Find Romantic Hotels in Hillsdale, NY

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Check availability on Hillsdale Romantic Hotels

Top Hillsdale Romantic Hotels

Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
8.0 out of 10, Very Good, (962)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is NT$2,789
NT$3,116 total
includes taxes & fees
Nov 29 - Nov 30
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1006)
"Great stay!"
United States
Ann
The price is NT$2,584
NT$2,886 total
includes taxes & fees
Dec 5 - Dec 6
The Yankee, Trademark Collection by Wyndham
Interior
Berkshires Untold

Berkshires Untold

3.5 star property
Lenox
9.0 out of 10, Wonderful, (800)
"We had a nice room and the food was delicious. Great place to stay. "
United States
Vincent
The price is NT$2,895
NT$3,233 total
includes taxes & fees
Nov 23 - Nov 24
Berkshires Untold
Outdoor pool, sun loungers
The Red Lion Inn

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1002)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is NT$5,090
NT$7,081 total
includes taxes & fees
Dec 21 - Dec 22
The Red Lion Inn
Porch
Interlaken Inn & Resort

Interlaken Inn & Resort

3.5 star property
Lakeville
8.2 out of 10, Very Good, (270)
"The staff is courteous and accommodating especially the restaurant staff."
United States
Christian
The price is NT$5,874
NT$6,755 total
includes taxes & fees
Nov 25 - Nov 26
Interlaken Inn & Resort
Library
Blackberry River Inn

Blackberry River Inn

3.0 star property
Norfolk
9.4 out of 10, Exceptional, (159)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is NT$5,132
NT$5,902 total
includes taxes & fees
Nov 25 - Nov 26
Blackberry River Inn
Balcony
The Nest Hudson

The Nest Hudson

3.5 star property
Hudson
9.6 out of 10, Exceptional, (208)
"What a beautiful stay right in the heart of Hudson. Cute, cozy, super clean with everything you need! "
United States
Kseniya
The Nest Hudson
Loft, Private Bathroom (Skylight Loft) | 1 bedroom, premium bedding, iron/ironing board, rollaway beds
Brook Farm Inn

Brook Farm Inn

3.5 star property
Lenox
9.4 out of 10, Exceptional, (162)
"Comfortable, quiet, convenient location, very friendly staff. "
United States
Susan
Brook Farm Inn
Deluxe Room, 1 King Bed, Balcony | Premium bedding, pillowtop beds, minibar, in-room safe
Diamond Mills Resort

Diamond Mills Resort

3.5 star property
Saugerties
9.4 out of 10, Exceptional, (343)
"Amazing view from the room. We had a great stay. "
United States
Adam
The price is NT$8,399
NT$10,188 total
includes taxes & fees
Dec 1 - Dec 2
Diamond Mills Resort
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

Diamond Mills Resort

Diamond Mills Resort

10/10 Excellent
"Staff was great. Clean room. Massages were great and the bar was great. If I can change anything it would be they need a pool there. The spa needs to be attached to the hotel and a bigger place to have breakfast."
Ken 2-night trip
Posted 5 days ago
Diamond Mills Resort

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Frequently asked questions

Searching for romantic hotels in Hillsdale?
If you and your partner need some romantic time away, we've got just the ticket. If you'd like to explore some of the area's notable sights, you might make a stop by Catamount Aerial Adventure Park, Catamount Ski Area, or Copake Lake. If you're interested in staying near a certain attraction, you can sort properties by neighborhood and proximity to top sights, so you'll be able to see everything on your list.
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, check out these details about year-round temperatures in Hillsdale: The hottest months are usually July and August with an average temp of 68°F, while the coldest months are January and February with an average of 29°F. The snowiest months in Hillsdale are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What is there to do in Hillsdale?
There's nothing better than seeing 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 Hudson, NY (HCC-Columbia County), located 12.5 mi (20.1 km) from the city center. If you'd like to explore around the area, you may want to rent a car for your trip.