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Check prices for these dates

Next weekend
10 Oct - 12 Oct
In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov

Featured Cottages in Winchendon

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

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

10.0 out of 10, Exceptional, (21)
"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
Waterfront Cottage on Scenic Sportsman Pond
Exterior

Waterfront Cottage on Scenic Sportsman Pond

9.6 out of 10, Exceptional, (44)
"Excellent location,plenty of water activities and equipment,fun place, Owners very nice and very helpful."
Waterfront Cottage on Scenic Sportsman Pond
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)
"Nice location and a very cool place to stay "
The price is NZ$683
includes taxes & fees
7 Oct - 8 Oct
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
2 queen and 2 twin beds
Exterior

2 queen and 2 twin beds

9.8 out of 10, Exceptional, (12)
"We really enjoyed our stay. The seating outside was lovely!"
2 queen and 2 twin beds
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, (35)
"The Host is very easy to contact and works well with our travelers."
Vacationer's oasis on the waterfront of picturesque Pearly Pond.
Lemon Drop Cottage a private cottage getaway
Property grounds

Lemon Drop Cottage a private cottage getaway

9.4 out of 10, Exceptional, (47)
"Straightforward check-in, very nice host. Great short stay."
The price is NZ$432
includes taxes & fees
7 Oct - 8 Oct
Lemon Drop Cottage a private cottage 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
Cottage beside a waterfall
Property grounds

Cottage beside a waterfall

9.6 out of 10, Exceptional, (5)
"The location was amazing. The cottage was cute, cozy, well appointed. The bed was super comfortable. Falling asleep to the waterfall sounds was similar to sleeping to ocean waves. Next time we visit NH we will certainly try to stay here again. "
The price is NZ$438
includes taxes & fees
13 Oct - 14 Oct
Cottage beside a waterfall
Cottage on Partridge Pond
Interior

Cottage on Partridge Pond

10.0 out of 10, Exceptional, (24)
"Nicely appointed with pretty view. "
Cottage on Partridge Pond
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)
"The cottage was a great place to stay. Very conveniently located to where we wanted to travel to. It has a great view of the lake, very clean and comfortable."
The price is NZ$623
includes taxes & fees
5 Oct - 6 Oct
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
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!
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."
The price is NZ$633
includes taxes & fees
20 Oct - 21 Oct
Finnish 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, (5)
"Very nice well kept and a great location to Monadnock Hospital."
Cozy Tiny House on Main Street. Fully Renovated.
Grey Cabin with Sauna on Lake Monomonac
Exterior

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"
The price is NZ$629
includes taxes & fees
19 Oct - 20 Oct
Grey Cabin with Sauna on Lake Monomonac
Cottage Lake Nubanusit
Exterior

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
House (2 Bedrooms) | 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
House (2 Bedrooms) | Interior

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
Beach Front Stay on Fully Recreational Lake at the base of Wachusett Mountain
Property grounds

Beach Front Stay on Fully Recreational Lake at the base of Wachusett Mountain

Beach Front Stay on Fully Recreational Lake at the base of Wachusett Mountain
Artist's Cottage in Woods
Exterior

Artist's Cottage in Woods

Artist's Cottage in Woods
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

Doubletree by Hilton Hotel Leominster

Doubletree by Hilton Hotel Leominster

10/10 Excellent
"The room was quite clean and the staff are extremely pleasant. Also great breakfast!"
Brian 3-night trip
Posted 2 days ago
Doubletree by Hilton Hotel Leominster

Find out more about Winchendon

Find out more about Winchendon

Winchendon Cottages information

Number of reviews
225
Accommodation
27 Cottages
Lowest Price
NZ$432
Highest Price
NZ$683

Frequently asked questions

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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia