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Compare 42 Vacation Homes in Winchendon with updated reviews, rates, and availability.

Cozy Home Near Downtown, Shops, and Restaurants.

2.0 star property
10.0 out of 10, Exceptional, (3)
"Online info was accurate. Nice spot to rent with family."
The price is SAR 1,328
SAR 2,198 total
includes taxes & fees
12 May - 13 May
Cozy Home Near Downtown, Shops, and Restaurants.

Dog-Friendly Fitchburg Vacation Rental, Hike & Ski

9.4 out of 10, Exceptional, (16)
"Very comfortable VRBO in good location. Quiet, clean without hassles."
Dog-Friendly Fitchburg Vacation Rental, Hike & Ski

Beautiful Lakefront home - perfect getaway for every season!

10.0 out of 10, Exceptional, (4)
"We had an incredible stay at the lake house. Michelle and Patrick were absolutely wonderful to work with and very responsive throughout our stay. The home is beautiful. Waking up to the lake each morning was such a treat. We definitely hope to visit again!"
Beautiful Lakefront home - perfect getaway for every season!

Modern Waterfront Gem w/ Dock on Lake Monomonac

10.0 out of 10, Exceptional, (4)
"Beautiful cottage on the lake. Everything seams new and spotless. Would definitely stay again."
Modern Waterfront Gem w/ Dock on Lake Monomonac

Wachusett Mountain Getaway, Lake Adjacent Home! Near 1761 Old Mill and Trails!

9.8 out of 10, Exceptional, (86)
"My family stayed here while in town for a family wedding. The house was very spacious and well stocked. Location was convenient for our events in Westminster. "
The price is SAR 1,313
SAR 2,321 total
includes taxes & fees
31 May - 1 Jun
Wachusett Mountain Getaway, Lake Adjacent Home! Near 1761 Old Mill and Trails!

Spacious Pet Friendly Waterfront w/ Hot Tub & Yogo Studio-Sleeps 10!

8.0 out of 10, Very Good, (1)
"The inside of these cabins was exceptionally clean and quaint. We loved the upstairs master bedroom loft! One of our guests needed to use the chair lift on the stairs, and it worked perfectly. The two second bedrooms were nicely equipped and pleasantly decorated. The kitchen had new appliances with a coffee bar. The view of the lake was stunning from multiple views. There were many activities available to take advantage of the outdoor spaces (boats, fire pit, grill, seating, etc.). We really...
Spacious Pet Friendly Waterfront w/ Hot Tub & Yogo Studio-Sleeps 10!

Waterfont log home nestled in the pines

10.0 out of 10, Exceptional, (52)
"Second time staying at this property ! Very relaxing, beds super comfortable. Would highly recommend."
Waterfont log home nestled in the pines

Lovely 3-bedroom City Escape

9.8 out of 10, Exceptional, (19)
"Our family gets together for Christmas and this home is the ideal place for part of the family to stay."
Lovely 3-bedroom City Escape

Nestled on the edge of the woods near Mount Monadnock

9.4 out of 10, Exceptional, (6)
"Very nice stay at railtrail retreat."
Nestled on the edge of the woods near Mount Monadnock

Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower

10.0 out of 10, Exceptional, (14)
"We had a great time. The house was very nice and clean. The lake was really lovely for boating and swimming."
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower

Downtown Hot Tub Escape

9.4 out of 10, Exceptional, (11)
"Brought my parents and my Brother to this rental - It was a nice place."
The price is SAR 743
SAR 1,367 total
includes taxes & fees
21 May - 22 May
Downtown Hot Tub Escape

Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby

9.8 out of 10, Exceptional, (16)
"Very nice house and property! "
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby

LAKE FRONT: Cozy 4-bedroom lake CAMP with WiFi and an outdoor firepit!

2.0 star property
9.0 out of 10, Wonderful, (8)
"Needed place to stay in Ashburnham large enough to sleep extended family traveling in for the holidays. Cabin was quaint, rustic and fit all of us. Overall good stay. "
LAKE FRONT: Cozy 4-bedroom lake CAMP with WiFi and an outdoor firepit!

Amazing Mid-Century Modern Mountain Top Home on 160 Acres

10.0 out of 10, Exceptional, (43)
"We had a great stay, house is amazing."
Amazing Mid-Century Modern Mountain Top Home on 160 Acres

Quiet private pond getaway

9.4 out of 10, Exceptional, (8)
"Beautiful property and accommodations. Can't wait to return soon!"
Quiet private pond getaway

Spacious Estate With Mtn Views! Private Setting, Great Family Home!!

10.0 out of 10, Exceptional, (65)
"There house is large and comfortable. Wayne was very helpful and accommodating. Highly recommend. "
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!

Charming 3-bedroom waterfront house in Harrisville

10.0 out of 10, Exceptional, (2)
"Very nice house with great amenities ! Beautiful location right on the lake (we may come back for a summer get together!) Highly recommend (just note - there’s plenty of room - but there is only one bed/bedroom)"
Charming 3-bedroom waterfront house in Harrisville

Charming Waterfront Log Cabin

9.4 out of 10, Exceptional, (38)
"We really appreciated the solitude and quiet retreat this cabin offered. "
Charming Waterfront Log Cabin

earthship forest exile

10.0 out of 10, Exceptional, (3)
"Great house for myself and my staff who run the NEW HAMPSHIRE OUTDOOR EXPO to stay and chill. House is clean, nice layout and the woodstove is awesome. We will be coming back to this property as our event is ANNUAL."
The price is SAR 750
SAR 1,579 total
includes taxes & fees
13 May - 14 May
earthship forest exile

3 Beautiful Finnish Cabins with Sauna on Lake Monomonac

2.0 star property
The price is SAR 3,372
SAR 5,262 total
includes taxes & fees
13 May - 14 May
3 Beautiful Finnish Cabins with Sauna on Lake Monomonac
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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Other property types in Winchendon

Modern Waterfront Gem w/ Dock on Lake Monomonac

10.0 out of 10, Exceptional, (4)
"Beautiful cottage on the lake. Everything seams new and spotless. Would definitely stay again."
Modern Waterfront Gem w/ Dock on Lake Monomonac

Downtown Hot Tub Escape

9.4 out of 10, Exceptional, (11)
"Brought my parents and my Brother to this rental - It was a nice place."
The price is SAR 743
SAR 1,367 total
includes taxes & fees
21 May - 22 May
Downtown Hot Tub Escape

Cottage beside a waterfall

The price is SAR 544
SAR 965 total
includes taxes & fees
11 May - 12 May
Cottage beside a waterfall
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.