Winchendon Vacations from $640
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
The Colonial Hotel
$744
per person
Nov 10 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Sacramento (SMF) to Worcester (ORH)
9/10 Wonderful! (1,009 reviews)
Stood here overnight since we were going to see a University up there. The room was clean and staff was very friendly. The place is beautiful. My son said he felt like he was in Hogwarts and I said it gave off The Shinning vibes. This place must be beautiful during the holidays. Will stay here again.
Reviewed on Sep 3, 2026
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.
Blueberry Island
Blueberry Island sits privately in Lake Monomonac, spanning the NH-MA border. While enjoying the lake's recreational offerings, respect the island's residential nature and focus on surrounding public areas instead.
Winchendon Community Park
Winchendon Community Park offers a picturesque amphitheater for concerts and community events during warmer months. Enjoy dog-friendly trails before settling in for performances under the stars.
Monument Park
Monument Park is just one of the places to see in Winchendon, so why not enjoy the other things to explore during your travels? While you're in the area, wander around the parks.
Wetmore Trailhead
Wetmore Trailhead opens to miles of serene forest and wetland paths in Birch Hill Wildlife Management Area. Bring sturdy shoes and binoculars for spotting native birds along the well-maintained trails.
Beals Memorial Library
This historic library houses literary treasures and sensory-friendly programs for neurodivergent visitors. Browse the collection, join a book club, or borrow unique items from their "Library of Things" like telescopes.
Hyde Park
Explore the great outdoors at Hyde Park, a lovely green space in Winchendon. While you're in the area, wander around the parks.
Winchendon Town Hall
The Winchendon Municipal Building serves as the town's administrative center. Visitors can observe civic operations during business hours and occasionally attend public meetings.
Winchendon Hotel Deals
Modern Waterfront Gem w/ Dock on Lake Monomonac
Winchendon MA
10/10 Exceptional! (9 reviews)
"The cottage was very cute and the lot was nice with a bit of elbow room between the cottage and the neighbors. Situated right on the lake it was a nice setting for relaxing which was exactly what we were looking for."
Reviewed on Jun 16, 2026
Cozy Lakefront Cottage
Winchendon MA
9.8/10 Exceptional! (24 reviews)
"What a wonderful way to bring the summer to a close. Our host was truly remarkable and so very quick to respond to each and every contact. Our stay was peaceful and relaxing which is exactly what I needed. The cottage is warm, comfortable and roomy. The lake is just beautiful and seeing a Loon up ..."
Reviewed on Aug 31, 2026
Great Wolf Lodge Boston / Fitchburg, MA
150 Great Wolf Dr Fitchburg MA
$184 nightly
$205 total
Sep 10 - Sep 11
Total with taxes and fees
8.6/10 Excellent! (1,009 reviews)
"Excellent service, clean room, bathroom. Good recreation area. Good attitude from employees. Very happy to be there. My family enjoyed."
Reviewed on Sep 2, 2026
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 |
More vacations you might like
Frequently asked questions
How much does a Winchendon vacation package cost?
Offering excellent value package deals from $640 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.
