Search Deals on
Freehold Vacation Packages

Build your package with 2 more options

Freehold Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
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
per person
Jun 1 - Jun 3
found 9 hours ago
Roundtrip flight included
Chicago (ORD) to Albany (ALB)
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood Music Center and Berkshire Theatre Festival are located nearby.
Life House Berkshires

Life House Berkshires

3.5 out of 5
per person
Jun 1 - Jun 3
found 9 hours ago
Roundtrip flight included
Chicago (ORD) to Albany (ALB)
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.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
per person
Jun 1 - Jun 3
found 9 hours ago
Roundtrip flight included
Chicago (ORD) to Albany (ALB)
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.
The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA

3.5 out of 5
per person
Jun 1 - Jun 3
found 9 hours ago
Roundtrip flight included
Chicago (ORD) to Albany (ALB)
Stay at this 3.5-star business-friendly hotel in North Adams. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Bracewell Park and Massachusetts Museum of Contemporary Art are located nearby.
The Constance, The Whitlock, & The Dewey By The Lenox Collection

The Constance, The Whitlock, & The Dewey By The Lenox Collection

3.5 out of 5
per person
Jun 1 - Jun 3
found 9 hours ago
Roundtrip flight included
Chicago (ORD) to Albany (ALB)
Stay at this 3.5-star hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Tanglewood Music Center and Lenox Library are located nearby.
The Little Lion

The Little Lion

3 out of 5
per person
Jun 1 - Jun 3
found 9 hours ago
Roundtrip flight included
Chicago (ORD) to Albany (ALB)
Stay at this 3-star motel in Great Barrington. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions Art et Industrie and Lake Mansfield Park are located nearby.
Hotel On North

Hotel On North

3.5 out of 5
per person
Jun 1 - Jun 3
found 9 hours ago
Roundtrip flight included
Chicago (ORD) to Albany (ALB)
Stay at this 3.5-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Barrington Stage Company and Berkshire Athenaeum are located nearby.
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 out of 5
per person
Jun 1 - Jun 3
found 9 hours ago
Roundtrip flight included
Chicago (ORD) to Albany (ALB)
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Tracy Brook Wildlife Sanctuary are located nearby.

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

American Airlines
Wed, May 21 - Tue, Jun 3
CLT
Charlotte-Douglas Intl.
ALB
Albany Intl.
$145 Roundtrip, found 3 days ago
$145
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, May 21 from Charlotte-Douglas Intl. to Albany Intl., returning Tue, Jun 3, priced at $145 found 3 days ago
JetBlue Airways
Fri, Mar 21 - Tue, Mar 25
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$193 Roundtrip, found 4 days ago
$193
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Fri, Mar 21 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Tue, Mar 25, priced at $193 found 4 days ago
American Airlines
Sat, May 3 - Mon, May 12
SFO
San Francisco Intl.
ALB
Albany Intl.
$247 Roundtrip, found 17 hours ago
$247
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Sat, May 3 from San Francisco Intl. to Albany Intl., returning Mon, May 12, priced at $247 found 17 hours ago
Delta
Thu, Mar 20 - Fri, Mar 28
ATL
Hartsfield-Jackson Atlanta Intl.
ALB
Albany Intl.
$326 Roundtrip, found 5 days ago
$326
Roundtrip
found 5 days ago
Select Delta flight, departing Thu, Mar 20 from Hartsfield-Jackson Atlanta Intl. to Albany Intl., returning Fri, Mar 28, priced at $326 found 5 days ago