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Check prices in Hillsdale for tonight, Jun 18 - Jun 19
Jun 18 - Jun 19
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Check prices in Hillsdale for tomorrow night, Jun 19 - Jun 20
Jun 19 - Jun 20
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Check prices in Hillsdale for this weekend, Jun 19 - Jun 21
Jun 19 - Jun 21
Next weekend
Check prices in Hillsdale for next weekend, Jun 26 - Jun 28
Jun 26 - Jun 28

Most frequently booked Hillsdale hotels

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
The price is CA $170 per night
CA $170
CA $221 total
Jun 25 - Jun 26
includes taxes & fees
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 Tanglewood Music Center and Guido's Marketplace are located nearby.
Pool
Hot tub
The Yankee Inn

The Yankee Inn

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 $178 per night
CA $178
CA $199 total
Jun 22 - Jun 23
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 Tanglewood Music Center and Guido's Marketplace are located nearby.
Pool
Hot tub
Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
Free cancellation
13.28 km from city centre
The price is CA $146 per night
CA $146
CA $163 total
Jun 21 - Jun 22
includes taxes & fees
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Mahaiwe Performing Arts Center and Housatonic River Walk are located nearby.
Breakfast included
Parking included
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 $192 per night
CA $192
CA $214 total
Jun 23 - Jun 24
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 Tanglewood Music Center and Kennedy Park are located nearby.
Pet-friendly
Parking included
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

2 out of 5
282 Cairo Junction Rd Catskill NY
35.72 km from city centre
The price is CA $225 per night
CA $225
CA $303 total
Jun 24 - Jun 25
includes taxes & fees
Stay at this cabin in Catskill. Enjoy free parking, furnished patios, and climate control. Popular attractions Catskill Golf Club and Angelo Canna Town Park are located nearby.
Kitchen
Pet-friendly
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 $209 per night
CA $209
CA $296 total
Jul 1 - Jul 2
includes taxes & fees
Book a stay at this historic hotel in Stockbridge. Enjoy free WiFi, free parking, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions National Shrine of the Divine Mercy and Tanglewood Music Center are located nearby.
Pool
Spa
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
23.24 km from city centre
The price is CA $170 per night
CA $170
CA $217 total
Jun 21 - Jun 22
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 National Shrine of the Divine Mercy and Norman Rockwell Museum are located nearby.
Pool
Air conditioning
Hotel On North

Hotel On North

3.5 out of 5
297 North Street Pittsfield MA
Free cancellation
Reserve now, pay when you stay
37.75 km from city centre
The price is CA $323 per night
CA $323
CA $361 total
Jun 21 - Jun 22
includes taxes & fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Barrington Stage Company and Lichtenstein Center for the Arts are located nearby.
Pet-friendly
Parking included
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

2.5 out of 5
1055 South Street Pittsfield MA
Free cancellation
33.28 km from city centre
The price is CA $197 per night
CA $197
CA $220 total
Jun 22 - Jun 23
includes taxes & fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.
Pool
Hot tub
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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

Micosta Leisure Inn

Micosta Leisure Inn

3007 County Rd 20 Hudson NY
The price is CA $183 per night from Jun 30 to Jul 1
CA $183
CA $205 total
Jun 30 - Jul 1
includes taxes & fees
9.2/10 Wonderful! (154 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
1,850 hotels
Lowest Price
CA $163
Highest Price
CA $361
Popular hotels
Berkshire Mountain Lodge, The Yankee Inn, Quality Inn Great Barrington, Berkshires Untold, Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy, The Red Lion Inn, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, Hotel On North, Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

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 $163 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 1,850 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

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

5 out of 5
Posted 9 hours ago
Travelocity Verified Review
"Had a wonderful stay. Staff is friendly and helpful. Breakfast was great, especially the automatic pancake maker. Had a wonderful dinner from Mint restaurant. The room was very clean and had the most comfortable hotel bed ever. The shower was a gleaming white as if it had never been used. The swan soap dish was a lovely touch. The view of the lake and mountains is spectacular. Would definitely stay here again."
A verified traveller stayed at The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel