Glendale Vacations from $595

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The Latest Glendale Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A large, white, multi-story building with a central courtyard, surrounded by lush greenery and a hilly landscape.
    Dec 11 - Dec 14

    Wylder Hotel Windham + Flight

    Windham
    3 nights
    3.5 star property
    9.0/10 - Wonderful (135 reviews)
    "Room super clean and beautiful property!"
    Reviewed November 2, 2026
    Roundtrip • Orlando (MCO) - Hudson (HCC)
    MCO - LGA • Nonstop EWR - MCO • Nonstop
    $700
    $595
    per traveler
    found 1 day ago
    Wylder Hotel Windham
  • An outdoor dining area with tables and chairs, surrounded by plants and trees.
    Dec 29 - Jan 3

    Delamar West Hartford + Flight

    West Hartford
    5 nights
    4.0 star property
    9.8/10 - Exceptional (1,000 reviews)
    "The staff was knowledgeable, professional, friendly and very helpful. The restaurant was excellent for dinner and the room was comfortable and lovely."
    Reviewed November 2, 2026
    Roundtrip • Tampa (TPA) - Hartford (BDL)
    TPA - BDL • Nonstop BDL - TPA • Nonstop
    $1,593
    $1,172
    per traveler
    found 1 day ago
    Delamar West Hartford
  • A lakeside property with a swimming pool, a house, and a well-maintained lawn.
    Dec 19 - Dec 24

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

    Hensonville
    5 nights
    3.0 star property
    Roundtrip • San Juan (SJU) - Hudson (HCC)
    SJU - ALB • 1 stop ALB - SJU • 2 stops
    $6,077
    $4,712
    per traveler
    found 1 day ago
    Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain
  • A kitchen with white cabinets, a refrigerator, and a dining area with a table and chairs.
    Dec 11 - Dec 14

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

    Hensonville
    3 nights
    3.0 star property
    Roundtrip • Orlando (MCO) - Hudson (HCC)
    MCO - LGA • Nonstop EWR - MCO • Nonstop
    $3,204
    $2,555
    per traveler
    found 1 day ago
    Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain
  • A living room with a sofa, a wooden cabinet, a dining table with a vase of flowers, and a glass of wine.
    Jan 21 - Jan 25

    Blackberry River Inn + Flight

    Norfolk
    4 nights
    3.0 star property
    9.4/10 - Exceptional (251 reviews)
    Roundtrip • San Juan (SJU) - Hartford (BDL)
    SJU - BDL • Nonstop BDL - SJU • 1 stop
    $676
    $597
    per traveler
    found 12 hours ago
    Blackberry River Inn

Where to stay near Glendale

Glendale, Massachusetts offers a charming blend of outdoor adventures, romantic getaways, and cultural experiences. Nearby cities provide family-friendly entertainment, scenic landscapes, and a relaxing atmosphere, making it an ideal destination for those seeking skiing, sports, and memorable moments with loved ones.
A large white house with multiple chimneys, surrounded by lush greenery and trees.

Lenox

Discover Lenox, a charming destination perfectly suited for travelers seeking a blend of culture, nature, and entertainment. With its scenic mountains and serene lakes, Lenox invites families and couples alike to explore attractions like the National Shrine of the Divine Mercy, The Mount, and the Norman Rockwell Museum. Located about 8 miles by car from Glendale, Lenox offers a delightful escape, making it a smart choice for your next hotel booking.

A building with a marquee sign reading "MAHAIWE Performing Arts Center" and a smaller sign for "Black Violin" performances.

Great Barrington

Experience the charm of Great Barrington, an excellent hub for family and nature lovers seeking a delightful weekend getaway. Enjoy outdoor adventures at nearby ski resorts, explore the serene Housatonic River, or take in the beauty of Lake Buel and the surrounding national state park. Just about a 7-mile drive from Glendale, Great Barrington offers a perfect mix of relaxation and adventure, making it a smart choice for your next vacation.

A historic building with a clock, a flag, and a street lamp.

Pittsfield

Make your vacation planning effortless by staying in Pittsfield, a haven for family and nature enthusiasts thanks to its stunning landscapes and engaging attractions. Visitors can explore the historic Hancock Shaker Village, delve into the natural wonders at the Berkshire Museum, or enjoy serene moments at the National Shrine of the Divine Mercy. Located about 16 miles by car from Glendale, Pittsfield's diverse offerings make it a smart choice for your next getaway.

A stone staircase leading up to a blue arched entrance, surrounded by lush greenery and birch trees.

Stockbridge

Immerse yourself in Stockbridge, where cultural enthusiasts can easily access attractions like the Norman Rockwell Museum, the National Shrine of the Divine Mercy, and the historic Naumkeag Museum. With its charming blend of nature and entertainment, Stockbridge offers a delightful escape, perfect for families or couples seeking romance. Located about 0.9 mile by car from Glendale, this city serves as a smart choice for travelers looking to enjoy a rich experience in the heart of Massachusetts.

A historic street with brick buildings, storefronts, and parked cars.

Lee

Travelers visiting the area often choose Lee, especially families and nature lovers seeking close proximity to cultural attractions and outdoor experiences. With highlights like the National Shrine of the Divine Mercy, The Mount historic house, and the Norman Rockwell Museum, Lee offers a rich blend of history and art. Located about 5 miles by car from Glendale, it provides easy access to these sites while ensuring a delightful atmosphere for romance and entertainment. Lee makes for a smart hotel booking choice for an unforgettable getaway.

Glendale Hotel Deals

An indoor swimming pool with a 6 feet 18 meters depth, surrounded by chairs and tables, with large windows offering views of trees.

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
4.5 mi from Glendale
8.8 out of 10, Excellent, (853 reviews)
$83 nightly
The price is $93
Dec 3 - Dec 4
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
See all properties in Glendale

Frequently Asked Questions

How to find the best Glendale package deals?

Start your search for a Glendale package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply a few filters, like "Property type" and "Popular locations," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Glendale package deal right away, simply switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Glendale adventure off to a flying start.

When to book a vacation package to Glendale?

Land incredible bargains by reserving your flights ahead of time with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Glendale break.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.