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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured Cottages in Winchendon and around

Cottage beside a waterfall
Property grounds

Cottage beside a waterfall

9.4 out of 10, Exceptional, (3)
"What a unique place to stay with a waterfall in the backyard! Quiet, beautiful grounds on the property. Clean, private and well appointed. "
The price is €226
includes taxes & fees
28 Aug - 29 Aug
Cottage beside a waterfall
2 queen and 2 twin beds
Interior

2 queen and 2 twin beds

9.6 out of 10, Exceptional, (10)
"We really enjoyed our stay. The seating outside was lovely!"
2 queen and 2 twin beds
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
Terrace/patio

2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock

10.0 out of 10, Exceptional, (17)
"It was a great place for what I needed. I was working in the area and it was a great quiet location, with nice scenery. The place was clean and spacious, with plenty of space to cook. I would definitely stay here again."
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Exterior

Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board

9.6 out of 10, Exceptional, (26)
"We stayed for 3 nights and had a lot of fun fishing. We caught so many fish. The cottage was cozy and we had everything we needed. "
The price is €438
includes taxes & fees
26 Aug - 27 Aug
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Cottage on Partridge Pond
Interior

Cottage on Partridge Pond

10.0 out of 10, Exceptional, (21)
"Property was spotless and well stocked"
Cottage on Partridge Pond
Finnish Cabin with Sauna on Lake Monomonac
Exterior

Finnish Cabin with Sauna on Lake Monomonac

2.0 star property
10.0 out of 10, Exceptional, (10)
"This was a very nice cozy cottage, with a nice view of the water. The host was friendly and accommodating. We look forward to staying again."
Finnish Cabin with Sauna on Lake Monomonac
Lemon Drop Cottage a private cottage getaway
Property grounds

Lemon Drop Cottage a private cottage getaway

9.4 out of 10, Exceptional, (46)
"Straightforward check-in, very nice host. Great short stay."
The price is €222
includes taxes & fees
3 Sept - 4 Sept
Lemon Drop Cottage a private cottage getaway
Beautiful Waterfront Cottage With a HOT TUB For Your Family Getaway!
Exterior

Beautiful Waterfront Cottage With a HOT TUB For Your Family Getaway!

10.0 out of 10, Exceptional, (14)
"Really enjoyed our time on the lake and loved the house. Everything was very clean and well maintained."
Beautiful Waterfront Cottage With a HOT TUB For Your Family Getaway!
Historic Home w/ Modern Updates on < 4 Acres
House (4 Bedrooms) | Interior

Historic Home w/ Modern Updates on < 4 Acres

3.0 star property
10.0 out of 10, Exceptional, (1)
Historic Home w/ Modern Updates on < 4 Acres
Charming Jaffrey Cottage w/ Deck & Grill!
Cottage (4 Bedrooms) | Interior

Charming Jaffrey Cottage w/ Deck & Grill!

3.0 star property
Charming Jaffrey Cottage w/ Deck & Grill!
Waterfront Cottage on Scenic Sportsman Pond
Exterior

Waterfront Cottage on Scenic Sportsman Pond

9.6 out of 10, Exceptional, (43)
"Excellent location,plenty of water activities and equipment,fun place, Owners very nice and very helpful."
Waterfront Cottage on Scenic Sportsman Pond
Vacationer's oasis on the waterfront of picturesque Pearly Pond.
Exterior

Vacationer's oasis on the waterfront of picturesque Pearly Pond.

10.0 out of 10, Exceptional, (34)
"The Host is very easy to contact and works well with our travelers."
Vacationer's oasis on the waterfront of picturesque Pearly Pond.
Waterfront Cottage 5 minutes to Mount Wachusett, Dock, Pet Friendly, Kayaks
Outdoor dining

Waterfront Cottage 5 minutes to Mount Wachusett, Dock, Pet Friendly, Kayaks

10.0 out of 10, Exceptional, (20)
"If you want to relax in a serene lake setting with a spectacular outdoor patio - this is the place to be! Enjoy the lake and get out on the water with kayaks and don’t miss a pontoon boat ride."
Waterfront Cottage 5 minutes to Mount Wachusett, Dock, Pet Friendly, Kayaks
Charming Jaffrey Cottage w/ Deck & Grill!
Fridge, microwave, stovetop, dishwasher

Charming Jaffrey Cottage w/ Deck & Grill!

10.0 out of 10, Exceptional, (43)
"Great stay for family, nice gathering for grandparents and adult children."
Charming Jaffrey Cottage w/ Deck & Grill!
Grey Cabin with Sauna on Lake Monomonac
Property grounds

Grey Cabin with Sauna on Lake Monomonac

2.0 star property
7.6 out of 10, Good, (4)
"Great location host was on it.anything u needed he was there.no ac was the only thing.but it was unusally hot.i would go again"
Grey Cabin with Sauna on Lake Monomonac
Cozy Tiny House on Main Street. Fully Renovated.
Exterior

Cozy Tiny House on Main Street. Fully Renovated.

10.0 out of 10, Exceptional, (4)
"I was in Dublin visiting my daughter who goes to high school here and it was the perfect place for me to stay and she stayed with me two nights. The owner thought of everything you would need. It was super clean and everything looked brand new. Really well decorated. The owner was super helpful and I’m sure I’ll be back before my girl graduates. Highly recommend!"
The price is €257
includes taxes & fees
21 Aug - 22 Aug
Cozy Tiny House on Main Street. Fully Renovated.
Cottage Lake Nubanusit
Fridge, microwave, oven, stovetop

Cottage Lake Nubanusit

10.0 out of 10, Exceptional, (2)
"Me and the wife wanted a place to get away from the daily grind. This small cabin was perfect."
Cottage Lake Nubanusit
Dog-friendly Fitchburg Vacation Rental, Hike & Ski
Interior

Dog-friendly Fitchburg Vacation Rental, Hike & Ski

3.0 star property
Dog-friendly Fitchburg Vacation Rental, Hike & Ski
Modern Waterfront Gem w/ Dock on Lake Monomonac
Front of property

Modern Waterfront Gem w/ Dock on Lake Monomonac

3.0 star property
Modern Waterfront Gem w/ Dock on Lake Monomonac
Magical Lakefront Home in Forest Lake
Terrace/patio

Magical Lakefront Home in Forest Lake

9.6 out of 10, Exceptional, (23)
"This house was a wonderful getaway for my family. The boys loved the swimming and fishing. The upper deck was a wonderful place to sit and relax. The house was very clean and ready to use. The street was very quiet and there were no jet skis or other loud boats out on the water. We brought our own kayaks and went around the lake numerous times. Overall, this house was perfect for our family (and pup as well). My boys want to us rent this house again next year!"
Magical Lakefront Home in Forest Lake
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.
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Top Winchendon Hotel Reviews

Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA

10/10 Excellent
"I like the bed comfort and the tv!!"
ERIC 1-night trip
Posted 2 days ago
Great Wolf Lodge Boston / Fitchburg, MA

Frequently asked questions

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What is there to do in Winchendon near my cottage?
After you've unpacked your suitcases, venture out and explore the amazing things Winchendon has to offer. Lake Dennison State Recreation Area is a top attraction to add to your must-do list.