Hillsdale Vacation Packages 2026 from $519

Hillsdale flight + hotel vacation packages

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

Vacation Village in the Berkshires

$519

per person

Aug 18 - Aug 21

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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.

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

$661

per person

Aug 18 - Aug 21

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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.

Brook Bound Inn

$916

per person

Sep 12 - Sep 16

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) 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.

South Shire

$887

per person

Sep 12 - Sep 16

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Albany (ALB)

A restaurant and a bar/lounge are featured at this bed & breakfast. Guests will appreciate free perks like free self parking and WiFi in public areas. A business center, express check-in, and express check-out are also on offer.

The White House Inn

$852

per person

Sep 12 - Sep 16

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Albany (ALB)

A restaurant and a bar/lounge are featured at this hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A terrace and a garden are also provided.

Top Hillsdale hotels deals

The Yankee Inn

461 Pittsfield Rd Lenox MA

Free Cancellation

Reserve now, pay when you stay

$159 nightly

$178 total

Jul 6 - Jul 7

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

8 Dan Fox Dr Pittsfield MA

$162 nightly

$181 total

Jul 29 - Jul 30

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.

The Red Lion Inn

30 Main Street Stockbridge MA

$184 nightly

$205 total

Jul 1 - Jul 2

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

Berkshires Untold

194 Pittsfield Rd Lenox MA

Free Cancellation

Reserve now, pay when you stay

$167 nightly

$187 total

Jul 1 - Jul 2

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

282 Cairo Junction Rd Catskill NY

$209 nightly

$226 total

Jul 29 - Jul 30

Total with taxes and fees

This cabin features a virtual front desk. Take advantage of the free self parking.

Kitchen

Pet friendly

Quality Inn Great Barrington

372 Main Street Great Barrington MA

$118 nightly

$132 total

Jul 20 - Jul 21

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

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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.

Copake Lake

Commune with nature and explore the great outdoors at Copake Lake during your travels in 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.

Frequently asked questions

How much are vacation packages to Hillsdale?

Travelocity offers hotel and flight vacation packages starting from just $519. 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.