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

Hillsdale Hotel Guide - 4 Stars Hotels in Hillsdale, New York

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Check availability on Hillsdale 4 Star Hotels

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 Rp3.858.820
Rp4.360.465 total
includes taxes & fees
4 Aug - 5 Aug
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 Rp1.866.592
Rp2.085.019 total
includes taxes & fees
23 Jul - 24 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
7.6 out of 10, Good, (32 reviews)
"The warmth of the owners!"
United States
Evangelia
The price is Rp3.209.651
Rp3.630.919 total
includes taxes & fees
29 Jul - 30 Jul
it's a good thing
John Harney Suite | Minibar, desk, iron/ironing board, free WiFi

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 Rp6.153.175
Rp7.076.107 total
includes taxes & fees
2 Aug - 3 Aug
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 Rp5.916.977
Rp7.157.825 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 Rp6.645.107
Rp7.793.843 total
includes taxes & fees
29 Jul - 30 Jul
The Inn at Stockbridge
The Garden Suite | 1 bedroom, Egyptian cotton sheets, premium bedding, pillow-top 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 Rp9.590.962
Rp11.029.606 total
includes taxes & fees
16 Aug - 17 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 Rp7.879.172
Rp8.800.981 total
includes taxes & fees
19 Aug - 20 Aug
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 Rp5.722.002
Rp6.904.775 total
includes taxes & fees
22 Jul - 23 Jul
The Old Inn On The Green
Luxury Room, 1 King Bed, Bathtub | Premium bedding, iron/ironing board, free WiFi, 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 Rp13.427.258
Rp14.998.246 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 Rp5.559.094
Rp6.209.447 total
includes taxes & fees
29 Jul - 30 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?
With Expedia's filter tool, locking in a great deal on a 4-star hotel in Hillsdale just got easier. Start by keying in your chosen travel dates and length of your break. Then list the results by price and pick a property that best fits your budget and style.

  • Search for the lowest price from Rp2.085.019

What's the difference between 5-star and 4-star hotels in Hillsdale?
Offering a friendly traveller experience and upmarket décor, 4-star hotels are a terrific option for your Hillsdale holiday. These types of accommodation generally come with loads of handy amenities that make it a breeze to kick back and relax — think pillowtop mattresses, gyms and restaurants. Or live the high life at a 5-star hotel designed to pamper with high-end perks and amenities. Full-service health clubs, premium toiletries and world-class dining are typically featured at these plush properties.
Does Hillsdale have any 4-star all-inclusive resorts?
Enjoy a relaxing holiday experience where everything is included in the one upfront rate by using our "All inclusive" filter. Staying within budget is a cinch when your room, food and many activities are already taken care of. Want more options? Browse the great deals on our standard 4-star resorts in and around Hillsdale too.