Family-friendly holiday rentals in Lake Winnipesaukee

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

Indoor spaces · Kitchen · Bathroom

Camp Oscar Waterfront Lake Winnipesaukee

Experience the true meaning of Lake Life at Camp Oscar. This classic Lake Winnipesaukee waterfront retreat in Moultonborough offers the perfect setting for a memorable Lakes Region getaway. Featuring 4 bedrooms, 1.5 baths, warm wood finishes throughout, a private dock, and a walk-out sandy beach, Camp Oscar is ideal for swimming, boating, fishing, and relaxing by the water. Enjoy beautiful lake views, timeless camp charm, and everything you need to create lasting memories with family and friends

Family · Indoor spaces · Hospitality

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

Indoor spaces · Family · Accuracy

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!

Indoor spaces · Family · Pets

Dreamy Lakefront: Hot Tub, Kayaks, & Kid-friendly

This romantic & family-friendly lakefront chalet comes with a private beach, hot tub, kayaks & stunning views and is packed with amenities. It’s a serene home base to explore some of the best New England towns and is in the heart of the Lakes Region. Swim, kayak, bike a scenic trail, fish, hike, explore historic towns, farms & food scene, or simply grill with a view & play board games. We have poured our heart into making this a romantic yet very kid-friendly retreat (kids gear included).

Kitchen · Indoor spaces · Backyard

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.

Indoor spaces · Family · Pool

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!

Indoor spaces · Kitchen · Breakfast

Peaceful 4 bedroom lakehouse retreat

Beautiful four bedroom two bath home located on Balch Lake in West Newfield Maine. Two private docks and your own boat launch. Sandy beach area on the south side of the house receives lots of sunshine. Take out kayaks or pedal boat to explore Balch Lake! Updated kitchen and a magnificent view of the lake from the living room. Relax in the shade under 2 motor canopies on the deck off of the master bedroom. Enjoy a barbeque and go for a swim at this hidden gem.

Indoor spaces · Kitchen · Outdoor spaces

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!

Indoor spaces · Family · Beach

The Quaint Escape - Built in 2024 - Lake Access

The Quaint Escape is a newly built 2024 custom home set in one of New Hampshire’s most sought-after locations. Designed as our modern take on a cozy cottage, it blends clean, simple elegance with thoughtful details to comfortably host 4–6 guests seeking a more elevated getaway. One of its standout features is private dock access directly on Lake Winnipesaukee. Follow us on IG @thequaintescape to watch a full video tour of the home.

Family · Indoor spaces · View

Cozy Chalet - Heart of NH Lakes Region

Our cozy chalet is nestled among tall trees in the heart of the Lakes Region. 5 minutes from Lake Winnipesaukee and 1 minute from Gunstock Mountain Resort, our hideaway offers instant access to the best of New England no matter the season, including hiking, beaches, kayaking, skiing, and more. Our family-friendly cottage has a two-story great room, a separate office, and an outdoor firepit. It is perfect for couples and families.

Kitchen · Family · Comfort

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.

Family · Kitchen · Checkout