Book Exclusive Hillsdale Vacation Packages
Hillsdale flight + hotel packages
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Suites Clifton Park by IHG
per person
Jun. 6 - Jun. 10
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
Book a stay at this business-friendly hotel in Clifton Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions The Edge Halfmoon and Clifton Common are located nearby.
Brookmere
Save 100% on your flight
per person
Jun. 6 - Jun. 10
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
Book a stay at this spa hotel in Saratoga Springs. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Saratoga Race Course and Saratoga Performing Arts Center are located nearby.
Lodges At Cresthaven
per person
Jun. 6 - Jun. 10
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
Stay at this 4-star beach lodge in Lake George. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Fort William Henry and Hearthstone Point Campground are located nearby.
The Equinox Golf Resort & Spa
per person
Jun. 6 - Jun. 10
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
Stay at this 4.5-star luxury hotel in Manchester. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the property condition in our reviews. Popular attractions Golf Club at Equinox and American Museum of Fly Fishing are located nearby.
Sundowner on Lake George
per person
Jul. 23 - Jul. 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
Book a stay at this beach motel in Lake George. Enjoy free parking, an outdoor pool, and a private beach. Popular attractions Fort William Henry and Six Flags Great Escape are located nearby.
Top Hillsdale hotels deals
Life House Berkshires
194 Pittsfield Rd, Lenox, MA
Free cancellation
Reserve now, pay when you stay
The price is CA $143 per night
CA $143
CA $159 total
includes taxes & fees
May 5 - May 6
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Kennedy Park are located nearby.
Pet-friendly
Parking included
Quality Inn
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Free cancellation
Reserve now, pay when you stay
The price is CA $104 per night
CA $104
CA $117 total
includes taxes & fees
May 18 - May 19
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Mahaiwe Performing Arts Center and Housatonic River Walk are located nearby.
Breakfast included
Parking included
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd, Lenox, MA
Free cancellation
Reserve now, pay when you stay
The price is CA $148 per night
CA $148
CA $165 total
includes taxes & fees
May 5 - May 6
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.
Pool
Hot tub
The Black Swan Lee - Lenox, Ascend Hotel Collection
435 Laurel St, Lee, MA
Free cancellation
Reserve now, pay when you stay
The price is CA $153 per night
CA $153
CA $170 total
includes taxes & fees
May 11 - May 12
Stay at this 3-star hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Tanglewood Music Center and Berkshire Mountain Country Store are located nearby.
Breakfast included
Pet-friendly
Howard Johnson by Wyndham Saugerties
2764 Route 32, Saugerties, NY
Free cancellation
Reserve now, pay when you stay
The price is CA $141 per night
CA $141
CA $158 total
includes taxes & fees
May 6 - May 7
Book a stay at this business-friendly hotel in Saugerties. Enjoy free WiFi, free parking, and a sauna. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Kiwanis Ice Arena and Esopus Bend Nature Preserve are located nearby.
Pool
Parking included
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street, South Lee, MA
Free cancellation
Reserve now, pay when you stay
The price is CA $148 per night
CA $148
CA $185 total
includes taxes & fees
May 15 - May 16
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood Music Center and Berkshire Theatre Festival are located nearby.
Pool
Air conditioning
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.
Hillsdale Vacations
We know, geography isn't everyone's strong suit. If you're unsure where Hillsdale lies on a map, it's a good idea to acquaint yourself with its location before you fly off!
This town is located 11 miles (18 kilometers) east of Hudson. It's also 20 miles (32 kilometers) southwest of Pittsfield.
Places to visit in Hillsdale
You don't need to know your Rubens from your Rembrandts to roam the corridors of Norman Rockwell Museum. It boasts an excellent array of exhibits that'll engage your interest and fuel your appreciation for art. Need more options? Whether you're a seasoned professional or total beginner, it's time to dig out your skis and tear up the slopes. Ski Butternut guarantees plenty of fun for all skill levels! And, there's more going on in the surrounding area. They say that history is the best teacher. Travel back through time for a fascinating lesson at Chesterwood.Where do you fly into for Hillsdale?
Coming in to land at Bradley International Airport (BDL)? Once you step off the aircraft, central Hillsdale is about 50 miles (80 kilometers) northwest away. Slide into a cab and enjoy the ride — your vacation has only just started!Photos of local treasures
Browse Hillsdale vacation photos for more inspiration