Winchendon Holiday Rentals

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Holiday Rentals in Winchendon

Enjoy your stay in an antique home in an antique toy museum!
9.2 out of 10, Wonderful, 7 reviews
"A unique enjoyable experience "
The price is AU$795
per night
4 June - 5 June
Enjoy your stay in an antique home in an antique toy museum!
Charming Waterfront Log Cabin
9.8 out of 10, Exceptional, 26 reviews
"Had some work in the area and decided to avoid hotels, etc. Found the property to be really peaceful and relaxing."
The price is AU$590
per night
11 June - 12 June
Charming Waterfront Log Cabin
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!
10.0 out of 10, Exceptional, 54 reviews
"Great location for our destination wedding nearby. Spacious home with a nice sunroom. Loved how you felt away from it all yet were very close to groceries, shops and restaurants."
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!
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Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower
9.8 out of 10, Exceptional, 10 reviews
"We had a great time at the cottage and were pleasantly surprised at the quaintness of the pond and surrounding community. Wonderful stay overall! We skied Wachusett. Which was 5 min drive and Wachusett Brewery was amazing! We recommend checking the sauna hookup first and more adult sized towels! Everything else was lovely!"
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower
Cozy Cabin in a Rural Setting #16 near Temple,NH
9.6 out of 10, Exceptional, 5 reviews
"Nice and clean cottage. Water is undrinkable and even too smelly to shower with. "
The price is AU$358
per night
4 June - 5 June
Cozy Cabin in a Rural Setting #16 near Temple,NH
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
10.0 out of 10, Exceptional, 8 reviews
"The house was superb for our family visit! We enjoyed it all! Linda was a perfect hostess…,so attentive!"
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
Sweet Retreat and Yurt Farm
10.0 out of 10, Exceptional, 3 reviews
"The Yurt was clean, everything that you need to stay is provided. The host was super friendly, and it was a great pleasure to see his farm animals as they were friendly too."
The price is AU$320
per night
9 June - 10 June
Sweet Retreat and Yurt Farm
Relaxing Retreat
10.0 out of 10, Exceptional, 17 reviews
"It was a pleasant stay"
Relaxing Retreat
Peaceful lake & boat house! Full kitchen. Fire pit, boat dock, canoes & a kayak
10.0 out of 10, Exceptional, 60 reviews
"Place was perfect for the 4 of us in town for a wedding. All new finishes and furnishings. Not one thing lacking. Want to come back in the summer."
Peaceful lake & boat house! Full kitchen. Fire pit, boat dock, canoes & a kayak
- Pet Friendly - 45 Mins to Boston - Ocean - Lakes - Mountains -
9.8 out of 10, Exceptional, 10 reviews
"Loved the ease of check in and check out, great location for our purpose!!"
- Pet Friendly - 45 Mins to Boston - Ocean - Lakes - Mountains -
Lakefront Orange Vacation Rental - Pet Friendly!
10.0 out of 10, Exceptional, 7 reviews
"The setting was beautiful and quiet. The creature comforts (snacks, lots of towels, toiletries) were thoughtful and plentiful. I went paddle-boarding (brought my own) and a swim. I will definitely stay there again!"
Lakefront Orange Vacation Rental - Pet Friendly!
Waterfront Cottage on Scenic Sportsman Pond
9.4 out of 10, Exceptional, 35 reviews
"Had a wonderful weekend kayaking and fishing. Very private and quiet. Great relaxing spot in nature"
Waterfront Cottage on Scenic Sportsman Pond
Quiet private pond getaway
9.6 out of 10, Exceptional, 4 reviews
"Needed a long weekend getaway. Perfect spot located in nature, great fishing and fall foliage."
Quiet private pond getaway
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
10.0 out of 10, Exceptional, 8 reviews
"Beautiful home in a beautiful area. Home was spacious, comfortable and well furnished. Played golf at a course nearby and visited a terrific brewery--both within a few miles of the home. Outdoor area was useful and private. Plenty of parking."
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
Charming Cottage by the Lake
Charming Cottage by the Lake
Historic Home w/ Modern Updates on < 4 Acres
10.0 out of 10, Exceptional, 5 reviews
"The property was awesome! Old, quaint and brought memories back of our grandparents homes…Family sat around table and enjoyed shared memories"
Historic Home w/ Modern Updates on < 4 Acres
Cozy Cabin in a rural setting (#12) in Temple NH
10.0 out of 10, Exceptional, 11 reviews
"Great little spot for an overnight. Clean and very comfortable! Had everything we needed!"
The price is AU$325
per night
4 June - 5 June
Cozy Cabin in a rural setting (#12) in Temple NH
Lake Adjacent Family Home Ready To Host Your Next Trip To Wachusett Mountain!
9.8 out of 10, Exceptional, 78 reviews
"We had a great get-away down to Wachusett Mountain with our two famlies, lots of room for everyone and very comfortable and close to the ski area and restaurants/groceries. Thank you!"
Lake Adjacent Family Home Ready To Host Your Next Trip To Wachusett Mountain!
Cottage on Laurel Lake, Private lake access, picture perfect sunsets
9.0 out of 10, Wonderful, 2 reviews
"It is a fun place for kids with a beautiful lake to enjoy. We made many fun memories and enjoyed our stay very much."
Cottage on Laurel Lake, Private lake access, picture perfect sunsets
Private Field House - Spacious 4 Bedroom Home
10.0 out of 10, Exceptional, 12 reviews
"We had a wonderful stay at the Dublin field house. Brie was an attentive host answering questions about local dining and offering to pick up groceries ahead of our arrival. Our party arrived in stages so knowing there were already snacks in the fridge was a huge relief. On our way home we were already talking about when we could stay again!"
Private Field House - Spacious 4 Bedroom Home
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See all available properties in Winchendon
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.

Winchendon Holiday Home Travel Info

Other types of properties in Winchendon you may be interested in

Enjoy your stay in an antique home in an antique toy museum!
9.2 out of 10, Wonderful, 7 reviews
"A unique enjoyable experience "
The price is AU$795
per night
4 June - 5 June
Enjoy your stay in an antique home in an antique toy museum!
Great Wolf Lodge Boston / Fitchburg, MA
3.5 star property
8.6 out of 10, Excellent, 701 reviews
"We had a wonderful time with our family. The only bad experience we had was when calling front end for service . They dont answer the phones for nothing ! I had to physical go down to the check in desk ask for extra pillow and blanket because my kids were cold. The lady at the front desk said someone should be up in a few. Well, we waited and waited for somone to knock on our door to bring us the pillow and blanket. NOBODY SHOWN UP ! the next morning we open up our door and it was left on the...
The price is AU$353
per night
4 June - 5 June
Great Wolf Lodge Boston / Fitchburg, MA
Motel 6 Leominster, MA
2.0 star property
7.4 out of 10, Good, 1,011 reviews
"This is a nicer Motel 6 with very clean rooms and modern amenities. The area has plenty of food choices within walking distance. As some have noted it does house migrants and the homeless but I avoided them and they did not bother me. I am not sure how safe a woman staying by herself would be here so thought I would mention this. Other than that not a bad choice. "
The price is AU$163
per night
16 June - 17 June
Motel 6 Leominster, MA
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.

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$320 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?

Charming Waterfront Log Cabin: This holiday home rental outside of Winchendon is located on the waterfront, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

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?

Lake Dennison State Recreation Area and Millers River are a couple of lovely local spots to get outside and enjoy nature. The Winchendon School and Wetmore Trailhead are a couple of places you'll find in the wider area.

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.

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