Hillsdale Hotels

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Filter by

Guest rating
Guest rating
Property class

Top 10 trending Hillsdale hotels

The Brooks Motel

2.0 star property
7.8 out of 10, Good, (90)
"Basic, clean and good value for the money."
The price is €129
includes taxes & fees
3 Aug - 4 Aug
The Brooks Motel

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.2 out of 10, Wonderful, (1000)
"Loved the Yankee Inn!"
The price is €153
includes taxes & fees
1 Sept - 2 Sept
The Yankee, Trademark Collection by Wyndham

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1000)
"Beautiful location!"
The price is €122
includes taxes & fees
1 Sept - 2 Sept
The Black Swan Lee - Lenox, Ascend Hotel Collection

The Constance by the Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (507)
"Property was excellent "
The price is €155
includes taxes & fees
2 Sept - 3 Sept
The Constance by the Lenox Collection

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1001)
"Breakfast each day was phenomenal, staff were all so friendly, hotel & room were beautifully decorated. We had a wonderful time & would stay here again!"
The price is €165
includes taxes & fees
27 Aug - 28 Aug
The Cornell Inn, Lenox & The Berkshires

Berkshires Untold

3.5 star property
9.2 out of 10, Wonderful, (655)
"It's a clean, nice place. And easy to get to the surrounding towns."
The price is €415
includes taxes & fees
8 Aug - 9 Aug
Berkshires Untold

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1002)
"Loved our visit"
The price is €221
includes taxes & fees
27 Aug - 28 Aug
The Red Lion Inn

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
9.0 out of 10, Wonderful, (683)
"Terrific place. Spacious, clean, comfortable."
The price is €127
includes taxes & fees
2 Sept - 3 Sept
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Econo Lodge Lee - Great Barrington

2.0 star property
6.4 out of 10, (615)
"It was a clean, well-run, low cost option. "
The price is €61
includes taxes & fees
17 Aug - 18 Aug
Econo Lodge Lee - Great Barrington

Catskill Motor Court Motel

2.5 star property
5.8 out of 10, (105)
"Pool was filled in years ago not like the picture on Expedia. Smells like sewage. I didn’t stay. I left. Place was disgusting "
The price is €97
includes taxes & fees
14 Aug - 15 Aug
Catskill Motor Court Motel

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (843)
"I like this place a lot and have stayed here many times over the years. Comfortable stay at a reasonable price at a convenient location in Pittsfield. "
The price is €111
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn & Suites Pittsfield-Berkshires by IHG

FairBridge Inn Express

2.5 star property
5.4 out of 10, (758)
"Close to our target event a plus"
The price is €69
includes taxes & fees
31 Aug - 1 Sept
FairBridge Inn Express

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1001)
"Very nice stay"
The price is €115
includes taxes & fees
1 Sept - 2 Sept
Best Western Plus Berkshire Hills Inn & Suites

St. Charles Hotel

2.0 star property
6.8 out of 10, (767)
"Very nice staff and comfy stay"
The price is €157
includes taxes & fees
5 Aug - 6 Aug
St. Charles Hotel

Chatham Travel Lodge

2.5 star property
7.6 out of 10, Good, (184)
"Nice and quiet"
The price is €108
includes taxes & fees
4 Aug - 5 Aug
Chatham Travel Lodge

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
9.4 out of 10, Exceptional, (723)
"Was the perfect stop over for our way home. All the employees were extremely friendly. "
The price is €146
includes taxes & fees
27 Aug - 28 Aug
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

The Whitlock

2.0 star property
8.6 out of 10, Excellent, (261)
"Lovely hotel in the heart of Lenox. The rooms and property were very nice. The staff was great. We would definitely stay here again!"
The price is €179
includes taxes & fees
2 Sept - 3 Sept
The Whitlock

Travelodge by Wyndham Great Barrington Berkshires

2.0 star property
7.4 out of 10, Good, (536)
"Run down old property , room smelled , dirty carpet "
The price is €72
includes taxes & fees
1 Sept - 2 Sept
Travelodge by Wyndham Great Barrington Berkshires

Howard Johnson by Wyndham Saugerties

2.0 star property
7.6 out of 10, Good, (1003)
"Hotels, very nice and very clean"
The price is €119
includes taxes & fees
3 Aug - 4 Aug
Howard Johnson by Wyndham Saugerties

Berkshire Travel Lodge

2.5 star property
5.4 out of 10, (429)
"A good, affordable place to sleep close to many scenic attractions."
The price is €65
includes taxes & fees
3 Aug - 4 Aug
Berkshire Travel Lodge
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.
Save an average of 15% on thousands of hotels when you're signed in

Learn more about Hillsdale

Quaint Hillsdale is calling! Discover its coffee, library, skiing and more.

Top Hillsdale Hotel Reviews

Frequently asked questions

Where is the best place to stay in Hillsdale?

Based on Expedia's traveller preferences, The Brooks Motel is a top place to stay in Hillsdale. Two other options for your trip to the area are Postcard Cabins Eastern Catskills and Berkshires Untold. See all available top hotels, or vacation rentals in Hillsdale.

What are some of the best holiday rentals that Hillsdale has to offer?

Spacious 5-bedroom house in charming Lee with WiFi: This holiday home rental outside of Hillsdale offers a fireplace, a BBQ and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities such as a dishwasher and a microwave can make your holiday run smoothly. See all vacation rentals in Hillsdale.

If I need to cancel my hotel reservation in Hillsdale, will I receive a refund?

Yes! Most hotel reservations are refundable provided that you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before check in. If you have a non-refundable reservation, you might be able to still cancel and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Hillsdale.

What's the best hotel for families in Hillsdale?

Holiday House Motel is a property with free parking and free WiFi, and it's a top choice on Expedia for families. Also, children of all ages will enjoy a visit to Catamount Aerial Adventure Park.

What's the best dog-friendly place to stay in Hillsdale?

The Brooks Motel is a top dog-friendly option for your stay. Hudson valley and The Berkshires Cottage is another good option for you and your pet. See more pet-friendly hotel accommodations in Hillsdale.

What's the best hotel for a trip to the slopes in Hillsdale?

Little Cat Lodge is a top hotel for a winter getaway, and features ski storage and free WiFiThis hotel is adjacent to Catamount Ski Area. The Brooks Motel is another good choice for your winter getaway. See all ski hotels in Hillsdale.

What are some accommodation options with pools in Hillsdale?

Howard Johnson by Wyndham Saugerties: Features a sauna, an indoor pool and free self parking. Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG and Holiday Inn & Suites Pittsfield-Berkshires by IHG are a couple of other choices that feature an on-site pool. View all hotels with pools in Hillsdale.

What's it like staying in Hillsdale?

Visitors can enjoy all that Hillsdale has to offer, including the coffee shops and ski areas. This city also attracts tourists with its relaxing and quaint setting. In Hillsdale, there are 72 hotels and other accommodation options to choose from. Find out more about Hillsdale.

What should I see while I'm in Hillsdale?

The picturesque setting of Copake Lake and Mosquito Island exemplify the area's natural beauty. A couple of additional sights to add to your itinerary are Catamount Aerial Adventure Park and Catamount Ski Area. Take a look at what more there is to see and do in Expedia's Hillsdale guide.

What's the seasonal weather 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.