Holiday houses in Lake Winnepocket

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Top-rated holiday rentals in Lake Winnepocket

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Top Guest favourite
A trio of sculpted birds rests on a wooden surface, with a lush green yard and stone wall in the background. Tall trees frame the scene, revealing a peaceful natural setting. The absence of leaves suggests a serene winter landscape.
Guest suite in New London
4.99 out of 5 average rating, 137 reviews

Cozy nest in historic home, close to town

Just minutes from town yet in a quaint residential neighborhood, the apartment attached to our 1820 historic home is a warm and inviting place to stay while visiting lovely New London, New Hampshire. The town includes many shops and restaurants, along with Colby Sawyer College and The New London Barn Playhouse. Minutes from Little Lake Sunapee and Pleasant Lake, both with beach areas and boating access for summer visitors, and close to Mts Sunapee, Kearsarge and Ragged, for hiking and skiing.

Top Guest favourite
Guesthouse in Alton
4.98 out of 5 average rating, 296 reviews

Vineyard Terrace - Modern & Beautiful

Step into a secluded vineyard retreat where elegance and breathtaking scenery meet. This suite offers a king bed, modern comforts, and a spacious patio pergola with sweeping vineyard and mountain views. Enjoy a well-equipped kitchen, dining and living area, or unwind in the new shared hot tub — perfect for romantic getaways or extended stays. Though other guests share the property, this space is yours to enjoy. 5 min to Lake Winni, 20 min to Wolfeboro, 25 min to Gunstock & Bank of NH Pavilion.

Top Guest favourite
A charming two-story house showcases white exterior siding and black shutters. A brick chimney rises from the sloped roof. A walkway leads to the front door, framed by a small porch. Lush greenery surrounds the property, providing a serene atmosphere.
Home in Concord
4.97 out of 5 average rating, 218 reviews

Charming 3 Bedroom Concord New Englander

Your family & friends will be close to everything when you stay at The Charles House. Renovated & modern kitchen & bath, living/dining and separate den. Sleeping for 7, private & spacious yard & seasonal views of the Contoocook River! Walking distance to food, day spa, and hardware store. Within a few miles: apple orchard, a canoe/kayak adventure park, a grocery store/liquor store, retail & Northern Rail Trail. North 15 minutes, the Tilton Outlets! 6 miles to downtown Concord! Sorry, no pets.

Guest favourite
A lofted sleeping area features a spacious bed, framed by a beautifully crafted wooden ceiling. A lantern-style light fixture hangs overhead, and large glass doors lead to the balcony, allowing natural light to illuminate the space.
Barn in Canterbury
4.93 out of 5 average rating, 279 reviews

The Barn

Welcome to The BARN! You can expect to feel tucked away in the trees in this cozy, rustic, yet chic space. Thoughtful lighting, fine linens and furnishings with a spacious and private deck off the back to sit and enjoy nature or entertain. Miles of wooded forest is this location; if you’re looking to escape the city or a busy life, this is the perfect place to explore, relax and revive. At the main house (across the way), there are horses, barn kitties, cattle dogs and other friendly animals.

Top Guest favourite
The bedroom features a spacious bed with an ochre yellow duvet and two matching pillows. A large wooden wardrobe is positioned against the wall. Natural light enters through a window dressed with sheer curtains, illuminating the soft beige walls and patterned area rug.
Guest suite in Andover
4.98 out of 5 average rating, 296 reviews

Guest Suite - Andover Village

Cozy, clean, comfortable and convenient to Proctor Academy's campus, Upper Valley and local Lakes Region attractions. You have a private keyed entrance to a one bedroom and one bath suite in a bungalow home with off street parking. Although attached to the primary home, you enter from your own covered patio and have the suite entirely to yourself. The bedroom has a queen bed, compact bathroom with shower and pleasant sitting area for two. A relaxing atmosphere with a morning coffee amenity!

Top Guest favourite
The studio features a spacious bed with white linens, accented by decorative throw pillows. A vibrant piece of art adorns the wall above the bed. A modern vanity area with a sink is visible, along with natural light filtering through windows that offer views of the surrounding woods.
Guest suite in Milford
5 out of 5 average rating, 155 reviews

New England Village Luxury Studio

Kick back and relax in this stylish studio! Our house is in a quiet neighborhood of older homes surrounded by woodlands yet conveniently located downtown, a half mile from our village green (Milford Oval). A short stroll over the river will take you to cafes, restaurants, pubs with live music, post office, library, shops & useful stores such as CVS. Whatever brings you…business, skiing, hiking, antiques, a family celebration or a romantic weekend away…we are looking forward to hosting you!

