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Vacation Homes in Winchendon

Story Book Lake Front Chateau with Private Beach!

10.0 out of 10, Exceptional, (8)
"We had a wonderful stay here over three nights in mid-April. We loved the style and personal touches of the property, and our dog loved how dog friendly it was and especially loved being able to prance around the beach and pull sticks out of the lake. Our visit was fantastic, and we’d happily come back sometime — well worth it!"
Story Book Lake Front Chateau with Private Beach!

Downtown Hot Tub Escape

9.6 out of 10, Exceptional, (14)
"Property was easy to locate. The rooms were perfect! Hot tub was fantastic! "
Downtown Hot Tub Escape

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!

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 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

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

9.8 out of 10, Exceptional, (87)
"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!

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

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

9.8 out of 10, Exceptional, (18)
"Beautiful place"
The price is AED 1,102
AED 2,244 total
includes taxes & fees
27 Jul - 28 Jul
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower

earthship forest exile

10.0 out of 10, Exceptional, (5)
"Host is wonderful and communication was great. We visited the Temple/ Wilton farm to table cafe and scones were excellent. Home is unique, but as stated and had everything we needed. Would definitely stay again. Thank you for share your house"
The price is AED 735
AED 1,586 total
includes taxes & fees
22 Jul - 23 Jul
earthship forest exile

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

9.8 out of 10, Exceptional, (16)
"Wonderful home. Owners are very helpful & hands on. Completely enjoyed the property. "
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby

Cozy Home Near Downtown, Shops, and Restaurants.

2.0 star property
10.0 out of 10, Exceptional, (5)
"This was just a few minutes drive from the city of Keene and was a perfect family rental. It had everything we needed. "
The price is AED 1,170
AED 1,995 total
includes taxes & fees
21 Jul - 22 Jul
Cozy Home Near Downtown, Shops, and Restaurants.

Waterfont log home nestled in the pines

10.0 out of 10, Exceptional, (54)
"Its a great retreat to stay at .we enjoyed the kayaks and paddle boards,roasted marshmellows,played games all in all a very relaxing time"
Waterfont log home nestled in the pines

Lovely 3-bedroom City Escape

9.8 out of 10, Exceptional, (22)
"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

3 Beautiful Finnish Cabins with Sauna on Lake Monomonac

2.0 star property
3 Beautiful Finnish Cabins with Sauna on Lake Monomonac

Dog-Friendly Fitchburg Vacation Rental, Hike & Ski

9.4 out of 10, Exceptional, (19)
"This was our second time and definitely not the last. Great location for the ski week. Has everything you need. Pet friendly which is a big plus for us. Welcoming basket very much appreciated. "
Dog-Friendly Fitchburg Vacation Rental, Hike & Ski

Quiet private pond getaway

9.2 out of 10, Wonderful, (10)
"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

Charming 4-BR + 6 bathroom chateau with WiFi, in Marlborough view on Monadnock

Charming 4-BR + 6 bathroom chateau with WiFi, in Marlborough view on Monadnock

Cozy 3 bedroom home

10.0 out of 10, Exceptional, (9)
"Communication excellent, back yard, had everything we needed, well stocked. "
Cozy 3 bedroom home

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!

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!
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