Winchendon Vacation Packages 2026 from $670

Winchendon flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Gardner Inn

$670

per person

Oct 14 - Oct 18

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Worcester (ORH)

Free WiFi in public areas is available at this hotel. Take advantage of the free self parking.

The Colonial Hotel

$928

per person

Oct 14 - Oct 18

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Worcester (ORH)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.

Top Winchendon hotels deals

Cozy Lakefront Cottage

Winchendon MA

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This vacation home features a garden, a picnic area, and laundry facilities. Barbecue grills are provided for your convenience.

Kitchen

Washer

Modern Waterfront Gem w/ Dock on Lake Monomonac

Winchendon MA

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This vacation home features barbecue grills.

Kitchen

Air conditioning

Enjoy your stay in an antique home in an antique toy museum!

Winchendon MA

$372 nightly

$393 total

Sep 1 - Sep 2

Total with taxes and fees

A garden is available at this vacation home.

Great Wolf Lodge Boston / Fitchburg, MA

150 Great Wolf Dr Fitchburg MA

$187 nightly

$209 total

Sep 1 - Sep 2

Total with taxes and fees

This smoke-free resort features free water park access, 4 indoor pools, and a restaurant. Bring the family and enjoy the lazy river, bowling alley, and mini golf. Enjoy the seasonal outdoor pool and unwind at the bar/lounge and poolside bar.

The Colonial Hotel

625 Betty Spring Road Gardner MA

Free Cancellation

Reserve now, pay when you stay

$153 nightly

$171 total

Sep 9 - Sep 10

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.

Motel 6 Leominster, MA

48 Commercial Rd Leominster MA

Free Cancellation

$81 nightly

$91 total

Sep 3 - Sep 4

Total with taxes and fees

This motel includes free WiFi in public areas and laundry facilities. Staff at the 24-hour front desk can provide around-the-clock assistance.

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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)

You can take time to visit Lake Dennison State Recreation Area during your travels to Winchendon. Discover the area's waterfalls and mountain views.

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Frequently asked questions

How much are vacation packages to Winchendon?

Vacation packages, including flights and hotels in Winchendon, start from as little as $670. Make your travel fantasies come to life and secure your vacation with Travelocity today.

Where can I get the best vacation package deals for Winchendon?

Find your dream escape at Travelocity. With access to 400 airlines and an incredible 1,000,000 properties worldwide, creating the perfect Winchendon package deal couldn't be simpler.

Why should I purchase my Winchendon vacation bundle via Travelocity?

Nothing beats the peace of mind knowing you've scored the best price available — that's our Price Match Guarantee. Add to that our inspiring range of magical destinations and 24/7 team of customer service professionals and you've got the blueprint for an unforgettable vacation.

Will I save money on my Winchendon car rental if I bundle it with my hotel or flight?

Combining your car, flight and hotel into a Winchendon vacation package is a surefire way to score the best deal. Plus, having your own rental car gives you total freedom to find your way to all those landmarks you'd like to see. Sitting 55 mi away from Winchendon, Fenway Park is one attraction that should be on your itinerary. Top up the tank and make a day trip of it.

Which airport is best for Winchendon?

Logan Intl. Airport (BOS) is 55 mi from the city center and is the starting point for many fun adventures. Alternatively, Bradley Intl. Airport (BDL) is 60 mi away from central Winchendon and Manchester-Boston Regional Airport (MHT) is 35 mi away from central Winchendon.

What is there to do in Winchendon?

Lake Dennison State Recreation Area is one of the memorable sights that make Winchendon such a popular tourist destination. But allow some extra time to experience its lesser-known attractions too. This is often where the best vacation memories are made.

Where should I stay when visiting Winchendon?

The Amazing Lakefront property, Private in ground pool, Epic views of Lake Monomonac is the first choice of many visitors. Book soon before it's too late.