House holiday rentals in Wolfeboro

20 Mile Bay - Tuftonboro - Lake View Pet friendly

Directly across from 20 Mile Bay on Lake Winnipesaukee in Tuftonboro. This 4 bedroom / 2.5 bathroom home sleeps up to 10 adults or 15 total people. The front deck overlooks the lake with unobstructed views. We provide kayaks, inflatable boats, & beach chairs for guests. We are pet friendly with $50 Fee only for pets registered at the time of booking. No unregistered pets allowed. The property is surrounded by conservation land. The Chandler Wild Park Trail has an entrance right in front o

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

Gram's House

Enjoy easy access to town from this historic home. Relax on the deck overlooking Wolfeboro Bay. Enjoy a swim whenever you want. There are 4-season activities in the area: bike, hiking and ski trails close by. Private beach, raft (no dock), canoe/kayaks, and beach toys. Great gathering place: our family has enjoyed many special events here! HOWEVER, if you are looking for a place to have loud parties, this is not for you. This rental is in a neighborhood and we respect our neighbors.

Derby House

Relax with the whole family at this peaceful quintessential lake house. Located on the shore of Lake Winnipesaukee in Chestnut Cove. The Derby house has 100 feet of private waterfront, beach and a large deep water crib dock. Relax and dine on the large deck by day and sit by the waters edge and enjoy a crackling fire while star gazing at night. There is plenty of space for your boat, kayak, canue etc. Kids and adults alike will enjoy the sandy beach with easy access to swimming & snorkeling.

Peaceful Lakefront Retreat

Rest, relax and recharge at this tranquil waterfront getaway on stunning Mirror Lake. Unplug from the hurry and enjoy this entire lakefront home in the privacy of a quiet street just minutes from downtown Wolfboro. Dining area, living space, kitchen and two bedrooms offer all the comforts you need with stunning lake views. Cozy cabin-like downstairs den has entertainment space, tables and seating for movies and games. Perfect spot for a quiet getaway to connect with friends, family and self.

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.

Cozy Basin House in Wolfeboro, NH

This home holds a special place in our heart. It belonged to a wonderful person who treasured the beauty of Wolfeboro, and the peacefulness that this house provides. Tucked into Fernald's basin, adjacent to Lake Wentworth in Wolfeboro, New Hampshire, this is a true retreat. Perfect for a family or a small group to get together and enjoy all that Wolfeboro has to offer. Water views and access, close to downtown, and plenty of space to relax, we hope you'll enjoy this home as much as we do.

Cozy Lake Cabin with Jacuzzi Tub

★ Cozy Lake Cabin Near Wolfeboro ★ Escape to a cozy cabin near Lake Wentworth, just a 2-minute drive to the water and minutes from downtown Wolfeboro. Enjoy included 2026 Wolfeboro beach parking permits, two kayaks, a fire pit under the stars, and a brand-new bathroom with jacuzzi tub and walk-in shower. Tucked away on a quiet dead-end road, this cabin is a peaceful retreat for families, couples, and responsible friends looking to relax and recharge.

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.

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.

Fall Foliage HQ- The Cottage on Paugus Bay

Enjoy peace and tranquility along the shores of Winnipesaukee's Paugus Bay. This Brand New waterfront Cottage is one of the most popular in Lakes Region and is central to all the Lakes Region has to offer. Along the western tip of the lake, easy access to I-93. The community comes with a day dock and easy access to boating and other lake activities. Come back year after year. We love repeat guests and offer discounts for second stays!

Gilford Getaway - Pool & Hot Tub + Sleeps 18

Welcome to the stunning, private escape of Gilford! This 6 bedroom, 4 full bathroom is the ideal vacation spot for you and your family- accommodating up to 18 guests. Sit back and relax by the pool and hot tub, or cozy up inside for a game night with a fully stocked game room: pool table, shuffle board, cards, board games, and more! Brand NEW outdoor fire pit! This house can accommodate ample parking.