Winchendon Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Winchendon

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
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 S$285 per night from 17 Jul to 18 Jul
S$285
17 Jul - 18 Jul
includes taxes & fees
8.4/10 Very Good! (1,025 reviews)
"Really enjoyed the wolf den suite. Plenty of room, microwave/mini fridge in room. Free ears at gift shop after check in! Download the app before going, willow will help you with anything."

Reviewed on 13 Jul, 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
8.6/10 Excellent! (1,011 reviews)
"Restaurant onsite was delicious, staff were welcoming and willing to answer any questions that may come up. Hotel rooms are newer but still a little outdated and there is a strong smell of "old" building in the hallways."

Reviewed on 13 Jul, 2025

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The Colonial Hotel
See all 195 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 holiday package cost?
Offering excellent value package deals on Expedia, you'll be pleasantly surprised at how much a holiday 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 holiday packages. Bear in mind that school holiday periods and local events and festivals can have an impact on prices, so do a little research before booking.
How many days is enough for Winchendon?
With a well-organised itinerary, you can easily hit the most popular Winchendon attractions in a few days. But if you prefer to venture off the beaten track or go on day trips, consider booking your Winchendon holiday for longer.
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 holiday as a package?
You can enjoy significant savings on your Winchendon escape by booking a customised holiday 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 holiday 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 favourite 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 holiday. 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 holiday package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.