Family-friendly vacation rentals in Madison

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Top-rated family-friendly rentals in Madison

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

A clean and bright bathroom is equipped with a toilet, a vanity sink, and a large mirror. A colorful shower curtain, featuring playful elephant designs, complements the light-colored walls. Natural light streams through a window, enhancing the inviting space.

Home in Gilford

4.88 out of 5 average rating, 201 reviews

Fun & Fabulous Getaway

Welcome to our exceptional vacation home, where stunning mountain views meet the serene beauty of Lake Winnipesaukee. Just minutes from Gunstock Mountain Resort, our home offers year-round fun and relaxation Enjoy a spacious interior ideal for socializing and dining. The lower-level family room is perfect for entertainment with a foosball table, air hockey, PlayStation, board games, and a flat-screen TV. Unwind in our hot tub for 8 and take in the beautiful surroundings both in summer and winter

Superhost

A spacious backyard is surrounded by lush trees, providing a natural setting. A wooden playground structure with a slide and swings is visible, inviting outdoor play and family activities. The grassy area shows fallen leaves, indicating the change of seasons.

Home in Conway

4.83 out of 5 average rating, 114 reviews

A Large Vacation Home with hot tub, game room +

My place is close to family-friendly activities, skiing, snowboarding, golf, shopping, hiking, restaurants, night life, shoe shoeing, ice skating, sleigh rides, tubing, Saco River tubing/canoeing, Echo Lake, Gondloa rides to summit, mini golf much more. You’ll love my place because of the quiet neighborhood, comfy beds, the kitchen, the hot tub and fireplaces and the space for large reunions and gatherings . My place is good for couples, business travelers, families (with kids), and big groups.

Guest favorite

A charming two-story cabin is surrounded by trees and illuminated by warm exterior lighting. The night sky above showcases a scattering of stars, creating a serene and inviting outdoor setting.

Cabin in Carroll County

4.84 out of 5 average rating, 745 reviews

The Overlook/Cozy 2 bed/Hot Tub/Wood Stove/Firepit

Great location! .5 mile to scenic overlook! Central to all attractions, private yard, fire pit, wood stove, outdoor space, hot tub, new furniture, cozy mattresses & linens. Walk to ice cream & scenic overlook, less than 5 mins to Saco River path, Golf, North Conway Village, Whitaker Woods, scenic train station, coffee shops, shopping, skating, nightlife, restaurants, kayaking, skiing, adventure parks, sleigh rides (discounts available), skiing, story land, hiking, Outlets, snowshoeing, etc.

Guest favorite

The exterior of a spacious mountain townhome is captured, featuring a warm wood façade and large windows that allow natural light inside. A deck extends from the front, overlooking a snowy landscape, with tall trees framing the serene setting.

Home in Carroll

4.94 out of 5 average rating, 161 reviews

Cozy Townhouse: Bretton Woods Mt. Washington Place

In the Mount Washington Resort (Bretton Woods) and near Cannon Mountain. Inviting four-season end-unit town home with warm ambiance, all the comforts you need, and great views. A mountain vacation getaway at a great value. Modern kitchen, comfortable dining and living room with fireplace. Four bedrooms, three floors, each with private bathroom (three full, one with shower). Large entertainment / recreation room for the family, outside deck with seating to enjoy the wildlife and a grill.

Guest favorite

A wooden deck is depicted, featuring a hot tub gently steaming in the cool evening air. Comfortable seating includes a red cushioned chair and a metal table. The surrounding trees add a serene natural backdrop, while warm light glows from a window nearby.

Home in Conway

4.87 out of 5 average rating, 130 reviews

Hot tub with country setting, close to village.

Must bring Bathing & hot tub towels We will supply everything else. ALL Major 3 day holiday weekends is a min of 3 nights!! Now close to the new Mt Washington Recreation Path. Country setting, quiet, three bedroom home close to village. All major ski resorts are minutes away. Hiking paths as well as TAX FREE OUTLETS. Brand new hot tub and wood stove works, wood is mostly supplied Storyland and Santa's village is also minutes away. Great country feeling in a good location.

Guest favorite

A large two-story white house is depicted, featuring multiple gabled roofs and blue accent doors. Surrounding trees provide shade, and a driveway is visible leading to a side parking area. The property is situated on a quiet road with ample outdoor space.

