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Vacation Rentals in Winchendon, Massachusetts

about Winchendon

Search vacation deals on homes, villas, cabins, cottages, apartments and condos in destinations all over the world. Click the "rental results" tab to browse Winchendon, Massachusetts vacation rentals and inquire about your favorites. If you cant find what youre looking for, consider nearby destinations, or come back for a visit - vacation home rentals in Winchendon are added and updated every week!

Compared to hotels, Winchendon vacation rentals are much more family-friendly and flexible, offering a lot more space, a lot more savings, and a lot more amenities - like private pools, gourmet kitchens, and pet-friendly accommodations! Tip: Save money by taking advantage of cheap weekly rates.

Winchendon, Massachusetts Vacation Rentals and Tourism

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Winchendon things to do


Monadnock State Park

I love hiking here. Tons of people come on the weekends with their kids so it's fun to take the slightly harder trails up and down. It's easy and only more


Woodbound Inn

I had stumbled on this quant inn, with my 2 young daughter, while making our way to see my horse. They were hungry; it was lunch time. We ate a nice, more


Lake Dennison

I'm sure the camping is fun, but don't let your six year old fish in ankle deep water or the power hungry DCR employee will stop traffic to explain how more


Gardner Cinemas

Not bad. The prices are reasonable and the theater is as clean as some of the others. This isn't a top notch theater you should go out of your way more


Cruiser's Malt Shoppe

Ewwwwwh! If you want fat laden fast food served by dirty people this is your place! And you can even leave smelling like the place! yUCKread more


Rails to Trails

This Rails to Trails starts in Jaffrey and goes all the way to Winchedon, MA. Parking is available at the Jaffrey end at the town lot, or along the more


Gardner Municipal Golf Course

Oh - GREAT course. Nice clubhouse. Restaurant was recently taken over by new management. Not that it needed it, but whatever. 18 holes. First nine more


Shattuck Golf Club

So far, so good! We'll update in November after the wedding. The Shattuck is a gorgeous location at the foot of Mt. Monadnock. We're getting married more


North Ridge Mountain Guides

I did a mount Washington winter climb with NRMG in Feb 2013. Jamie was our guide. He is a true professional and an expert at what he does. It was always more


Penguin Roadracing School

Motorcycle roadracing school run by former AMA Pro and many CCS national champion Eric Wood. The Advanced school is an excellent value for the money. more


Otter River State Forest

Really spacious and gorgeous without the crowds of other state forests. A nice shallow pond for the kids. Only downside is that you can still here more


Frederick Historic Piano Collection

This is a world-class antique piano collection, located about 70 miles outside Boston. What makes this place outstanding, however, is that the more


Winchendon Rod & Gun Club

The Winchendon Rod & Gun Club hosted Project Appleseed over Columbus Day Weekend. I'd never been to the club before, but for a small, rural club I more


Mount Watatic

Great, short hike with very rewarding summit views! Easy hike for winter too, just bring spikes / traction. Entire summit covered in blueberry bushes - more


Humiston Field & Playground

Pros: Lighted baseball/soccer field (with timed sprinklers) with bleachers, dugouts. Lighted basket ball court that they flood & turn into an outdoor more

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