Winchendon Vacation Packages 2026 from $425

Winchendon flight + hotel vacation packages

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

Gardner Inn

$425

per person

Oct 3 - Oct 5

found 4 hours ago

Roundtrip flight included

Nashville (BNA) to Worcester (ORH)

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

The Colonial Hotel

$723

per person

Oct 2 - Oct 4

found 1 day ago

Roundtrip non-stop flight included

Philadelphia (PHL) 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

Get rates

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

Kitchen

Washer

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

Winchendon MA

$371 nightly

$392 total

Jul 14 - Jul 15

Total with taxes and fees

A garden is available at this vacation home.

Kitchen

Free WiFi

Great Wolf Lodge Boston / Fitchburg, MA

150 Great Wolf Dr Fitchburg MA

$149 nightly

$166 total

Jul 14 - Jul 15

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.

Pool

Restaurant

The Colonial Hotel

625 Betty Spring Road Gardner MA

Free Cancellation

Reserve now, pay when you stay

$170 nightly

$190 total

Jul 19 - Jul 20

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.

Pool

Hot Tub

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH

Free Cancellation

Reserve now, pay when you stay

$119 nightly

$129 total

Jul 15 - Jul 16

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Pool

Breakfast included

Best Western Plus Keene Hotel

401 Winchester St Keene NH

Free Cancellation

Reserve now, pay when you stay

$119 nightly

$129 total

Jul 14 - Jul 15

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 24-hour gym and free perks like buffet breakfast and free self parking.

Pool

Breakfast included

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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 $425. 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.