Entire home

Hudson Valley and The Berkshires getaway

Photo gallery for Hudson Valley and The Berkshires getaway

Kitchen and dining room
Open living room to kitchen and dining room
Open living room to kitchen and dining room
Outside dining table off open kitchen, dining, and living room
Bathroom next to open kitchen, dining, and living room

Reviews

10 out of 10
Exceptional
4 bedrooms3 bathroomsSleeps 9

Popular amenities

  • Parking available
  • Dryer
  • Pet-friendly
  • Washer
  • Barbecue grill
  • Kitchen

Explore the area

Map
Hillsdale, NY
  • Catamount Aerial Adventure Park
    ‪15 min drive‬
  • Catamount Ski Area
    ‪17 min drive‬
  • Ski Butternut
    ‪22 min drive‬
  • Great Barrington, MA (GBR-Walter J. Koladza)
    ‪13 min drive‬

Rooms & beds

4 bedrooms (sleeps 9)

Bedroom 1

1 Single Bed and 1 Single Bunk Bed

Bedroom 2

1 Double Sofa Bed

Bedroom 3

1 King Bed

Bedroom 4

1 Queen Bed

3 bathrooms

Bathroom 1

Bathtub · Toilet · Shower only

Bathroom 2

Toilet · Shower only

Bathroom 3

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Balcony
Garden
Dining area

About this property

Hudson Valley and The Berkshires getaway

The space
Completely renovated, the space has 2 beautifully decorated open concept living areas with a modern kitchen stocked with amenities, 3 large bedrooms, an office with pullout couch, and 3 bathrooms.

What sets this villa apart are the floor-to ceiling windows surrounding the home, bringing warm natural light and tranquility to every corner. Additionally, the primary bedroom is truly stunning, boasting a high ceiling with natural wooden beams, a gorgeous en suite bathroom, and access to the wrap-around deck.

High-speed WiFi is available throughout the property and the office setup is available when inspiration (or those pesky emails) hits.

Take in the picturesque landscape and fresh air from the enormous wrap-around deck, furnished with a large outdoor dining table with seating for 13. Serene views and access to the stream provides a total sense of calm and relaxation, perfect for those looking to be in nature, while still enjoying luxury.

Parking is in the driveway with stone steps leading directly to the entrance.
Guest access
Guests will receive an entry door code 12 hours prior to their arrival.
Other things to note
Explore the Hudson Valley by starting in Hillsdale, NY. With plenty of things to do within a short drive, you can find everything you'll need to getaway across Upstate New York and the Berkshires:

Restaurants/Breweries - All Within 15 minutes
1) Roe Jan Brewing Co
2) Barrington Brewery & Restaurant
3) Chatham Brewing
4) Four Brothers Pizza Inn
5) Hillsdale House
6) Sweet Peas Country Diner
7) Little Cat Lodge


Attractions/Things To Do:
1) Ski Resorts:
- Catamount Mountain Resort - 15 minutes
- Jiminy Peak Ski Resort - 35 minutes

3) Chatham, NY - 15 minutes
- Idyllic Hudson Valley town with charming storefronts, restaurants, breweries, and galleries

4) Great Barrington, MA - 15 minutes
- Great Barrington is the hub of Southern Berkshire County with a vibrant Main Street and side streets packed with shops, theaters, and restaurants. While tourism is its biggest draw, its hidden open spaces and vistas has made this beautiful southern town ideal for vacation- and second-home owners.

5) Hudson, NY - 30 minutes
- Hudson has a historical richness and contemporary vibrancy far bigger than its size would suggest. Hudson’s compact urban core makes it an eminently walkable city. You'll find history, art galleries, culture, and restaurants, making Hudson an extraordinary city to visit, offering sights, sounds, curiosities and great food around every corner.

6) Lenox, MA

7)Tanglewood - 25 minutes
- A World-Class Outdoor Performing Arts Venue! The famous performing arts venue of Tanglewood is nestled away in the Berkshire Hills of western Massachusetts and sets high standards for musical festivals, especially in the warmer months. Home to the famous Boston Symphony Orchestra, and the site of one of the world’s best-known music festivals, Tanglewood hosts the Festival of Contemporary Music, along with many other events including concerts of various genres from jazz to pop and frequent visits from James Taylor, John Williams, and the Boston Pops.

8) Taconic State Park
- Bish Bash Falls - 60 foot waterfall and highest waterfall in Massachusetts.
- Copake Iron Works Historic Site
- Hiking, Simming, cross-coutry skiing, and snow shoeing

9) Art OMI - 25 minutes
- Situated on one-hundred and twenty acres in the Hudson Valley, Art Omi presents the works of contemporary artists and architects, and offers a range of large-scale works in nature, plus a 1,500 square foot gallery. The Sculpture & Architecture Park currently offers more than 60 works by artists and architects on view, with pieces added or exchanged each year.

10) Mass MoCA - 60 minutes
- The Massachusetts Museum of Contemporary Art (MASS MoCA) is one of the world’s liveliest centers for making and enjoying today’s most evocative art. With vast galleries and a stunning collection of indoor and outdoor performing arts venues, MASS MoCA is able to embrace all forms of art: music, sculpture, dance, film, painting, photography, theater, and new, boundary-crossing works of art that defy easy classification.

