Family-friendly holiday rentals in Hillsborough

Vermont Mirror House

Escape to our stunning glass house nestled in the Vermont forest. This modern retreat offers breathtaking 360-degree views of lush wilderness and beautiful waterways. Unwind in the hot tub, warm up by the cozy fireplace, or rejuvenate in the sauna. Floor-to-ceiling windows bring nature indoors! Perfect for romantic getaways, small families or simply work away from work with fiber wifi. Experience tranquility during all seasons in this one-of-a-kind hideaway. Book now for an unforgettable escape!

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

Cozy Cabin with Lake Access

Our cabin is situated in a private, peaceful setting surrounded by trees. Inside you will find a timeless lake house decor and everything you need for a relaxing vacation. A 1/4 mile walk or drive brings you to our private community lake access and boat ramp on beautiful Highland Lake. We offer use of our 3 kayaks (2 single/1 tandem) located next to the boat ramp. Nearby are great hiking trails and quaint villages. This is a wonderful place to unwind and have a truly fun & relaxing vacation!

Cottage beside a waterfall

Our 1840’s renovated grist mill is located in the beautiful Monadnock Region. The house and cottage are situated on twelve acres and includes gardens, an orchard, berry bushes, grape vines, beehives, a dog, and a tremendous waterfall. We are close to many of nature’s gems including Mount Monadnock, Pack Monadnock, the Heald Tract hiking trails, skiing, snowshoeing and swimming. Also the acclaimed MacDowell Arts Center, Andy’s Summer Playhouse, Andres Institute of Art and the Waldorf Schools.

Sugar River Treehouse

Welcome to Sugar River Treehouse! If you’re looking for serenity, peace and quiet, in the most unique, breathtaking, beautiful setting, you have found it. On top of the trees, overlooking the Sugar River in the quaint town of Newport, NH you will find plenty of year round activities including swimming, floating, fishing on the beautiful, clear Sugar River, right outside the back door. You will find the treehouse sits up in between 2 beautiful northern hemlocks and is fully equipped inside.

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

River's View Cozy Getaway

Secluded, tranquil, woodland retreat. Unique home overlooks river-cathedral ceilings and large windows throughout. Stay cozy indoors by the wood stove or explore acres of conservation land abutting the property. All you need for quiet getaway or ski vacation. Sleeps 6 in winter months; extra bed on sleeping porch overlooking river in warmer months. Master bath has deep soaking jacuzzi tub. Skiing 20 minutes away at Pat's Peak & Crotched Mt. Trails nearby for hiking, snowshoeing & x-country.

Treehouse Haven in Putney-All Seasons

Peaceful, private & fully equipped four-season treehouse, surrounded by nature. ☽ Private & secluded ☽ Central to activities & necessities ☽ Firepit, pellet stove, deck, grill & fully stocked kitchen ☽ Scrupulously clean, unscented products ☽ Clean composting outhouse ☽ Tea & local coffee ☽ Hot outdoor shower-Closed Nov-April ☽ 45min to ski resorts ☽ Swimming holes & hikes ☽ WiFi & electricity Retreat from the business of life; romance, with the family, or even a remote work sanctuary.

Rustic & Renovated Hot Tub/Game Room Sleeps 8ppl

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 Fire Pit, Grill, Hammock, Gym equipment Xbox Series S, Life Size Janga, Yahtzee, Darts, Corn Hole, ping pong tables, mini pool tables 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, backyard on 2 private acres

Beautiful Log Cabin on Highland Lake

Take it easy at this unique and tranquil getaway. A gorgeous log cabin nestled right on Highland Lake in Washington, NH. An outdoor lovers paradise that welcomes you any season. Nearby Mount Sunapee, Mount Manodnock, Crotched Mountain, Pillsbury State Park and Pats Peak. fall foliage, fire pit, grilling, ATV trails ice fishing, nearby skiing, snowmobile trails boating, kayaking, swimming, fishing Get the full New England experience at this incredible lakeside location!

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!

Luxury Glamping NH - Geodome Sanctuary

Escape to a private luxury sanctuary retreat tucked behind a charming Christmas tree farm in Sutton, New Hampshire. This adults-only geodome features a private hot tub, wood-fired cedar sauna, cold plunge, and fire pit beneath a sky full of stars. Created for couples seeking rest, connection, and renewal, it’s the perfect place to slow down, reconnect, and experience the beauty of New Hampshire. Just 90 minutes from Boston, yet a world away.