A snow-covered river flowing through a town with brick buildings and a tall chimney in the background.

Ware Vacations from $379

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Your Ware Vacation

When a city escape is calling, answer it with a vacation package to Ware. With all your travel plans in place before you go, all you have to do here is focus on enjoying yourself. You'll want to go sightseeing during your trip to Ware. Swing by popular attractions like Palmer Motorsports Park, Hardwick Vineyard and Winery and Rock House Reservation. No matter your travel plans or budget, putting together the ultimate tailored Ware vacation is a piece of cake with Expedia.

The Latest Ware Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A Candlewood Suites hotel with a modern design, featuring multiple floors and a well-lit entrance.
    Jan 15 - Jan 18

    Candlewood Suites Windsor Locks Bradley Arpt by IHG + Flight

    Windsor Locks
    3 nights
    2.5 star property
    8.4/10 - Very good (1,245 reviews)
    Roundtrip • San Juan (SJU) - Hartford (BDL)
    SJU - BDL • 1 stop BDL - SJU • Nonstop
    $463
    $379
    per traveler
    found 1 day ago
    Candlewood Suites Windsor Locks Bradley Arpt by IHG
  • An outdoor dining area with tables and chairs, surrounded by plants and trees.
    Jan 15 - Jan 18

    Delamar West Hartford + Flight

    West Hartford
    3 nights
    4.0 star property
    9.8/10 - Exceptional (1,004 reviews)
    "Clean, nice property. Highly recommend."
    Reviewed November 9, 2026
    Roundtrip • San Juan (SJU) - Hartford (BDL)
    SJU - BDL • 1 stop BDL - SJU • Nonstop
    $1,148
    $777
    per traveler
    found 1 day ago
    Delamar West Hartford
  • A buffet setup with various food items in metal containers, a sign indicating 'Cheese Omelet', and a patterned wall in the background.
    Jan 15 - Jan 18

    Holiday Inn Express Vernon - Manchester by IHG + Flight

    Vernon
    3 nights
    2.5 star property
    8.6/10 - Excellent (1,004 reviews)
    Roundtrip • San Juan (SJU) - Hartford (BDL)
    SJU - BDL • 1 stop BDL - SJU • Nonstop
    $589
    $471
    per traveler
    found 1 day ago
    Holiday Inn Express Vernon - Manchester by IHG
  • A large, two-story house with a wrap-around porch, a central entrance, and a flag.
    Dec 24 - Dec 28

    Belden House & Mews + Flight

    Litchfield Historic District
    4 nights
    5.0 star property
    9.4/10 - Exceptional (14 reviews)
    "Absolutely beautiful property. The restaurant was amazing and delicious. The room was perfect and cozy and the staff, from the front desk to the restaurant, were all on point! Highly, highly, highly recommend and would return again."
    Reviewed November 2, 2026
    Roundtrip • Orlando (MCO) - Hartford (BDL)
    MCO - BDL • Nonstop BDL - MCO • Nonstop
    $1,735
    $1,430
    per traveler
    found 18 hours ago
    Belden House & Mews
  • A breakfast buffet area with various food options and a bakery section.
    Jan 15 - Jan 18

    Holiday Inn Express Southington by IHG + Flight

    Southington
    3 nights
    2.5 star property
    8.6/10 - Excellent (1,469 reviews)
    Roundtrip • San Juan (SJU) - Hartford (BDL)
    SJU - BDL • Nonstop BDL - SJU • Nonstop
    $572
    $479
    per traveler
    found 0 hours ago
    Holiday Inn Express Southington by IHG

Where to stay near Ware

Discover the charm of Ware, MA, where the city center offers a blend of outdoor activities and scenic views. Explore Hall Rd for a romantic stroll, or enjoy family-friendly experiences nearby. Whether for leisure or business travel, Ware provides a welcoming atmosphere to relax and explore.
A rural farm with stone walls, wooden barns, and a cow in a fenced area.

