Vacation rentals in Winchendon

Cider House Cottage

Antique guest cottage on a becountry farm property with acres of fields, ponds, forests and streams, adjoining Quabbin Reservoir domain. Ideal for hikers, bird watchers, and bicyclists, this quiet country retreat offers trails and terrain to explore, only 3 miles away from small historic New England town. Make yourself at home in the comfortably furnished post and beam home with terrace and pond views, adventure in the surroundings, dip in fresh water streams, and relax in the claw foot bathtub

Fully Renovated Cottage

Come for a short or long stay in this cozy, efficient, newly renovated cottage. Located less than a mile from the New Hampshire border in Winchendon, MA, the cottage provides easy access to hiking, skiing, fishing, and other outdoor activities in both the Monadnock Region, and North Central Worcester County. Brand new mini-splits provide AC throughout the house and brand new beds and mattresses will help ensure a comfortable and restful stay. 25 Min from Wachusett Ski Area for winter getaways!

"The Porch" Your cozy home away from home!

Welcome to The Porch! Ready for a mini vacation, or just a place to hang out, or work from? You are most welcome here! . This cozy cabin is very flexible and user friendly! It is private to only your group! The downstairs with all it offers, is for one or two person stays. The upstairs becomes available if you enter 3 or more people. This building is in the backyard of our home, as in photos on our Airbnb site, Other info is listed there also! Info book is in room! Welcome! (no pets)

Cabin & Sauna on Lake Monomonac

Beautiful Finnish House and a Sauna on Lake Monomonac. 2 Queen bedrooms, full kitchen and bathroom. Maximum occupancy 4. Perfect for a family reunion, get together or event. Authentic Finnish wood burning sauna, boat dock, kayaks, canoes, nature, wildlife, birding, walking, running, hiking, biking, snow skiing ATV, UTV, snowmobiling. Close to Mt Monadnock, Mt. Wachusett, Pats Peak, Granite Gorge Mountain Peak, and Crotched Mountain for hiking and skiing. 1 hr. from Boston 4 hrs. from NYC

Cozy, year-round Lakefront Retreat.

Nestled in nature at the end of a quiet, wooded road, this cozy waterfront home overlooks peaceful Winnekeag Lake and is surrounded by cedars and maple trees. Wake to glowing sunrises over the water and the call of loons. Spend summer days swimming, kayaking, and fishing, or explore scenic hiking trails nearby. In winter, enjoy and unwind by the fireplace after skiing, and , relax in the radiant sunroom with heated floors and windows on 3 sides—perfect for taking in the beauty of the lake.

Lakefront 3BR Log Cabin w/ Dock & Fire Pit

Escape to our true log cabin on Lake Contoocook. Wake up to sparkling water views, step onto the private dock, and spend the day swimming, kayaking or fishing. Inside you’ll find soaring timber ceilings, a fully equipped kitchen, fast Wi-Fi and three comfy bedrooms that sleep eight. Lakefront deck for sunset drinks, fire pit & BBQ grill Board games & books for rainy days. Only 90 minutes from Boston yet a world away in the pines—perfect for families and friend getaways year-round.

Willow Falls Home ~Hot tub & Waterfront

Constructed waterfall views are just feet away from you! Not far from Boston, RI or CT, this newly designed home is located at a privately viewed pond, in New England, near Mt. Monadnock! Kick back, relax & listen to the water falling in a screened-in gazebo, or in the outdoor hot tub! Or view it all at the picture windows and enjoy the solitude at this picturesque retreat! Inside you'll find multiple lounging areas, luxurious beds, a fully stocked kitchen and a fun game room.

Escape to the Lake!

Relax with family or friends at this little slice of heaven directly on Sunset Lake. The west facing views make the lake live up to its name. We purchased this home in fall 2023 so all furniture, paint and fixtures are relatively new! While this home is outdoor living at its best, we do have WiFi and TV for those who want it. There are 2 kayaks for use as well as a covered hot tub with lake views. You can walk into the shallow water from shore and jump off the dock with ease.

Lakefront Mid-Century Cottage with Sandy Beach

Welcome to Hudson's Hideaway- a peaceful lakeside retreat where simple charm meets unforgettable views. Tucked among the pine trees at the end of a quiet, bumpy dirt road, this classic 1940's three season cottage is the kind of place that lets you slow down and reconnect with nature. While the cottage proudly shows its vintage character, it has been lovingly maintained and thoughtfully stocked with everything you need for a comfortable stay. The real star is the location.

Lake Monomonac Cottage with Private Beach & Dock

Relax at a lakefront cottage on a peninsula on desirable Lake Monomonac. Enjoy a private beach, dock, patio, kayaks, rowboat, swimming, fishing, boating, and water sports. Inside is a cozy 1BR, 1BA cottage with a queen bed and small pull-out sofa, full kitchen, Wi-Fi, AC, and plenty of parking. Wooded hiking trails are within walking distance. Bringing a boat? Guests may use the dock. Launch at the public boat ramp at North of the Border, 1207 US-202, Rindge, NH 03461.

The little house on Mirror Pond

Escape to our fully renovated tiny pond house on the serene Mirror Pond. Perfect for up to 4 guests, enjoy swimming, kayaking, or floating on tubes. Unwind by the fire pit, barbecue on the deck, or cozy up by the fireplace with board games on cooler days. With great WiFi, it’s also ideal for a peaceful work retreat. Whether you're here to relax, or get some work done, this tranquil hideaway offers the perfect blend of adventure and relaxation.

The Shoreline

Welcome to The Shoreline. This Classic New England Lakehouse is located on Lake Monomonac, minutes away from amenities but tucked away in small town America. This property is the ideal getaway for a relaxing peaceful vacation. The kitchen and living areas are comfortable and clean, but the real star is the lake itself—perfect for boating, kayaking, swimming, and fishing. Enjoy the 180 degree water views and over 600 ft of beautiful shoreline.