Hillsdale Hotels from S$91

    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
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
17 Jul - 18 Jul
Tomorrow
18 Jul - 19 Jul
This weekend
18 Jul - 20 Jul
Next weekend
25 Jul - 27 Jul

Filter by

Guest rating
Guest rating
Property class

Top 10 trending Hillsdale hotels

The Brooks Motel
Two beds with white bedding, a unique wall paneling, and a cozy reading area.

The Brooks Motel

2.0 star property
7.8 out of 10, Good, (85)
" Wry nice and clean. "
The price is S$183
includes taxes & fees
20 Jul - 21 Jul
The Brooks Motel
Blackberry River Inn
Cozy living room with a traditional fireplace, armchairs, and a sofa, perfect for relaxing.

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (116)
"We had a vey clean room with a comfortable bed The breakfast was awesome as was the entire staff. Enjoyed our stay"
The price is S$245
includes taxes & fees
21 Jul - 22 Jul
Blackberry River Inn
Gedney Farm
Enjoy a serene dining experience in a picturesque countryside setting at Gedney Farm.

Gedney Farm

3.5 star property
9.2 out of 10, Wonderful, (122)
"Beautiful, clean property that is well run."
Gedney Farm
The Old Inn On The Green
Relax in a serene bedroom with a large bed, window, and comfortable chair.

The Old Inn On The Green

4.0 star property
9.2 out of 10, Wonderful, (86)
"Beautiful room and property. Perfect weekend getaway!"
The price is S$449
includes taxes & fees
20 Jul - 21 Jul
The Old Inn On The Green
Locust Tree Bed and Breakfast LLC
Relax on the covered porch with two comfortable rocking chairs and lush green surroundings.

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (392)
"A positively delightful B&B in a beautiful town. "
The price is S$155
includes taxes & fees
20 Jul - 21 Jul
Locust Tree Bed and Breakfast LLC
Pilgrim Inn
Enjoy meals in the dining area with a round table and comfortable seating.

Pilgrim Inn

2.5 star property
5.8 out of 10, (310)
"Great location but no staff at check-in or checkout!"
The price is S$112
includes taxes & fees
31 Jul - 1 Aug
Pilgrim Inn
Quality Inn
Welcome to our reception area, featuring a comfortable seating space with a fireplace, flat-screen TV, and stunning views of the outside.

Quality Inn

2.5 star property
8.2 out of 10, Very good, (1000)
"Friendly staff, easy parking"
The price is S$181
includes taxes & fees
30 Jul - 31 Jul
Quality Inn
Sunset Inn
Enjoy a refreshing swim in our pool surrounded by a tiled edge.

Sunset Inn

2.0 star property
7.6 out of 10, Good, (391)
"No frills but it was a great stay!"
The price is S$172
includes taxes & fees
21 Jul - 22 Jul
Sunset Inn
FairBridge Inn Express
Relax in a spacious room with a large bed, two bedside tables, and a separate bathtub area.

FairBridge Inn Express

2.5 star property
5.4 out of 10, (742)
"Close to our target event a plus"
The price is S$102
includes taxes & fees
31 Jul - 1 Aug
FairBridge Inn Express
Chambery Inn
Chambery Inn features a traditional two-story building with a pitched roof and multiple windows.

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (368)
"We returned to the Chambery Inn to celebrate my wife's birthday and the Memorial Day weekend. We were very happy with our choice. We stayed in a beautiful room (203), which included a spacious sitting area and a well-appointed bath. The breakfast were nicely prepared and presented. The Inn provided timely information prior and during our stay. We will be back in the future. "
Chambery Inn
Econo Lodge Lee - Great Barrington
Relax in comfort with a large bed, two bedside tables, and a balcony with a view.

Econo Lodge Lee - Great Barrington

2.0 star property
6.4 out of 10, (610)
"It is clean and reasonably priced. We were comfortable and close to Tanglewood. "
The price is S$91
includes taxes & fees
3 Aug - 4 Aug
Econo Lodge Lee - Great Barrington
Devonfield Inn B&B
Stunning two-story house with a central entrance and beautifully manicured lawn.

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (128)
"Very enjoyable comfortable stay"
Devonfield Inn B&B
The Black Swan Lee - Lenox, Ascend Hotel Collection
Relax in a serene lakeside setting with Adirondack chairs and a tranquil atmosphere.

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1002)
"Beautiful location!"
The price is S$279
includes taxes & fees
30 Jul - 31 Jul
The Black Swan Lee - Lenox, Ascend Hotel Collection
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Play a round of golf amidst lush surroundings and scenic obstacles.

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

3.5 star property
9.0 out of 10, Wonderful, (675)
"Had a great time"
The price is S$262
includes taxes & fees
21 Jul - 22 Jul
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires
Relax in our stylish lobby with a seating area, desk, and comfortable sofa.

Holiday Inn Express & Suites Pittsfield - Berkshires

2.5 star property
10.0 out of 10, Exceptional, (3)
"Our stay was terrific, and we appreciated the staff's attentiveness, especially Anthony's."
The price is S$267
includes taxes & fees
20 Jul - 21 Jul
Holiday Inn Express & Suites Pittsfield - Berkshires
Hilton Garden Inn Lenox Pittsfield
Relax on the patio with wicker sofas and armchairs, surrounded by a fire feature and a beautiful garden view.

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (637)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service. "
The price is S$295
includes taxes & fees
17 Aug - 18 Aug
Hilton Garden Inn Lenox Pittsfield
Wagon Wheel Inn
Enjoy a serene outdoor setting with two picnic tables on a well-maintained lawn.

Wagon Wheel Inn

2.0 star property
7.0 out of 10, Good, (610)
"Convenient location for my trip"
The price is S$99
includes taxes & fees
20 Jul - 21 Jul
Wagon Wheel Inn
Howard Johnson by Wyndham Lenox
Stylish motel with a central entrance and two wings, featuring individual rooms with doors and windows.

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (760)
"Was great loved the jacuzzi tub "
The price is S$142
includes taxes & fees
20 Jul - 21 Jul
Howard Johnson by Wyndham Lenox
Berkshire Mountain Lodge
Enjoy cooking in this well-equipped kitchen with a double sink, oven, and gas range.

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (516)
"Clean, comfortable and great staff. Highly recommend and will be staying there again in the future."
Berkshire Mountain Lodge
Hampton Inn & Suites Berkshires-Lenox
Hotel features a two-story design with a flat roof and a mix of brick and siding.

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1000)
"Good lodgings in a great area to visit."
The price is S$230
includes taxes & fees
30 Jul - 31 Jul
Hampton Inn & Suites Berkshires-Lenox
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
Sign in
Sign up, it's free

Learn more about Hillsdale

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

See all hotels in Hillsdale

Top Hillsdale Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Great place for tooling around the Berkshires. Nice suite with frig, TVs, table, kitchen, etc. "
Carolyn 1-night trip
Posted 2 days ago
Berkshire Mountain Lodge

Frequently asked questions

Where is the best place to stay in Hillsdale?

Located 23.9 mi (38.4 km) from the heart of Hillsdale, Howard Johnson by Wyndham Saugerties is a top choice for your stay, based on our traveller data. Two other options for your trip to the area are Best Western Plus Berkshire Hills Inn & Suites and Holiday Inn & Suites Pittsfield-Berkshires by IHG. See all available top hotels, or 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. 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.

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 & Suites Pittsfield-Berkshires by IHG and Holiday Inn Club Vacations Oak n’ Spruce Resort in the 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 73 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.