House holiday rentals in Wolfeboro

Tranquil Pondside Retreat

Welcome to this clean, bright, airy cabin with floor-to-ceiling windows and stunning views of Sargent's Pond in all seasons. At 62 acres and with just twelve homes, Sargent's Pond is the perfect place for simpler pursuits and peace and quiet. Enjoy two comfortable double bedrooms, a pull-out sofa in the living room, a bathroom with tub, washer, and dryer, a fully equipped kitchen with dishwasher, Wifi, bluetooth stereo system (bring your vinyl!), and Smart TV. Enjoy dining and relaxing on the spacious deck with commanding water views, and for the little ones, swinging and sliding on the swing set. Above the garage is a recreation room with a ping pong table as well as a smashing children's playroom filled with toys, board games, puzzles, and books. Enjoy the TV/ DVD player with a variety of favorite kids' flicks. Perfect for rainy days or down time, this extra living space is sure to please kids and adults alike! Please note that a pack-and-play, toddler mattress, and toddler high chair are available upon request.

Lake Access + Kayaks+Arcade+Bike Path+Private deck

Welcome to the Striped Loon! Our newly updated 2bd/1ba cottage is just steps away from Crescent Lake (great for kayaking) and Cotton Valley Rail-trail walking/bike path leading directly into downtown. Perfect for families , small friend groups, or couples our home offers the below amenities to enhance your stay! -Beach pass & towels, chairs, blanket -Two player arcade, Board games, pickleball set -TV for streaming -Private deck with grill, dining area and deck fire pit -Kayaks, lifejackets

Perfect Family Getaway On Lake Ossipee

Our 10 year old home has four bedrooms three baths, theater room, gas fireplace, bar outdoor fire pit, open concept kitchen, nestled in a mountain landscape. Beautiful private beach with a playground, picnic area and boat launch only a short walk away. Tennis courts and a basketball court centrally located within the community. Boat rentals available on the lake. Multiple ski areas close by. Easy access to local and state snowmobile trails and the lake for ice fishing right out of the driveway.

5-Stars!! Cozy Home near the lake

Please answer our questions when requesting to book. If they are not answers, your request will be declined. Cozy home near the lake is a peaceful place to relax or adventure in the lakes region.The house is located right next to the Glendale Yacht Club and 0.3 miles or a 6 min walk (based on Google) to the Breeze Restaurant and water access at the Glendale Public Docks (no swim area). The house comes with a fully stocked kitchen, a grill, relatively fast internet and a 55" TV (no cable)

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.

Waterfront w Kayaks, Pool table, Pergola, Firepit

Waterfront location nestled in the heart of Laconia. Located on a river connected to Lake Opechee.. Less than 5 minute walk the lake, beaches and downtown. A beautiful 7 mile walking trail “wow trail” right near the property. 2 water facing decks, 1 front porch, 2 grills, fire pit under the pergola, Sundeck on the river, and 2 kayaks are provided with the home. Close to lake Winni, Weirs beach, Bank of NH Pavilion, Gunstock ski and many more local attractions all 10 minutes away

The LOTUS welcomes you, stay a while

The Lotus is your zen home away from home. Enjoy peace and tranquility on your private back deck, the amazing salt water hot tub (exclusively use) new sauna, heated seasonal outdoor shower, deep bathtub (showering is tricky for people taller then 5'5)with bluetooth speaker.Comfortable king size bed with European bedding and a single fold out foam mattress on the 1st floor, that was just finished as another relax area, with 70" TV, record player, hammock & hanging chair.

20 Mile Bay - Tuftonboro - Lake View

Directly across from 20 Mile Bay on Lake Winnipesaukee in Tuftonboro. This 4 bedroom / 2.5 bathroom home comfortably sleeps up to 12 guests. The front deck overlooks the lake with unobstructed views. We provide kayaks, inflatable boats, & beach chairs for guests. The property is surrounded by conservation land. The Chandler Wild Park Trail has an entrance right in front of the property. It is perfect for hiking, snow shoeing, cross country skiing, and walking.

Relaxing hidden gem in Wolfeboro

Located within just 7 minutes from Lake Winnipesaukee, Wolfeboro Center, Allen Albee Beach, and Lake Wentworth, Beach Pond Acres is your perfect year round vacation resting place. Indulge in the abundance of activities in the nation’s oldest summer resort, including fishing, water sports, and relaxing lake beaches and Gunstock Ski Resort. Enjoy the privacy of an open, cozy, and light filled home, sitting on five acres of abundant wildlife and vivid greenery.

Wren Cabin + Wood fired Sauna

We built the Wren Cabin to be a serene space filled with light and art and with lots of cozy details. Lofted ceilings, a spiral staircase and large open concept with lofted bedroom. The cabin also has a gorgeous wood-fired sauna for those colder days. Wren cabin has a large wraparound deck for relaxing and an outdoor fire pit, as well as shared access to Adams Pond. The space is modern Scandinavian, light and aery, and filled with thoughtful details.

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.

Piece of Heaven

Available starting in spring of 2025. Welcome to our "little piece of heaven" located in Wolfeboro New Hampshire just outside downtown filled with multiple shops and restaurants! Our home on Crescent Lake, with private beach access and dock with a boat slip. The home is located off of Wolfeboro Cotton Rail Trail, a peaceful walking path that begins in downtown and passes through several towns New construction to be completed by the spring.