Deals on vacations and trips to Hillsdale

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The Landing Hotel at Rivers Casino & Resort

The Landing Hotel at Rivers Casino & Resort

4 out of 5
Nothside
Price was $743, price is now $587 per person
$587
per person
Feb 5 - Feb 8
found 18 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Albany (ALB)
A casino, 5 restaurants, and a 24-hour gym are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference space. Free self parking is free for guests, and you can enjoy a meal in one of the 2 coffee shops/cafes.
Church Des Artistes Guest House

Church Des Artistes Guest House

3 out of 5
Rondout
Save 100% on your flight
Price was $7,543, price is now $5,066 per person
$5,066
per person
Feb 24 - Mar 3
found 19 hours ago
Roundtrip non-stop flight included
Portland (PWM) to Albany (ALB)
This guesthouse features an area shuttle, free self parking, and free WiFi in public areas. Enjoy the free continental breakfast each morning. A business center, a terrace, and a garden are also on offer.
The Old Catskill Game Farm Inn

The Old Catskill Game Farm Inn

3.5 out of 5
Save 100% on your flight
Price was $5,960, price is now $4,362 per person
$4,362
per person
Feb 24 - Mar 3
found 19 hours ago
Roundtrip non-stop flight included
Portland (PWM) to Albany (ALB)
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A communal living room, a picnic area, and laundry facilities are also on offer.
Urban Cowboy Lodge

Urban Cowboy Lodge

5 out of 5
Save 100% on your flight
Price was $2,388, price is now $1,802 per person
$1,802
per person
Feb 24 - Mar 3
found 19 hours ago
Roundtrip non-stop flight included
Portland (PWM) to Albany (ALB)
This lodge features a restaurant, a sauna, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A snack bar/deli, a lobby fireplace, and a communal living room are also on offer.
Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

2 out of 5
Price was $1,252, price is now $998 per person
$998
per person
Feb 24 - Mar 3
found 19 hours ago
Roundtrip non-stop flight included
Portland (PWM) to Albany (ALB)
A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. A coffee shop is provided and the front desk is staffed around-the-clock.

Top Hillsdale hotels deals

The Brooks Motel

The Brooks Motel

2 out of 5
2871 New York 23 Hillsdale NY
Free Cancellation
Reserve now, pay when you stay
$135 nightly
The price is $151 total per night
$151 total
Dec 19 - Dec 20
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A virtual front desk are provided for your convenience.
Pet friendly
Parking included
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Free Cancellation
$93 nightly
The price is $104 total per night
$104 total
Dec 17 - Dec 18
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Pool
Pet friendly
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
$79 nightly
The price is $88 total per night
$88 total
Dec 24 - Dec 25
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking.
Pool
Hot Tub
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
$108 nightly
The price is $120 total per night
$120 total
Jan 14 - Jan 15, 2026
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
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
$180 nightly
The price is $202 total per night
$202 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
This smoke-free 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. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.
Pool
Spa
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$110 nightly
The price is $123 total per night
$123 total
Dec 21 - Dec 22
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
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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 $587. 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