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Check prices for these dates

Next weekend
21 Saf. - 23 Saf.
In two weeks
28 Saf. - 2 Rab. I
In one month
14 Rab. I - 16 Rab. I
In two months
11 Rab. II - 13 Rab. II

Compare 43 Vacation Homes in Winchendon with updated reviews, rates, and availability.

Charming Waterfront Log Cabin
Exterior

Charming Waterfront Log Cabin

9.6 out of 10, Exceptional, (37)
"We really appreciated the solitude and quiet retreat this cabin offered. "
Charming Waterfront Log Cabin
earthship forest exile
Outdoor dining

earthship forest exile

The price is SAR 731
SAR 1,579 total
includes taxes & fees
18 Feb - 19 Feb
earthship forest exile
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!
Front View of The Thrushwood Estate

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

10.0 out of 10, Exceptional, (65)
"My husband, myself, 3 of my adult kids and 5 grandchildren under 7 stayed very comfortably. So many nice rooms. Although very updated had a very nostalgic feel. All of the living spaces were extra large and plenty of seating. The kitchen had everything that we needed and the yard was humongous. We were fortunate to get snow while we were there and the kids had never seen snow since we’re from Georgia. It was a wonderful stay. Thank you so much, Wayne. "
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!
Historic Home w/ Modern Updates on < 4 Acres
Royalston Vacation Rental | 4BR | 2BA | Stairs to Access | 3,200 Sq Ft

Historic Home w/ Modern Updates on < 4 Acres

10.0 out of 10, Exceptional, (6)
"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
Waterfont log home nestled in the pines
Cabin on Lake Contoocook

Waterfont log home nestled in the pines

10.0 out of 10, Exceptional, (52)
"Anther fantastic time at this beautiful location. Owner is always so geeat to work work "
Waterfont log home nestled in the pines
Nestled on the edge of the woods near Mount Monadnock
Exterior

Nestled on the edge of the woods near Mount Monadnock

9.4 out of 10, Exceptional, (6)
"House is comfortable and well stocked."
Nestled on the edge of the woods near Mount Monadnock
VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac
Exterior

VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac

10.0 out of 10, Exceptional, (6)
"Everything about this property was beautiful. The home itself being located right on the water was perfect for kayaking, fishing, evenings by the fire, relaxing and reconnecting. The house is gorgeous, comfortable, and had everything you might need/want. We enjoyed the game room - jenga and family air hockey tournaments. A lovely experience and we hope to return at some point. Thank you for sharing your beautiful home with us!"
VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac
Downtown Hot Tub Escape
Property grounds

Downtown Hot Tub Escape

9.4 out of 10, Exceptional, (10)
"Brought my parents and my Brother to this rental - It was a nice place."
The price is SAR 746
SAR 1,384 total
includes taxes & fees
18 Feb - 19 Feb
Downtown Hot Tub Escape
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower
Miscellaneous

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

10.0 out of 10, Exceptional, (12)
"We had a great time. The house was very nice and clean. The lake was really lovely for boating and swimming."
The price is SAR 1,500
SAR 2,785 total
includes taxes & fees
21 Feb - 22 Feb
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower
Amazing Lakefront property, Private Pool on Lake Monomonac at Tatum's Place
Pool

Amazing Lakefront property, Private Pool on Lake Monomonac at Tatum's Place

10.0 out of 10, Exceptional, (2)
"Stunning property, we had the best time for our annual friendsgiving. The kids loved the backyard and the two kitchens was awesome! "
Amazing Lakefront property, Private Pool on Lake Monomonac at Tatum's Place
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, (7)
"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 Family Home!
Summer at the House

Wachusett Mountain Getaway - Lake Adjacent Family Home!

