Hillsdale Vacations

Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*

Choose two or more items and save on your trip:

Top Hotel Deals

The Brooks Motel

The Brooks Motel

2 out of 5
2871 New York 23 Hillsdale NY
1.64 km from city center
Stay at this motel in Hillsdale. Enjoy free WiFi, free parking, and premium bedding. Popular attractions Catamount Aerial Adventure Park and Community Library ...
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
33.68 km from city center
Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
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
35.72 km from city center
Stay at this cabin in Catskill. Enjoy free parking, furnished patios, and climate control. Popular attractions Catskill Golf Club and Angelo Canna Town Park ...
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
23.24 km from city center
Book a stay at this 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 ...
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
30.95 km from city center
Stay at this lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
37.23 km from city center
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd Lenox MA
32.71 km from city center
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 ...
Hotel On North

Hotel On North

3.5 out of 5
297 North Street Pittsfield MA
37.75 km from city center
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean ...
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
20.96 km from city center
Book a stay at this historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3 out of 5
435 Laurel St Lee MA
26.95 km from city center
Stay at this hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions ...
Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
13.28 km from city center
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 ...
Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

2.5 out of 5
2777 ROUTE 32 Saugerties NY
38.4 km from city center
Book a stay at this business-friendly hotel in Saugerties. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 out of 5
415 Stockbridge Rd Great Barrington MA
15.28 km from city center
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3 out of 5
70 Pittsfield Rd Lenox MA
30.17 km from city center
Book a stay at this business-friendly hotel in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
voco James Newbury Hudson Valley by IHG

voco James Newbury Hudson Valley by IHG

3.5 out of 5
60 S River St Coxsackie NY
29.25 km from city center
Book a stay at this spa hotel in Coxsackie. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in ...
Don't see what you're looking for?
See all available properties in Hillsdale
View all properties
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.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Breeze Airways
Thu, May 7 - Sun, May 10
TPA
Tampa Intl.
ALB
Albany Intl.
$328 Roundtrip, found 4 hours ago
$328
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Thu, May 7 from Tampa Intl. to Albany Intl., returning Sun, May 10, priced at $328 found 4 hours ago
Southwest Airlines
Thu, May 7 - Sun, May 10
TPA
Tampa Intl.
ALB
Albany Intl.
$344 Roundtrip, found 4 hours ago
$344
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Thu, May 7 from Tampa Intl. to Albany Intl., returning Sun, May 10, priced at $344 found 4 hours ago
American Airlines
Thu, May 7 - Sun, May 10
TPA
Tampa Intl.
ALB
Albany Intl.
$354 Roundtrip, found 4 hours ago
$354
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Thu, May 7 from Tampa Intl. to Albany Intl., returning Sun, May 10, priced at $354 found 4 hours ago
Delta
Thu, May 7 - Sun, May 10
TPA
Tampa Intl.
ALB
Albany Intl.
$359 Roundtrip, found 4 hours ago
$359
Roundtrip
found 4 hours ago
Select Delta flight, departing Thu, May 7 from Tampa Intl. to Albany Intl., returning Sun, May 10, priced at $359 found 4 hours ago
United
Thu, May 7 - Sun, May 10
TPA
Tampa Intl.
ALB
Albany Intl.
$369 Roundtrip, found 4 hours ago
$369
Roundtrip
found 4 hours ago
Select United flight, departing Thu, May 7 from Tampa Intl. to Albany Intl., returning Sun, May 10, priced at $369 found 4 hours ago