Hudson Valley and The Berkshires getaway

Photo gallery for Hudson Valley and The Berkshires getaway

A modern building with a balcony, large windows, and a metal railing.
A modern two-story cabin with a stone foundation, surrounded by a snowy forest.
A modern kitchen with a central island, bar stools, and a dining table.
A modern living room with a blue sofa, a wooden coffee table, and large windows offering a view of trees.
Room

Reviews

10 out of 10
Exceptional

Highlights

  • Room to spread out
    Enjoy spacious layout that give everyone more room to relax.
  • Centrally-located
    You're never far from where you need to be with this convenient location.

Popular amenities

  • Balcony
  • Barbecue
  • Air-conditioning
  • Refrigerator
  • Pet-friendly
  • Internet

Explore the area

View map
Hillsdale, NY
  • Place, Catamount Aerial Adventure Park
    ‪16 min drive‬
  • Place, Catamount Ski Area
    ‪17 min drive‬
  • Place, Taconic State Park
    ‪18 min drive‬
  • Airport, Hudson, NY (HCC-Columbia County)
    ‪36 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

Bathtub · Toilet · Shower only

Bathroom 3

Bathtub · Toilet · Shower only

Spaces

Kitchen
Balcony
Garden

Add dates for prices

Similar properties

Daytime balcony view
Summer in the Berkshires!
Stockbridge
  • Spa pool
  • Kitchen
  • Washing machine
  • Dryer
9.8 out of 10, Exceptional, (6 reviews)
Summer in the Berkshires!

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 Charles H. Baldwin & Sons. Hoffman's Pottery and Berkshire Botanical Garden are also worth visiting.
View more Holiday homes in HillsdaleOpens in a new window
Map
Hillsdale, NY

What's nearby

  • Hillsdale Town Hall - 15 min drive - 19.9 km
  • W.E.B. Du Bois Boyhood Homesite - 16 min drive - 15.6 km
  • Catamount Aerial Adventure Park - 16 min drive - 22.0 km
  • Catamount Ski Area - 17 min drive - 23.1 km
  • Taconic State Park - 18 min drive - 24.8 km

Getting around

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

Restaurants

  • ‪Four Brothers Pizza Inn - ‬13 min drive
  • ‪Stewart's Shops - ‬13 min drive
  • ‪Berkshire Mountain Bakery - ‬22 min drive
  • ‪Common Or Garden Pub - ‬22 min drive
  • ‪The Cliff House - ‬9 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.

How much does it cost to stay at Hudson Valley and The Berkshires getaway?

As of 3 November 2026, prices found for a 1-night stay for 2 adults at Hudson Valley and The Berkshires getaway on 16 November 2026 start from NZ$1,391, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Hudson Valley and The Berkshires getaway?

On-site parking is available at the property.

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, Monument Mountain and Great Barrington Historical Society & Museum. Hillsdale Town Hall and Mahaiwe Performing Arts Center are also within 9 miles (15 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 14 out of 15 reviews
Rating 8 - Good. 1 out of 15 reviews
Rating 6 - Okay. 0 out of 15 reviews
Rating 4 - Poor. 0 out of 15 reviews
Rating 2 - Terrible. 0 out of 15 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had such an incredible stay, this home is gorgeous and was the perfect quiet sanctuary for our weekend. I would stay again without a doubt.
Stayed 3 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very comfortable home in a great area!
Stayed 3 nights in Dec 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful stay. Very responsive host. Clean, spacious home that is in a great location with easy access to many activities.
Stayed 3 nights in Feb 2026
Response from VrboOwner on 19 February 2026
Thank you so much Mary! You were a wonderful guest and are welcome back any time.
Verified review

10/10 Excellent

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

Peaceful stay in the woods

Place was decorated very nicely and it was very quiet and peaceful.
Stayed 2 nights in May 2025
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Ben and Andrew's communication was outstanding. Whenever I reached out they responded immediately. We stayed at the their property for 2 months this summer. The home was clean when we arrived.We had everything we needed for cooking. It as a great stay,
Stayed 59 nights in Aug 2025
Response from VrboOwner on 16 October 2025
It was truly a pleasure to host you this past summer Amy! Thank you for putting your trust in us and our property for a long period of time. You are welcome back any time!
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
What a great house. Perfect for our group. Kids stayed downstairs and watched movies. We played games every night around the dinning room table. The sectionals were comfy, allowing us all to relax. Also the throw blankets were a nice homey touch. Kitchen was easy to navigate. Nice open concept layout. The master bedroom and bathroom are so nice. The bed was delightful the blankets dreamy. For real didn’t want to get out of bed. We went out one night. Went to Barrington for dinner one night. FYI a lot of restaurants in Hillsdale are closed on Mondays and Tuesday. Which is why we went to Barrington. But it was really close and supper cute town. Some of us relaxed and did a puzzle others went skiing at catamountOverall a great stay for skiing, hiking or just relaxing. Thanks again for the wonderful stay.
Stayed 3 nights in Feb 2026
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Long term stay (9 weeks). Wonderful Summer at Ben and Andrew’s house in the woods. Felt like living in a treehouse or terrarium. Not our first long term stay and there are always a hiccup or two. Hosts were super, super responsive with texts back immediately and resolutions sooner than any reasonable expectation. Would definitely stay again.
Stayed 63 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This home was so lovely--tucked away in rolling hills and surrounded by greenery. A great place to escape from Washington, DC, and explore the Hudson Valley. Ben is very responsive. Highly recommend it!
Stayed 3 nights in Jun 2026
Response from VrboOwner on 10 July 2026
Thank you very much Lisa! You are welcome back any time.
Verified review

8/10 Good

Stayed 5 nights in Mar 2026
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