Book Exclusive Hillsdale Vacation Packages

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Hillsdale flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Albany Airport Inn

Albany Airport Inn

2.5 out of 5
Price was CA $595, price is now CA $542 per person
CA $542
per person
Jan 8 - Jan 11
found 1 day 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 parking, and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Colonie Center Mall and Palace Theater are located nearby.
Marriott Albany

Marriott Albany

3.5 out of 5
Price was CA $1,475, price is now CA $1,346 per person
CA $1,346
per person
Dec 14 - Dec 18
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Albany (ALB)
Book a stay at this business-friendly hotel in Albany. Enjoy an outdoor pool, a free airport shuttle, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Colonie Center Mall and Palace Theater are located nearby.
Brook Bound Inn

Brook Bound Inn

2 out of 5
Price was CA $1,286, price is now CA $1,183 per person
CA $1,183
per person
Dec 15 - Dec 18
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
Book a stay at this golf hotel in Wilmington. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Mount Snow and North Branch Deerfield River are located nearby.
The White House Inn

The White House Inn

3.5 out of 5
Price was CA $1,156, price is now CA $1,065 per person
CA $1,065
per person
Dec 15 - Dec 18
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) 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.
Super 8 by Wyndham Latham/Albany Airport

Super 8 by Wyndham Latham/Albany Airport

2 out of 5
Price was CA $591, price is now CA $547 per person
CA $547
per person
Jan 8 - Jan 11
found 1 day 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 helpful staff and the clean rooms in our reviews. Popular attractions Colonie Center Mall and Latham Farms 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 $116 per night
CA $116
CA $161 total
Nov 8 - Nov 9
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
Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
Free cancellation
The price is CA $106 per night
CA $106
CA $119 total
Nov 23 - Nov 24
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
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 $225 per night
CA $225
CA $304 total
Nov 29 - Nov 30
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
Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

4.5 out of 5
549 Washington Street Hudson NY
Free cancellation
Reserve now, pay when you stay
The price is CA $327 per night
CA $327
CA $433 total
Nov 18 - Nov 19
includes taxes & fees
Book a stay at this luxury hotel in Hudson. Enjoy free WiFi, free parking, and 3 indoor pools. Popular attractions Oakdale Beach and Hudson Area Library are located nearby.
Pool
Spa
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 $134 per night
CA $134
CA $150 total
Nov 1 - Nov 2
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
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

3.5 out of 5
190 Meadow Street South Lee MA
Free cancellation
The price is CA $175 per night
CA $175
CA $223 total
Nov 1 - Nov 2
includes taxes & fees
Book a stay at this ski 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 Tanglewood Music Center and Berkshire Theatre Festival are located nearby.
Pool
Air conditioning
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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.

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 $542. 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.