Property manager

Ben Lockspeiser and Andrew D’Agostino
Premier Host

Languages

English

Add dates for prices

Amenities

Kitchen
Washer
Dryer
Pet-friendly
Air conditioning
Outdoor space

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House Rules

Check in after 3:00 PM
Minimum age to rent: 18
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed: dogs and cats less than 23 kg per pet (limit one pet total)
Charge may apply
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Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher

About the area

Hillsdale

Hillsdale is home to this holiday home. W.E.B. Du Bois Boyhood Homesite and Mahaiwe Performing Arts Center are local landmarks, and some of the area's attractions include Ebenezer II Gifts and Antiques and Hotchkiss Mobile Studio. Charles H. Baldwin & Sons and Hoffman's Pottery are also worth visiting.
Map
Hillsdale, NY

What's nearby

  • Catamount Aerial Adventure Park - 15 min drive - 16.4 km
  • Housatonic River Walk - 16 min drive - 15.1 km
  • Catamount Ski Area - 17 min drive - 17.4 km
  • Ski Butternut - 22 min drive - 19.6 km
  • National Shrine of the Divine Mercy - 27 min drive - 28.0 km

Getting around

  • Pittsfield Intermodal Transportation Center - 35 min drive
  • Hudson, NY (HCC-Columbia County) - 34 min drive

Restaurants

  • ‪Pleasant and Main - ‬21 min drive
  • ‪Berkshire Mountain Bakery - ‬22 min drive
  • ‪Roe Jan Brewing - ‬13 min drive
  • ‪Housie Market Cafe - ‬22 min drive
  • ‪Little Cat Lodge - ‬17 min drive

Frequently asked questions

Is Hudson Valley and The Berkshires getaway pet-friendly?

Yes, this property allows cats and dogs (limit 1 total) with a maximum weight of up to 23 kg per pet.

What time is check-in at Hudson Valley and The Berkshires getaway?

Check-in begins at 3:00 PM.

What time is check-out at Hudson Valley and The Berkshires getaway?

Checkout is at 10:00 AM.

Where is Hudson Valley and The Berkshires getaway located?

Situated in Hillsdale, this holiday home is within 9 miles (15 km) of W.E.B. Du Bois Boyhood Homesite, Hillsdale Town Hall and Mahaiwe Performing Arts Center. Housatonic River Walk and Community Library are also within 12 miles (20 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 6 out of 6 reviews
Rating 8 - Good. 0 out of 6 reviews
Rating 6 - Okay. 0 out of 6 reviews
Rating 4 - Poor. 0 out of 6 reviews
Rating 2 - Terrible. 0 out of 6 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Lori S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great little hideaway

The house was clean, well-maintained and easy to navigate. Communication with the owners was seamless, and they kindly extended our check-out due to inclement weather. Highly recommend this rental!
Stayed 2 nights in Feb 2025

10/10 Excellent

Derek N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Location in Hillsdale

We loved our stay on Stone Ledge Rd in Hillsdale. We have stayed at Vrbo properties in Hillsdale two prior holiday weeks leading up to the New Year and this was by far the best set-up for us—gorgeous views through the wrap-around windows, easy and comfortable sleeping arrangements for the 6 of us, plenty of sofa space for reading, watching movies, just hanging out. Ben was very responsive when a mixture of drizzle and freezing temperatures made the driveway slippery and we were able to park in an alternative spot just below the house. The road is a dead end and so very quiet, great for walking our dogs, and also not far from three or four trails that we’ve discovered over the years. We will keep coming back, and hope when we’re ready to book for next year that this house is available.
Stayed 5 nights in Dec 2024

10/10 Excellent

Jessica W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Cozy, quiet, and close to attractions!

This property is close to many Berkshires and Hudson Valley attractions. In addition to its great location, it is clean, has new appliances, and is on such a peaceful street! There is a lot of space, but it's still incredibly cozy. The beds were extra comfy, as well! I will stay here again if the opportunity presents itself. Thanks for a great stay and the easy check-in/check-out process!
Stayed 2 nights in Nov 2024

10/10 Excellent

Jennifer H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely Stay

We very much enjoyed our stay at this lovely home. The hosts were wonderful communicators!
Stayed 4 nights in Jul 2024

10/10 Excellent

Joe F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Weekend

Took a trip upstate to see a concert at Tanglewood, not far from the property. The area was quiet, peaceful and overall beautiful. All the features in the home seem to be brand new and it was extremely clean. Benjamin, the owner, is very easy to get a hold of and extremely accessible. Would recommend to anyone thinking about staying here!
Stayed 1 night in Jun 2024

10/10 Excellent

John C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Golf trip

Overnight golf trip with cousins and father. Perfect accommodations not far from the copake country club. Great time
Stayed 1 night in Apr 2024

About the host

Hosted by Ben Lockspeiser and Andrew D’Agostino

Host profile image
Andrew and Ben have been friends since college, living in different parts of the NorthEast. They wanted a place to get together in the Hudson Valley to enjoy the beautiful landscape and host others in a wonderful part of New York State.

Languages:

English

Premier Host

They consistently provide great experiences for their guests