Townhouse in Kennebunkport

4.94 out of 5 average rating, 167 reviews

Great get away spot,historic home in Kennebunkport

Located 1.8 mi-dock square, 2.6 mi- Colony Beach, .7 mi -Cape Arundel Golf Course. Plenty of onsite parking, beach pass provided for Kbunk Beaches, a large back yard for fun and relaxation. Just on the outside of town in a country setting. Comfortable setting for relaxation. This is a daily reservation from Oct.1st-June. I love to make sure my guests have as much fun as they can while they are visiting and will help out in anyway possible. No dogs of any kind are allowed

Guest favorite

A wooden deck features two red Adirondack chairs, positioned to overlook rolling green hills and distant mountains. The sky is painted with soft hues of pink and blue, hinting at a tranquil sunset. Lush trees and greenery surround the area, enhancing the natural ambiance.

Chalet in Bartlett

4.92 out of 5 average rating, 277 reviews

Chalet in the Sky| NorthConway+StoryLand| Outlets

This gorgeous 2-bedroom chalet, styled by the Homme team, is the ultimate mountain escape! Tucked away in North Conway’s White Mountains, it’s great for families, friends, or ski enthusiasts. Take in stunning views, free onsite parking, modern comforts, and quick access to top area attractions for a getaway to remember! 🌿✨ 🎢 Story Land - 10 min 🌿 Diana’s Baths - 10 min 🚠 Mt. Washington Auto Rd - 35 min 🏞️ Echo Lake State Park - 15 min See below to learn more!

Top guest favorite

An aerial view of a rustic home with a red metal roof, surrounded by trees. Two vehicles are parked in the driveway, highlighting the home's accessible location. A gravel path leads to the front door, which is illuminated by warm lighting.

Home in Intervale

4.97 out of 5 average rating, 179 reviews

Spacious 3 level family friendly home.Dog friendly

Private home 3 Levels Sleeps 14 Plus! Large fire pit! Great for family gatherings! rustic weddings and celebrations. close to Cranmore, Story Land, Local Breweries, skiing & shopping. Amazing view of the Moat mountains Close to great local restaurants. Dishwasher, Wi-Fi PacMan Arcade, Washer/Dryer, Lg backyard, deck, BBQ grill Spacious Family Room! Full home generator! We are proud of our great reviews and as a host I look forward to hosting you. Dog friendly

Guest favorite

A modern kitchen features sleek cabinetry and a granite countertop, with appliances and cookware neatly arranged. A color-coordinated backsplash adds depth to the design. In the background, a living area is visible, furnished with comfortable seating and a smart TV on the wall.

Home in Kennebunk

4.95 out of 5 average rating, 151 reviews

Quiet cozy cottage close to restaurants, beach

Winter-wonderland, close to skiing and a walk from great dining. In the summer, enjoy the quiet backyard or walk to the beach! No need to find parking, my place is 3/10 of a mile from downtown Kennebunkport and 7/10 of a mile to Gooch's Beach. You will love my place because of the kitchen, the coziness, and the location. My place is good for couples. It has a tempurpedic king-sized bed and a queen sized pull out bed in the living room.

Guest favorite

The exterior of a cedar home is highlighted, surrounded by lush greenery and trees. The structure features large windows and a spacious deck, showcasing a distinct A-frame design. A stone pathway leads to the entrance, enhancing accessibility to the outdoor space.

Home in Kennebunk

4.91 out of 5 average rating, 111 reviews

A Great Space in a Great Place

This Lindal Cedar Home overlooks the tidal marsh. Walking distance to beach and Kennebunkport. Second story duplex with master bedroom loft. Complete kitchen. Children's play park, pitch and putt golf, kayak and bike rentals, bakery, restaurants, market, antiquing, whale watching, Shipyard brewery and retail shopping; all within walking distance. Owners on site.

Guest favorite

The entrance of the condo is marked by a large, welcoming sign surrounded by well-maintained greenery. Two tall trees frame the view, and a rock formation is positioned nearby, adding to the natural setting. An American flag gently waves in the breeze.

Chalet in Intervale

4.91 out of 5 average rating, 246 reviews

Spacious, air-conditioned condo next to Storyland!

Large, mountainside condo just minutes to Storyland and all attractions in the Mt Washington Valley! Features king BR with en suite bathroom and a queen BR on the 1st fl. The 2nd level features a giant bedroom with 4 twins. Brand new ductless AC system. Perfect for families or groups! Use the condo as home base for all of your vacation adventures.

Superhost

A single-story mobile home is set among trees, featuring a light yellow exterior with maroon shutters. A small porch is positioned at the front, while flower beds with blooming plants and a stone border enhance the well-maintained yard.

Home in Paris

4.92 out of 5 average rating, 146 reviews

Just a get away!!

My place is close to great views - for fall time - half hour to ski area's -oxford casino 7 miles away - hour drive to Mt Washington or Portland - Plenty of hiking area's- Oxford plains speed way 3 miles - , restaurants and dining . Read all { House Rules } it's under things to know, on the bottom left, before making reservation - Thank You