Search Holiday Rentals in Winchendon

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
2 Jan - 4 Jan
In two months
13 Feb - 15 Feb
In three months
13 Mar - 15 Mar
In four months
10 Apr - 12 Apr

Our top choices for Winchendon holiday rentals

House (2 Bedrooms) | Front of property
Modern Waterfront Gem w/ Dock on Lake Monomonac

Modern Waterfront Gem w/ Dock on Lake Monomonac

Modern Waterfront Gem w/ Dock on Lake Monomonac
3.0 star property
Winchendon
Modern Waterfront Gem w/ Dock on Lake Monomonac
House (4 Bedrooms) | Interior
Historic Home w/ Modern Updates on < 4 Acres

Historic Home w/ Modern Updates on < 4 Acres

Historic Home w/ Modern Updates on < 4 Acres
3.0 star property
Royalston
10.0 out of 10, Exceptional, (2)
"Great place. Enjoyed our stay. Wish it wasn’t raining so we could’ve enjoyed more of the outdoors."
United States
Melissa
Historic Home w/ Modern Updates on < 4 Acres
Apartment (1 Bedroom) | Interior
Cozy Getaway - 10 Miles to Mount Wachusett Skiing!

Cozy Getaway - 10 Miles to Mount Wachusett Skiing!

Cozy Getaway - 10 Miles to Mount Wachusett Skiing!
3.5 star property
Leominster
Cozy Getaway - 10 Miles to Mount Wachusett Skiing!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchendon Hotel Reviews

Motel 6 Leominster, MA

Motel 6 Leominster, MA

10/10 Excellent
"Very clean room and helpful, friendly staff !"
Ralph 1-night trip
Posted 23 hours ago
Motel 6 Leominster, MA

Frequently asked questions

Are there holiday rentals in Winchendon?

Yes, there are holiday rentals close to the most popular sights in Winchendon, or you can select a more secluded option if you're looking for a relaxing stay. Winchendon is known for its parks.

How many holiday rentals will I find in Winchendon?

Choose from 5 Expedia holiday rentals in Winchendon for a memorable holiday.

What’s there to see and do in Winchendon?

Wendall P. Clark Memorial and Millers River are a couple of scenic spots to enjoy the outdoors, whereas The Robinson-Broadhurst Foundation Performing Arts Ampitheater is one of the cultural attractions. Lake Dennison State Recreation Area and Winchendon Town Hall are other places to visit while you're in town.

What’s a holiday rental in Winchendon like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchendon. Holiday rentals provide amenities such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from public hotel lifts and bustling concierge desks while still allowing you to travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for a family trip.