Hillsdale Hotels from S$102

    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
21 Aug - 22 Aug
Tomorrow
22 Aug - 23 Aug
This weekend
22 Aug - 24 Aug
Next weekend
29 Aug - 31 Aug

Filter by

Guest rating
Guest rating
Property class

Top 10 trending Hillsdale hotels

Our top choices for Hillsdale hotels

Locust Tree Bed and Breakfast LLC
Terrace/patio

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (400)
"A positively delightful B&B in a beautiful town. "
The price is S$155
includes taxes & fees
24 Aug - 25 Aug
Locust Tree Bed and Breakfast LLC
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (584)
"Amazing place to stay. Can’t wait to go again. "
The price is S$123
includes taxes & fees
7 Sept - 8 Sept
Berkshire Mountain Lodge
Element Lenox Berkshires
Free daily continental breakfast

Element Lenox Berkshires

3.0 star property
9.6 out of 10, Exceptional, (4)
"New hotel very nice"
The price is S$218
includes taxes & fees
1 Sept - 2 Sept
Element Lenox Berkshires
The Brooks Motel
1 bedroom, Egyptian cotton sheets, premium bedding, memory-foam beds

The Brooks Motel

2.0 star property
7.8 out of 10, Good, (96)
"Basic, clean and good value for the money."
The Brooks Motel
Micosta Leisure Inn
Balcony

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (116)
"Great stay!"
The price is S$187
includes taxes & fees
24 Aug - 25 Aug
Micosta Leisure Inn
Quality Inn
Lobby

Quality Inn

2.5 star property
8.2 out of 10, Very good, (1001)
"nice place"
The price is S$133
includes taxes & fees
4 Sept - 5 Sept
Quality Inn
The Black Swan Lee - Lenox, Ascend Hotel Collection
Exterior

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1001)
"Very comfortable stay with reasonable pricing if you are coming at the right time. The lake view is beautiful "
The price is S$182
includes taxes & fees
1 Sept - 2 Sept
The Black Swan Lee - Lenox, Ascend Hotel Collection
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (691)
"Fun place and very clean. Friendly staff and an amazing outdoor area to hang out."
The price is S$230
includes taxes & fees
26 Aug - 27 Aug
Berkshires Untold
Travelodge by Wyndham Great Barrington Berkshires
In-room safe, desk, free cots/infant beds, free rollaway beds

Travelodge by Wyndham Great Barrington Berkshires

2.0 star property
7.4 out of 10, Good, (544)
"Excellent location, friendly service, clean, comfortable room."
The price is S$108
includes taxes & fees
2 Sept - 3 Sept
Travelodge by Wyndham Great Barrington Berkshires
Overlook Hotel
Exterior

Overlook Hotel

2.0 star property
7.8 out of 10, Good, (7)
"设备不齐全"
The price is S$242
includes taxes & fees
24 Aug - 25 Aug
Overlook Hotel
Postcard Cabins Eastern Catskills
Exterior

Postcard Cabins Eastern Catskills

2.0 star property
9.6 out of 10, Exceptional, (59)
"Really beautiful place to enjoy nature with family!!"
The price is S$283
includes taxes & fees
24 Aug - 25 Aug
Postcard Cabins Eastern Catskills
the Alander
American cuisine

the Alander

2.5 star property
9.0 out of 10, Wonderful, (155)
"Loved our stay, staff very attentive and helpful!! "
The price is S$230
includes taxes & fees
24 Aug - 25 Aug
the Alander
The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1001)
"We have stayed at the Cornell Inn in the past. Always a comfortable, convenient and friendly stay. The food, staff and accommodations are perfect."
The price is S$234
includes taxes & fees
1 Sept - 2 Sept
The Cornell Inn, Lenox & The Berkshires
Monument Mountain Motel
Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi

Monument Mountain Motel

2.5 star property
8.8 out of 10, Excellent, (740)
"A great mom & pop motel. Clean and friendly "
Monument Mountain Motel
Howard Johnson by Wyndham Lenox
Exterior

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (786)
"My stay was perfect. I can't wait to stay there again. "
The price is S$113
includes taxes & fees
2 Sept - 3 Sept
Howard Johnson by Wyndham Lenox
Courtyard by Marriott Lenox Berkshires
Property amenity

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (570)
"Fabulous place"
The price is S$218
includes taxes & fees
2 Sept - 3 Sept
Courtyard by Marriott Lenox Berkshires
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Hypo-allergenic bedding, iron/ironing board, free cots/infant beds

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.6 out of 10, Exceptional, (20)
"Really enjoyed my stay here, definitely need a car to get around"
The price is S$194
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Best Western Plus Berkshire Hills Inn & Suites
Lobby sitting area

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1000)
"Very clean rooms and excellent staff."
The price is S$153
includes taxes & fees
1 Sept - 2 Sept
Best Western Plus Berkshire Hills Inn & Suites
The Nest Hudson
Balcony

The Nest Hudson

3.5 star property
9.6 out of 10, Exceptional, (200)
"The Nest Hudson is a gem with great amenities and very comfortable bedding. We are riding our bicycles up the state and over to Buffalo, and this place was an oasis that helped us recharge and prep for the next leg of our journey. Food tips: Feast and Floret for an excellent meal and WYLDE Hudson for a morning cafe, both within a short walk. "
The price is S$234
includes taxes & fees
7 Sept - 8 Sept
The Nest Hudson
Blackberry River Inn
Library

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (127)
"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$243
includes taxes & fees
2 Sept - 3 Sept
Blackberry River Inn
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

Tucked in the Hudson Valley, this rural hamlet offers scenic hikes through Taconic State Park and charming farm-to-table dining. Explore nearby art galleries in Copake or visit Catamount Mountain Resort for outdoor adventures in all seasons.

See all hotels in Hillsdale

Top Hillsdale Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"It was fine , no complaints "
Roberta 1-night trip
Posted 2 days ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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 Berkshire Mountain Lodge and Berkshires Untold. 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 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 are some accommodation options with pools in Hillsdale?

Berkshire Mountain Lodge: Offers free self parking, an indoor pool and complimentary wireless Internet access. Howard Johnson by Wyndham Lenox 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 71 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.