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

Hillsdale Hotel Guide - Romantic Hotels in Hillsdale, New York

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Our top choices for Hillsdale romantic hotels

Superior Room, 1 King Bed, Jetted Tub | Jetted bathtub

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,013 reviews)
"Great location with easy parking Excellent cleaning staff. Done promptly and right. Very helpful front desk staff."
United States
Brian
The price is €148
includes taxes & fees
12 Jul - 13 Jul
The Yankee Inn
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (463 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is €183
includes taxes & fees
13 Jul - 14 Jul
Shaker Mill Inn
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1,005 reviews)
The price is €117
includes taxes & fees
14 Jul - 15 Jul
Best Western Plus Berkshire Hills Inn & Suites
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,011 reviews)
"Great place"
United States
Michelle
The price is €140
includes taxes & fees
28 Jul - 29 Jul
Quality Inn Lee - Lenox South
Restaurant

Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.6 out of 10, Exceptional, (95 reviews)
"Really sweet quality, details. Kind and helpful staff and management. Truly enjoyed my stay."
United States
Koryn
The price is €167
includes taxes & fees
13 Jul - 14 Jul
Little Cat Lodge
Exterior

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (789 reviews)
"very responsive staff excellent check in and check out"
United States
Kathleen
The price is €151
includes taxes & fees
26 Jul - 27 Jul
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Indoor pool

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (127 reviews)
"Breakfast was good, good location, friendly staff."
United States
Courtney
The price is €154
includes taxes & fees
16 Jul - 17 Jul
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Lobby

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.6 out of 10, Excellent, (1,014 reviews)
"Great staff. Clean comfortable rooms. Good pillows and mattress and cold A/C"
United States
sarah
The price is €116
includes taxes & fees
10 Aug - 11 Aug
Quality Inn Great Barrington
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Hillsdale Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Clean room. Arrived late."
Nick 1-night trip
Posted 1 day ago
The Red Lion Inn
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

8/10 Good
"Room was a good size.Front desk associate when we arrived helped with suggestions for dinner. In the morning another front desk associate helped to replenish the coffee when I let them know it was empty."
Debra 1-night trip
Posted 2 days ago
Hampton Inn & Suites Berkshires-Lenox

Frequently asked questions

Searching for romantic hotels in Hillsdale?
If you and your partner need some romantic time away, we'd like to help you plan for it. While you're in Hillsdale, you'll find plenty to see and do. If you want to explore the sights and attractions with your partner, you might consider stopping by Catamount Aerial Adventure Park, Catamount Ski Area or Copake Lake. Whether you'd like to sip a glass of champagne or get a couples' massage, you'll be sure to find your ideal accommodation in Hillsdale to make for the perfect couples' weekend.
What's the best hotel for a couple going to Hillsdale?
Farm House Getaway on beautiful horse farm! is a favourite country house for couples, and features in-room fireplaces and a garden.
When is the best time of year for a romantic getaway to Hillsdale?
If you're hoping to get lost in the rain on your romantic getaway, take a look at these details about year-round temperatures in Hillsdale: The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Hillsdale are January, March, February and November, with each month seeing an average of 18 cm of snowfall.
What is there to do in Hillsdale?
There's nothing better than experiencing a new destination with your sweetheart, so consider checking out all there is to see and do in Hillsdale. You might consider a visit to Catamount Aerial Adventure Park, Catamount Ski Area or Copake Lake.
What's the best way to get to Hillsdale and around town during my romantic getaway?
These transportation options in Hillsdale might help your romantic trip go off without a hitch: If you're looking to fly to Hillsdale, the closest major airport is in Hudson, NY (HCC-Columbia County), located 12.5 mi (20.1 km) from the city centre. If you'd like to explore around the area, you may want a rental car for your journey.