Romantic Hotels & Resorts in Hillsdale from AU$376

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Check availability on Hillsdale Romantic Hotels

Our top choices for Hillsdale romantic hotels

Terrace/patio

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
9.8 out of 10, Exceptional, (281 reviews)
"Beautiful “New England” layout and area!!!"
United States
Peter S.
The price is AU$376
includes taxes & fees
10 June - 11 June
Berkshire Village Carriage House - Super Private!!
Interior

Brand New House w gated backyard that is located right at the Saugerties Village

Brand New House w gated backyard that is located right at the Saugerties Village
Saugerties
10.0 out of 10, Exceptional, (41 reviews)
"Great new and clean property! Very close to downtown, supermarket, and a short drive to Hunter Mountain & Kaaterskill falls. "
United States
Michael
The price is AU$574
includes taxes & fees
14 June - 15 June
Brand New House w gated backyard that is located right at the Saugerties Village
Interior

rural, serene + sophisticated space

rural, serene + sophisticated space
Red Hook
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful property with unique accommodations in the Hudson Valley"
United States
BRIAN PATRICK M.
The price is AU$566
includes taxes & fees
15 June - 16 June
rural, serene + sophisticated space
Fridge, microwave, oven, stovetop

A Country Lodge Straight Out of the Pages of a Great Novel

A Country Lodge Straight Out of the Pages of a Great Novel
Pine Plains
10.0 out of 10, Exceptional, (13 reviews)
"Our group of parents and riders had a great stay during the Millbrook Horse Trials in July. Clean facility, ample room, responsive host. Would stay again."
United States
Hessie S.
The price is AU$2,038
includes taxes & fees
10 June - 11 June
A Country Lodge Straight Out of the Pages of a Great Novel
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

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

2/10 Terrible
"The hotel is under construction. This was not mentioned when reservations made. The only available parking was down the street at the bank. The television channels did not come in had to call for assistance. Then tv continued to have issues. On the ceiling and the wall there was dark colored “something” mold? dust? GROSS! Not worth the price."
Brenda 1-night trip
Posted 21 hours ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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.