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.
Brook Bound Inn

Brook Bound Inn

2 out of 5
Price was $842, price is now $708 per person
$708
per person
Dec 18 - Dec 20
found 1 day ago
Roundtrip non-stop flight included
Fort Myers (RSW) to Albany (ALB)
A seasonal outdoor pool, free self parking, and barbecue grills are featured at this hotel. WiFi in public areas is free. A garden, a lobby fireplace, and a communal living room are also on offer.
Aspen At Manchester

Aspen At Manchester

2.5 out of 5
Price was $1,291, price is now $1,012 per person
$1,012
per person
Dec 22 - Dec 29
found 17 hours ago
Roundtrip non-stop flight included
Fort Myers (RSW) to Albany (ALB)
A seasonal outdoor pool, free self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. A terrace, a garden, and a lobby fireplace are also on offer.
Weathervane Motel

Weathervane Motel

2 out of 5
Price was $979, price is now $874 per person
$874
per person
Dec 22 - Dec 29
found 17 hours ago
Roundtrip non-stop flight included
Fort Myers (RSW) to Albany (ALB)
Free WiFi in public areas is available at this motel.
The Manchester View

The Manchester View

2.5 out of 5
Price was $1,441, price is now $1,293 per person
$1,293
per person
Dec 22 - Dec 29
found 17 hours ago
Roundtrip non-stop flight included
Fort Myers (RSW) to Albany (ALB)
A seasonal outdoor pool is featured at this hotel, along with free self parking. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and luggage storage are also on offer.
The Rosendale Roost

The Rosendale Roost

2 out of 5
Price was $1,319, price is now $1,193 per person
$1,193
per person
Dec 28 - Jan 1
found 1 day ago
Roundtrip flight included
Fort Myers (RSW) to Albany (ALB)
This vacation home features a virtual front desk. Take advantage of the free self parking.

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
$106 nightly
The price is $118 total per night
$118 total
Dec 14 - Dec 15
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.
Pool
Hot Tub
Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
Free Cancellation
$76 nightly
The price is $85 total per night
$85 total
Dec 3 - Dec 4
Total with taxes and fees
A gym, free self parking, and free newspapers are featured at this hotel. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. A picnic area and barbecue grills are also provided.
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
$192 nightly
The price is $207 total per night
$207 total
Dec 14 - Dec 15
Total with taxes and fees
This cabin features a virtual front desk. Take advantage of the free self parking.
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
$241 nightly
The price is $272 total per night
$272 total
Dec 7 - Dec 8
Total with taxes and fees
This smoke-free hotel features 3 indoor pools, a restaurant, and a bar/lounge. Enjoy the steam room and perks like free valet parking and free WiFi. Free self parking, a coffee shop, and a garden are also offered.
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
$126 nightly
The price is $141 total per night
$141 total
Dec 12 - Dec 13
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.
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
$128 nightly
The price is $143 total per night
$143 total
Nov 15 - Nov 16
Total with taxes and fees
This hotel features 2 outdoor pools, 2 indoor pools, and a poolside bar. There's fun for all ages with mini golf and a playground, and families will appreciate the picnic area. Enjoy the seasonal outdoor pool and conveniences like a coffee shop and barbecue grills.
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.
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Frequently asked questions

How much are vacation packages to Hillsdale?
Travelocity offers hotel and flight vacation packages starting from just $708. 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 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.
A rural landscape with snow-covered fields, a winding road, and scattered trees.
A snow-covered landscape with fields, trees, and distant mountains.