Hillsdale is home to this guesthouse. Tanglewood Music Center and Great Barrington Historical Society & Museum are cultural highlights, and some of the area's landmarks include W.E.B. Du Bois Boyhood Homesite and Mahaiwe Performing Arts Center. Ebenezer II Gifts and Antiques and Charles H. Baldwin & Sons are also worth visiting. Take the opportunity to explore the area for outdoor excitement like cycling.
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 Cottage 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 Cottage?
As of 1 November 2026, prices found for a 1-night stay for 2 adults at Hudson valley and The Berkshires Cottage on 30 March 2027 start from NZ$685, 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 Cottage?
On-site parking is available at the property.
What time is check-in at Hudson valley and The Berkshires Cottage?
Check-in begins at 3:00 PM.
What time is check-out at Hudson valley and The Berkshires Cottage?
Checkout is at 10:00 AM.
Where is Hudson valley and The Berkshires Cottage located?
Situated in Hillsdale, this guesthouse 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).
Hudson valley and The Berkshires Cottage Reviews
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Clean, great communication and a very cute spot. Our neighbors at the main house were also respectful and we had zero issues. If possible get there before dark so you can easily see the steps that lead up to the cottage. Would book again!
We had a great weekend stay at The Cottage. We loved the accommodations- great decor! Very clean and comfortable accommodations. Will definitely come back!
Hosts had great communication, house was very clean and had great amenities. No lists or hassle at check-out. My only comment would be that the parking/stairs might be hard to find if you arrive after dark.
This might be the cleanest VRBO I've ever stayed in, spotless and sparkling. Ben let me know I could contact him anytime if I had problems. It was quiet and serene on a dirt road, would definitely love to go back sometime!
We were in town for a concert and this cottage was perfect for our quick overnight trip! The owners were very communicative. The cottage is immaculate! Highly recommend! Thank you!
We had a wonderful stay at this charming cottage in Hillsdale, NY. The location was absolutely beautiful—peaceful and quiet, perfect for a relaxing getaway. The house itself was clean, with a modern design that felt both stylish and incredibly hospitable. The communication with the host was fantastic—attentive and responsive throughout our stay. Highly recommend this spot for anyone looking for a peaceful retreat!
A great stay in this well situated getaway. The owners were helpful and communicative, and the house was easy driving distance to Great Barrington, Hillsdale and Lenox. The unit is open and airy and decorated in a very pet friendly way.
Would stay again without hesitation.
This was a great experience and hit all the buttons. With a secluded location only 15 minutes from most attractions you really get have both the social excitement before retreating to comfortable seclusion. The cottage was perfect offering exactly the small things that are needed i.e coffee, pre-programmed netflix login, and a terrific layout. It was a true Berkshire stay with the blizzard, being able to just hunker down, or enjoy snowboarding on the mountain that was 10 min away. Great communication provided a safe and comfortable getaway. We look forward to booking again.
From start to finish everything went smoothly! Visiting family in the Hillsdale NY area - this clean & serene dog friendly one bedroom provided a place to recharge in the morning & evenings. Thanks Ben & Andrew!
I enjoyed my stay. The cottage was immaculate upon arrival and is gorgeously decorated. Beautiful kitchen with stunning countertop, comfortable couch, spacious bathroom, beautiful flooring, and wonderful high ceilings on the top (kitchen and living room) level. There is another rental property (owned by the same owner) just steps away from the back door of the cottage, and there was some brief construction noise at 10 am one morning during my stay which luckily did not occur again. Otherwise it was a blissfully peaceful stay. Communication with the owners was excellent, they were very responsive to messages before and during my stay.
The property was beautiful! We did not get to stay as long as we wanted but we will definitely be coming back to this little cottage. It was very clean and decorated well! The host was immediately responsive but we should note that there was absolutely no cellphone service which made communicating with guests a little difficult.
Lovely little cabin, beautifully renovated and spotless! My only concern is the steps to the property are steep, (we are in our 70s). If your fit, go for it! We loved it!
Stayed 6 nights in Sep 2024
Verified review
8/10 Good
Michael N.
9 April 2026
Liked: Cleanliness, check-in, communication
No pets. The kitchen could use better lighting, measuring cups, another pot with lid, a cheese grater. Otherwise, the kitchen worked well.
This cottage offered us just what we needed. It is located close to the shops in Hillsdale and neighboring towns in Massachusetts. The property is very clean, the bed is comfortable. Easy to adjust the temp to handle the daytime heat and humidity, along with the chilly nights. Plenty of places to sit, great kitchen - everything just as the pictures suggest. The owners were very responsive and eager to be helpful when/if needed.
The cottage was spacious and comfortable. We appreciated the quiet and the relaxation. It was close to all of the venues and towns we wanted to visit. Ben and Andrew were gracious hosts and quick to respond to questions. Check in/out was a breeze. We truly appreciated their “no chore list” philosophy. One teeny-tiny suggestion, put some sort of lamp on the kitchen counter. When it was dark out it was impossible to use the kitchen without turning on the bright overhead lights. Thanks for a wonderful stay!
This oasis in the woods is a perfect week long or weekend respite. It is very clean and comfortable with all the necessary amenities. The location is quiet and peaceful with chirping birds and a nearby babbling brook. Easy access to nearby country towns for groceries, restaurants or browsing. Hiking trails are abundant. WiFi was robust enough for me to connect remotely with work when needed. The owner is pleasant, responsive and accommodating. I would highly recommend for anyone looking for an escape to rejuvenate and boost their well-being.
We loved our get away at the Cottage! Comfortable mattress and pillows. Great temp control. It’s not often my husband and I sleep that well when traveling. You’re surrounded by beautiful lush forest, so much that a couple small windows don’t need blinds. Check-in was slick with the keypad. Check-out the same with the no-chores philosophy. To access the cabin you walk up a concrete step path, so make sure you’re able to carry your luggage. The neighborhood is beautiful for walks/runs. Bunnies abound!