Winchendon Vacation Rentals

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Vacation 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 ￥62,011
￥82,140 total
includes taxes & fees
May 28 - May 29
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 ￥29,671
￥63,876 total
includes taxes & fees
Jun 11 - Jun 12
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 ￥20,409
￥28,847 total
includes taxes & fees
Jun 2 - Jun 3
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 ￥14,914
￥32,704 total
includes taxes & fees
Jun 2 - Jun 3
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 ￥13,344
￥35,941 total
includes taxes & fees
May 28 - May 29
- 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
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.

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 ￥62,011
￥82,140 total
includes taxes & fees
May 28 - May 29
Enjoy your stay in an antique home in an antique toy museum!
4 indoor pools, seasonal outdoor 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 ￥28,101
￥36,852 total
includes taxes & fees
Jun 2 - Jun 3
Great Wolf Lodge Boston / Fitchburg, MA
Lobby
Motel 6 Leominster, MA
2.0 star property
7.4 out of 10, Good, (1011)
"Good"
The price is ￥15,258
￥17,357 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.

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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

Motel 6 Leominster, MA

Motel 6 Leominster, MA

5/5 Excellent
"Good"
A verified traveler stayed at Motel 6 Leominster, MA
Posted 1 day ago
Motel 6 Leominster, MA