Book Exclusive Hillsdale Vacation Packages

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Hillsdale flight + hotel packages

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Hampton Inn & Suites Albany-Downtown

Hampton Inn & Suites Albany-Downtown

2.5 out of 5
Downtown Albany
Price was CA $1,303, price is now CA $1,107 per person
CA $1,107
per person
Jul 22 - Jul 26
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
Book a stay at this business-friendly hotel in Albany. Enjoy free breakfast, free WiFi, and 2 restaurants. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions MVP Arena and Colonie Center Mall are located nearby.
Hampton Inn Albany-Wolf Road (Airport)

Hampton Inn Albany-Wolf Road (Airport)

2.5 out of 5
Price was CA $1,570, price is now CA $1,236 per person
CA $1,236
per person
Jul 22 - Jul 26
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
Book a stay at this business-friendly hotel in Albany. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Colonie Center Mall and MVP Arena are located nearby.
Best Western Plus Franklin Square Inn Troy/Albany

Best Western Plus Franklin Square Inn Troy/Albany

2.5 out of 5
Price was CA $1,349, price is now CA $1,160 per person
CA $1,160
per person
Jul 22 - Jul 26
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
Stay at this hotel in Troy. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Arts Center of the Capital Region and Troy Waterfront Farmers' Market are located nearby.
La Quinta Inn & Suites by Wyndham Latham Albany Airport

La Quinta Inn & Suites by Wyndham Latham Albany Airport

3 out of 5
Price was CA $1,282, price is now CA $1,133 per person
CA $1,133
per person
Jul 22 - Jul 26
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
Book a stay at this business-friendly hotel in Latham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular attractions Colonie Center Mall and Latham Farms are located nearby.
Hyatt Place Albany/Downtown

Hyatt Place Albany/Downtown

3 out of 5
Downtown Albany
Price was CA $1,417, price is now CA $1,252 per person
CA $1,252
per person
Jul 22 - Jul 26
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
Book a stay at this business-friendly hotel in Albany. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions MVP Arena and Colonie Center Mall are located nearby.

Top Hillsdale hotels deals

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 $119 per night
CA $119
CA $163 total
May 31 - Jun 1
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
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 $113 per night
CA $113
CA $127 total
May 5 - May 6
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
The price is CA $218 per night
CA $218
CA $294 total
May 12 - May 13
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
The price is CA $199 per night
CA $199
CA $284 total
May 4 - May 5
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
Free cancellation
The price is CA $175 per night
CA $175
CA $222 total
May 5 - May 6
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 Tanglewood Music Center are located nearby.
Pool
Air conditioning
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

2.5 out of 5
445 Pittsfield Rd Lenox MA
Free cancellation
Reserve now, pay when you stay
The price is CA $163 per night
CA $163
CA $182 total
May 17 - May 18
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 helpful staff in our reviews. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.
Pool
Breakfast included
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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.

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 $1,107. 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

Bird's eye view of the cityscape of Hillsdale, New York under a cloudy sky in winter
Red and Green Norway Maple Trees and Wood Fence
USA, New York, Hillsdale, Green fields and blue sky