Family-friendly holiday rentals in Hillsborough

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Top-rated family-friendly rentals in Hillsborough

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

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Top Guest favourite

Sunset is seen through a row of trees along the lake, casting gentle reflections on the water's surface. A boat is visible in the distance, leaving ripples as it moves across the calm lake, while the sky transitions from blue to shades of orange and gold.

Home in Washington

5.0 out of 5 average rating, 135 reviews

Newer Home on quiet 200 acre lake - sleeps 6

Less than an hour from Manchester, Concord & Keene, this new home offers relaxation & year-round adventure. This lakefront property has a dock, with kayaks & paddleboards. You could also walk down the paved road to the neighborhood beach & swim platform. About 30 minutes to Pats Peak, Sunapee, or Crotched Mtn ski resorts. Beds for 6, 2 full baths, W/D, fully equipped kitchen, open living space, gas fireplace, water views, gas grill, parking, firepit, internet. We do not allow pets or smoking.

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Top Guest favourite

The cabin features a wooden exterior with large windows and a sloped roof, surrounded by natural greenery. A front porch extends from the building, providing access through stairs. The entrance is framed by a welcoming entryway and a small outdoor area.

Cabin in Henniker

4.97 out of 5 average rating, 178 reviews

The SugarShack at Sweetwater

Welcome to our off-the-grid cabin, sleeping 2-4 people with an upstairs loft & downstairs custom Murphy bed. It's equipped with lights, mini-fridge, Bluetooth speakers & an indoor/outdoor bar. Outside you'll find a private fire pit & charcoal grill, a shared outdoor kitchen pavilion w/ gas grill (stocked with cooking supplies) & the outdoor bathroom w/ a real flushing toilet, sink and outdoor shower. Access the Tooky River just steps away and enjoy plenty of space, privacy & beautiful scenery!

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Top Guest favourite

Cabin in Bradford

4.98 out of 5 average rating, 439 reviews

Deer Valley Retreat, Lovely Log Cabin

This Lake Sunapee Region cabin retreat is perfect for romantics, artists, writers, outdoor enthusiasts, gardeners, friends, & family. Centrally located between the area's best lakes and mountains, convenient to area attractions, and outdoor activities. Still, the cabin feels like a destination in itself, where you can relax, recharge, and reconnect. Cozy up by the stone fireplace, relax on the porch, see nature, read, listen, play, cook, stargaze, and enjoy just being! M&R license #: 063685

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Guest favourite

The view showcases a rustic cottage nestled among trees along the lake. A wooden dock extends from the rocky shoreline, featuring a ladder for easy water access. The cabin's light yellow exterior complements the natural surroundings, providing a serene escape by the water.

Cottage in Marlow

4.88 out of 5 average rating, 112 reviews

Sunapee area lakeside cottages trio on Sand Pond

Three cottages, each with lake view and shared dock, on pristine, quiet Sand Pond are perfect for a family gathering. Three cottages for one rental, offering privacy and indoor and outdoor space for being together. The main cottage sleeps four, has a full kitchen and a screened-in porch; the two studio cottages have kitchenettes and sleep two. It is not ideal for very young children or those who have difficulty walking up and down hill on uneven ground. 8.5% NH Meals & Rental tax applies.

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Top Guest favourite

A serene lakeside scene features a plush chair by the water, where a golden retriever is comfortably resting. Lush greenery surrounds the lake, and a kayak is seen moored nearby, adding to the tranquil atmosphere.

Cottage in Newbury

4.95 out of 5 average rating, 251 reviews

Large Private Lake House

Spacious lake house with a private beach, directly on Lake Todd in Newbury, NH, located within the Lake Sunapee Region. Fish for bass, pickerel or swim/boat to one of the lake's three islands. Relax on the water or on one of the large decks overlooking the lake. Enjoy local outdoor activities such as hiking, biking, golfing, fishing & kayaking. Mt Sunapee ski area is only 10 minutes down the road. Enjoy ice skating and cross country skiing right out your door in the winter or cozy by the fire.

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Guest favourite

Two kayaks are positioned on the grassy shore next to a tranquil lake. A private dock extends into the water, where an individual is fishing while another person relaxes in an Adirondack chair, surrounded by lush green treetops and a partly cloudy sky.

Home in Dunbarton

4.94 out of 5 average rating, 188 reviews

Picturesque Dunbarton Waterfront Cottage

New dock coming in 2026. Lakefront cottage in the center of New England. Our home has everything you need for your waterfront retreat. Enjoy morning coffee or go fishing on your private dock. Step out the front door and you are at the community park and playground. Walk 2 minutes to the community beach or 5 minutes to the start of 7 miles of hiking trails. Golf is less than 5 minutes' drive and skiing is 25 minutes away. Breathtaking fall foliage, and snowmobiling and ice fishing in winter.

