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Monterey Vacation Packages

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Monterey Flight + Hotel Packages

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

Berkshire Mountain Lodge

3 out of 5
Price was $666, price is now $499 per person
$499
per person
Dec 22 - Dec 27
found 21 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Book a stay at this golf aparthotel in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.
Lots of space. Very comfy beds. Toilet was really short though! Didn't use kitchen at all but looked great.

Reviewed on Oct 2, 2026

Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

3.5 out of 5
Price was $755, price is now $537 per person
$537
per person
Dec 22 - Dec 27
found 21 hours ago
Roundtrip flight included
New York (NYC) 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.
Wonderful resort

Reviewed on Sep 29, 2026

Hotel On North

Hotel On North

3.5 out of 5
Price was $743, price is now $545 per person
$545
per person
Dec 22 - Dec 27
found 21 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Book a stay at this family-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Barrington Stage Company and Lichtenstein Center for the Arts are located nearby.
Delightful place with charm and warmth and character. I would love to come back.

Reviewed on Oct 2, 2026

The Perch Hotel

The Perch Hotel

2 out of 5
Price was $1,296, price is now $962 per person
$962
per person
Nov 5 - Nov 9
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.

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was $698, price is now $521 per person
$521
per person
Dec 22 - Dec 27
found 21 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Book a stay at this family-friendly aparthotel in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located nearby.

Brook Bound Inn

Brook Bound Inn

2 out of 5
Price was $1,435, price is now $1,142 per person
$1,142
per person
Dec 23 - Dec 27
just found
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
Book a stay at this golf hotel in Wilmington. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Mount Snow and North Branch Deerfield River are located nearby.
Our weeklong trip meandering the roads of Vermont was made more memorable by our stay at the Brook Bound Inn! The property is gorgeous and impeccably maintained! Our room was clean and so quiet! The bed was comfortable, and the blackout window blinds allowed us to sleep a little later than normal. The bathroom was very clean with a large shower and great smelling body wash, shampoo, etc. Jake and Hope were so helpful before and during our stay. We also appreciated the robust WIFI. We didn’t try the amazing pool this time, but we will for sure on our next trip!

Reviewed on Aug 30, 2026

The Williams Inn

The Williams Inn

4 out of 5
Price was $1,057, price is now $848 per person
$848
per person
Dec 22 - Dec 27
found 21 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Book a stay at this business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Williams College Schow Science Library and Denison Park are located nearby.
Great

Reviewed on Sep 29, 2026

The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA

3.5 out of 5
Price was $953, price is now $774 per person
$774
per person
Dec 22 - Dec 27
found 20 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Book a stay at this business-friendly hotel in North Adams. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Bracewell Park and Massachusetts Museum of Contemporary Art are located nearby.
Excellent staff. Friendly and helpful. Enjoyed the pool and sauna. Breakfast above average. One little quirk with the room. There was a frosted window on the wall of the bathroom so when you turned on the bathroom light it illuminated the bedroom. Could have done without that. But all the rooms are different. Good location across from Mass MoCA. Overall would recommend.

Reviewed on Sep 30, 2026

Monterey Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Landing Hotel at Rivers Casino Schenectady

The Landing Hotel at Rivers Casino Schenectady

4 out of 5
Nothside
Price was $688, price is now $607 per person
$607
per person
Nov 20 - Nov 23
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 $1,296, price is now $962 per person
$962
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Brook Bound Inn

Brook Bound Inn

2 out of 5
Price was $1,435, price is now $1,142 per person
$1,142
per person
Dec 23 - Dec 27
just found
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
Aspen At Manchester

Aspen At Manchester

2.5 out of 5
Price was $1,170, price is now $985 per person
$985
per person
Dec 23 - Dec 27
just found
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)

Monterey Vacation Packages 5-7 Night Stays

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

Berkshire Mountain Lodge

3 out of 5
Price was $666, price is now $499 per person
$499
per person
Dec 22 - Dec 27
found 21 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

3.5 out of 5
Price was $755, price is now $537 per person
$537
per person
Dec 22 - Dec 27
found 21 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Hotel On North

Hotel On North

3.5 out of 5
Price was $743, price is now $545 per person
$545
per person
Dec 22 - Dec 27
found 21 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was $698, price is now $521 per person
$521
per person
Dec 22 - Dec 27
found 21 hours 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.

Breeze Airways
Wed, Dec 2 - Mon, Dec 14
MCO
Orlando Intl.
BDL
Bradley Intl.
$162 Roundtrip, just found
$162
Roundtrip
just found
Select Breeze Airways flight, departing Wed, Dec 2 from Orlando Intl. to Bradley Intl., returning Mon, Dec 14, priced at $162 just found
Frontier Airlines
Wed, Oct 21 - Mon, Oct 26
SJU
Luis Munoz Marin Intl.
BDL
Bradley Intl.
$179 Roundtrip, found 1 day ago
$179
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Oct 21 from Luis Munoz Marin Intl. to Bradley Intl., returning Mon, Oct 26, priced at $179 found 1 day ago
Breeze Airways
Thu, Nov 12 - Mon, Nov 16
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$187 Roundtrip, found 4 hours ago
$187
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Thu, Nov 12 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Mon, Nov 16, priced at $187 found 4 hours ago
Breeze Airways
Wed, Jan 27 - Mon, Feb 1
TPA
Tampa Intl.
BDL
Bradley Intl.
$191 Roundtrip, found 1 day ago
$191
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Jan 27 from Tampa Intl. to Bradley Intl., returning Mon, Feb 1, priced at $191 found 1 day ago