Hillsdale, NY Country Houses from AED 4,384

Bird's eye view of the cityscape of Hillsdale, New York under a cloudy sky in winter

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Our top choices for Hillsdale country houses

NEW RENO - Historic Loft w/views of the Berkshires

New Lebanon

John

AED 804 total

includes taxes & fees

7 Jun - 8 Jun

the suite @ barn & bike - private, bucolic, serene setting

Red Hook

William D.

AED 831 total

includes taxes & fees

9 Jun - 10 Jun

Private bed& bath in 1860s farmhouse, access to total house and patio, porch.

Clinton Corners

Tony A.

AED 889 total

includes taxes & fees

6 Jun - 7 Jun

1789 Shaker Farmhouse in Berkshires/Hudson Valley

Canaan

Christine C.

AED 1,798 total

includes taxes & fees

9 Jun - 10 Jun

Charming 5-bedroom farmhouse with AC, WiFi in delightful Ghent

Ghent

elizabeth K.

AED 2,090 total

includes taxes & fees

7 Jun - 8 Jun

Farmhouse Retreat, Infrared Sauna, Fire-Pit, Fast Wifi, Golf & 3-Acre Privacy

Valatie

Tabish T.

AED 3,308 total

includes taxes & fees

30 Jun - 1 Jul

Charming 6 Bdrm Countryside Stay

Great Barrington

AED 4,384 total

includes taxes & fees

6 Jul - 7 Jul

NEW RENO - Chalet-style farm loft near Tanglewood

New Lebanon

Joanna P.

AED 756 total

includes taxes & fees

7 Jun - 8 Jun

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Top Hillsdale Hotel Reviews

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

10/10 Excellent

"I went on a solo cabin trip and it was so relaxed and peaceful! The condition of the cabin was better than I expected it to be and the staff were super friendly and accommodating. Definitely plan to go again next year! The cabin had so many supplies from cooking material, mini fridge (no freezer portion), lighters, books, games, stereo! I will say if you're able to rent a car, please do so. It was easy to Uber from New York City to the property, but to get an Uber back into the city was very hard. I ended up calling a taxi service. Lesson learned lol"

The Whitlock

8/10 Good

"We had a late arrival, which worked out with self checkout. Left the next morning after 9am, didn't see a single staff member during our whole stay, Was a bit of a challenge getting luggage up to the top floor without an elevator but we probably should have realized that when we booked. Nice property, nice big room with separate area for visiting. TV channel choices, which included streaming services, was excellent. Overall a good experience, just didn't see anyone there."

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"Wonderful hidden gem of a little hotel. Right on lake laurel we had a beautiful lake view. Rooms were very clean. Decent breakfast. Well Located and close to Lee downtown main st, the Lennox Main Street and Stockbridge as well. Looking forward to returning"

Berkshires Untold

8/10 Good

"Here’s what we liked: If we were just reviewing BERKSHIRES UNTOLD based on the staff, we’d be giving it a 5. The staff were extremely friendly, helpful and gracious. When we asked for extra towels and requested a room change, they accommodated those requests immediately. After we switched rooms they checked to see if we were happier. This is exactly the kind of service you want in a hotel or inn. Other good things - The bed was comfortable and there was enough counter space in the bathroom and at the desk area. We also liked that there was a breakfast seating area, bar and small indoor seating area plus outdoor seating with gas fire pits. So, why are we giving the place a 3 overall? It really needed more attention to detail. The carpet in our original room was not in good shape and the fitted bed sheet had a small rip on my side. Some of the room furniture was dinged up and a sofa in the common seating area had some shredded fabric. One thing we didn’t like (that they couldn’t exactly help) was that we were there on a late spring wedding weekend, so there were buses idling in front of our room with loud talkers and smokers nearby. It felt like they were in our room along with the smoke and fumes. The trend of turning motels into better motels is interesting. They’re less expensive and are sometimes more original. But you’re still in a motel. If you value soundproofing and consistently better quality, a mid range chain may be a better choice."

Berkshire Mountain Lodge

10/10 Excellent

"We love the Bershire Mountain Lodge. We've stayed here five other times but this time we do have a few very minor negatives. 1) The cabinet door under the kitchenette sink had a loose hinge. We messaged the staff and requested that they wait until after we checked out to repair the hinge. We hope the hinge was repaired before the next guest checked in. 2) The toilet flush handle was slightly cracked but still functional. We forgot to notify the staff; it was barely noticeable. 3) The guest or owner in the room above our room walked very loudly. We were used to hearing noises from people walking in the hall but this was our first time hearing footsteps through the ceiling. Other than those three items, our stay was excellent. The front desk staff were courteous and helpful. The housekeeping crew were unobtrusive. The long driveway to the ample parking lot gives enough distance from the busy"

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Treat yourself

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Check prices for these dates

Our top choices for Hillsdale country houses

NEW RENO - Historic Loft w/views of the Berkshires

the suite @ barn & bike - private, bucolic, serene setting

Private bed& bath in 1860s farmhouse, access to total house and patio, porch.

1789 Shaker Farmhouse in Berkshires/Hudson Valley

Charming 5-bedroom farmhouse with AC, WiFi in delightful Ghent

Farmhouse Retreat, Infrared Sauna, Fire-Pit, Fast Wifi, Golf & 3-Acre Privacy

Charming 6 Bdrm Countryside Stay

NEW RENO - Chalet-style farm loft near Tanglewood

1800s Carriage house in Berkshires / Hudson Valley

NEW RENO Historic Creamery in Berkshires w/hot tub

Top Hillsdale Hotel Reviews

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

The Whitlock

The Black Swan Lee - Lenox, an Ascend Collection Hotel

voco James Newbury Hudson Valley by IHG

Berkshires Untold

Berkshire Mountain Lodge

Spark by Hilton West Coxsackie

Hampton Inn & Suites Berkshires-Lenox

Quality Inn Great Barrington

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Search Country Houses in Hillsdale

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Hillsdale country houses

NEW RENO - Historic Loft w/views of the Berkshires

the suite @ barn & bike - private, bucolic, serene setting

Private bed& bath in 1860s farmhouse, access to total house and patio, porch.

1789 Shaker Farmhouse in Berkshires/Hudson Valley

Charming 5-bedroom farmhouse with AC, WiFi in delightful Ghent

Farmhouse Retreat, Infrared Sauna, Fire-Pit, Fast Wifi, Golf & 3-Acre Privacy

Charming 6 Bdrm Countryside Stay

NEW RENO - Chalet-style farm loft near Tanglewood

1800s Carriage house in Berkshires / Hudson Valley

NEW RENO Historic Creamery in Berkshires w/hot tub

Top Hillsdale Hotel Reviews

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Explore a world of travel with Expedia

Popular Destinations

Top Country Houses in Other Destinations

More Accommodation Types in Hillsdale