Winchendon Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Winchendon

Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA

3.5 out of 5
150 Great Wolf Dr Fitchburg MA
The price is 3.918.104 ₫ per night from 31 Aug to 1 Sept
3.918.104 ₫
4.376.523 ₫ total
31 Aug - 1 Sept
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"Clean room, great staff, food is good, the house cleaner lady from 360 did a wonderful job with all the questions we needed. 👍👍👍👍🙏🙏. Will come again."

Reviewed on 2 Aug 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
The price is 4.021.973 ₫ per night from 4 Aug to 5 Aug
4.021.973 ₫
4.492.671 ₫ total
4 Aug - 5 Aug
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
"The hotel was great by most accounts. However, apparently there was a leak when I bathed and it leaked downstairs. Our complaint was maintenance making repairs at 8am without any notice. We were literally in the bed when the whole floor started shaking and the loudness of the tools to go through ..."

Reviewed on 2 Aug 2026

The Colonial Hotel
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 out of 5
175 Key Rd Keene NH
Fully refundableReserve now, pay when you stay
The price is 3.102.928 ₫ per night from 1 Sept to 2 Sept
3.102.928 ₫
3.366.677 ₫ total
1 Sept - 2 Sept
includes taxes & fees
Keene Elm City Hotel, an Ascend Collection Hotel
See all 228 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.

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.
See properties

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.