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Western Massachusetts Vacation Packages

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Western Massachusetts Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
Price was $976, price is now $708 per person
$708
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.
Our unit was very comfortable for 2 senior couples. We were only there for the weekend so we didn’t use any of the amenities but, the property is lovely.

Reviewed on Sep 4, 2026

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Price was $1,348, price is now $924 per person
$924
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
New York (NYC) 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 Lenox Library are located nearby.

Prospect Berkshires

Prospect Berkshires

3 out of 5
Price was $3,109, price is now $2,191 per person
$2,191
per person
Oct 22 - Oct 29
found 1 day ago
Roundtrip flight included
New York (NYC) 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.

The Perch Hotel

The Perch Hotel

2 out of 5
Price was $2,094, price is now $1,594 per person
$1,594
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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.

Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

2 out of 5
Price was $1,376, price is now $1,091 per person
$1,091
per person
Oct 22 - Oct 26
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 Oakdale Beach and Hudson Area Library are located nearby.
We stay here all the time. Love everything about this place. Front staff is amazing. The dipping pools are amazing. Rudy, the bartender best guy ever at the bar, have to see him. You will not be disappointed. Great location also

Reviewed on Sep 8, 2026

Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

3.5 out of 5
Price was $933, price is now $741 per person
$741
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)
Book a stay at this ski hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood Music Center and Berkshire Theatre Festival are located nearby.
Our room was amazingly spacious and clean, and the area is also very peaceful and quiet. We were only there for 2 nights but it was a good experience. Would consider staying there again next time we visit the Berkshires.

Reviewed on Sep 7, 2026

Aspen At Manchester

Aspen At Manchester

2.5 out of 5
Price was $1,651, price is now $1,343 per person
$1,343
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)
Stay at this hotel in Manchester Center. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Bromley Mountain Ski Resort and Dana L. Thompson Memorial Park are located nearby.
Thank you so much for a wonderful stay. Will definitely be back.

Reviewed on Sep 7, 2026

The Manchester View

The Manchester View

2.5 out of 5
Price was $1,810, price is now $1,476 per person
$1,476
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Albany (ALB)
Book a stay at this business-friendly hotel in Manchester Center. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Bromley Mountain Ski Resort and Dana L. Thompson Memorial Park are located nearby.
We had a great stay at the Manchester View with my whole family. The staff is very nice, friendly and helpful. Highly recommended!

Reviewed on Sep 8, 2026

Western Massachusetts Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
Price was $976, price is now $708 per person
$708
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Price was $1,348, price is now $924 per person
$924
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
The Perch Hotel

The Perch Hotel

2 out of 5
Price was $2,094, price is now $1,594 per person
$1,594
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Albany (ALB)
Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

2 out of 5
Price was $1,376, price is now $1,091 per person
$1,091
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)

Western Massachusetts Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

3.5 out of 5
Price was $886, price is now $640 per person
$640
per person
Oct 22 - Oct 29
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Price was $1,777, price is now $1,188 per person
$1,188
per person
Oct 22 - Oct 29
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
Price was $1,460, price is now $1,018 per person
$1,018
per person
Oct 22 - Oct 29
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Prospect Berkshires

Prospect Berkshires

3 out of 5
Price was $3,109, price is now $2,191 per person
$2,191
per person
Oct 22 - Oct 29
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)

Top Flight Deals

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

Frontier Airlines
Thu, Dec 3 - Sat, Dec 12
MCO
Orlando Intl.
BDL
Bradley Intl.
$82 Roundtrip, found 23 hours ago
$82
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Thu, Dec 3 from Orlando Intl. to Bradley Intl., returning Sat, Dec 12, priced at $82 found 23 hours ago
Allegiant Air
Thu, Sep 17 - Sun, Sep 27
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$144 Roundtrip, found 3 days ago
$144
Roundtrip
found 3 days ago
Select Allegiant Air flight, departing Thu, Sep 17 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Sun, Sep 27, priced at $144 found 3 days ago
Frontier Airlines
Wed, Oct 14 - Fri, Oct 23
SJU
Luis Munoz Marin Intl.
BDL
Bradley Intl.
$161 Roundtrip, found 1 day ago
$161
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Oct 14 from Luis Munoz Marin Intl. to Bradley Intl., returning Fri, Oct 23, priced at $161 found 1 day ago
Breeze Airways
Thu, Nov 12 - Mon, Nov 16
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$179 Roundtrip, found 1 day ago
$179
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Nov 12 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Mon, Nov 16, priced at $179 found 1 day ago