9.8 out of 10, Exceptional, (86)
"My niece was getting married at the Colonial Hotel. This house was only a short drive away and a great place for a family to gather. "
Wachusett Mountain Getaway - Lake Adjacent Family Home!
Lovely 3-bedroom City Escape
Exterior

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
Modern Waterfront Gem w/ Dock on Lake Monomonac
Winchendon Vacation Rental | 2BR | 1BA | 658 Sq Ft | 1 Step Required

Modern Waterfront Gem w/ Dock on Lake Monomonac

10.0 out of 10, Exceptional, (1)
""Our stay at the Lake Monomonac cottage was absolutely perfect! The home was impeccably clean, beautifully decorated, and had everything we needed for a comfortable stay. The location was ideal for us to visit family nearby. The host was incredibly responsive and accommodating. We will definitely book again!"
Modern Waterfront Gem w/ Dock on Lake Monomonac
Spacious Pet Friendly Waterfront w/ Hot Tub & Yogo Studio-Sleeps 10!
Outdoor Dining Seating

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

Spacious Pet Friendly Waterfront w/ Hot Tub & Yogo Studio-Sleeps 10!
Dog-Friendly Fitchburg Vacation Rental, Hike & Ski
Fitchburg Vacation Rental | 2BR | 1BA | Stairs Required | 720 Sq Ft

Dog-Friendly Fitchburg Vacation Rental, Hike & Ski

9.4 out of 10, Exceptional, (11)
"Nice private location on a woodsy lot. Cute 4 room, 2 bedroom, 1 bath, with the necessary amenities. Landlord very cooperative and prompt in responses. Would book again"
Dog-Friendly Fitchburg Vacation Rental, Hike & Ski
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
Rear Deck for barbecues looking across rear yard.

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

9.8 out of 10, Exceptional, (15)
"Very nice house and property! "
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
Charming 3-bedroom waterfront house in Harrisville
Exterior

Charming 3-bedroom waterfront house in Harrisville

10.0 out of 10, Exceptional, (2)
"The home is absolutley beautiful with everything you could need from linens and kitchen needs to shampoos and lotions. The view and access to the lake were unbeatable. We stayed in the winter and got some snow overnight that was cleared perfectly by the time we woke up. Property owner was responsive and pleasant. we woke up."
Charming 3-bedroom waterfront house in Harrisville
Charming barn studio apt, in lovely Peterborough NH overlooking the downtown.
Private kitchen

Charming barn studio apt, in lovely Peterborough NH overlooking the downtown.

2.0 star property
10.0 out of 10, Exceptional, (4)
"Loved the barn, very comfortable and toasty warm. This is our second time visiting and it will not be the last. The host is awesome and the fresh eggs are a nice touch."
Charming barn studio apt, in lovely Peterborough NH overlooking the downtown.
Private Field House - Spacious 4 Bedroom Home
House from backyard

Private Field House - Spacious 4 Bedroom Home

10.0 out of 10, Exceptional, (15)
"Very nice home, quiet location, and house had everything we needed and more. Property manager timely communicated all necessary information."
Private Field House - Spacious 4 Bedroom Home
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

Amazing Lakefront property, Private Pool on Lake Monomonac at Tatum's Place
Pool

Amazing Lakefront property, Private Pool on Lake Monomonac at Tatum's Place

10.0 out of 10, Exceptional, (2)
"Stunning property, we had the best time for our annual friendsgiving. The kids loved the backyard and the two kitchens was awesome! "
Amazing Lakefront property, Private Pool on Lake Monomonac at Tatum's Place
VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac
Exterior

VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac

10.0 out of 10, Exceptional, (6)
"Everything about this property was beautiful. The home itself being located right on the water was perfect for kayaking, fishing, evenings by the fire, relaxing and reconnecting. The house is gorgeous, comfortable, and had everything you might need/want. We enjoyed the game room - jenga and family air hockey tournaments. A lovely experience and we hope to return at some point. Thank you for sharing your beautiful home with us!"
VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac
Modern Waterfront Gem w/ Dock on Lake Monomonac
Winchendon Vacation Rental | 2BR | 1BA | 658 Sq Ft | 1 Step Required

Modern Waterfront Gem w/ Dock on Lake Monomonac

10.0 out of 10, Exceptional, (1)
""Our stay at the Lake Monomonac cottage was absolutely perfect! The home was impeccably clean, beautifully decorated, and had everything we needed for a comfortable stay. The location was ideal for us to visit family nearby. The host was incredibly responsive and accommodating. We will definitely book again!"
Modern Waterfront Gem w/ Dock 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.