Winchendon Holiday Rentals

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Our top choices for Winchendon holiday rentals

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 AU$440
includes taxes & fees
22 Dec - 23 Dec
Cottage beside a waterfall
10.0 out of 10, Exceptional, (13)
"Loved the area"
United States
Jose R.
The price is AU$347
includes taxes & fees
5 Jan - 6 Jan 2026
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna
9.8 out of 10, Exceptional, (30)
"Fully equipped kitchen, comfortable open floor plan, easy walk to downtown and very hospitable—thank you—we’d like to stay here again next year!"
United States
Mark
The price is AU$243
includes taxes & fees
20 Dec - 21 Dec
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
9.6 out of 10, Exceptional, (30)
"Nice location and a very cool place to stay "
United States
Samson M.
The price is AU$755
includes taxes & fees
21 Dec - 22 Dec
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
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 AU$564
includes taxes & fees
21 Dec - 22 Dec
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
10.0 out of 10, Exceptional, (12)
"Wonderful place to stay. Everything was very clean, comfortable, and spacious, with a warm, welcoming feel. I highly recommend the place to stay. "
United States
Catherine
The price is AU$595
includes taxes & fees
27 Dec - 28 Dec
Modern 3BR Near FSU • 15 Min to Wachusett
10.0 out of 10, Exceptional, (3)
"Had a great time, the grounds are spectacular with the river waterfall in the background. The Bathroom was stunning. Had everything we needed. The bed was super comfy too. The screened-in porch was convenient, too."
United States
Romie G.
The price is AU$438
includes taxes & fees
20 Dec - 21 Dec
River Room overlooking the waterfall
9.8 out of 10, Exceptional, (9)
"Its was great clean, quite and comfortable. "
United States
John G.
The price is AU$402
includes taxes & fees
19 Dec - 20 Dec
Charming cabin in delightful Greenfield New Hampshire with WiFi access

Holiday Home in Keene

Downtown Hot Tub Escape
9.6 out of 10, Exceptional, (21)
"Good location for some event staff to stay while we were hosting a conference in town. Simple check-in/out. Would rent again."
United States
Jack P.
The price is AU$426
includes taxes & fees
22 Dec - 23 Dec
Downtown Hot Tub Escape
10.0 out of 10, Exceptional, (24)
"Our stay at the beautiful cabin was absolutely delightful. Everything was exactly as described, and Kathleen went above and beyond to make sure we had a wonderful time. We highly recommend this place and will definitely be bringing our family back again next time we are in the area! Thank you for providing us with a relaxing and peaceful stay. "
United States
Nancy G.
The price is AU$840
includes taxes & fees
5 Jan - 6 Jan 2026
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
10.0 out of 10, Exceptional, (2)
"Wonderful and thoughtful hosts that went above and beyond to make us feel at home. We appreciated the coziness of the house and your kindness. "
United States
Kadie H.
The price is AU$558
includes taxes & fees
21 Dec - 22 Dec
Spacious & Historic 2-Bed – 5 Min Drive to High Mowing, 25 Min to Dublin School
2.0 star property
10.0 out of 10, Exceptional, (1)
"Friendly hosts and excellent location to walk to downtown."
United States
Joshua
Central Large 3-bedroom apartment in Keene
10.0 out of 10, Exceptional, (27)
"The house had everything our family needed for a fun and relaxing stay. Great house and yard on a beautiful spot on the lake! Highly recommend!!"
United States
Carol W.
The price is AU$763
includes taxes & fees
30 Dec - 31 Dec
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower
The price is AU$707
includes taxes & fees
26 Dec - 27 Dec
Feels Like Home - BBQ, Yard, Fire Pit

Holiday Home in Keene

Charming Home Walk to Downtown!
10.0 out of 10, Exceptional, (2)
"Thanks to Bill and Angela. We had a wonderful few days staying in your clean, quiet, and very comfortable home. We often choose VRBOs for our travels, whether in the U.S. or abroad—Freiburg, Paris, Bangkok—and this has truly been one of the best experiences.The highlight: this home is the most well-equipped place we’ve ever stayed in—everything we could possibly need was provided, and more. Complete in every way!On top of that, the location is perfect—close to shopping, hiking, fishing, and even...
United States
Xilin J.
The price is AU$944
includes taxes & fees
5 Jan - 6 Jan 2026
Charming Home Walk to Downtown!
10.0 out of 10, Exceptional, (25)
"Good place to stay during a wedding week"
United States
Veronique S.
The price is AU$939
includes taxes & fees
21 Dec - 22 Dec
Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region
9.8 out of 10, Exceptional, (7)
"very clean, well decorated, comfortable and peaceful"
United States
Dan G.
The price is AU$660
includes taxes & fees
23 Dec - 24 Dec
Unique Cozy private 1-bedroom apartment in charming Temple
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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Top Winchendon Hotel Reviews

Find out more about Winchendon

Everything you need to know about Winchendon holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchendon holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchendon holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winchendon holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchendon. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchendon holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchendon holiday rentals we have selected for you start as low as AU$402 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winchendon rentals

At Expedia, we put the best Winchendon holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winchendon rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchendon holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchendon. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 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.