A rural landscape with snow-covered fields, a winding road, and scattered trees.

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Our top choices for Hillsdale 4-star hotels

Hiking

The Wick, Hudson, A Tribute Portfolio Hotel

The Wick, Hudson, A Tribute Portfolio Hotel
4.0 star property
Hudson
8.8 out of 10, Excellent, (572 reviews)
"Friendly and helpful staff. Great location for those traveling by train. A pool would elevate the experience :)"
United States
Claudette
The price is SAR 860
SAR 972 total
includes taxes & fees
26 Jul - 27 Jul
The Wick, Hudson, A Tribute Portfolio Hotel
Exterior

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (379 reviews)
"Central location!"
United States
Brenda
The price is SAR 402
SAR 449 total
includes taxes & fees
21 Jul - 22 Jul
The Central Downtown Inn & Suites
Front of property

it's a good thing

it's a good thing
4.5 star property
Clinton Corners
7.8 out of 10, Good, (31 reviews)
"The warmth of the owners!"
United States
Evangelia
The price is SAR 673
SAR 761 total
includes taxes & fees
21 Jul - 22 Jul
it's a good thing
John Harney Suite | Minibar, desk, iron/ironing board, WiFi (free)

The White Hart

The White Hart
4.0 star property
Salisbury
9.8 out of 10, Exceptional, (151 reviews)
"It’s an exceptional place in every aspect. "
United States
William
The price is SAR 1,289
SAR 1,483 total
includes taxes & fees
22 Jul - 23 Jul
The White Hart
Suite, Private Bathroom (RedBird Suite) | View from room

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (113 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is SAR 1,240
SAR 1,500 total
includes taxes & fees
3 Aug - 4 Aug
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Front of property

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.8 out of 10, Exceptional, (99 reviews)
"Great spot close to town. Cozy, tasteful, comfortable room. Nice breakfasts and pleasant interaction with the staff. We love the Berkshires and we’ll definitely stay here again."
United States
Stephen
The price is SAR 1,393
SAR 1,633 total
includes taxes & fees
27 Jul - 28 Jul
The Inn at Stockbridge
The Garden Suite | 1 bedroom, Egyptian cotton sheets, premium bedding, pillowtop beds

9 Academy

9 Academy
4.0 star property
Salisbury
9.4 out of 10, Exceptional, (13 reviews)
"Extremely clean and the rooms are beautifully decorated with warm minimal decor. We will definitely be back!"
United States
Gina
The price is SAR 1,895
SAR 2,180 total
includes taxes & fees
12 Aug - 13 Aug
9 Academy
Front of property

Seven Hills Inn

Seven Hills Inn
4.0 star property
Lenox
7.8 out of 10, Good, (467 reviews)
"Great location, nice breakfast and clean rooms"
United States
Christopher
Seven Hills Inn
Front of property - evening/night

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (139 reviews)
"Room was great, staff was awesome, amenities were cool"
United States
Francis
The price is SAR 1,649
SAR 1,842 total
includes taxes & fees
21 Jul - 22 Jul
Devonfield Inn B&B
Breakfast, lunch, dinner and brunch served

The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (91 reviews)
"Beautiful Inn and outstanding chef"
United States
Catherine
The price is SAR 1,197
SAR 1,445 total
includes taxes & fees
21 Jul - 22 Jul
The Old Inn On The Green
Luxury Room, 1 King Bed, Bathtub | Premium bedding, iron/ironing board, WiFi (free), individually decorated

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is SAR 2,613
SAR 2,919 total
includes taxes & fees
16 Aug - 17 Aug
33 Main
Porch

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (303 reviews)
"Clean rooms and staff were very knowledgeable about the area. Breakfast was very good. Beautiful room and view on second floor. Would recommend as a place to get away from it all!!"
United States
Angela
Lakehouse Inn
Exterior detail

Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
Lenox
9.0 out of 10, Wonderful, (44 reviews)
"Comfortable bed. Quiet location. Excellent breakfast. Friendly host."
United States
Kathleen
The price is SAR 1,202
SAR 1,343 total
includes taxes & fees
22 Jul - 23 Jul
Hampton Terrace Inn
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Learn more about Hillsdale

Tucked in the Hudson Valley, this rural hamlet offers scenic hikes through Taconic State Park and charming farm-to-table dining. Explore nearby art galleries in Copake or visit Catamount Mountain Resort for outdoor adventures in all seasons.

See all hotels in Hillsdale
A landscape with a row of trees in autumn colors, a wooden fence, and a hilly background.

Top Hillsdale Hotel Reviews

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Hillsdale?
To lock in a 4-star hotel in Hillsdale that fits your budget, use Expedia's search and sort filters. Take a look at the availability during your vacation dates and use our pricing filter to set your maximum rate. You can also list your results by the most affordable escape first.

  • Search for the lowest price from SAR 449

What's the difference between 5-star and 4-star hotels in Hillsdale?
Offering a welcoming guest experience and upmarket surroundings, 4-star hotels are a fantastic option for your Hillsdale escape. These kinds of stays generally come with lots of handy amenities that make it simple to unpack and recharge — think complimentary bathrobes, pools and restaurants. Or live in the lap of luxury at a 5-star hotel designed to pamper with high-end perks and amenities. Round-the-clock concierge service, premium toiletries and world-class dining are typically featured at these deluxe retreats.
Does Hillsdale have any 4-star all-inclusive resorts?
Finding vacation bliss in Hillsdale is as simple as typing in your travel details and clicking on our "All inclusive" filter. Stay and play where almost everything is already taken care of like your meals, room, entertainment and activities, or choose a standard 4-star resort in or around this leading destination.

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