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Pittsfield Vacation Packages

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A historic building with a clock, a flag, and a street lamp.

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.

The Ponds at Foxhollow

3 out of 5

Save 100% on your flight

Price was $936, price is now $648 per person

$648

per person

Oct 22 - Oct 26

found 1 day ago

Roundtrip flight included

New York (NYC) to Albany (ALB)

Stay at this aparthotel in Lenox. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Tanglewood Music Center and The Mount are located nearby.

Quiet property. Convenient location.

Reviewed on Aug 2, 2026

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5

Save 100% on your flight

Price was $1,108, price is now $784 per person

$784

per person

Sep 24 - Sep 27

found 1 day ago

Roundtrip 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 Tanglewood Music Center and The Bookstore are located nearby.

Lake Haven Motel

2.5 out of 5

Save 100% on your flight

Price was $879, price is now $660 per person

$660

per person

Sep 20 - Sep 26

found 1 day ago

Roundtrip flight included

New York (NYC) to Albany (ALB)

Stay at this motel in Lake George. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Lake George Steamboat Company and Fort William Henry Museum are located nearby.

Room was clean and staff was helpful when asked for things like toilet paper and towels. Out of their control but the whole village lost power Friday 7/3 from about 8:00 am - 2:00 pm. They don’t open their pool until 10:00 am I would have thought with the no power and heat they would have opened sooner. Only other thing is if you are on the ground floor you can definitely hear everything above you.

Reviewed on Jul 5, 2026

Lodges At Cresthaven

4 out of 5

Price was $1,070, price is now $821 per person

$821

per person

Oct 19 - Oct 23

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Albany (ALB)

Book a stay at this 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 Lake George Steamboat Company and Fort William Henry Museum are located nearby.

Overall is really nice to stay here with my family.

Reviewed on Aug 17, 2026

Saratoga Casino Hotel

4 out of 5

Price was $943, price is now $735 per person

$735

per person

Oct 3 - Oct 8

found 1 day ago

Roundtrip flight included

Fort Lauderdale (FLL) to Albany (ALB)

Stay at this hotel in Saratoga Springs. Enjoy free WiFi, free parking, and a casino. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Saratoga Casino and Saratoga Racetrack are located nearby.

Convenient location, clean comfortable rooms, beautiful grounds, worth the cost.

Reviewed on Aug 19, 2026

The Whitlock

2 out of 5

Price was $1,025, price is now $811 per person

$811

per person

Oct 13 - Oct 17

found 14 hours ago

Roundtrip flight included

Dallas (DFW) to Albany (ALB)

Stay at this hotel in Lenox. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood Music Center and The Bookstore are located nearby.

Lovely room, nice amenities.

Reviewed on Aug 17, 2026

Historic & Secluded Estate on the Hudson River w/ Pool Sleeps 24 River House by Avantstay

3.5 out of 5

Save 100% on your flight

Price was $3,218, price is now $2,583 per person

$2,583

per person

Sep 21 - Sep 24

found 1 day ago

Roundtrip flight included

New York (NYC) to Albany (ALB)

Book a stay at this business-friendly condo in Catskill. Enjoy free parking, concierge services, and a pool table. Popular attractions Thomas Cole National Historic Site and Catskill Golf Club are located nearby.

The Wiltwyck

3.5 out of 5

Price was $1,303, price is now $1,047 per person

$1,047

per person

Oct 9 - Oct 13

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Albany (ALB)

Stay at this guesthouse in Kingston. Enjoy free WiFi, free parking, and Netflix. Popular attractions Senate House State Historic Site and Volunteer Fireman's Hall and Museum of Kingston are located nearby.

It's a very cute apartment and perfect for a two-person stay. I love that it has a little sitting area outside of the bedroom. The host is very professional, thoughtful and communicative. I'd stay here again.

Reviewed on Aug 14, 2026