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Check prices for these dates

Next weekend
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun
In one month
4 Jul - 6 Jul
In two months
1 Aug - 3 Aug

Compare 23 Cottages in Winchendon with updated reviews, rates, and availability.

Cottage beside a waterfall
Property grounds

Cottage beside a waterfall

8.0 out of 10, Very Good, (1)
"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 AED 533
AED 944 total
includes taxes & fees
6 Jun - 7 Jun
Cottage beside a waterfall
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Aerial view

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

9.4 out of 10, Exceptional, (23)
"This was a very clean property. "
The price is AED 1,469
AED 2,498 total
includes taxes & fees
22 Jun - 23 Jun
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Waterfront Cottage on Scenic Sportsman Pond
Exterior

Waterfront Cottage on Scenic Sportsman Pond

9.6 out of 10, Exceptional, (41)
"Very clean, very private and secluded. What a hidden gem!"
Waterfront Cottage on Scenic Sportsman Pond
Cottage on Partridge Pond
Interior

Cottage on Partridge Pond

10.0 out of 10, Exceptional, (19)
"This cute cottage served our family of 5 adults. It was clean and well decorated. Would definitely recommend. "
Cottage on Partridge Pond
2 queen and 2 twin beds
2 bedrooms, desk, iron/ironing board, free WiFi

2 queen and 2 twin beds

10.0 out of 10, Exceptional, (7)
"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.
Pool

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

10.0 out of 10, Exceptional, (29)
"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, (14)
"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
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 AED 823
AED 1,232 total
includes taxes & fees
9 Jun - 10 Jun
Finnish Cabin with Sauna on Lake Monomonac
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
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, (13)
"This house was great! It provided an amazing place to stay for our son’s wedding! Would rent again! Jacuzzi was a nice addition!"
Beautiful Waterfront Cottage With a HOT TUB For Your Family Getaway!
Charming Jaffrey Cottage w/ Deck & Grill!
Fridge, microwave, stovetop, dishwasher

Charming Jaffrey Cottage w/ Deck & Grill!

10.0 out of 10, Exceptional, (39)
"Stayed four nights. Perfect weather and the foliage was fabulous.The cottage was ideal for us. Tastefully decorated and everything labeled. Wish we lived closer so we could go again in other seasons."
Charming Jaffrey Cottage w/ Deck & Grill!
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!
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
Grey Cabin with Sauna on Lake Monomonac
Property grounds

Grey Cabin with Sauna on Lake Monomonac

2.0 star property
7.4 out of 10, Good, (3)
"Hit the jackpot at this stay .Awesome area with many things to keep busy outside ,hiking all around ,lake for all kind of activities .Jim was a great host filled us in on activities in the area and was a message away for any help u may need .I will be back ."
The price is AED 922
AED 1,467 total
includes taxes & fees
6 Jun - 7 Jun
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)
"This was a perfect place to stay for my solo trip into town for a family wedding. The host was incredibly responsive and friendly and I'd recommend this place to anyone visiting the area!"
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
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
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
Beach Front Stay on Fully Recreational Lake at the base of Wachusett Mountain
Fridge, microwave, oven, stovetop

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
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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