Winchendon Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    one key icon
    Treat yourself
    Save instantly and earn perks with One Key
    Learn about One Key
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Winchendon

Enjoy your stay in an antique home in an antique toy museum!
Interior
Enjoy your stay in an antique home in an antique toy museum!
9.2 out of 10, Wonderful, (7)
"A unique enjoyable experience "
The price is $395
$523 total
includes taxes & fees
Jun 4 - Jun 5
Enjoy your stay in an antique home in an antique toy museum!
Charming Waterfront Log Cabin
Interior
Charming Waterfront Log Cabin
9.8 out of 10, Exceptional, (26)
"Had some work in the area and decided to avoid hotels, etc. Found the property to be really peaceful and relaxing."
The price is $210
$432 total
includes taxes & fees
Jun 18 - Jun 19
Charming Waterfront Log Cabin
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!
Exterior
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!
10.0 out of 10, Exceptional, (54)
"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!!
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower
Lake
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower
9.8 out of 10, Exceptional, (10)
"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
Fridge, microwave, stovetop, coffee/tea maker
Cozy Cabin in a Rural Setting #16 near Temple,NH
9.6 out of 10, Exceptional, (5)
"Nice and clean cottage. Water is undrinkable and even too smelly to shower with. "
The price is $130
$235 total
includes taxes & fees
Jun 4 - Jun 5
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
Lake
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
10.0 out of 10, Exceptional, (8)
"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
Interior
Sweet Retreat and Yurt Farm
10.0 out of 10, Exceptional, (3)
"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 $95
$210 total
includes taxes & fees
Jun 9 - Jun 10
Sweet Retreat and Yurt Farm
Relaxing Retreat
Interior
Relaxing Retreat
10.0 out of 10, Exceptional, (17)
"It was a pleasant stay"
Relaxing Retreat
Peaceful lake & boat house! Full kitchen. Fire pit, boat dock, canoes & a kayak
Property grounds
Peaceful lake & boat house! Full kitchen. Fire pit, boat dock, canoes & a kayak
10.0 out of 10, Exceptional, (60)
"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 -
Aerial view
- Pet Friendly - 45 Mins to Boston - Ocean - Lakes - Mountains -
9.8 out of 10, Exceptional, (10)
"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!
Property grounds
Lakefront Orange Vacation Rental - Pet Friendly!
10.0 out of 10, Exceptional, (7)
"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
Exterior
Waterfront Cottage on Scenic Sportsman Pond
9.4 out of 10, Exceptional, (35)
"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
Property grounds
Quiet private pond getaway
9.6 out of 10, Exceptional, (4)
"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
Smart TV
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
10.0 out of 10, Exceptional, (8)
"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
Property grounds
Charming Cottage by the Lake
Charming Cottage by the Lake
Historic Home w/ Modern Updates on < 4 Acres
4 bedrooms, desk, iron/ironing board, internet
Historic Home w/ Modern Updates on < 4 Acres
10.0 out of 10, Exceptional, (5)
"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
Exterior
Cozy Cabin in a rural setting (#12) in Temple NH
10.0 out of 10, Exceptional, (11)
"Great little spot for an overnight. Clean and very comfortable! Had everything we needed!"
The price is $115
$214 total
includes taxes & fees
Jun 4 - Jun 5
Cozy Cabin in a rural setting (#12) in Temple NH
Lake Adjacent Family Home Ready To Host Your Next Trip To Wachusett Mountain!
Exterior
Lake Adjacent Family Home Ready To Host Your Next Trip To Wachusett Mountain!
9.8 out of 10, Exceptional, (78)
"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
Interior
Cottage on Laurel Lake, Private lake access, picture perfect sunsets
9.0 out of 10, Wonderful, (2)
"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
Fridge, microwave, oven, stovetop
Private Field House - Spacious 4 Bedroom Home
10.0 out of 10, Exceptional, (12)
"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
Don't see what you're looking for?
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 Vacation Rental Travel Info

Popular accommodation
Winchendon private vacation homes
Known landmarks
Doane's Falls, Dunn State Park and Lake Dennison State Recreation Area
International airport
Boston, MA (BOS-Logan Intl.)

Other types of properties in Winchendon you may be interested in

Enjoy your stay in an antique home in an antique toy museum!
Interior
Enjoy your stay in an antique home in an antique toy museum!
9.2 out of 10, Wonderful, (7)
"A unique enjoyable experience "
The price is $395
$523 total
includes taxes & fees
Jun 4 - Jun 5
Enjoy your stay in an antique home in an antique toy museum!
Great Wolf Lodge Boston / Fitchburg, MA
4 indoor pools, seasonal outdoor pool, cabanas (surcharge)
Great Wolf Lodge Boston / Fitchburg, MA
3.5 star property
8.6 out of 10, Excellent, (701)
"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 $179
$235 total
includes taxes & fees
Jun 4 - Jun 5
Great Wolf Lodge Boston / Fitchburg, MA
Motel 6 Leominster, MA
Lobby
Motel 6 Leominster, MA
2.0 star property
7.4 out of 10, Good, (1011)
"The staff member tjat checked us in was amazing "
The price is $97
$111 total
includes taxes & fees
Jun 16 - Jun 17
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchendon vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchendon vacation 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 low season months. For more hustle and bustle, you may prefer to visit Winchendon in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $95 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winchendon rentals

At Expedia, we put the best Winchendon vacation 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 vacation.

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 vacation rentals in Winchendon?

Yes, we offer vacation rentals near well known points of interest in Winchendon, or you can choose a secluded option if you're looking for relaxation. Winchendon is known for its parks.

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

Charming Waterfront Log Cabin: This vacation home near Winchendon is located on the waterfront and has a garden, a barbecue grill, 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 you can cook with friends or family.

How many vacation rentals will I find in Winchendon?

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

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 larger area.

What’s a vacation rental in Winchendon like?

Vacation rentals are private properties you can book for a few weeks or just a few days in Winchendon. Vacation rentals offer extras such as hot tubs, fire pits, and patios so your stay will be comfortable. If you're concerned about a clean environment, a vacation rental can offer a sense of safety away from public hotel elevators and busy lobbies while still allowing you to travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for family trips or small group gatherings.

Recent reviews of Winchendon properties
Expedia verified reviews

The Birchwood Inn

The Birchwood Inn

5/5 Excellent
"I travel a lot for work on my own in remote areas of NH & VT, so finding a safe and comfortable place to stay is very important to me. The staff at Birchwood were so kind and welcoming. My room was well prepared and very clean. The only thing that made me a little nervous was the back door in the room because I was unsure if the lock actually worked and only a thin see through drape covered the window. Just something to be cognizant of for young women traveling alone! Overall, I loved my stay and would definitely come again! "
A verified traveler from Conway stayed at The Birchwood Inn
Posted 3 days ago
The Birchwood Inn