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Western Massachusetts Vacation Packages

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A panoramic view of a valley with autumn foliage, a town in the distance, and rolling hills.

Western Massachusetts
Massachusetts
United States of America
North America
Hotwire.com

Western Massachusetts Flight + Hotel Packages

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

The Yankee Inn

2.5 out of 5

Price was $605, price is now $500 per person

$500

per person

Aug 4 - Aug 7

found 13 hours ago

Roundtrip non-stop flight included

Orlando (MCO) to Albany (ALB)

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.

Amaya Bed&Breakfast

2 out of 5

Save 100% on your flight

Price was $1,119, price is now $832 per person

$832

per person

Jul 31 - Aug 3

found 1 day ago

Roundtrip flight included

New York (NYC) to Albany (ALB)

Stay at this B&B in Oak Hill. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Durham Center Museum and Zoom Flume are located nearby.

The Perch Hotel

2 out of 5

Price was $865, price is now $667 per person

$667

per person

Jul 31 - Aug 3

found 1 day ago

Roundtrip flight included

New York (NYC) to Albany (ALB)

Stay at this hotel in Cornwallville. Enjoy free WiFi, free parking, and a garden. Popular attractions Elm Ridge Wild Forest and Zoom Flume are located nearby.

Hotel Kinsley

3.5 out of 5

Price was $958, price is now $771 per person

$771

per person

Jul 31 - Aug 3

found 1 day ago

Roundtrip flight included

New York (NYC) to Albany (ALB)

Book a stay at this business-friendly hotel in Kingston. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Birch Body Care and Volunteer Fireman's Hall and Museum of Kingston are located nearby.

Urban Cowboy Lodge

5 out of 5

Price was $990, price is now $822 per person

$822

per person

Jul 31 - Aug 3

found 1 day ago

Roundtrip flight included

New York (NYC) to Albany (ALB)

Book a stay at this luxury lodge in Big Indian. Enjoy free WiFi, free parking, and a sauna. Our guests praise the helpful staff in our reviews. Popular attractions Catskill Mountains and Catskill State Park are located nearby.

The Haüs Windham

2 out of 5

Price was $848, price is now $722 per person

$722

per person

Jul 31 - Aug 3

found 1 day ago

Roundtrip flight included

New York (NYC) to Hudson (HCC)

Stay at this hotel in Windham. Enjoy free WiFi, free parking, and a 24-hour fitness center. Popular attractions Windham Country Club and Windham Mountain Resort are located nearby.

Pocketbook Hotel and Bath

2 out of 5

Price was $961, price is now $830 per person

$830

per person

Jul 31 - Aug 3

found 1 day ago

Roundtrip flight included

New York (NYC) to Albany (ALB)

Stay at this hotel in Hudson. Enjoy free WiFi, free parking, and 3 indoor pools. Popular attractions Olana State Historic Site and Oakdale Beach are located nearby.

Best Western Plus Kingston Hotel And Conference Center

2.5 out of 5

Price was $625, price is now $540 per person

$540

per person

Jul 31 - Aug 3

found 1 day ago

Roundtrip flight included

New York (NYC) to Albany (ALB)

Book a stay at this business-friendly hotel in Kingston. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Dietz Stadium and Birch Body Care are located nearby.