Search Deals onWestern Massachusetts Vacation Packages
Western Massachusetts Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Hotel Vervana, Trademark Collection by Wyndham
Price was $512, price is now $443 per person
$443
per person
Jan 27 - Jan 30
found 7 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Book a stay at this ski hotel in Bennington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Bennington Museum and Fiddlehead at Four Corners are located nearby.

Wylder Hotel Windham
Price was $708, price is now $606 per person
$606
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Hudson (HCC)
Stay at this hotel in Windham. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Windham Mountain Resort and Windham Country Club are located nearby.

Saratoga Casino Hotel
Price was $613, price is now $526 per person
$526
per person
Dec 18 - Dec 20
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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 Racetrack and Saratoga Performing Arts Center are located nearby.

South Shire
Price was $630, price is now $545 per person
$545
per person
Dec 18 - Dec 20
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this B&B in Bennington. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Bennington Arts Guild Gallery and Fiddlehead at Four Corners are located nearby.

Lodges At Cresthaven
Price was $649, price is now $567 per person
$567
per person
Dec 18 - Dec 20
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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 Hearthstone Point Campground and Lakeside Trail are located nearby.
The grounds were lovely, the views from our balcony were beautiful. as well. The room was spotless. We dined at the Boathouse restaurant on site and it was very good.
Reviewed on Nov 9, 2026

Hotel Vienna
Price was $540, price is now $474 per person
$474
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Hudson (HCC)
Book a stay at this golf hotel in Windham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Windham Mountain Resort and Windham Country Club are located nearby.
The property was beautiful overall, but I encountered a staff member who was unfortunately very rude. Although I am 18 and booked through Expedia, the hotel policy requires guests to be 21. Expedia verified my age, and I didn’t encounter any issues until I arrived. I checked in and paid the remaining balance for my two-night stay, but was then confronted by a man who claimed there was an issue due to the age policy. He did not speak to me kindly, leaving me on edge for the remainder of my stay, fearing I would be evicted over a discrepancy with their Expedia listing. To make matters worse, the sauna was broken, and the breakfast was inadequate. Furthermore, checkout is at 11:00 AM or earlier; when I went to check out at 6:30 AM, there was no staff present, so I simply left my keys on the counter to get to work. As someone who works in customer service, I would never speak to a guest the way he spoke to me; if not for that interaction, I would have had a pleasant stay.
Reviewed on Nov 8, 2026

Howland House
Price was $594, price is now $523 per person
$523
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this hotel in Mount Tremper. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mount Tremper Arts and Emerson Place Kaleidoscope are located nearby.
A very nice experience, the Howland House is a very charming guesthouse with cozy, rooms, an excellent restaurant, Oliver’s, right downstairs and a really welcoming atmosphere. Staff were helpful and friendly, really couldn’t have asked for a nicer stay. We had a standard room with a shared bathroom, but the way it was setup made it totally comfortable. Highly recommended place if you’re in the area and we’ll almost certainly return.
Reviewed on Nov 8, 2026

Hyatt House Schenectady / Mohawk Harbor
Price was $521, price is now $459 per person
$459
per person
Jan 27 - Jan 30
found 6 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this hotel in Schenectady. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Rivers Casino & Resort and Schenectady City Hall are located nearby.
Western Massachusetts Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



Western Massachusetts Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.



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

Fri, Dec 4 - Mon, Dec 7
MCO
Orlando Intl.
BDL
Bradley Intl.
$176 Roundtrip, found 4 hours ago
$176
Roundtrip
found 4 hours ago

Wed, Jan 27 - Tue, Feb 2
TPA
Tampa Intl.
BDL
Bradley Intl.
$192 Roundtrip, found 11 hours ago
$192
Roundtrip
found 11 hours ago

Sat, Dec 19 - Wed, Dec 23
DCA
Ronald Reagan Washington National
ALB
Albany Intl.
$203 Roundtrip, found 1 day ago
$203
Roundtrip
found 1 day ago

Wed, Jan 13 - Sat, Jan 23
CLT
Charlotte-Douglas Intl.
BDL
Bradley Intl.
$209 Roundtrip, found 1 day ago
$209
Roundtrip
found 1 day ago
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