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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 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 $1,093, price is now $770 per person

$770

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 21 hours 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

Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain

3 out of 5

Save 100% on your flight

Price was $3,378, price is now $2,604 per person

$2,604

per person

Sep 21 - Sep 24

found 1 day ago

Roundtrip flight included

New York (NYC) to Hudson (HCC)

Stay at this cottage in Hensonville. Enjoy free parking and air conditioning. Popular attractions Windham Mountain Resort and Hunter Mountain are located nearby.

Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain

3 out of 5

Save 100% on your flight

Price was $3,490, price is now $2,716 per person

$2,716

per person

Sep 21 - Sep 24

found 1 day ago

Roundtrip flight included

New York (NYC) to Hudson (HCC)

Stay at this cottage in Hensonville. Enjoy free parking, volleyball on site, and a pool table. Popular attractions Windham Mountain Resort and Hunter Mountain are located nearby.

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 8 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