Deals on vacations and trips to Hillsdale

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Hillsdale flight + hotel vacation packages

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

The Wiltwyck

3.5 out of 5
Price was $941, price is now $743 per person
$743
per person
Nov 5 - Nov 10
found 16 hours ago
Roundtrip non-stop flight included
Greensboro (GSO) to Albany (ALB)
Free WiFi in public areas is available at this guesthouse. Take advantage of the free self parking.
The Old Catskill Game Farm Inn

The Old Catskill Game Farm Inn

3.5 out of 5
Save 100% on your flight
Price was $5,305, price is now $3,825 per person
$3,825
per person
Nov 5 - Nov 10
found 16 hours ago
Roundtrip non-stop flight included
Greensboro (GSO) to Albany (ALB)
A sauna, free self parking, and laundry facilities are featured at this guesthouse. WiFi in public areas is free. A communal living room, a picnic area, and free newspapers are also on offer.
The Perch Hotel

The Perch Hotel

2 out of 5
Save 100% on your flight
Price was $1,575, price is now $1,137 per person
$1,137
per person
Nov 5 - Nov 10
found 16 hours ago
Roundtrip non-stop flight included
Greensboro (GSO) to Albany (ALB)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.
Hotel Kinsley

Hotel Kinsley

3.5 out of 5
Stockade District
Price was $1,209, price is now $948 per person
$948
per person
Nov 5 - Nov 10
found 16 hours ago
Roundtrip non-stop flight included
Greensboro (GSO) to Albany (ALB)
This hotel features a restaurant, a gym, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the sauna and free perks like continental breakfast and free self parking.
Farmhouse at Leeds by Avantstay Catskills Farmhouse + Barn Suite + Firepit Mins to Hudson + Kaaterskill Falls

Farmhouse at Leeds by Avantstay Catskills Farmhouse + Barn Suite + Firepit Mins to Hudson + Kaaterskill Falls

3 out of 5
Save 100% on your flight
Price was $1,987, price is now $1,582 per person
$1,582
per person
Nov 5 - Nov 10
found 16 hours ago
Roundtrip non-stop flight included
Greensboro (GSO) to Albany (ALB)
This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. Barbecue grills are provided for your convenience.

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
$158 nightly
The price is $176 total per night
$176 total
Sep 14 - Sep 15
Total with taxes and fees
This hotel features an outdoor pool and an indoor pool. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the 24-hour gym and free perks like buffet breakfast and free self parking.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$125 nightly
The price is $139 total per night
$139 total
Aug 31 - Sep 1
Total with taxes and fees
This aparthotel features an indoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, laundry facilities, and barbecue grills are also on offer.
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road Pittsfield MA
$61 nightly
The price is $68 total per night
$68 total
Aug 31 - Sep 1
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the business center. The front desk is staffed around-the-clock and laundry facilities are on offer.
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$145 nightly
The price is $162 total per night
$162 total
Sep 8 - Sep 9
Total with taxes and fees
A restaurant and a bar/lounge are featured at this lodge. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a lobby fireplace, and express check-in are also on offer.
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
$201 nightly
The price is $217 total per night
$217 total
Sep 13 - Sep 14
Total with taxes and fees
This cabin features a virtual front desk. Take advantage of the free self parking.
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
$119 nightly
The price is $133 total per night
$133 total
Sep 14 - Sep 15
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.
Pool
Hot Tub
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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.
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Frequently asked questions

How much are vacation packages to Hillsdale?
Travelocity offers hotel and flight vacation packages starting from just $743. 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 100 mi from Hillsdale.
Which airport is best for Hillsdale?
There's a good chance you'll touch down at Bradley Intl. Airport (BDL), which is 45 mi east of inner Hillsdale. Albany Intl. Airport (ALB) (40 mi away from central Hillsdale) and Stewart Intl. Airport (SWF) (55 mi 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.