Holiday houses in Lake Wentworth

Luxury Year-round Treehouse with private hot tub

The Canopy is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

Family · Location · Heating

Lake Winnipesaukee/9min to Gunstock Mtn. Alton Bay

Family lake house built over the water on Lake Winnipesaukee. Great place for families and children. Only 9 min. to Gunstock Mountain for exceptional NH skiing. Close to many amazing hikes and set in the middle of world class foliage! Quiet, serene, and restful cottage that offers something for everyone. Whether is swimming, paddle boarding, and hiking in the summer or skiing, ice fishing and relaxing by the wood stove in the winter, this cottage will relax and revive you and your loved ones.

Family · Value · Decor

Luxury Lakehouse| Sunsets| Cen. Air| Private Dock

Crystal clear Rust Pond contemporary waterfront home with picturesque lake views from every angle and multiple decks. Your vacation home has central AC for hot days and a cozy gas fireplace and central heat for chilly nights. Rust Pond is an oligotrophic lake with excellent swimming, SUP boarding, kayaking, fishing, etc. The home offers privacy in a peaceful lakeside setting, yet is just 10 mins from Wolfeboro downtown restaurants, farm to table fare, art galleries and boutique shopping.

Family · Location · Getting around

Clean, quaint studio apartment on small farm

Enjoy the Old Farm cottage, a studio apartment on our small homestead in the beautiful Lakes Region. It’s a perfect spot for couples, small families, or traveling nurses. We are within 20 minutes to many beaches, including Lake Winnipesaukee, and provide easy access to head south to the ocean or north to the mountains. You will have your own separate parking/entrance, but are welcome to enjoy our cozy fire pit, stylish treehouse, and backyard access to the network of snowmobile trails.

Location · Value · Decor

Peaceful horse farm retreat

Gorgeous foliage views from the big bay window. A nice 1 mile walking trail. A full kitchen to make homemade meals. A large TV to settle in and relax. A workspace if needed. Laundry. Extra space could be used for storage/air mattress/kid space. Come experience farm life and let us know if you want a visit with any of the animals. Horses, chickens & dogs. Our place is a perfect getaway for a couple or small family. Escape the busy city noise. Relax at our firepit and check out the stars

Location · Family · Layout

Waterfront Chalk Pond | Fireplace | Kayaks

Birch Hill House on Chalk Pond is a bright waterfront retreat for every season. Cathedral ceilings and expansive windows frame glowing sunset water views while a cozy electric fireplace warms crisp evenings. Enjoy hiking, birding, kayaking, fishing, and swimming from the private beach, then unwind by the fire pit or relax on the spacious deck. Watch for loons and eagles and explore nearby Birch Ridge trails, Powder Mill snowmobile routes, and the Lakes Region. 90 minutes from Boston.

Location · Family · View

Kings Cottage

Relax in this cozy 2BR, 1.5BA lakeside retreat with beautiful water views. Enjoy a spacious living room, open-concept kitchen with island, full bath with a rain shower and deep soaking tub; and a uniquely designed half bath. Just 10 min from Lake Winnipesaukee (Wolfeboro center) and 25 min from Mt. Major, with endless options for hiking, boating, dining, and exploring nearby. Perfect for a peaceful getaway with plenty of adventure close by. unwind at this peaceful oasis.

Family · Location · Comfort

Fall Lakefront Luxe I Cozy I Bonfire I Hot Tub

Welcome to Camp Lollywood where lakefront magic meets your perfect spring escape on Balch Lake! Sip coffee as the mist lifts off the water, soak in the hot tub with stunning lake views, and gather around the bonfire pit for golden-hour s'mores. Kayak, swim, and soak up warm NH afternoons. The game room keeps the fun going after sunset. Luxury comfort, pure magic, and the best of a New Hampshire spring right outside your door. Come for the lake. Stay for the magic. ✨🌿

Location · Family · Accuracy

Peaceful 4 bedroom lakehouse retreat

Beautiful four bedroom two bath home located on Balch Lake in West Newfield Maine. Two private docks and your own boat launch. Sandy beach area on the south side of the house receives lots of sunshine. Take out kayaks or pedal boat to explore Balch Lake! Updated kitchen and a magnificent view of the lake from the living room. Relax in the shade under 2 motor canopies on the deck off of the master bedroom. Enjoy a barbeque and go for a swim at this hidden gem.

Location · Family · Beach

Cozy Wolfeboro Getaway | Lake, Ski & Fireplace

Welcome to Lake a Dream - your cozy, family-friendly Wolfeboro getaway in EVERY season! Enjoy our neighborhood beach just a 5-minute walk away or explore charming downtown Wolfeboro, only 5 minutes from the cottage. Winter is just as magical! Ski at Wolfeboro’s hidden gem, Abenaki Ski Area, skate, snowshoe or simply cozy up by the fireplace with hot cocoa & family games. Looking for a bigger mountain day? Gunstock & King Pine are nearby too!

Family · Location · Decor

Romantic Mirror cabin in the woods

Stay at Hidden Pines Cabins. The Mirror cabin is Maines only 3 sided floor to ceiling mirrored glass cabin. Unwind in the hot tub while looking up at the sky full of stars. Take a sauna while surrounded by nature all around. Located in the majestic forest of mount Agamenticus, the extensive trail system is off of our road. Short drive to the Ogunquit/York beaches, Outlets at Kittery and near Portsmouth, Dover and Portland restaurant scenes.

Location · Value · Amenities

Lakeside Getaway - Lake Access/PrivateDock/Firepit

Escape to this cozy lakeside retreat with direct access to Crescent Lake - perfect for swimming, kayaking, or simply enjoying the view. Bring your own boat and take advantage of the private dock, offering effortless access to the water for fishing, cruising, or sunset rides. In the evening, gather around the fire pit and unwind under the stars.​ This house is ideal for couples, families, or groups seeking comfort, nature, and connection.

Location · Family · Bathroom