Winchendon Vacations from $590

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Your Winchendon Vacation

When you choose a Winchendon vacation package, it's all about enjoying your adventure to the fullest. Delve into the highlights of this unique city knowing that all your travel needs have been worked out in advance. If seeing the sights is on your list of things to do during your trip to Winchendon, head over to popular attractions like Lake Dennison State Recreation Area. Your dream Winchendon vacation is just clicks away. Browse flights, hotels and more on Expedia for a getaway that's tailored to suit your style.

The Latest Winchendon vacation packages

Price found within the past 48 hours. Click for updated prices.
Trainmasters Inn

Trainmasters Inn

3 out of 5
Price was $598, price is now $590 per person
$590
per person
Dec 22 - Dec 28
found 21 hours ago
Roundtrip flight included
Washington (DCA) to Worcester (ORH)
19.2/10 Exceptional! (381 reviews)
It was beyond our expectations. Great room and great muffins.

Reviewed on Nov 10, 2025

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Discover the most popular places to visit in Winchendon

The Winchendon School

Explore the campus of The Winchendon School as part of your travels around Winchendon. While you're in the area, wander around the parks.

The Winchendon School

Lake Dennison State Recreation Area

You can take time to visit Lake Dennison State Recreation Area during your travels to Winchendon. Discover the area's waterfalls and mountain views.

Lake Dennison State Recreation Area

Winchendon Hotel Deals

Cozy Lakefront Cottage

Cozy Lakefront Cottage

Winchendon
9.8/10 Exceptional! (19 reviews)
Spend your time enjoying nature and the outdoors. Do your grocery shopping during the day as the road is winding and dark. Enjoy evenings sitting around the firepit or on the porchswing literally on the water!! Access to canoes and paddles at your leisure. Full kitchen.

Reviewed on Sep 28, 2025

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Cozy Lakefront Cottage
Modern Waterfront Gem w/ Dock on Lake Monomonac

Modern Waterfront Gem w/ Dock on Lake Monomonac

3 out of 5
Winchendon
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Modern Waterfront Gem w/ Dock on Lake Monomonac
The Colonial Hotel

The Colonial Hotel

3 out of 5
625 Betty Spring Road, Gardner, MA
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $161 total per night from Nov 19 to Nov 20
$161 total
Nov 19 - Nov 20
Total with taxes and fees
8.8/10 Excellent! (1,002 reviews)
Very nice hotel.

Reviewed on Nov 13, 2025

The Colonial Hotel
See all 208 properties in Winchendon
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.

Find the Best Winchendon Vacation Packages

Winchendon Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Worcester Regional Airport (ORH)
Population
4,200
Top Sights
Doanes Falls, Royalston Falls and Dunn State Park

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Frequently asked questions

How much does a Winchendon vacation package cost?
Offering excellent value package deals from $590 on Expedia, you'll be pleasantly surprised at how much a vacation to Winchendon costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Winchendon?
You can typically find lower prices and better availability in November, December and January. Check out our cheap Winchendon vacation packages and you could land some excellent off-season deals.
How many days is enough for Winchendon?
Usually, a handful of days is enough to visit the main attractions during your Winchendon vacation. However, if you want to have some time to rest or take day tours, consider extending your trip.
How to find the best Winchendon package deals?
Start your search for a Winchendon package deal by entering your preferred trip dates and destination under our "Packages" tab. Then select a few filters, like "Popular locations" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Winchendon package deal right away, just change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Winchendon getaway off to a flying start.
Is it cheaper to book a Winchendon vacation as a package?
You can enjoy significant savings on your Winchendon escape by booking a customized vacation package. Click on the "Package" heading, then enter your travel dates and destination to browse some great airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Winchendon?
Score amazing discounts by booking your flights in advance with Expedia. If spontaneity is more your style, grab one of our last-minute deals for a spur-of-the-moment Winchendon adventure.
Does Expedia offer Book Now, Pay Later Winchendon vacation packages?
If you're anything like us, you love jet-setting around the world but don't love the big price tag that can sometimes come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the cost of your Winchendon break over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure cheap 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.