Winchendon Holiday Rentals

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Holiday Rentals in Winchendon

VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac
10.0 out of 10, Exceptional, (6)
"Everything about this property was beautiful. The home itself being located right on the water was perfect for kayaking, fishing, evenings by the fire, relaxing and reconnecting. The house is gorgeous, comfortable, and had everything you might need/want. We enjoyed the game room - jenga and family air hockey tournaments. A lovely experience and we hope to return at some point. Thank you for sharing your beautiful home with us!"
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
10.0 out of 10, Exceptional, (4)
"This property was great. Wonderfully modern lake front home. Recommend renting the pontoon to fish for larger fish. Kayaks, Paddleboards, great restaurants and sauna. Picture perfect scenery. "
VRBO Top 10 - Copley's Lakefront Cottage and Guest House on its own Peninsula
Amazing Lakefront property, Private Pool on Lake Monomonac at Tatum's Place
10.0 out of 10, Exceptional, (1)
"Very nice house on lake with great pool area. Close to town, but not too close. Comfortable beds. Co-located and adjacent to other VRBO houses able to accomadate large family gatherings."
Amazing Lakefront property, Private Pool on Lake Monomonac at Tatum's Place
Lovely 3-bedroom City Escape
9.8 out of 10, Exceptional, (17)
"A couple friends and I stayed for a long weekend to play local disc golf and thoroughly enjoyed our stay. We loved how spacious, comfortable, and clean Christopher's place was and were thankful to each have our own bedroom. Will definitely be back!"
Lovely 3-bedroom City Escape
Charming Waterfront Log Cabin
9.4 out of 10, Exceptional, (34)
"Awesome"
Charming Waterfront Log Cabin
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
9.8 out of 10, Exceptional, (14)
"Wonderful home. Owners are very helpful & hands on. Completely enjoyed the property. "
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
Lake Adjacent Family Home Ready To Host Your Next Trip To Wachusett Mountain!
9.8 out of 10, Exceptional, (85)
"Home was clean and comfortable. My extended family and I stayed two nights for a wedding in the area and a good time was had by all. No complaints with the accommodations and the hosts communicated well."
Lake Adjacent Family Home Ready To Host Your Next Trip To Wachusett Mountain!
Relaxing Retreat
9.8 out of 10, Exceptional, (23)
"Had a wonderful stay here."
Relaxing Retreat
Dog-Friendly Fitchburg Vacation Rental, Hike & Ski
9.4 out of 10, Exceptional, (8)
"We stayed for a lacrosse tournament in Devens MA. Only 20 minutes away and the house was perfect!"
Dog-Friendly Fitchburg Vacation Rental, Hike & Ski
Cottage on Partridge Pond
10.0 out of 10, Exceptional, (16)
"Lovely home with a small dock in a large pond! Kayaks in the back yard. Beautiful looking out to the pond. Very comfortable home. Hosts are very responsive. We would definitely stay here again. Nice job!"
Cottage on Partridge Pond
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
10.0 out of 10, Exceptional, (14)
"The property is lovely. It suited our needs and fully equipped. "
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
Historic Home w/ Modern Updates on < 4 Acres
10.0 out of 10, Exceptional, (6)
"Stayed here with my brothers and cousins.. had a great time. Close proximity to Royalston Falls and a great hike through the forest "
Historic Home w/ Modern Updates on < 4 Acres
Waterfont log home nestled in the pines
10.0 out of 10, Exceptional, (49)
"Beautiful secluded location. Quiet neighborhood right on the lake. Wonderful to go down to the dock in the morning and watch the lake come alive with a good cup of coffee. Plenty of room for the family. The log cabin interior was very cozy, clean and inviting. Kitchen had everything needed. The kayaks and fishing poles were put to good use. We stayed here to attend a nearby family wedding and it was SOOO much nicer than being in a hotel, having the family all together. Alfred made sure to check...
Waterfont log home nestled in the pines
Stunning brand new 2 bedroom Loft amidst nature
10.0 out of 10, Exceptional, (16)
"Place was great! Roomy, comfortable, we felt so welcome! Took my dog for a nice walk around the area in the morning and the country roads were safe and well maintained for a walk. "
Stunning brand new 2 bedroom Loft amidst nature
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
9.2 out of 10, Wonderful, (7)
"The studio apartment was nice. The owner resolved quickly to our questions. The only issue was the traffic noise."
The price is NZ$282
includes taxes & fees
4 Nov - 5 Nov
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Waterfront Cottage on Scenic Sportsman Pond
9.6 out of 10, Exceptional, (41)
"Sportsman's Pond and Blueberry Cottage provided the ideal location for disconnecting from the noise and busyness of every day life. The pond was beautifully serene, without outboard motors, jet skis, etc. The fall colors were gorgeous. The hosts provided every sort of watercraft one might want. I kayaked everyday exploring the shoreline and watching for birds. The cottage was well equipped, the bed was comfortable and an assortment of chairs and couches were available for lounging, viewing the...
Waterfront Cottage on Scenic Sportsman Pond
Cottage on Laurel Lake, Private lake access, picture perfect sunsets
9.4 out of 10, Exceptional, (3)
"We loved the lake and the location. Very nice lake. My kids loved swimming, kayaks and paddle boats. Lovely dock with gorgeous sunset. House is very rustic. The stairs are steep and slippery. Could use a handle rail for safety and may not be appropriate for those with small kids or mobility issues. Beds very small. Screened porch room had some defects in the screen and because of this there were lots of bugs. Otherwise comfortable and very fun. Owners responsive and cabin quite cute and...
Cottage on Laurel Lake, Private lake access, picture perfect sunsets
Welcome to your dream lake getaway! Lovely views of 150 feet lakefront bliss!
10.0 out of 10, Exceptional, (71)
"Perfect place. We were very comfortable and happy with our stay! "
Welcome to your dream lake getaway! Lovely views of 150 feet lakefront bliss!
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower
10.0 out of 10, Exceptional, (12)
"We had a great time. The house was very nice and clean. The lake was really lovely for boating and swimming."
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower
VERY LUXURIOUS QUIET AND PEACEFUL APARTMENT ..PRIVATE ENTRANCE
8.0 out of 10, Very good, (5)
"the hosts were fantastic! They were so welcoming and went out of their way to be take care of our every need even during the Christmas holiday. We were so thankful for how dog friendly they were and the neighborhood was perfect for dog walking. I would definitely stay here again."
The price is NZ$559
includes taxes & fees
12 Nov - 13 Nov
VERY LUXURIOUS QUIET AND PEACEFUL APARTMENT ..PRIVATE ENTRANCE
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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Other types of properties in Winchendon you may be interested in

VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac
10.0 out of 10, Exceptional, (6)
"Everything about this property was beautiful. The home itself being located right on the water was perfect for kayaking, fishing, evenings by the fire, relaxing and reconnecting. The house is gorgeous, comfortable, and had everything you might need/want. We enjoyed the game room - jenga and family air hockey tournaments. A lovely experience and we hope to return at some point. Thank you for sharing your beautiful home with us!"
VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac
Amazing Lakefront property, Private Pool on Lake Monomonac at Tatum's Place
10.0 out of 10, Exceptional, (1)
"Very nice house on lake with great pool area. Close to town, but not too close. Comfortable beds. Co-located and adjacent to other VRBO houses able to accomadate large family gatherings."
Amazing Lakefront property, Private Pool on Lake Monomonac at Tatum's Place
VRBO Top 10 - Copley's Lakefront Cottage and Guest House on its own Peninsula
10.0 out of 10, Exceptional, (4)
"This property was great. Wonderfully modern lake front home. Recommend renting the pontoon to fish for larger fish. Kayaks, Paddleboards, great restaurants and sauna. Picture perfect scenery. "
VRBO Top 10 - Copley's Lakefront Cottage and Guest House on its own Peninsula
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.

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?

VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac: This highly rated holiday home rental in Winchendon offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals will I find in Winchendon?

Choose from 5 Expedia holiday rentals in Winchendon for a memorable holiday.

What’s there to see and do in Winchendon?

Lake Dennison State Recreation Area and Wendall P. Clark Memorial are a couple of scenic spots to enjoy the outdoors, whereas The Robinson-Broadhurst Foundation Performing Arts Ampitheater is one of the cultural attractions. Beals Memorial Library and Winchendon Town Hall are other places to visit while you're in town.

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.