Holiday rentals with lake access 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

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.

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.

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.

Elegant condo on the water in downtown Wolfeboro!

Often described as Wolfeboro's favorite house, this historic Victorian sits right downtown Wolfeboro and on the water looking across to the town docks, Brewster Academy and Wolfeboro Bay. This two-story unit, occupying the second and third floors, has a beautiful porch overlooking the bay and is located by the famous Yum Yum Shop. Walk to most places in town or just sit on your porch or the Adirondack chairs beside the lake. Hard to beat our location.

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.

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!

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.

Lovely cottage on Sunrise Lake, Middleton, NH.

A lovely lake-front cottage with a private beach on quaint Sunrise Lake! The house has a great view overlooking the water. Enjoy a beautiful morning view of the sun rising onto the lake with a cup of coffee or tea, grilling a tasty dinner on the deck, and toasting marshmallows in the fire pit for dessert. We also provide a double kayak so you can explore the mile-long lake from the easy launch point in front of the house.

The Barn at Crescent Lake

Welcome to Wolfeboro, New Hampshire! Our barn is located just outside of downtown Wolfeboro, filled with multiple shops and eateries! Our home is on Crescent Lake, with private beach access and a dock with a boat slips if needed. The home is located off of Wolfeboro's Cotton Valley Rail tail, a peaceful walking path that begins in downtown and passes through several towns!