Winchendon Vacations from $438

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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 $474, price is now $438 per person
$438
per person
Sep 26 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Jackson (JAN) to Worcester (ORH)
7.2/10 Good! (27 reviews)
Staff and owners do not speak any English, communication was very difficult. There seem to be some long term renters living here as well.

Reviewed on Jul 15, 2026

The Colonial Hotel

The Colonial Hotel

3 out of 5
Price was $590, price is now $540 per person
$540
per person
Sep 26 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Jackson (JAN) to Worcester (ORH)
8.8/10 Excellent! (1,005 reviews)
Did eat breakfast at the hotel. Room was clean

Reviewed on Jul 14, 2026

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Stay near popular Winchendon attractions

Lake Dennison State Recreation Area

10.0/10 (1 review)
This serene 85-acre lake offers swimming, fishing, and access to 50+ miles of mountain biking trails. Reserve one of the 150 wooded campsites early for a prime lakeside spot to fully experience this natural retreat.
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Winchendon Hotel Deals

Cozy Lakefront Cottage

Cozy Lakefront Cottage

Winchendon MA
9.8/10 Exceptional! (20 reviews)
"Such a cute cottage on a gorgeous lake. Our host was wonderful and happened to be on the other side of the property when we arrived and we had a chance to chat. She was super accommodating. The place had everything we needed to cook meals in the kitchen and on the grill. The house was well stocked ..."

Reviewed on May 27, 2026

Get rates
Cozy Lakefront Cottage
Enjoy your stay in an antique home in an antique toy museum!

Enjoy your stay in an antique home in an antique toy museum!

Winchendon MA
$367 nightly
The price is $388 total per night from Jul 16 to Jul 17
$388 total
Jul 16 - Jul 17
Total with taxes and fees
9.4/10 Exceptional! (8 reviews)
Quick stop between baseball games
"Perfect location between game locations. Easy walk to restaurants. House was clean and tidy. Easy check in/out process Owner was easy to communicate with."

Reviewed on Jul 3, 2024

Enjoy your stay in an antique home in an antique toy museum!
Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA

3.5 out of 5
150 Great Wolf Dr Fitchburg MA
$149 nightly
The price is $166 total per night from Jul 16 to Jul 17
$166 total
Jul 16 - Jul 17
Total with taxes and fees
8.6/10 Excellent! (1,026 reviews)
"Family friendly, my kids really enjoyed it."

Reviewed on Jul 13, 2026

Great Wolf Lodge Boston / Fitchburg, MA
See all 234 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 $438 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.