Holiday Homes in Winchendon

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Find holiday rentals that suit your style

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Cabins
Cabins
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Apartments
Apartments

Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Winchendon holiday homes

A staircase with a wooden handrail and white steps, leading to a landing with a wooden table and a clock.

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 AU$532
includes taxes & fees
9 Nov - 10 Nov
Enjoy your stay in an antique home in an antique toy museum!
A lake surrounded by trees, with a wooden deck leading to a white railing.

2. 2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.

2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.
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 AU$406
includes taxes & fees
9 Nov - 10 Nov
2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.
A modern interior with a dining area, a black chair, and a wall-mounted artwork.

3. Cozy & Stylish 2-bedroom Home in Leominster

Cozy & Stylish 2-bedroom Home in Leominster
Leominster
The price is AU$329
includes taxes & fees
9 Nov - 10 Nov
Cozy & Stylish 2-bedroom Home in Leominster
A modern kitchen with a wooden countertop, dark cabinets, and a large window.

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 AU$515
includes taxes & fees
9 Nov - 10 Nov
Modern Downtown Escape HotTub Fire Pit Games 12ppl
A modern kitchen with granite countertops, stainless steel appliances, and a central island.

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 AU$659
includes taxes & fees
9 Nov - 10 Nov
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
A red house with a stone pathway leading to it, surrounded by autumn foliage.

6. 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 AU$986
includes taxes & fees
9 Nov - 10 Nov
Cobb Meadow House: Cozy 5 Bedroom Retreat
A wooden cabin bedroom with a bed, a nightstand, a lamp, and a bunk bed.

7. The Christmas Cottage, 4BR New England Escape

The Christmas Cottage, 4BR New England Escape
Rutland
The price is AU$1,063
includes taxes & fees
9 Nov - 10 Nov
The Christmas Cottage, 4BR New England Escape
A modern kitchen with a marble island, white cabinetry, and pendant lighting.

8. Entire home in Sterling, Massachusetts, United States

Entire home in Sterling, Massachusetts, United States
Sterling
The price is AU$1,038
includes taxes & fees
10 Nov - 11 Nov
Entire home in Sterling, Massachusetts, United States
A room with a large window overlooking a lake at sunset.

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 AU$1,103
includes taxes & fees
10 Nov - 11 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.
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Learn more about Winchendon

Toy Town's charm comes alive at the Old Murdock Senior Centre, 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.

See all hotels in Winchendon
A river reflecting autumn trees and a dense forest.

Top reviews in Winchendon

A dining area with wooden tables and chairs, large windows with a view of trees, and a bench along the wall.
The Carriage Barn Inn

The Carriage Barn Inn

The Carriage Barn Inn
Keene

10/10 Excellent

Great host , scenic setting , easy parking , charming house. Hope to return .
Australia
Maree
Reviewed July 2, 2025
The Carriage Barn Inn