Book Cheap Hotels in Hillsdale

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Check hotel availability in Hillsdale

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Check prices in Hillsdale for tonight, Dec 8 - Dec 9
Dec 8 - Dec 9
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Check prices in Hillsdale for tomorrow night, Dec 9 - Dec 10
Dec 9 - Dec 10
This weekend
Check prices in Hillsdale for this weekend, Dec 12 - Dec 14
Dec 12 - Dec 14
Next weekend
Check prices in Hillsdale for next weekend, Dec 19 - Dec 21
Dec 19 - Dec 21

Most frequently booked Hillsdale hotels

The Brooks Motel

The Brooks Motel

2 out of 5
2871 New York 23 Hillsdale NY
Free cancellation
Reserve now, pay when you stay
1.64 km from city centre
Get rates
Stay at this motel in Hillsdale. Enjoy free WiFi, free parking, and premium bedding. Popular attractions Catamount Aerial Adventure Park and Community Library are located nearby.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free cancellation
Reserve now, pay when you stay
33.68 km from city centre
Get rates
Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Guido's Marketplace and Herman Melville's Arrowhead are located nearby.
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Free cancellation
37.23 km from city centre
The price is CA $127 per night
CA $127
CA $142 total
Dec 12 - Dec 13
includes taxes & fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Berkshire Museum and Colonial Theater are located nearby.
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd Lenox MA
Free cancellation
Reserve now, pay when you stay
32.71 km from city centre
The price is CA $123 per night
CA $123
CA $138 total
Dec 15 - Dec 16
includes taxes & fees
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Guido's Marketplace and Bousquet Ski Area are located nearby.
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Free cancellation
Reserve now, pay when you stay
30.95 km from city centre
The price is CA $152 per night
CA $152
CA $169 total
Dec 9 - Dec 10
includes taxes & fees
Stay at this lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Kennedy Park and Pleasant Valley Wilderness Sanctuary are located nearby.
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
Free cancellation
Reserve now, pay when you stay
20.96 km from city centre
The price is CA $208 per night
CA $208
CA $295 total
Jan 8 - Jan 9, 2026
includes taxes & fees
Book a stay at this historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Schantz Galleries and Mission House are located nearby.
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

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

3.5 out of 5
190 Meadow Street South Lee MA
Free cancellation
23.24 km from city centre
The price is CA $157 per night
CA $157
CA $203 total
Dec 11 - Dec 12
includes taxes & fees
Book a stay at this family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff in our reviews. Popular attractions Berkshire Theatre Festival and Schantz Galleries are located nearby.
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3 out of 5
435 Laurel St Lee MA
Free cancellation
26.95 km from city centre
The price is CA $140 per night
CA $140
CA $156 total
Dec 18 - Dec 19
includes taxes & fees
Stay at this hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Berkshire Mountain Country Store and Animagic Museum of Animation are located nearby.
Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

2 out of 5
549 Washington Street Hudson NY
22.71 km from city centre
The price is CA $323 per night
CA $323
CA $428 total
Dec 29 - Dec 30
includes taxes & fees
Book a stay at this spa hotel in Hudson. Enjoy free WiFi, a full-service spa, and a 24-hour front desk. Popular attractions Hudson Area Library and Stoddard Corner are located nearby.
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See all available properties in Hillsdale
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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.

Top hotels in Hillsdale for Extended Stay

Suite 4 - Quiet and private accommodations in a country setting.

Suite 4 - Quiet and private accommodations in a country setting.

Spencertown NY
10/10 Exceptional! (3 reviews)
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.

Hillsdale hotels essential information

Accommodation
1,823 hotels
Lowest Price
CA $138
Highest Price
CA $428
Popular hotels
The Brooks Motel, Berkshire Mountain Lodge, Holiday Inn & Suites Pittsfield-Berkshires by IHG, The Yankee, Trademark Collection by Wyndham, Berkshires Untold, The Red Lion Inn, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, The Black Swan Lee - Lenox, an Ascend Collection Hotel, Pocketbook Hotel and Bath

Frequently asked questions

What are the top kid-friendly hotels in Hillsdale?
From fun amenities to bigger rooms, kid-friendly hotels come with features that can help turn an everyday family vacation into an amazing one. These Hillsdale properties make traveling with little ones child's play: Ideal location for summer and winter activities with plenty of outdoor space. will help make your trip the best one yet. It comes with a range of conveniences aimed at families, such as a travel crib and a firepit. Alternatively, spend your Hillsdale escape at Holiday House Motel Hillsdale. Make the most of pet-friendly facilities, express check-out services and more here.
Where can I find cheap hotels in Hillsdale?
At Travelocity you'll find really nice hotels in Hillsdale at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Hillsdale rather than in Hillsdale. We may find you even better rates, too.
How do I find the best Hillsdale hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Hillsdale then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Hillsdale?
The cheapest hotel in Hillsdale is CA $138 This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Hillsdale?
There are 1,823 hotels in Hillsdale on Travelocity.
What are the best hotels in Hillsdale?
Hillsdale has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Hillsdale for you!
When is the best time to visit Hillsdale?
If you want the joy of a fun-filled trip in peak season, visit Hillsdale during February, May and September. If you'd prefer the peace of off-season, book a stay during quieter months, such as March, June and December.
When is the cheapest time to stay in Hillsdale?
Based on historic data is usually the cheapest month to visit Hillsdale. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Hillsdale?
There are multiple hotels in Hillsdale that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Hillsdale. We have plenty of kid-friendly hotels in Hillsdale to choose from on Travelocity!
Why book a hotel in Hillsdale through Travelocity?
Because we have the top hotels in Hillsdale! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Hillsdale on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Hillsdale hotel reviews by fellow wanderers

Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

5 out of 5
Posted 3 days ago
Travelocity Verified Review
"We loved our stay at the brand new Pocketbook Hotel! Our room was lovely and the bed/pillows were great."
A verified traveller stayed at Pocketbook Hotel and Bath
Pocketbook Hotel and Bath

Hotels near…

Areas of Hillsdale