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

Downtown Hot Tub Escape
Fridge, microwave, oven, stovetop

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 AED 808
AED 1,439 total
includes taxes & fees
10 Jun - 11 Jun
Downtown Hot Tub Escape
Story Book Lake Front Chateau with Private Beach!
Miscellaneous

Story Book Lake Front Chateau with Private Beach!

10.0 out of 10, Exceptional, (7)
"We loved staying here! The property was sparkling clean and very well stocked with everything you need. Comfortable beds and space. The view was beautiful and the privacy and yard created great memories for our family. Thank you sharing your beautiful house with us!"
Story Book Lake Front Chateau with Private Beach!
Lovely 3-bedroom City Escape
Property grounds

Lovely 3-bedroom City Escape

9.8 out of 10, Exceptional, (20)
"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
Quiet private pond getaway
Property grounds

Quiet private pond getaway

9.4 out of 10, Exceptional, (9)
"We really enjoyed our time at the lake house! The deck and fire pit was fun and everything was very nicely decorated and had enough supplies to make it very easy and a quiet peaceful setting!"
Quiet private pond getaway
LAKE FRONT: Cozy 4-bedroom lake CAMP with WiFi and an outdoor firepit!
Terrace/patio

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

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. "
Wachusett Mountain Getaway, Lake Adjacent Home! Near 1761 Old Mill and Trails!
Charming Waterfront Log Cabin
3 bedrooms, travel crib, free WiFi, bed sheets

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

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

9.8 out of 10, Exceptional, (15)
"Beautiful place"
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower
Modern Waterfront Gem w/ Dock on Lake Monomonac
Fridge, coffee/tea maker, toaster, cookware/dishes/utensils

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

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
earthship forest exile
Fridge, microwave, oven, stovetop

earthship forest exile

10.0 out of 10, Exceptional, (4)
"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."
earthship forest exile
Nestled on the edge of the woods near Mount Monadnock
Fridge, microwave, oven, stovetop

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
Meadow House at Powder Mill Pond - a nature lover's paradise
Terrace/patio

Meadow House at Powder Mill Pond - a nature lover's paradise

10.0 out of 10, Exceptional, (18)
"Great house on an amazing property"
Meadow House at Powder Mill Pond - a nature lover's paradise
Dog-Friendly Fitchburg Vacation Rental, Hike & Ski
Exterior

Dog-Friendly Fitchburg Vacation Rental, Hike & Ski

9.4 out of 10, Exceptional, (19)
"Very comfortable VRBO in good location. Quiet, clean without hassles."
Dog-Friendly Fitchburg Vacation Rental, Hike & Ski
3 Beautiful Finnish Cabins with Sauna on Lake Monomonac
Exterior

3 Beautiful Finnish Cabins with Sauna on Lake Monomonac

2.0 star property
The price is AED 2,972
AED 4,699 total
includes taxes & fees
17 Jun - 18 Jun
3 Beautiful Finnish Cabins with Sauna on Lake Monomonac
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!
Exterior

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!!
Historic Home w/ Modern Updates on < 4 Acres
4 bedrooms, desk, iron/ironing board, WiFi

Historic Home w/ Modern Updates on < 4 Acres

10.0 out of 10, Exceptional, (7)
"Stayed here with my brothers and cousins.. had a great time. Close proximity to Royalston Falls and a great hike through the forest "
Historic Home w/ Modern Updates on < 4 Acres
Spacious Pet Friendly Waterfront w/ Hot Tub & Yogo Studio-Sleeps 10!
Fridge, microwave, oven, stovetop

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!
Beautiful Lakefront home - perfect getaway for every season!
Miscellaneous

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!
5 Bedroom cozy New England home - Cobb Meadow House
Interior

5 Bedroom cozy New England home - Cobb Meadow House

10.0 out of 10, Exceptional, (23)
"Good place to stay during a wedding week"
The price is AED 1,543
AED 2,606 total
includes taxes & fees
8 Jun - 9 Jun
5 Bedroom cozy New England home - Cobb Meadow House
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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