Deals on vacations and trips to Winchendon

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Hunters Grille and Tap at The Grafton Inn

Hunters Grille and Tap at The Grafton Inn

2.5 out of 5
Price was $389, price is now $355 per person
$355
per person
Feb 19 - Feb 22
found 17 hours ago
Roundtrip non-stop flight included
Houston (HOU) to Worcester (ORH)
This inn doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace and a fireplace in the lobby are also provided.
The Colonial Hotel

The Colonial Hotel

3 out of 5
Price was $559, price is now $525 per person
$525
per person
Mar 2 - Mar 5
found 20 hours ago
Roundtrip flight included
Houston (HOU) 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.
Gardner Inn

Gardner Inn

2 out of 5
Price was $482, price is now $478 per person
$478
per person
Mar 2 - Mar 5
found 20 hours ago
Roundtrip flight included
Houston (HOU) to Worcester (ORH)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.

Top Winchendon hotels deals

Cozy Lakefront Cottage

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
Modern Waterfront Gem w/ Dock on Lake Monomonac

Modern Waterfront Gem w/ Dock on Lake Monomonac

3 out of 5
Winchendon MA
Get rates
This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. Barbecue grills are provided for your convenience.
Kitchen
Parking included
Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA

3.5 out of 5
150 Great Wolf Dr Fitchburg MA
Free Cancellation
$179 nightly
The price is $200 total per night
$200 total
Jan 20 - Jan 21
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

The Colonial Hotel

3 out of 5
625 Betty Spring Road Gardner MA
Free Cancellation
Reserve now, pay when you stay
$160 nightly
The price is $179 total per night
$179 total
Jan 14 - Jan 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 gym and perks like free self parking.
Pool
Hot Tub
Motel 6 Leominster, MA

Motel 6 Leominster, MA

2 out of 5
48 Commercial Rd Leominster MA
Free Cancellation
$83 nightly
The price is $92 total per night
$92 total
Jan 20 - Jan 21
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.
Pet friendly
Free WiFi
Doubletree by Hilton Hotel Leominster

Doubletree by Hilton Hotel Leominster

4 out of 5
99 Erdman Way Leominster MA
Free Cancellation
Reserve now, pay when you stay
$141 nightly
The price is $158 total per night
$158 total
Jan 25 - Jan 26
Total with taxes and fees
This hotel features 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.
Pool
Parking included
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See all available properties in Winchendon
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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.

Popular places to visit

The Winchendon School

Explore the campus of The Winchendon School as part of your travels around Winchendon. While you're in the area, wander around the parks.

The Winchendon School

Lake Dennison State Recreation Area

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

Lake Dennison State Recreation Area

Wendall P. Clark Memorial

After visiting Wendall P. Clark Memorial, make a plan to see the other sights and activities in Winchendon. While you're in the area, wander around the parks.

Wendall P. Clark Memorial

Frequently asked questions

How much are vacation packages to Winchendon?
Vacation packages, including flights and hotels in Winchendon, start from as little as $355. 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.

Photos of local treasures

Browse Winchendon vacation photos for more inspiration