Book Exclusive Hillsdale Vacation Packages

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Hillsdale flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
The Wiltwyck

The Wiltwyck

2 out of 5
per person
Apr. 9 - Apr. 15
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Albany (ALB)
Stay at this guesthouse in Kingston. Enjoy free WiFi, free parking, and Netflix. Popular attractions Senate House State Historic Site and Volunteer Fireman's Hall and Museum of Kingston are located nearby.
Brookmere

Brookmere

2.5 out of 5
per person
Mar. 9 - Mar. 16
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
Book a stay at this spa hotel in Saratoga Springs. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Saratoga National Golf Course and Yaddo Gardens are located nearby.
Hotel Kinsley

Hotel Kinsley

3.5 out of 5
Kingston Stockade District
Save 100% on your flight
per person
Apr. 9 - Apr. 15
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Albany (ALB)
Stay at this 3.5-star business-friendly hotel in Kingston. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Birch Body Care and Volunteer Fireman's Hall and Museum of Kingston are located nearby.
Kingston Carriage House

Kingston Carriage House

4 out of 5
Roundout
Save 100% on your flight
per person
Apr. 9 - Apr. 15
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Albany (ALB)
Stay at this 4-star ski B&B in Kingston. Enjoy free breakfast, free WiFi, and onsite spa services. Popular attractions Hudson River Maritime Museum and Trolley Museum of New York are located nearby.
Hilton Garden Inn Saratoga Springs

Hilton Garden Inn Saratoga Springs

3 out of 5
per person
Mar. 9 - Mar. 16
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
Stay at this 3-star business-friendly hotel in Saratoga Springs. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions National Museum of Dance and Congress Park are located nearby.

Top Hillsdale hotels deals

Life House Berkshires

Life House Berkshires

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Free cancellation
Reserve now, pay when you stay
The price is CA $141 per night
CA $141
CA $158 total
includes taxes & fees
20 Feb - 21 Feb
Stay at this 3.5-star 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
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

3.5 out of 5
190 Meadow Street, South Lee, MA
Free cancellation
The price is CA $170 per night
CA $170
CA $210 total
includes taxes & fees
9 Feb - 10 Feb
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood Music Center and Berkshire Theatre Festival are located nearby.
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

3 out of 5
One West Street, Pittsfield, MA
Free cancellation
The price is CA $156 per night
CA $156
CA $174 total
includes taxes & fees
9 Feb - 10 Feb
Stay at this 3-star 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.
Pool
Pet-friendly
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
The price is CA $156 per night
CA $156
CA $174 total
includes taxes & fees
9 Feb - 10 Feb
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.
Pool
Hot tub
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 $209 per night
CA $209
CA $298 total
includes taxes & fees
10 Mar - 11 Mar
Stay at this 3.5-star historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Schantz Galleries and Mission House are located nearby.
Pool
Spa
Holiday Inn Express & Suites Saugerties - Hudson Valley, an IHG Hotel

Holiday Inn Express & Suites Saugerties - Hudson Valley, an IHG Hotel

2.5 out of 5
2777 ROUTE 32, Saugerties, NY
Free cancellation
The price is CA $176 per night
CA $176
CA $197 total
includes taxes & fees
9 Mar - 10 Mar
Book a stay at this business-friendly hotel in Saugerties. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Kiwanis Ice Arena and Esopus Bend Nature Preserve are located nearby.
Pool
Breakfast included
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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.

Popular places to visit

Catamount Aerial Adventure Park

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.

Catamount Aerial Adventure Park

Copake Lake

Commune with nature and explore the great outdoors at Copake Lake during your travels in Copake Lake.

Copake Lake

Community Library

Community Library is just one of the places to see in Hillsdale, so why not enjoy the other things to explore during your travels? Discover the sunrises while you're in the area.

Community Library

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 $825. 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