Book Exclusive Hillsdale Vacation Packages

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Hillsdale flight + hotel packages

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Super 8 by Wyndham Cobleskill NY

Super 8 by Wyndham Cobleskill NY

2.5 out of 5
per person
Jan. 21 - Jan. 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
Book a stay at this golf hotel in Cobleskill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Cobleskill Fairgrounds and Iroquois Indian Museum are located nearby.
Super 8 by Wyndham Albany

Super 8 by Wyndham Albany

2 out of 5
per person
Jan. 21 - Jan. 26
found 1 day ago
Roundtrip 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 property condition in our reviews. Popular attractions Colonie Center Mall and Crossgates Mall are located nearby.
Best Western Plus Kingston Hotel And Conference Center

Best Western Plus Kingston Hotel And Conference Center

2.5 out of 5
per person
Jan. 21 - Jan. 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
Book a stay at this family-friendly hotel in Kingston. Enjoy free breakfast, free parking, and room service. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Dietz Stadium and Birch Body Care are located nearby.
Hampton Inn Albany-Wolf Road (Airport)

Hampton Inn Albany-Wolf Road (Airport)

2.5 out of 5
per person
Jan. 21 - Jan. 26
found 1 day ago
Roundtrip 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 Crossgates Mall are located nearby.
Holiday Inn Express Hotel & Suites West Coxsackie, an IHG Hotel

Holiday Inn Express Hotel & Suites West Coxsackie, an IHG Hotel

2.5 out of 5
per person
Jan. 21 - Jan. 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
Book a stay at this business-friendly hotel in West Coxsackie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Parks Dairy and Bronck Island 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 $137 per night
CA $137
CA $153 total
includes taxes & fees
17 Nov - 18 Nov
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
Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties

2 out of 5
2764 Route 32, Saugerties, NY
Free cancellation
Reserve now, pay when you stay
The price is CA $148 per night
CA $148
CA $165 total
includes taxes & fees
17 Nov - 18 Nov
Book a stay at this business-friendly hotel in Saugerties. Enjoy free WiFi, free parking, and a sauna. 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
Parking included
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 $195 per night
CA $195
CA $281 total
includes taxes & fees
25 Nov - 26 Nov
Stay at this 3.5-star spa hotel in Stockbridge. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Tanglewood Music Center and Schantz Galleries 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
The price is CA $136 per night
CA $136
CA $152 total
includes taxes & fees
25 Nov - 26 Nov
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
The Black Swan Lee - Lenox, Ascend Hotel Collection

The Black Swan Lee - Lenox, Ascend Hotel Collection

3 out of 5
435 Laurel St, Lee, MA
Free cancellation
Reserve now, pay when you stay
The price is CA $145 per night
CA $145
CA $162 total
includes taxes & fees
1 Dec - 2 Dec
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 Tanglewood Music Center and Berkshire Mountain Country Store are located nearby.
Breakfast included
Pet-friendly
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Free cancellation
Reserve now, pay when you stay
The price is CA $100 per night
CA $100
CA $112 total
includes taxes & fees
1 Dec - 2 Dec
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
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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 $570. 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