Pet-friendly holiday rentals in Wolfeboro

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.

🌟Winni Cottage beach, dock, kayaks, SUP & more! 🌈🍸

Great waterfront cottage on Wolfeboro’s Back Bay! Includes 5 kayaks, 2 canoes, a paddleboard & rowboat. 3 bedrooms, plus indoor & outdoor hot showers. Large deck, big grassy lawn, and cozy campfire area. Calm, protected bay—perfect for beginner paddlers. 40-ft dock, beach area, & swim platform on a mooring. Bring your boat or rent one to access main lake under the bridge. Just an 8-minute walk to town! Bring bikes explore scenic trails. A peaceful, relaxing retreat with all the lakefront fun.

Mountainside Chalet+Sauna near Lake Winnipesaukee

Enjoy everything Lake Winnipesaukee has to offer with private beach passes. Located directly between downtown Wolfeboro and Alton Bay, a quick 10min drive will get you to either. A 30min drive will get you to Gunstock Resort or Mount Major. Enjoy gorgeous sunsets and views from the elevated deck, while you sit around a gas fireplace. The interior provides a spacious open concept layout with a large couch, 75" TV and a stocked kitchen. Enjoy the health benefits of the relaxing Infrared Sauna.

Eclectic Lakefront Cottage on Great East Lake

Welcome to a relaxing stay on the shores of Great East Lake! The fall and winter are the definition of peace and quiet. Often you'll be the only folks on the cove! Come back inside after your outdoor adventures and warm your feet on the radiant slate floors .You can also prepare a home cooked meal in the vintage, fully applianced kitchen. This home is the perfect base for all your winter excursions, or enjoy family time inside with plenty of games, puzzles, ping pong, or air hockey! Enjoy!

The Lake house

Enjoy the southern exposure, a sugar sand walkout beach, an L-shaped dock, and classic Lake Winnipesaukee construction. The open concept includes a full kitchen and a living room. The spacious bathroom also includes a washer and dryer. It has one private bedroom, and a ships ladder guides you to a loft containing additional sleeping space, with a catwalk to a private balcony overlooking the lake. This property has a detached bunkhouse with two full-sized beds and a ¾ bath.

Farmhouse Retreat, Dog Friendly w/ view & deck

Welcome to Valley View Farm, your next getaway! The 3-bedroom, 2.5-bath is newly remodeled with an open concept and modern vibe. Overlooking 90 acres with sprawling fields and 180-degree views of the Mount Washington Valley from Lake Ossipee to Chocorua Mountain. Enjoy your morning coffee while gazing out the wall-to-wall windows or take it outside to the expansive deck. Family and Dog-Friendly! Air Conditioning Summer '25 Minutes from Lake Ossipee. 25 mins to North Conway.

Lakefront Home-Stunning Views-Hot Tub, 3100 sqft!

Experience ultimate relaxation with over 100 feet of sandy lakeside beach frontage, nestled among serene pine trees. This spacious lake house features: Open concept main floor 3 levels (3100 sq ft) for privacy Family & dog friendly Hot tub, kayaks, beach, game room, firepit & more! Ideal for large families wanting to share a vacation without compromising on privacy. Enjoy year-round activities and create lasting memories. Get 10% OFF for weekly or longer stays!

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.

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!

Melvin Village - 5 Bed/3 Bath - Lake Winnipesaukee

Melvin Village - 5 bedroom, 3 full bath newly renovated home for lease. Amenities include: minutes to the town beach, huge yard, grill, stainless steel kitchen, coffee bar with Nespresso machine & Keurig, arcade machines, board games, kayaks, hammock, corn hole, ladder ball, outdoor dining, and screened in porch. We are pet friendly with $50 Fee only for pets registered at the time of booking. No unregistered pets allowed.