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Superhost

An A-Frame cabin is set on a sloped hill, surrounded by trees. The cabin features a deck overlooking the water, with kayaks and a hammock visible on the lawn. A wooden dock extends into the pond, enhancing the serene outdoor setting.

Chalet in Antrim

4.9 out of 5 average rating, 155 reviews

Direct Waterfront A-Frame, Close to 3 Ski Areas!

My direct waterfront, year-round A-Frame cabin is 30 min to Mount Sunapee, 20 min to Crotched, and 15 min to Pat's Peak! It’s located on a small 32-acre pond near Franklin Pierce Lake with over 100 feet of waterfront. There is a 6 foot main dock to load kayaks, and a small fishing dock off to the side. The fishing on our pond gets rave reviews! The property sits on 1/3 of an acre, on a sloped hill. It's located between Keene and Concord, and nearby many great hiking and snowmobile trails

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Guest favourite

The open-concept kitchen and living area features natural wood paneling and high ceilings with exposed beams. A spacious kitchen island, accompanied by three wooden stools, provides ample counter space. Large windows allow natural light to illuminate the inviting space, while shelves filled with books line the walls.

Apartment in Nelson

4.88 out of 5 average rating, 112 reviews

Swiss Chalet Family Retreat!

Welcome to our family's Swiss style chalet! Inspired by trips to Davos, Switzerland, my grandparents built the chalet in the 1950s to be a family playhouse and gathering spot for their 6 children. It's kind of magical. Today, our large extended family still enjoys holiday celebrations here every year. Our kids love exploring the woodland trails and swimming in Center Pond. We hope you love it as much as we do! Note: the building also has two apartments on the first floor.

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Superhost

Home in Antrim

4.98 out of 5 average rating, 248 reviews

HotTub FirePit Games Huge Backyard Family Friendly

The ultimate experience for couples & families 5-10min from hiking trails & ski resorts A Mile from Gregg Lake Beach ALL YEAR PRIVATE/SECLUDED HOT TUB Grill, Hammock, Gym equipment XBox Series S, Life Size Janga, Yahtzee, Darts, Corn Hole, ping pong table, mini pool table Luxury KING PURPLE Brand Mattresses in every bedroom for the best nights rest with individual mini splits for optimal comfort Fully stocked kitchen High speed WiFi, house on 2 private acres

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Guest favourite

The A-frame chalet is surrounded by colorful fall foliage, showcasing vibrant orange and yellow leaves. A canoe is positioned by the entrance, complementing the cabin's rustic facade with green accents. A carpet of fallen leaves blankets the ground, creating a serene outdoor setting.

Chalet in Stoddard

4.93 out of 5 average rating, 327 reviews

Highland Haus | Cozy 70s Aframe | Lake Access

Authentic 1975 A-frame chalet nestled in peaceful Stoddard countryside. This cozy cabin sleeps 5 with two wood stoves and full kitchen. Perfect rural retreat just 2 hours from Boston! Explore nearby hiking trails, swimming spots, and fishing areas. Summer bonus: complimentary canoe access! Highland Haus offers a tranquil escape with vintage charm. Note for winter visitors: Shedd Hill Road requires AWD/4WD due to steep terrain. Your cozy retro hideaway awaits!

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Top Guest favourite

Apartment in Henniker

4.93 out of 5 average rating, 106 reviews

Henniker Haven Carriage House-Stroll to Town, Pool

Charming 3BR Above Rustic Barn – Walk to NEC & Downtown! Featured on Atlas’ must-visit NH towns! Great for families, NEC staff/students, wedding parties & workers. Updated open-concept 3BR above a rustic barn. Just 0.3 mi to NEC, 2.4 mi to Pats Peak, 17.7 mi to Mt. Sunapee, 19.2 mi to Crotched Mt. Steps from Country Spirit restaurant. Enjoy skiing, hiking, rafting, or leaf peeping. Walk to downtown bars & shops. Shared pool. Easy access via Rt 114.

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Top Guest favourite

A charming exterior of the rental reveals a gravel area with potted flowers. A dining table with umbrella sits next to the building, along with wicker chairs. The entrance features a white door and is surrounded by light-colored wooden shingles. Lush greenery provides a serene backdrop.

Apartment in Bradford

4.91 out of 5 average rating, 177 reviews

Lovely One level, spacious @ the 121 #3

Come stay at our lovely guest house in the back of The 121 Shop. Located a 15-minute drive from Lake Sunapee and Mount Sunapee. In the quaint village of Bradford. Comfortable and spacious (1400SF) all on one level with Central Air. Three bedrooms perfect for a family. Located in the quaint village of Bradford. Walkable to a few family restaurants, cafes, and shops in town to help you experience this rural small town.

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