Winchendon Holidays

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Your Winchendon Holiday

Our holiday packages to Winchendon provide countless opportunities to discover new sights, sounds and tastes. And with all the travel planning taken care of, you'll be free to enjoy your city break in the way that you deserve. During your trip to Winchendon, give yourself plenty of time for sightseeing. A popular place to start exploring is Lake Dennison State Recreation Area. Your dream Winchendon holiday is a couple of clicks away. Search airfares, hotels and more on Expedia for an adventure that's tailored just for you.

Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Winchendon Holiday

Winchendon Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Worcester Regional Airport (ORH)
Population
4,200
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Royalston Falls, Doanes Falls and Dunn State Park

Our pick of the best Winchendon Hotel Deals

VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac
VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac
Winchendon
10/10 Exceptional! (6 reviews)
Beautiful
"Everything about this property was beautiful. The home itself being located right on the water was perfect for kayaking, fishing, evenings by the fire, relaxing and reconnecting. The house is gorgeous, comfortable, and had everything you might need/want. We enjoyed the game room - jenga and family ..."

Reviewed on 4 Jul. 2024

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VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac
Amazing Lakefront property, Private Pool on Lake Monomonac at Tatum's Place
Amazing Lakefront property, Private Pool on Lake Monomonac at Tatum's Place
Winchendon
10/10 Exceptional! (1 review)
LAKE HOUSE
"Very nice house on lake with great pool area. Close to town, but not too close. Comfortable beds. Co-located and adjacent to other VRBO houses able to accomadate large family gatherings."

Reviewed on 27 Sep. 2024

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Amazing Lakefront property, Private Pool on Lake Monomonac at Tatum's Place
VRBO Top 10 - Copley's Lakefront Cottage and Guest House on its own Peninsula
VRBO Top 10 - Copley's Lakefront Cottage and Guest House on its own Peninsula
Winchendon
10/10 Exceptional! (4 reviews)
Getaway
"This property was great. Wonderfully modern lake front home. Recommend renting the pontoon to fish for larger fish. Kayaks, Paddleboards, great restaurants and sauna. Picture perfect scenery."

Reviewed on 24 Aug. 2024

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VRBO Top 10 - Copley's Lakefront Cottage and Guest House on its own Peninsula
See all 189 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.
All Inclusive Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Frequently asked questions

How much does a Winchendon holiday package cost?
The cheapest Winchendon holiday package is , so your dream trip can become a reality — without spending an arm and a leg. Combine flights, hotels, car rentals and more to create a package that matches your travel style.
How do I get a cheap travel package to Winchendon?
Imagine all the amazing things you could do in Winchendon with extra cash in your pocket. Watch your savings stack up when you bundle your flights, hotels and other bookings into a Winchendon holiday package. You have plenty of choice when you book with Expedia too. In fact, you can choose from more than 550 air carriers and 1 000 000 properties globally. Whether you’re taking a holiday with the family or adventuring alone, exploring Winchendon is better with a package.
Where should I stay in Winchendon?
A trip to Winchendon isn’t complete without checking out Lake Dennison State Recreation Area, Wetmore Trailhead and The Winchendon School. Stay close to these top attractions and make sightseeing a breeze.
How far in advance should I book my Winchendon holiday?
Your best bet is to book early. Air carriers typically release flights nearly 12 months ahead of departure, and this is a great opportunity to land some of the cheapest prices. Boss just told you to take all your holiday days next month? No sweat. Expedia are never short of fantastic bargains to send you on the getaway of your dreams, at a price you can afford.
What does an Expedia Winchendon travel package include?
You can choose from a combination of rental cars, hotels and flights. Once you’ve made your booking, you can add some activities and experiences. Want to pick your fare class? That’s easily done too. The choice is yours when it comes to creating your perfect Winchendon trip.
What should I know before booking a Winchendon travel package?
Whether it’s adventure or relaxation you’re seeking, a Winchendon holiday package lets you plan your escape your way. Plus, you’ll get access to great discounts when you combine your hotel with your rental car and flights. The more you bundle, the bigger the savings!
Can I choose my airline with a Winchendon Expedia holiday package?
With a holiday package, you’re the boss. Whether you want to fly to Winchendon in business or coach, simply choose from the available airline options. Expedia has access to over 550 airline partners worldwide.
If I'm not able to travel, can I cancel my Winchendon holiday package?
Don’t worry if you’re rethinking your Winchendon holiday package — you can cancel or change your booking. And if you’ve booked it within 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur a fee from your airline, hotel or car rental company. We totally get that your circumstances can suddenly change, so head to our Customer Service Portal if that occurs. When you’re ready to make changes, we’ll be here to help.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.