Winchendon Vacations from $587

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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.
Gardner Inn

Gardner Inn

2 out of 5
Price was $646, price is now $587 per person
$587
per person
May 15 - May 19
found 14 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Worcester (ORH)
5.4/10 (23 reviews)
Great for a quick stay while passing through!

Reviewed on Apr 10, 2026

The Colonial Hotel

The Colonial Hotel

3 out of 5
Price was $904, price is now $782 per person
$782
per person
May 15 - May 19
found 14 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Worcester (ORH)
8.8/10 Excellent! (1,002 reviews)
Bathroom should have a safety grab bar in the shower as well as hooks for towels.

Reviewed on Apr 5, 2026

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Discover the most popular places to visit in Winchendon

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

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

Winchendon Hotel Deals

Cozy Lakefront Cottage

Cozy Lakefront Cottage

Winchendon MA
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
Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA

3.5 out of 5
150 Great Wolf Dr Fitchburg MA
$179 nightly
The price is $200 total per night from May 3 to May 4
$200 total
May 3 - May 4
Total with taxes and fees
8.6/10 Excellent! (1,020 reviews)
The Spring Fest for Kids and family was excellent.

Reviewed on Apr 13, 2026

Great Wolf Lodge Boston / Fitchburg, MA
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 Apr 19 to Apr 20
$161 total
Apr 19 - Apr 20
Total with taxes and fees
8.8/10 Excellent! (1,010 reviews)
Yes it's safe

Reviewed on Apr 13, 2026

The Colonial Hotel
See all 227 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 $587 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.