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Our top choices for Winchendon vacation homes

1. Enjoy your stay in an antique home in an antique toy museum!
Enjoy your stay in an antique home in an antique toy museum!Winchendon
9.4 out of 10, Exceptional, (10 reviews)
The price is AED 1,194
AED 1,367 total
includes taxes & fees
10 Nov - 11 Nov

2. "Pondlife" - Waterfront home in a peaceful, wooded setting.
"Pondlife" - Waterfront home in a peaceful, wooded setting.Fitzwilliam
10.0 out of 10, Exceptional, (7 reviews)
The price is AED 876
AED 1,034 total
includes taxes & fees
5 Nov - 6 Nov

3. Cozy & Stylish 2-bedroom Home in Leominster
Cozy & Stylish 2-bedroom Home in LeominsterLeominster
The price is AED 731
AED 866 total
includes taxes & fees
5 Nov - 6 Nov

4. Modern Downtown Escape HotTub Fire Pit Games 12ppl
Modern Downtown Escape HotTub Fire Pit Games 12pplKeene
9.4 out of 10, Exceptional, (27 reviews)
The price is AED 757
AED 1,316 total
includes taxes & fees
9 Nov - 10 Nov

5. Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!Keene
9.8 out of 10, Exceptional, (6 reviews)
The price is AED 705
AED 1,682 total
includes taxes & fees
5 Nov - 6 Nov

6. The Christmas Cottage, 4BR New England Escape
The Christmas Cottage, 4BR New England EscapeRutland
The price is AED 1,286
AED 2,741 total
includes taxes & fees
8 Nov - 9 Nov

7. Cobb Meadow House: Cozy 5 Bedroom Retreat
Cobb Meadow House: Cozy 5 Bedroom RetreatDublin
10.0 out of 10, Exceptional, (27 reviews)
The price is AED 1,543
AED 2,518 total
includes taxes & fees
8 Nov - 9 Nov

8. Entire home in Sterling, Massachusetts, United States
Entire home in Sterling, Massachusetts, United StatesSterling
The price is AED 1,041
AED 2,505 total
includes taxes & fees
5 Nov - 6 Nov

9. 3br Lakefront Oasis in Shutesbury with central air and 180-deg views!
3br Lakefront Oasis in Shutesbury with central air and 180-deg views!Shutesbury
10.0 out of 10, Exceptional, (2 reviews)
The price is AED 1,652
AED 2,698 total
includes taxes & fees
8 Nov - 9 Nov
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.
Learn more about Winchendon
Toy Town's charm comes alive at the Old Murdock Senior Center, where the town's unique toy-making history is celebrated. Lake Dennison Recreation Area offers perfect summer swimming, while winter visitors can explore nearby Wachusett Mountain for skiing in Princeton.

Top reviews in Winchendon

The Maguire House Bed & Breakfast
The Maguire House Bed & BreakfastAshburnham
















































































