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

Hillsdale Hotel Guide - Romantic Hotels in Hillsdale, New York

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Hillsdale Romantic Hotels

Tonight
9 Oct - 10 Oct
Tomorrow
10 Oct - 11 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

Our top choices for Hillsdale romantic hotels

A two-story house with a balcony, a deck, and a view of the surrounding forest.
A spacious living room with a high ceiling, a fireplace, and a staircase leading to an upper level.
A modern kitchen with white cabinets and a built-in knife block.
A kitchen with wooden floors, a central island, a stainless steel refrigerator, and pendant lighting.

1. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
United States
Anne S.
€590
includes taxes & fees
18 Oct - 19 Oct
Gorgeous Mountain Views Retreat: Family & Nature
A stone patio with outdoor furniture, a small brick house with a green roof, and a forested area.
A kitchen with white cabinets, a granite countertop, a stainless steel sink, and a red pendant light.
A dog lying on a stone wall in a forested area.
A modern kitchen with white cabinets, a granite countertop, and a central island with stools.

2. Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
United States
Mary R.
€192
includes taxes & fees
12 Oct - 13 Oct
Berkshire Village Carriage House - Super Private!!
A bedroom with a large bed, a nightstand, an air conditioning unit, and a view through the window.
A cozy living room with a sectional sofa, a coffee table, and a ceiling fan.
A red building with a green door labeled "Apartment 1," a small garden with mulch and plants, and a white car parked in the background.
A modern kitchen with stainless steel appliances, a wooden dining table, and light-colored cabinetry.

3. 2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Stephentown
United States
Christine P.
€247
includes taxes & fees
12 Oct - 13 Oct
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
A modern kitchen with white cabinets, a large island, and a skylight.
A bedroom with a large bed, built-in bookshelves, a bedside table, and a window with curtains.
A two-story house with a gravel driveway leading to a garage.
A bedroom with a large bed, a red rug, a bookshelf, and a chair.

4. 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
United States
stephen r.
€1,291
includes taxes & fees
9 Nov - 10 Nov
A Country Lodge Straight Out of the Pages of a Great Novel
View all properties

Top Hillsdale Hotel Reviews

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

8/10 Good
"Nice Inn/B&B in Lenox MA, about a mile from downtown."
Anne 1-night trip
Posted 2 days ago
The Cornell Inn, Lenox & The Berkshires
The Red Lion Inn

The Red Lion Inn

8/10 Good
"Would go there again but would request to be in the main Inn, they have properties all over the town center that are considered the Inn. That was disappointing. A very unique property and super cute!"
Joanne 1-night trip
Posted 3 days ago
The Red Lion Inn

Frequently asked questions

Searching for romantic hotels in Hillsdale?
If you and your partner need a romantic holiday, we've got just the thing. 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 neighbourhood and proximity to top sights, so you'll be able to see everything on your list.
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.