Winchendon Vacations

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Find the Best Winchendon Vacation Packages

Winchendon Hotel Deals

Modern Waterfront Gem w/ Dock on Lake Monomonac
Modern Waterfront Gem w/ Dock on Lake Monomonac
Winchendon
10/10 Exceptional! (2 reviews)
Wonderful!
"We couldn’t have had a better experience! Such a beautiful cottage—immaculate, gorgeous decor, spectacular deck w/exquisite lake view, super-cozy beds, outstanding communication with hosts! We actually had local plans canceled due to a late March “wintry” ice storm, but couldn’t imagine a better ..."

Reviewed on 1 April 2025

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Modern Waterfront Gem w/ Dock on Lake Monomonac
Great Wolf Lodge Boston / Fitchburg, MA
Great Wolf Lodge Boston / Fitchburg, MA
3.5 out of 5
150 Great Wolf Dr, Fitchburg, MA
Fully refundableReserve now, pay when you stay
The price is AED 657 per night from May 4 to May 5
AED 657
AED 875 total
includes taxes & fees
4 May - 5 May
8.4/10 Very Good! (947 reviews)
"The stay has been great so far. Not sure why I payed $15 for parki bc though"

Reviewed on 18 April 2025

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
The price is AED 514 per night from Apr 21 to Apr 22
AED 514
AED 574 total
includes taxes & fees
21 Apr - 22 Apr
8.6/10 Excellent! (1,003 reviews)
"Very nice property. Lots of amenities"

Reviewed on 16 April 2025

The Colonial Hotel
See all 184 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.

Frequently asked questions

How much does a Winchendon vacation package cost?
Offering excellent value package deals 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?
Travel in the shoulder or low season and you’re likely to score cheap Winchendon vacation packages. Bear in mind that school vacation periods and local events and festivals can have an impact on prices, so do a little research before booking.
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.
How to plan a trip to Winchendon?

  1. Choose when to travel: Check your schedule and get packing. Your favorite time of year and the type of activities available will also help you decide when to escape to Winchendon.
  2. Set a budget: Factor in expenses like flights, food and transportation when working out how much to save for your trip to Winchendon. Then, select a hotel that fits your budget, whether that’s an affordable option or a deluxe retreat.
  3. Decide how long to go for: Now that you’re more familiar with Winchendon, you can work out the ideal length of your vacation. Create a draft itinerary and allocate enough time to get through everything on your must-do list.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that’s left is to find a Winchendon vacation package that brings all your bookings together.

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

Explore the great outdoors at Lake Dennison State Recreation Area, a lovely green space in Winchendon. Discover the area's waterfalls and mountain views.

Lake Dennison State Recreation Area