Winchendon Holiday Rentals

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

Tonight
18 Nov - 19 Nov
Tomorrow
19 Nov - 20 Nov
This weekend
21 Nov - 23 Nov
Next weekend
28 Nov - 30 Nov

Holiday Rentals in Winchendon

Exterior
Cozy Lakefront Cottage

Cozy Lakefront Cottage

Winchendon
9.8 out of 10, Exceptional, (19)
"We found a gem! Easy check in/out and right on the water! Extremely relaxing stay with a fully equipped kitchen where qe were abke to cook every meal and truly enjoy the lake the entire day."
United States
Greg P.
Cozy Lakefront Cottage
Front of property
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
Outdoor dining
Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.

Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.

Fitzwilliam
10.0 out of 10, Exceptional, (10)
"This comfortable 2-bedroom house on a tranquil NH pond was the perfect weekend escape! We absolutely loved the peaceful setting and beautiful views. It was incredibly relaxing and exactly what we needed. Highly recommend!"
United States
Seth K.
Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.
Fridge, microwave, oven, stovetop
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.

Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.

Peterborough
9.8 out of 10, Exceptional, (28)
"I had a great stay at Mary Anne and Ben’s place in Peterborough. The apartment was clean and comfortable, and the location cannot be beat."
United States
Joseph K.
The price is HK$560
HK$1,198 total
includes taxes & fees
2 Dec - 3 Dec
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Interior
Charming cabin in delightful Greenfield New Hampshire with WiFi access

Charming cabin in delightful Greenfield New Hampshire with WiFi access

Greenfield
9.8 out of 10, Exceptional, (8)
The price is HK$1,438
HK$2,049 total
includes taxes & fees
29 Nov - 30 Nov
Charming cabin in delightful Greenfield New Hampshire with WiFi access
Smart TV
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn

Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn

Westminster
10.0 out of 10, Exceptional, (23)
"Kathleen was an amazing host and the property exceeded our expectations. The kids loved the bunk room and loft and the surrounding area provided something for all interests. We will definitely be planning another stay. "
United States
Michael T.
The price is HK$1,749
HK$4,017 total
includes taxes & fees
1 Dec - 2 Dec
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
Fridge, microwave, stovetop, coffee/tea maker
Cozy Cabin in a Rural Setting #16 near Temple,NH

Cozy Cabin in a Rural Setting #16 near Temple,NH

Temple
9.4 out of 10, Exceptional, (17)
"Super cute cabin with updated features and it was cozy and recently updated. The bed was particularly comfortable and the efficient layout made it possible for four adults to stay. Parking was easy and checkin and communication with the host was excellent before and after our stay. Would highly reccommend!"
United States
Kevin H.
The price is HK$1,180
HK$1,921 total
includes taxes & fees
1 Dec - 2 Dec
Cozy Cabin in a Rural Setting #16 near Temple,NH
Exterior
Beautiful Adirondack Cabin with Sauna on Lake Monomonac

Beautiful Adirondack Cabin with Sauna on Lake Monomonac

2.0 star property
Rindge
10.0 out of 10, Exceptional, (24)
"This is a great property, and Jim is a wonderful host. He accommodated all our requests for sauna use and provided helpful tips about the area. We hope to return again one day!"
United States
Leigh C.
The price is HK$1,672
HK$2,759 total
includes taxes & fees
23 Nov - 24 Nov
Beautiful Adirondack Cabin with Sauna on Lake Monomonac
Property grounds
Cottage beside a waterfall

Cottage beside a waterfall

Wilton
9.8 out of 10, Exceptional, (10)
"What a unique place to stay with a waterfall in the backyard! Quiet, beautiful grounds on the property. Clean, private and well appointed. "
United States
Marcella J.
The price is HK$1,244
HK$2,235 total
includes taxes & fees
18 Dec - 19 Dec
Cottage beside a waterfall
Terrace/patio
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock

2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock

Rindge
10.0 out of 10, Exceptional, (22)
"The cottage was a great place to stay. Very conveniently located to where we wanted to travel to. It has a great view of the lake, very clean and comfortable."
United States
Nicole B.
The price is HK$1,329
HK$2,817 total
includes taxes & fees
1 Dec - 2 Dec
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
3 bedrooms, travel cot, free WiFi, bed sheets
Charming Waterfront Log Cabin

