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.

1840 Meredith Farmhouse w/ outdoor Sauna & Pool

This beautifully renovated antique 1840 Meredith Farmhouse combines timeless charm with modern comforts. Nestled on over 3 acres in the lakes and mountains, it features a snowmobiling trail in the backyard, easy access to hiking, skiing & lakes, and is less than 10 minutes from Mill Falls in downtown Meredith. Outdoor amenities include a barrel sauna, cozy fire pit, in-ground saltwater pool & a game room. Inside, the chef’s kitchen boasts Thermador appliances, a coffee & tea nook & a bar area

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 Lakes Region Escape. Fire Pit. Patio

Welcome to Buttercup Inn Tucked away in the peaceful lakes region, less than 2 miles from downtown Wakefield, this tastefully upgraded home may just surprise you. Every detail has been designed to make you feel right at home, from cozy furnishings to the brand new coffee bar- your go-to spot for a perfect brew. Whether you're unwinding or exploring the area, this charming retreat's proof that sometimes the best places are the ones you least expect. Message for further info.

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!

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.

Family Retreat in Wolfeboro: 5BR/3BA, Lake Views

A new opportunity for your large family or reunions to stay in “The Oldest Summer Resort in America” in a historic home located a few minutes from downtown. This 1870’s home was turned into “The Oaks” in the early 1900’s as an Inn for visitors over a hundred years ago to take in the Crescent Lake view. Your gathering will enjoy the beautiful character of the old Inn while utilizing modern amenities.