Search Deals on
Pittsfield Vacation Packages

Build your package with 2 more options

Leaving from

Going to

Departing

Returning

Travelers

Room 1

Adults

ChildrenAges 2 to 17

InfantsYounger than 2

Add specific hotel dates

Pittsfield
Massachusetts
United States of America
North America
Hotwire.com

Pittsfield Flight + Hotel Packages

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

Gedney Farm

3.5 out of 5

Price was $789, price is now $569 per person

$569

per person

Apr 10 - Apr 13

found 1 day ago

Roundtrip non-stop flight included

Fort Lauderdale (FLL) to Albany (ALB)

Stay at this hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Questing and New Marlborough Town Library are located nearby.

Prospect Berkshires

3 out of 5

Price was $1,103, price is now $740 per person

$740

per person

Apr 10 - Apr 13

found 1 day ago

Roundtrip non-stop flight included

Fort Lauderdale (FLL) to Albany (ALB)

Stay at this hotel in Great Barrington. Enjoy free WiFi, free parking, and a sauna. Popular attractions Catamount Aerial Adventure Park and Catamount Ski Area are located nearby.

Pocketbook Hotel and Bath

2 out of 5

Price was $927, price is now $664 per person

$664

per person

Apr 10 - Apr 13

found 1 day ago

Roundtrip non-stop flight included

Fort Lauderdale (FLL) to Albany (ALB)

Book a stay at this spa hotel in Hudson. Enjoy free WiFi, a full-service spa, and a 24-hour front desk. Popular attractions Hudson Area Library and Stoddard Corner are located nearby.

Secluded Estate w/ Guest House, Private Pond, Gym, & Movie Theater Sunny Pond

3 out of 5

Save 100% on your flight

Price was $4,008, price is now $2,960 per person

$2,960

per person

Apr 10 - Apr 13

found 1 day ago

Roundtrip non-stop flight included

Fort Lauderdale (FLL) to Albany (ALB)

Stay at this cottage in Austerlitz. Enjoy free parking, balconies, and in-room washers/dryers. Popular attractions Hoffman's Pottery and Ebenezer II Gifts and Antiques are located nearby.

The Dewey

3.5 out of 5

Price was $825, price is now $612 per person

$612

per person

Apr 10 - Apr 13

found 1 day ago

Roundtrip non-stop flight included

Fort Lauderdale (FLL) to Albany (ALB)

Stay at this guesthouse in Lenox. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the breakfast in our reviews. Popular attractions The Bookstore and Lenox Library are located nearby.

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5

Price was $879, price is now $662 per person

$662

per person

Apr 10 - Apr 13

found 1 day ago

Roundtrip non-stop flight included

Fort Lauderdale (FLL) to Albany (ALB)

Stay at this B&B in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the comfy rooms in our reviews. Popular attractions The Bookstore and Lenox Library are located nearby.

Wilder House Berkshires

2 out of 5

Price was $869, price is now $671 per person

$671

per person

Apr 10 - Apr 13

found 1 day ago

Roundtrip non-stop flight included

Fort Lauderdale (FLL) to Albany (ALB)

Stay at this B&B in Sheffield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Thom Reed UFO Monument Park and Lime Kiln Farm Wildlife Sanctuary are located nearby.

Relax in Style at Historic Modern on Main With Modern Amenities & Wooded Views

3 out of 5

Save 100% on your flight

Price was $967, price is now $755 per person

$755

per person

Apr 6 - Apr 10

found 18 hours ago

Roundtrip flight included

Atlanta (ATL) to Albany (ALB)

Stay at this cottage in Stone Ridge. Enjoy free parking, patios, and air conditioning. Popular attractions Tongore Park Beach and Century House Historical Society are located nearby.