Winchendon Vacation Rentals

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Vacation Rentals in Winchendon

VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac
Interior
VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac
10.0 out of 10, Exceptional, (5)
"Copley Cottage was phenomenal! Our group included family from Los Angeles, Pa and NJ. We wanted to introduce our newest family member to great grandpa who lives in the area. We were impressed with the design and lay out of the house. . High end kitchen and open concept made for easy enjoyable time together. Waking up to the views of the lake and area felt like a bit of paradise. The private beach, dock and sauna were outstanding additions. Overall a stay that will be remembered forever"
VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac
VRBO Top 10 - Copley's Lakefront Cottage and Guest House on its own Peninsula
Interior
VRBO Top 10 - Copley's Lakefront Cottage and Guest House on its own Peninsula
10.0 out of 10, Exceptional, (3)
"My family and I stayed here four nights over Christmas, and were extremely particular. This home exceeded expectations; from the cleanliness, to the aesthetics of both home and location. Made for a great Christmas holiday, filled with memories for years to come. We will absolutely be repeat customers of this property."
VRBO Top 10 - Copley's Lakefront Cottage and Guest House on its own Peninsula
Amazing Lakefront property, Private in ground pool, Epic views of Lake Monomonac
Fridge, microwave, oven, stovetop
Amazing Lakefront property, Private in ground pool, Epic views of Lake Monomonac
Amazing Lakefront property, Private in ground pool, Epic views of Lake Monomonac
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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
$525 total
includes taxes & fees
Jun 19 - Jun 20
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, (27)
"This cabin is so wonderful. The linens are exquisite and the beds are super comfortable. It is decorated so cute. There is everything you need! My favorite activity was sitting in the wooden rocking chair on the front porch each morning, drinking coffee, listening to nature (frogs, fish), and watching the lovely pond (which is so big it should be called a lake!) The owner responded to all my questions within minutes. You can even have pizza (regular AND gluten free) delivered!! If you visit, you...
Charming Waterfront Log Cabin
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, (9)
"The grounds were well kept. The house was remodeled and very clean. Lots of room. Equipped with everything you would need. Quiet. Owners were awesome to deal with and easy to get ahold of. I would definitely recommend people to stay there. "
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
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!"
The price is $600
$1,003 total
includes taxes & fees
Jun 23 - Jun 24
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
9.4 out of 10, Exceptional, (6)
"Nice and clean cottage. Water is undrinkable and even too smelly to shower with. "
The price is $130
$230 total
includes taxes & fees
Jun 19 - Jun 20
Cozy Cabin in a Rural Setting #16 near Temple,NH
Downtown Hot Tub Escape
Property grounds
Downtown Hot Tub Escape
9.6 out of 10, Exceptional, (4)
"We had a work get together and it is was perfect. There was a nice spot outside to socialize, and all of the sleeping areas were very comfy. Great stay."
The price is $185
$352 total
includes taxes & fees
Jun 25 - Jun 26
Downtown Hot Tub Escape
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!!
- 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!!"
The price is $80
$217 total
includes taxes & fees
Jun 23 - Jun 24
- Pet Friendly - 45 Mins to Boston - Ocean - Lakes - Mountains -
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!
Relaxing Retreat
Interior
Relaxing Retreat
9.8 out of 10, Exceptional, (18)
"It was a pleasant stay"
Relaxing Retreat
Welcome to your dream lake getaway! Divine views of 150 feet lakefront bliss!
Property grounds
Welcome to your dream lake getaway! Divine views of 150 feet lakefront bliss!
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."
Welcome to your dream lake getaway! Divine views of 150 feet lakefront bliss!
Lakefront Orange Vacation Rental - Pet Friendly!
Property grounds
Lakefront Orange Vacation Rental - Pet Friendly!
10.0 out of 10, Exceptional, (8)
"It’s a wonderful place to stay!!"
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
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
Sweet Retreat and Yurt Farm
Property grounds
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
$206 total
includes taxes & fees
Jun 23 - Jun 24
Sweet Retreat and Yurt Farm
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
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

VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac
Interior
VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac
10.0 out of 10, Exceptional, (5)
"Copley Cottage was phenomenal! Our group included family from Los Angeles, Pa and NJ. We wanted to introduce our newest family member to great grandpa who lives in the area. We were impressed with the design and lay out of the house. . High end kitchen and open concept made for easy enjoyable time together. Waking up to the views of the lake and area felt like a bit of paradise. The private beach, dock and sauna were outstanding additions. Overall a stay that will be remembered forever"
VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac
Amazing Lakefront property, Private in ground pool, Epic views of Lake Monomonac
Fridge, microwave, oven, stovetop
Amazing Lakefront property, Private in ground pool, Epic views of Lake Monomonac
Amazing Lakefront property, Private in ground pool, Epic views of Lake Monomonac
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
$525 total
includes taxes & fees
Jun 19 - Jun 20
Enjoy your stay in an antique home in an antique toy museum!
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 $80 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?

Amazing Lakefront property, Private in ground pool, Epic views of Lake Monomonac: Visitors give good reviews to this Winchendon vacation home rental, which is located on the waterfront and has an outdoor pool, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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

Doubletree by Hilton Hotel Leominster

Doubletree by Hilton Hotel Leominster

5/5 Excellent
"Cookies were great! Thanks!"
A verified traveler stayed at Doubletree by Hilton Hotel Leominster
Posted 3 days ago
Doubletree by Hilton Hotel Leominster