Deals on vacations and trips to Winchendon

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

Gardner Inn

2 out of 5
Price was $538, price is now $482 per person
$482
per person
Aug 13 - Aug 19
found 12 hours ago
Roundtrip flight included
Chicago (MDW) to Worcester (ORH)
Free WiFi in public areas is available at this hotel. Take advantage of the free self parking.
The Colonial Hotel

The Colonial Hotel

3 out of 5
Price was $947, price is now $879 per person
$879
per person
Aug 13 - Aug 19
found 12 hours ago
Roundtrip flight included
Chicago (MDW) 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

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
Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA

3.5 out of 5
150 Great Wolf Dr Fitchburg MA
$149 nightly
The price is $166 total per night
$166 total
Jun 30 - Jul 1
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
$170 nightly
The price is $190 total per night
$190 total
Jun 30 - Jul 1
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

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 out of 5
175 Key Rd Keene NH
Free Cancellation
Reserve now, pay when you stay
$109 nightly
The price is $118 total per night
$118 total
Jun 30 - Jul 1
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
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
$167 nightly
The price is $187 total per night
$187 total
Jul 12 - Jul 13
Total with taxes and fees
This smoke-free hotel includes 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
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St Keene NH
Free Cancellation
Reserve now, pay when you stay
$127 nightly
The price is $138 total per night
$138 total
Jul 1 - Jul 2
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.

Popular places to visit

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

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

Blueberry Island

Commune with nature and explore the great outdoors at Blueberry Island during your travels in Winchendon. While you're in the area, wander around the parks.

Blueberry Island

Frequently asked questions

How much are vacation packages to Winchendon?
Vacation packages, including flights and hotels in Winchendon, start from as little as $482. 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

A hilly landscape with a tower on top, dense forest, and a cloudy sky.
A river reflecting autumn trees and a dense forest.
A calm river reflecting autumn trees and a clear sky.
A calm lake reflecting autumn trees with red, orange, and yellow foliage.