Charming Waterfront Log Cabin

Fitzwilliam
9.4 out of 10, Exceptional, (45)
"Great cabin for a true NH getaway. The kayaks and pedal boat were so much fun. "
United States
Katherine M.
Charming Waterfront Log Cabin
Dining
Lakefront 3BR Log Cabin w/ Dock and Fire Pit

Lakefront 3BR Log Cabin w/ Dock and Fire Pit

Rindge
10.0 out of 10, Exceptional, (56)
"This is a roomy cabin with a great view and location! Our second year here!"
United States
Linda B.
Lakefront 3BR Log Cabin w/ Dock and Fire Pit
Exterior
Charming Lake Cottage est 1903! Private and relaxing waterfront, family fun!

Charming Lake Cottage est 1903! Private and relaxing waterfront, family fun!

Rindge
9.8 out of 10, Exceptional, (51)
"Ryan’s property is beautiful and peaceful. Its exactly what I would describe as a perfect summer getaway."
United States
Elizabeth S.
Charming Lake Cottage est 1903! Private and relaxing waterfront, family fun!
Fridge, microwave, oven, stovetop
Mid-Century Comfort & Style

Mid-Century Comfort & Style

Fitchburg
9.4 out of 10, Exceptional, (10)
"Great property close to where we needed to be."
United States
Justin
Mid-Century Comfort & Style
Outdoor dining
Beautiful Lakefront home - perfect getaway for every season!

Beautiful Lakefront home - perfect getaway for every season!

Ashburnham
10.0 out of 10, Exceptional, (6)
"We had an incredible stay at the lake house. Michelle and Patrick were absolutely wonderful to work with and very responsive throughout our stay. The home is beautiful. Waking up to the lake each morning was such a treat. We definitely hope to visit again!"
United States
Tory M.
Beautiful Lakefront home - perfect getaway for every season!
Exterior
Waterfront Cottage on Scenic Sportsman Pond

Waterfront Cottage on Scenic Sportsman Pond

Fitzwilliam
9.6 out of 10, Exceptional, (44)
"Excellent location,plenty of water activities and equipment,fun place, Owners very nice and very helpful."
United States
Cathy M.
Waterfront Cottage on Scenic Sportsman Pond
Fridge, microwave, oven, stovetop
Nestled on the edge of the woods near Mount Monadnock

Nestled on the edge of the woods near Mount Monadnock

Jaffrey
9.6 out of 10, Exceptional, (7)
"Very nice stay at railtrail retreat."
United States
David O.
Nestled on the edge of the woods near Mount Monadnock
Exterior detail
Cozy Cabin in a Rural setting #8

Cozy Cabin in a Rural setting #8

Temple
9.0 out of 10, Wonderful, (4)
"Cute, cozy and clean. "
United States
Jessica F.
The price is HK$913
HK$1,487 total
includes taxes & fees
1 Dec - 2 Dec
Cozy Cabin in a Rural setting #8
Interior
Story Book Lake Front Chateau with Private Beach!

Story Book Lake Front Chateau with Private Beach!

Winchester
10.0 out of 10, Exceptional, (10)
"The house was clean and as described. Very private location, nice and quite. We look forward to going back to this property but for a longer stay! "
United States
Edward Z.
Story Book Lake Front Chateau with Private Beach!
Interior
2 queen and 2 twin beds

2 queen and 2 twin beds

Milford
9.6 out of 10, Exceptional, (14)
"The property was very comfortable and had enough room for the 5 people who stayed there."
United States
Peggy K.
2 queen and 2 twin beds
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

Riverhouse by Weekender (Formerly Jack Daniels Inn)

Riverhouse by Weekender (Formerly Jack Daniels Inn)

10/10 Excellent
"The room was very clean and the place was quiet "
Rick 1-night trip
Posted 2 days ago
Riverhouse by Weekender (Formerly Jack Daniels Inn)

Find out more about Winchendon

Search for holiday rentals in Winchendon on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchendon using one of the methods below:

  • View our selection of featured holiday rentals in Winchendon
  • Use the map to find apartments and other holiday homes in the Winchendon neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winchendon while they last

Look no further and take a look at our great range of rental properties in Winchendon!

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.

What are some of the best holiday rentals that Winchendon has to offer?

Cozy Lakefront Cottage: This highly rated holiday home rental in Winchendon is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as a selection of books.

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 Militia Training Field 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 Birch Hill Wildlife Management Area 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.