Top Guest favourite
The interior dining area features a small wooden table surrounded by chairs and stools. A bright kitchen is visible with stainless steel appliances. Natural light enters through multiple windows, and a cozy seating area is positioned near the entrance, enhancing the welcoming ambiance.
Cottage in Newbury
4.96 out of 5 average rating, 447 reviews

Tranquil Getaway-Dartmouth Lake Sunapee Region

Welcome to your picturesque, peaceful getaway! Nestled along a historic country road, this charming, rustic cottage style home is just minutes from skiing at Mount Sunapee (6 mi), Pats Peak (12 mi), and many other nearby ski areas. Easy access to a network of scenic trails for hiking, snow shoeing, and snowmobiling to explore. Enjoy nearby pristine lakes like beautiful Lake Sunapee, or just relax and soak in the beautiful views — a perfect destination to make memories in any season!

Superhost
An open living area is shown, featuring a cozy seating arrangement with a striped couch, a flat-screen TV, and a round dining table with white chairs. The kitchen space is visible, equipped with stainless steel appliances and ample cabinet storage, illuminated by recessed ceiling lights.
Guest suite in Canterbury
4.88 out of 5 average rating, 254 reviews

Cozy Canterbury Suite

Discover the perfect retreat in Canterbury, NH! Our 1 bed, 1 bath unit is a cozy haven, centrally located for lakes and mountain adventures. Spanning 850 sq ft, it offers comfort with a queen size bed and a pull-out couch to sleep a total of 4. Nestled by snowmobile trails, minutes from Highland Mountain Bike Park, Canterbury country club, and the historic Shaker Village. Unwind in nature's embrace. December-February can be icy. Winter tire or 4x4 vehicle recommended.

Top Guest favourite
A cozy living area is highlighted by a spacious brown leather sofa positioned beside a decorative area rug. Natural light enters through a triangular window, illuminating wooden walls and ceiling beams. A small kitchen area with wooden countertops and carefully arranged decor adds to the inviting ambiance.
Apartment in Wilmot
4.99 out of 5 average rating, 162 reviews

Bog Mt Retreat Upstairs Suite

A unique crafty cozy 1 bedroom/1 bathroom UPSTAIRS suite with most of the comforts of home except a oven. Woodland trails on the property, moderate hikes nearby or bring your kayaks and explore the many ponds and lakes in the area. Ragged Mt and Mt Sunapee Ski Resorts are both under 30 minutes away. This newly designed suite is perfect for an individual or couple wanting to escape into the country but still be within an easy driving distance to local sites.

Top Guest favourite
A cozy living area features a comfortable sofa and a wooden table beneath a rustic wooden ceiling with exposed beams. A wooden ladder with handrails leads to a loft space above, adding charm and functionality to the cabin's interior.
Cabin in Andover
4.95 out of 5 average rating, 127 reviews

Little House on the Lake in the Forest

***7-night minimum in warmer months, Saturday check in/out*** Wake up to the call of loons in this tiny and cozy lakefront cabin. Nestled at the remote base of Mount Kearsarge, with unobstructed views of Ragged Mountain, this location affords year-round adventure on the protected south shore of Bradley Lake. Five minutes from Proctor Academy, 90 minutes from Boston. This retreat mixes ample amenities and high-speed internet with outdoor adventure!

Top Guest favourite
A large historic house is blanketed in snow, with heavy snowfall creating a serene winter scene. The front porch is visible, along with large windows partially obscured by the snow. An American flag can be seen waving in front of the building.
Apartment in Wilmot
4.94 out of 5 average rating, 105 reviews

Rustic Barn King Apt. at Deepwell Farm (2nd Floor)

Enjoy this one king bed, one bath cozy apartment on the second level of the old barn at Deepwell Farm, a 205 year old estate in lovely Wilmot, NH in the valley beneath Mount Kearsarge. The rustic exposed beams are a treat, while modern conveniences of a full kitchen and laundry can make any short to long-term stay enjoyable. A local pond with beach and amenities, and multiple hiking / biking trails await your outdoor adventures.

Top Guest favourite
A charming country cabin is presented, featuring wooden shingle siding and red trim. A welcoming front door is set within a gabled frame. Surrounding greenery includes well-maintained bushes and trees, with a wooden privacy fence visible to one side.
Cabin in Northfield
4.95 out of 5 average rating, 275 reviews

Adorable Country Cabin with Hot Tub

Get cozy in this country cabin off the beaten path yet close to everything. The cabin is a comfortable size with all of the amenities to make your stay comfortable. Including a 3/4 bathroom, and well sized kitchenette. Oh and of course the Hot Tub right outside your door. The cabin is about 30 minutes from mountains and lakes for all of you outdoor recreation wants. Also only minutes to dining and shopping.

Popular amenities for Lake Winnepocket holiday rentals