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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)
"What a fun stay! Great communication with the property manager Don, cute town, lots of American history to be discovered, fun stay. 10/10 highly recommend!!!"
United States
Katja Z.
The price is AED 1,194
AED 1,367 total
includes taxes & fees
10 Nov - 11 Nov
Enjoy your stay in an antique home in an antique toy museum!

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)
"Pondlife was clean, calm, cozy, and peaceful...exactly what we wanted...fall foliage was gorgeous....rail trail hiking adjacent to the property and plenty of mountain hiking nearby. If you want to be immersed in nature's beauty, this is perfect..."
United States
Margaret
The price is AED 876
AED 1,034 total
includes taxes & fees
5 Nov - 6 Nov
"Pondlife" - Waterfront home in a peaceful, wooded setting.

3. Cozy & Stylish 2-bedroom Home in Leominster

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

4. Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
9.4 out of 10, Exceptional, (27 reviews)
"Great stay, clean, accommodating and great location. Will stay again!"
United States
cody s.
The price is AED 757
AED 1,316 total
includes taxes & fees
9 Nov - 10 Nov
Modern Downtown Escape HotTub Fire Pit Games 12ppl

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)
"Communication with the host was easy and the house was great. I would definitely book this home again if/when I come back to Keene."
United States
Jeremy S.
The price is AED 705
AED 1,682 total
includes taxes & fees
5 Nov - 6 Nov
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!

6. The Christmas Cottage, 4BR New England Escape

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

7. Cobb Meadow House: Cozy 5 Bedroom Retreat

Cobb Meadow House: Cozy 5 Bedroom Retreat
Dublin
10.0 out of 10, Exceptional, (27 reviews)
"Good place to stay during a wedding week"
United States
Veronique S.
The price is AED 1,543
AED 2,518 total
includes taxes & fees
8 Nov - 9 Nov
Cobb Meadow House: Cozy 5 Bedroom Retreat

8. Entire home in Sterling, Massachusetts, United States

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

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)
"We had a great time at the house. Perfect for family and young kids. Very clean. View of lake and bald eagles! were amazing. Host was very responsive and provided a lot of extra info on location places to eat, events, etc. Would definitely stay again."
United States
Tara I.
The price is AED 1,652
AED 2,698 total
includes taxes & fees
8 Nov - 9 Nov
3br Lakefront Oasis in Shutesbury with central air and 180-deg views!
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.

A river reflecting autumn trees and a dense forest.

Top reviews in Winchendon