Book Exclusive Hillsdale Vacation Packages

Choose one or more items to build your trip:

Hillsdale flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Park Manor Hotel

Park Manor Hotel

4 out of 5
Price was CA $1,283, price is now CA $1,244 per person
CA $1,244
per person
Oct 19 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Albany (ALB)
Stay at this hotel in Clifton Park. Enjoy free parking, 24-hour room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Regal Clifton Park and Wicked Eatery Pub & Entertainment are located nearby.
The Landing Hotel at Rivers Casino Schenectady

The Landing Hotel at Rivers Casino Schenectady

4 out of 5
Nothside
Price was CA $1,705, price is now CA $1,570 per person
CA $1,570
per person
Oct 19 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Albany (ALB)
Book a stay at this business-friendly hotel in Schenectady. Enjoy free WiFi, free parking, and 5 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Rivers Casino & Resort and Schenectady Light Opera Performing Arts Center are located nearby.
South Shire

South Shire

4 out of 5
Price was CA $1,498, price is now CA $1,384 per person
CA $1,384
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Albany (ALB)
Stay at this B&B in Bennington. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Bennington Arts Guild Gallery and Fiddlehead at Four Corners are located nearby.
The White House Inn

The White House Inn

3.5 out of 5
Price was CA $1,577, price is now CA $1,468 per person
CA $1,468
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Albany (ALB)
Stay at this hotel in Wilmington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions South Main Street and Pettee Memorial Library are located nearby.
Knotty Pine

Knotty Pine

2.5 out of 5
Price was CA $1,300, price is now CA $1,271 per person
CA $1,271
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Albany (ALB)
Stay at this motel in Bennington. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Bennington Museum and Old First Congregational Church are located nearby.

Top Hillsdale hotels deals

The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
Free cancellation
Reserve now, pay when you stay
The price is CA $177 per night
CA $177
CA $198 total
Sep 16 - Sep 17
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.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free cancellation
Reserve now, pay when you stay
The price is CA $131 per night
CA $131
CA $178 total
Aug 31 - Sep 1
includes taxes & fees
Book a stay at this golf aparthotel 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
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road Pittsfield MA
The price is CA $84 per night
CA $84
CA $93 total
Aug 24 - Aug 25
includes taxes & fees
Book a stay at this business-friendly motel in Pittsfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Crane Museum of Papermaking and Crane Museum of Papermaking are located nearby.
Parking included
Free WiFi
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Free cancellation
Reserve now, pay when you stay
The price is CA $181 per night
CA $181
CA $202 total
Sep 8 - Sep 9
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

2.5 out of 5
282 Cairo Junction Rd Catskill NY
The price is CA $223 per night
CA $223
CA $301 total
Sep 14 - Sep 15
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.
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
The price is CA $165 per night
CA $165
CA $184 total
Sep 14 - Sep 15
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.
Don't see what you're looking for?
See all available properties in Hillsdale
View all properties
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.

Stay near popular Hillsdale attractions

Catamount Aerial Adventure Park

6.4/10 (5 reviews)
You can take time to visit Catamount Aerial Adventure Park during your travels to Hillsdale. Discover the area's mountain views and seek out the hiking trails.
See properties

Hillsdale Vacations

We know, geography isn't everyone's strong suit. If you're unsure where Hillsdale lies on a map, it's a good idea to acquaint yourself with its location before you fly off!

This town is located 11 miles (18 kilometers) east of Hudson. It's also 20 miles (32 kilometers) southwest of Pittsfield.

Places to visit in Hillsdale

You don't need to know your Rubens from your Rembrandts to roam the corridors of Norman Rockwell Museum. It boasts an excellent array of exhibits that'll engage your interest and fuel your appreciation for art. Need more options? Whether you're a seasoned professional or total beginner, it's time to dig out your skis and tear up the slopes. Ski Butternut guarantees plenty of fun for all skill levels! And, there's more going on in the surrounding area. They say that history is the best teacher. Travel back through time for a fascinating lesson at Chesterwood.

Where do you fly into for Hillsdale?

Coming in to land at Bradley International Airport (BDL)? Once you step off the aircraft, central Hillsdale is about 50 miles (80 kilometers) northwest away. Slide into a cab and enjoy the ride — your vacation has only just started!

Frequently asked questions

How much are vacation packages to Hillsdale?
Travelocity offers hotel and flight vacation packages starting from just CA $1,244. With such great bargains, you'll be exploring all of Hillsdale in a flash.
How long should my Hillsdale vacation be?
If you're looking for some guidance, most visitors spend roughly 2 nights vacationing in Hillsdale. But to discover the true spirit of this destination, stay a few extra days. That way you can see more and really experience the local culture.
Where can I get the best vacation package deals for Hillsdale?
You'll discover a terrific range of Hillsdale package deals on Travelocity. With 400 air carriers and 1,000,000 properties worldwide, organizing your ideal getaway will be a piece of cake.
Why should I book my Hillsdale vacation package via Travelocity?
Because life is one incredible journey, and we have all you need to help you on the way. With our first-rate service and Price Match Guarantee, you can book with confidence. And you can sleep easy while you're on the road knowing you can reach us with our round-the-clock support.
Can I save money on my Hillsdale car rental if I bundle it with a hotel or flight?
Sure can — combine your car, flight and hotel into a Hillsdale vacation package and you can save a ton. With so much to discover in the Hillsdale area, that rental vehicle will make exploring a joy. Once you've slid into the driver's seat, crank up the tunes and find your way to Times Square, a famous sight approximately 161 kilometers from Hillsdale.
Which airport is best for Hillsdale?
There's a good chance you'll touch down at Bradley Intl. Airport (BDL), which is 72 kilometers east of inner Hillsdale. Albany Intl. Airport (ALB) (64 kilometers away from central Hillsdale) and Stewart Intl. Airport (SWF) (88 kilometers away from central Hillsdale) are your other options.
What is there to do in Hillsdale?
You'll find some great photo-ops at Catamount Aerial Adventure Park, one of the most popular attractions in Hillsdale. There's plenty more to discover around this exciting city, so make sure you have enough time to see some of its off-the-beaten-path gems.
Where should I stay when visiting Hillsdale?
Many visitors opt to stay at the Hudson Valley and The Berkshires getaway. It's an excellent base for your Hillsdale escape.

Photos of local treasures

Browse Hillsdale vacation photos for more inspiration

A rural landscape with snow-covered fields, a winding road, and scattered trees.
A snow-covered landscape with fields, trees, and distant mountains.
A landscape with a row of trees in autumn colors, a wooden fence, and a hilly background.
A grassy field with wildflowers and a hill in the background.