Winchendon Holiday Rentals

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Holiday Rentals in Winchendon

Our top choices for Winchendon holiday rentals

Modern Waterfront Gem w/ Dock on Lake Monomonac

3.0 star property
Modern Waterfront Gem w/ Dock on Lake Monomonac

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

10.0 out of 10, Exceptional, (6)
"Beautiful property and great a host! My boys loved getting up early and fishing into the night! Perfect get away from the hustle and bustle of every day life. If you love nature this is a great place. Lots to explore! We had a GREAT also caught some good size BASS. Definitely will be back again. Thanks tons, The Gallant Family "
Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.

New and Modern 3 B- 5 min FSU - 15 min Wachusett's

10.0 out of 10, Exceptional, (5)
"Wonderful place to stay. Everything was very clean, comfortable, and spacious, with a warm, welcoming feel. I highly recommend the place to stay. "
The price is AU$503
includes taxes & fees
27 Sept - 28 Sept
New and Modern 3 B- 5 min FSU - 15 min Wachusett's

Quiet private pond getaway

9.4 out of 10, Exceptional, (15)
"We really enjoyed our time at the lake house! The deck and fire pit was fun and everything was very nicely decorated and had enough supplies to make it very easy and a quiet peaceful setting!"
Quiet private pond getaway

Downtown Hot Tub Escape

9.6 out of 10, Exceptional, (18)
"Property was easy to locate. The rooms were perfect! Hot tub was fantastic! "
The price is AU$621
includes taxes & fees
10 Sept - 11 Sept
Downtown Hot Tub Escape

Modern Mid-Century in Fitchburg

9.8 out of 10, Exceptional, (6)
"Great property close to where we needed to be."
Modern Mid-Century in Fitchburg

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

9.8 out of 10, Exceptional, (23)
"great location"
The price is AU$283
includes taxes & fees
15 Sept - 16 Sept
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.

Cozy Cabin in a Rural setting-14

8.8 out of 10, Excellent, (5)
"It was a cute nice space. Close to outlets and plenty of trails for hiking. The cabin was also just a nice space to relax."
The price is AU$266
includes taxes & fees
22 Sept - 23 Sept
Cozy Cabin in a Rural setting-14

Charming cabin in delightful Greenfield New Hampshire with WiFi access

9.6 out of 10, Exceptional, (5)
The price is AU$406
includes taxes & fees
9 Sept - 10 Sept
Charming cabin in delightful Greenfield New Hampshire with WiFi access

Charming Waterfront Log Cabin

9.4 out of 10, Exceptional, (41)
"We really appreciated the solitude and quiet retreat this cabin offered. "
Charming Waterfront Log Cabin

Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower

9.8 out of 10, Exceptional, (20)
"Beautiful place"
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower

Cozy Updated Log Cabin with Mountain Views close to Monadnock

9.4 out of 10, Exceptional, (26)
"a fantastic weekend getaway in the mountains! quiet neighborhood with stunning night time views of the stars. such a cozy cabin, very clean, linens provided, nice property with a little fire pit too! very friendly host, easy to contact and pleasant. "
Cozy Updated Log Cabin with Mountain Views close to Monadnock

River Room overlooking the waterfall

10.0 out of 10, Exceptional, (1)
"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."
The price is AU$396
includes taxes & fees
12 Sept - 13 Sept
River Room overlooking the waterfall

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

9.4 out of 10, Exceptional, (13)
"This is a little modern cabin in the woods type experience. It is fairly private, set apart from the road. It rained while we were there, but if it had been warm and dry we would have taken advantage of the outdoor table and chairs. A lovely little spot in rural New Hampshire for one or two."
The price is AU$381
includes taxes & fees
9 Sept - 10 Sept
Cozy Cabin in a Rural Setting #16 near Temple,NH

Cozy Cabin in a Rural setting #8

8.0 out of 10, Very good, (2)
"The cabins in New Hampshire are great place to stay. Everything you need in this efficient space. Would definitely recommend it to anyone. We hope to stay there again."
The price is AU$295
includes taxes & fees
9 Sept - 10 Sept
Cozy Cabin in a Rural setting #8

Unique Cozy private 1-bedroom apartment in charming Temple

9.6 out of 10, Exceptional, (4)
"very clean, well decorated, comfortable and peaceful"
The price is AU$657
includes taxes & fees
12 Sept - 13 Sept
Unique Cozy private 1-bedroom apartment in charming Temple

Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

10.0 out of 10, Exceptional, (13)
"Loved the area"
The price is AU$341
includes taxes & fees
9 Sept - 10 Sept
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

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

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

Waterfront Cottage on Scenic Sportsman Pond

9.6 out of 10, Exceptional, (43)
"Excellent location,plenty of water activities and equipment,fun place, Owners very nice and very helpful."
Waterfront Cottage on Scenic Sportsman Pond

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

10.0 out of 10, Exceptional, (21)
"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. "
The price is AU$791
includes taxes & fees
18 Sept - 19 Sept
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
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

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$266 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?

Modern Waterfront Gem w/ Dock on Lake Monomonac: This highly rated holiday home rental in Winchendon is located on a lake, and has a selection of games, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, kitchenware and a coffee maker.

How many holiday rentals will I find in Winchendon?

Choose from 6 Expedia holiday rentals in Winchendon for a memorable holiday.

What’s there to see and do in Winchendon?

Millers River and V F W Park 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 Blueberry Island 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.