Deals on vacations and trips to Hillsdale

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Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
Price was $489, price is now $356 per person
$356
per person
Jun 5 - Jun 8
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
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.
Saratoga Casino Hotel

Saratoga Casino Hotel

4 out of 5
Price was $1,202, price is now $866 per person
$866
per person
Jul 13 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Albany (ALB)
This smoke-free hotel features a casino, a nightclub, and a restaurant. Enjoy the indoor pool and perks like free self parking and a free area shuttle. You'll appreciate the 24-hour gym, bar/lounge, and snack bar/deli.
The Motel Montreal

The Motel Montreal

2 out of 5
Price was $1,111, price is now $845 per person
$845
per person
Jul 16 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
An outdoor pool, free self parking, and barbecue grills are featured at this motel. WiFi in public areas is free. A terrace and a picnic area are also provided.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was $501, price is now $385 per person
$385
per person
Jun 5 - Jun 8
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
This condo features an outdoor pool and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.
Sundowner on Lake George

Sundowner on Lake George

2.5 out of 5
Price was $1,828, price is now $1,406 per person
$1,406
per person
Jul 16 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
A private beach and a hot tub are featured at this smoke-free motel. Enjoy the seasonal outdoor pool and perks like free self parking. A terrace, a picnic area, and laundry facilities are also on offer.

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
$113 nightly
The price is $126 total per night
$126 total
May 24 - May 25
Total with taxes and fees
This lodge 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
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$92 nightly
The price is $103 total per night
$103 total
May 5 - May 6
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.
Pet friendly
Parking included
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

2 out of 5
282 Cairo Junction Rd Catskill NY
$192 nightly
The price is $207 total per night
$207 total
Jun 2 - Jun 3
Total with taxes and fees
This cabin features a virtual front desk. Take advantage of the free self parking.
Kitchen
Pet friendly
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
$186 nightly
The price is $208 total per night
$208 total
May 17 - May 18
Total with taxes and fees
This historic hotel includes 3 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.
Pool
Spa
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
190 Meadow Street South Lee MA
Free Cancellation
$145 nightly
The price is $162 total per night
$162 total
May 6 - May 7
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
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

2.5 out of 5
445 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$119 nightly
The price is $133 total per night
$133 total
May 17 - May 18
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
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See all available properties in Hillsdale
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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

Hillsdale Town Hall

Hillsdale Town Hall 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.

Hillsdale Town Hall

Frequently asked questions

How much are vacation packages to Hillsdale?
Travelocity offers hotel and flight vacation packages starting from just $356. 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

Bird's eye view of the cityscape of Hillsdale, New York under a cloudy sky in winter
Red and Green Norway Maple Trees and Wood Fence
USA, New York, Hillsdale, Green fields and blue sky