Sturbridge

For families and history enthusiasts seeking a memorable trip, Sturbridge offers a blend of culture and nature that makes it an ideal destination. Explore the charming Old Sturbridge Village, immerse yourself in the beauty of Wells State Park, and stroll through the historic Sturbridge Common Historic District. With its diverse attractions and activities year-round, Sturbridge is easily accessible, located about 18 miles by car from Ware. Choosing Sturbridge for your stay ensures a delightful experience filled with rich history and outdoor adventures.

A road flanked by trees with autumn foliage, a fence along one side, and a clear sky.

West Brookfield

Experience the charm of West Brookfield, an excellent hub for family and nature enthusiasts eager to explore attractions such as the Rock House Reservation and the historic Old Sturbridge Village. This picturesque city also offers serene views along the Quaboag River, making it perfect for those seeking outdoor adventures or a romantic getaway. Located about 4 miles from Ware, West Brookfield is a smart choice for travelers looking to immerse themselves in local culture while enjoying scenic beauty.

Warren

Make your vacation planning effortless by staying in Warren, a haven for family and nature travelers due to its charming outdoor scenery and a variety of attractions. Explore the cultural richness of Old Sturbridge Village, unwind at the serene Rock House Reservation, or enjoy a good read at the West Warren Library Association. Located about 4 miles from Ware, Warren's seasonal appeal peaks in March, June, and August, making it a smart choice for your trip.

Gilbertville

Immerse yourself in Gilbertville, where family and nature travelers can easily access a wealth of outdoor and cultural experiences. This charming city serves as a perfect base for exploring the nearby Rock House Reservation and the historic Old Sturbridge Village, while also being close to the University of Massachusetts Amherst. Just about 4 miles from Ware, Gilbertville offers a unique blend of recreational areas and cultural venues, making it a smart choice for your stay.

A calm river surrounded by autumn-colored trees.

Palmer

Travelers visiting the area often choose Palmer, especially families and adventure enthusiasts seeking close proximity to outdoor activities and cultural experiences. With attractions like Old Sturbridge Village and Rock House Reservation, Palmer offers a blend of history and nature that appeals to diverse interests. Just about 6 miles from Ware, it provides easy access to recreation, education, and local events. Palmer is a smart choice for your stay, ensuring a memorable vacation experience.

Discover the most popular places to visit in Ware

Hardwick Vineyard and Winery

This historic 1795 Federal-style mansion houses a charming vineyard producing distinctive New England wines. Sample cranberry-grape blends while enjoying scenic countryside views from the timber-frame barn.
See properties

Ware Hotel Deals

A hotel entrance with a covered walkway, columns, and a brick facade.

Holiday Inn Express & Suites Sturbridge by IHG

Holiday Inn Express & Suites Sturbridge by IHG
2.5 star property
12.8 mi from Ware
9.2 out of 10, Wonderful, (1,006 reviews)
$92 nightly
The price is $103
Nov 29 - Nov 30
Total with taxes and fees
Holiday Inn Express & Suites Sturbridge 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 Ware

Frequently Asked Questions

How much does a Ware vacation package cost?

Offering great value package deals from $379 on Expedia, you'll be pleasantly surprised at how much a vacation to Ware costs! Expedia's packages simplify travel planning and maximize your savings.

What are the cheapest months to go to Ware?

You can usually find reduced prices and better availability in January, October and December. Browse our cheap Ware vacation packages and you could get some excellent off-season deals.

How many days is enough for Ware?

Usually, a handful of days is enough to check out the main attractions during your Ware vacation. However, if you prefer to have more time to rest or take day trips, think about extending your trip.

How to find the best Ware package deals?

Use Expedia's handy filters to help you find some unbeatable Ware package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or search for Ware package deals in the off-season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.

Is it cheaper to book a Ware vacation as a package?

Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll generally score a better deal than booking each component individually. And you'll still have the freedom to create a personalized Ware vacation by choosing your favorite airline, accommodation type and car class.

When to book a vacation package to Ware?

If you're considering an impromptu Ware vacation, check out our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can land incredible deals on your hotels and flights by booking ahead.

Does Expedia offer Book Now, Pay Later Ware vacation packages?

If you're anything like us, you love traveling but are not a fan of the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the cost of your Ware vacation across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great vacation packages with payment plans as soon as you spot them.

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