Winchendon Holiday Rentals

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Holiday Rentals in Winchendon

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 NZ$855
includes taxes & fees
28 May - 29 May
Enjoy your stay in an antique home in an antique toy museum!
Interior
Charming Waterfront Log Cabin
10.0 out of 10, Exceptional, (25)
"Had some work in the area and decided to avoid hotels, etc. Found the property to be really peaceful and relaxing."
The price is NZ$665
includes taxes & fees
11 Jun - 12 Jun
Charming Waterfront Log Cabin
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 NZ$300
includes taxes & fees
2 Jun - 3 Jun
Cozy Cabin in a Rural Setting #16 near Temple,NH
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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!!
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
Exterior
Sweet Retreat and Yurt Farm
10.0 out of 10, Exceptional, (2)
"We had a really nice time in the yurt– it's beautifully decorated on the inside, very cozy and the hosts were super nice and welcoming. Would definitely recommend staying here!"
The price is NZ$340
includes taxes & fees
2 Jun - 3 Jun
Sweet Retreat and Yurt Farm
Interior
Relaxing Retreat
10.0 out of 10, Exceptional, (17)
"It was a pleasant stay"
Relaxing Retreat
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
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 -
Property grounds
Lakefront Orange Vacation Rental - Pet Friendly!
10.0 out of 10, Exceptional, (7)
"Crystal was an exceptional hostess! "
Lakefront Orange Vacation Rental - Pet Friendly!
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
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
Property grounds
Charming Cottage by the Lake
Charming Cottage by the Lake
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
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!
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
Fridge, microwave, stovetop, dishwasher
Charming Jaffrey Cottage w/ Deck & Grill!
10.0 out of 10, Exceptional, (34)
"Loved everything about it!"
Charming Jaffrey Cottage w/ Deck & Grill!
Fridge, microwave, stovetop, dishwasher
Updated Vintage Apartment < 1/2 Mi to Main St
9.8 out of 10, Exceptional, (8)
"Place is great! Pricing is deceiving…fees were double the actual rent. Small ramp from kitchen to living room is dangerous!"
Updated Vintage Apartment < 1/2 Mi to Main St
Fridge, microwave, oven, stovetop
- Pet Friendly - 45mins Lakes - Boston - Seacoast -
10.0 out of 10, Exceptional, (7)
"The rental in located in downtown Milford, a small quaint New England town with well kept nicely lanscaped late 19th and early 20th century homes. It is very close to restaurants. We chose Grill 603 and Asanm for dinner. Both were very satisfactory but Ansam was Haitian, delightfully different! Saturday morning we breakfasted at the Cafe on the Oval which also earns our recommendation. We will likely stay here again."
The price is NZ$374
includes taxes & fees
28 May - 29 May
- Pet Friendly - 45mins Lakes - Boston - Seacoast -
Exterior
Dog-Friendly Fitchburg Vacation Rental, Hike & Ski
9.6 out of 10, Exceptional, (4)
"We had a lovely stay at the house. It’s very clean and comfortable. The welcome basket was a nice touch upon arrival. We stayed at the house to visit Great Wolf Lodge and be able to have our dog with us. It’s about a 7 minute drive to Great Wolf and we had the best time. We had delicious dinners at 110 Grill and at Tacos Tequila. The house is next to a beautiful quiet cul de sac perfect for walking our dog. We would definitely stay again!"
Dog-Friendly Fitchburg Vacation Rental, Hike & Ski
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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.

Other types of properties in Winchendon you may be interested in

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 NZ$855
includes taxes & fees
28 May - 29 May
Enjoy your stay in an antique home in an antique toy museum!
4 indoor pools, seasonal outdoor pool, pool cabanas (surcharge)
Great Wolf Lodge Boston / Fitchburg, MA
3.5 star property
8.6 out of 10, Excellent, (695)
"Took my family here for the first time and they loved it and enjoyed it, we will definitely be back. The only thing they need to do is update the facility property, especially the rooms and the carpets had some stains all over it but overall a good fun place to go to. Staff were very nice, helpful and very attentive to everybody needs."
The price is NZ$384
includes taxes & fees
2 Jun - 3 Jun
Great Wolf Lodge Boston / Fitchburg, MA
Lobby
Motel 6 Leominster, MA
2.0 star property
7.4 out of 10, Good, (1011)
"All around good"
The price is NZ$181
includes taxes & fees
16 Jun - 17 Jun
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Winchendon holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Winchendon. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Winchendon. Seeing all the best attractions is bound to make you fall in love with Winchendon. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Winchendon short-term rentals, that won’t be hard to do.

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.

Recent reviews of Winchendon properties
Expedia verified reviews