as ...
From $416 per night (USD)
VRBO
From $1050 per night (USD)
VRBO
Beautiful Berkshire Farm House on 160+ Acres
Bedrooms:
4
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 $1050 per night (USD)
VRBO
From $1821 per night (USD)
Expedia
Peaceful Compound Perfect for Groups 12 Minutes from Great Barrington!
Bedrooms:
5
Bathrooms:
7
Sleeps:
17
In one of the most sought after destinations in New England, located just outside Great Barrington near the top of Baldw ...
From $1821 per night (USD)
Expedia
From $342 per night (USD)
VRBO
Family Ski House at Catamount !
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Experience the ultimate family ski getaway at this spacious 4-bedroom, 3-bath home across from Catamount Ski Area. With ...
From $342 per night (USD)
VRBO
Click For Pricing
Expedia
Near Catamount Resort & Tanglewood: Mtn-View Haven
Bedrooms:
3
Bathrooms:
7
Sleeps:
8
Dog Friendly w/ Fee | 40 Private Acres | Fire Pit | Foosball Table | Swimming Pond Nestled in the charming town of Aust ...
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Expedia
Click For Pricing
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 ...
Click For Pricing
VRBO
From $897 per night (USD)
Expedia
Grand Estate w/ Mountain Views 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 $897 per night (USD)
Expedia
From $506 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 $506 per night (USD)
VRBO
From $269 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 $269 per night (USD)
VRBO
From $367 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 $367 per night (USD)
VRBO
From $1063 per night (USD)
VRBO
Hudson Valley GetAway: Great for Skiing, family holidays and summers by the pool
Bedrooms:
3
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 $1063 per night (USD)
VRBO
From $1161 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 $1161 per night (USD)
VRBO
From $425 per night (USD)
Expedia
Luxury Barn Retreat . Year-Round Scenic “Park Like”Paradise.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Absolutely everyone that has been here loves the setting. It is truly one of a kind peaceful and serene setting. This ...
From $425 per night (USD)
Expedia
Click For Pricing
VRBO
Family friendly. In nature & all things Berkshire. Equidistant Hudson/GtBarr,MA
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
1791 farmhouse/cottage located just 3 miles East of the Taconic. A diamond in the rough. Peaceful farmland setting. S ...
Click For Pricing
VRBO
From $1047 per night (USD)
Expedia
Exclusive Estate, Heated Yearround Outdoor Pool
Bedrooms:
4
Bathrooms:
7
Sleeps:
17
Summary: Awaiting your next trip in our former horse farm turned luxury vacation rental, recently upgraded and re-furnis ...
From $1047 per night (USD)
Expedia
From $1633 per night (USD)
VRBO
Luxury Berkshires Family Vacation Rental on 45 Acres
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Surrounded by open fields, 15 minutes from Catamount, Tanglewood, Great Barrington and the center of Lenox, this house f ...
From $1633 per night (USD)
VRBO
From $869 per night (USD)
VRBO
Incredible Hillside Country House-Pool, Sleeps 8, 3 Bath-Available August
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Charming country home with pool on three beautifully landscaped acres, only two hours from NYC. The house is geared towa ...
From $869 per night (USD)
VRBO
From $345 per night (USD)
VRBO
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 $345 per night (USD)
VRBO
From $919 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 $919 per night (USD)
Expedia
From $245 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 $245 per night (USD)
VRBO
From $1106 per night (USD)
Expedia
Peaceful Retreat Compound 10 Minutes to Great Barrington!
Bedrooms:
3
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 $1106 per night (USD)
Expedia
From $478 per night (USD)
VRBO
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 $478 per night (USD)
VRBO
From $923 per night (USD)
Expedia
Chester by AvantStay | Amazing Views, Secluded Home, A True City Escape!
Bedrooms:
3
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 $923 per night (USD)
Expedia
From $515 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 $515 per night (USD)
VRBO
From $908 per night (USD)
VRBO
August in the Berkshires! Incredible Hillside Country House. Sleeps 10.
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 $908 per night (USD)
VRBO

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Town of Hillsdale Rentals

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Results: 72 Rentals