Holiday houses in Hillsborough

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Top-rated holiday rentals in Hillsborough

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Guest favourite
The exterior of a charming red house is shown, nestled among greenery. A spacious deck wraps around the front, offering access to outdoor seating. Lush ferns and bushes create a natural border, while tall trees provide a serene, wooded backdrop.
Apartment in Henniker
4.81 out of 5 average rating, 215 reviews

Birchwood at Stonehenge

Totally private self-contained private in-law studio in private home in Henniker, New Hampshire, near Pat’s Peak Ski Area, and New England College. 1 Queen bed sleeps 2 and 1 single bed 1. If the single bed is needed please notify us when you make the reservation. The walkout basement has its own entrance, kitchenette, bathroom, and patio with a small grill. Nice yard in wooded area, rivers, lakes and mountains with recreational activities nearby. Suitable for 2-3 people. No pets, no smoking.

Top Guest favourite
The open-concept living area features a cozy seating arrangement on a dark blue sofa, complemented by a patterned rug. Natural wood elements adorn the ceiling and walls, while large windows allow light to fill the space, enhancing the view of the snowy landscape outside.
Cabin in Hillsboro
4.99 out of 5 average rating, 85 reviews

Cozy, modern lakeside cabin with a rustic vibe

Modern, custom built lake cabin, perfect for a weekend getaway or a week of skiing or lakeside fun. Open concept living area, cathedral ceilings, natural wood, radiant floors and cozy gas fireplace. Enjoy your morning coffee listening to loons with a peek a boo view of the lake. Jump across the road for kayaking, fishing or go swimming at one of the Emerald Lake sand beaches. Skiing at Pat's Peak is 15 minutes away. Meet red newts and woodpeckers on a hike at Fox State Forest five min away!

Guest favourite
Chalet in Hillsboro
4.92 out of 5 average rating, 53 reviews

Summer getaway at Emerald lake fun for the family

Relax with the family at this peaceful 1970's style chalet. It's a beautiful place to unwind from the hustle and bustle, nice private deck to BBQ, Free access to 3 beaches 5 minut walk to Emerald lake. swimming, fishing, kayaking. beaches have hibachi, dock, some beach toys for kids. Three Ski resorts within 20 to 30 minutes from our home .New propane heating system .Old School wood stove just installed for ambiance to warm you up after a long day of Skiing. 15 minutes from New England college

Top Guest favourite
Apartment in Henniker
4.99 out of 5 average rating, 87 reviews

A Lovely In-Law Apt Near Pat’s Peak and NEC!

Kick back and relax in this peaceful, stylish space. Located 3 minutes to New England College and Pat’s Peak, this special, well-appointed and gorgeous apartment offers both convenience and seclusion wrapped into one. Enjoy New Hampshire’s beauty, including its small town charm, covered bridges, beautiful mountains, hiking trails, and ski hills. We are 25 minutes to downtown Concord, 25 to Sunapee Ski Area, and just over 30 minutes to Manchester. Experience a taste of New England charm with us!

Top Guest favourite
Cabin in Bradford
4.98 out of 5 average rating, 440 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

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, 156 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

Superhost
A spacious home nestled in a serene natural setting, surrounded by lush greenery. The property features a wooden exterior and a stone chimney, with a gravel driveway leading to the house. Scenic mountains can be faintly seen in the background beneath a partly cloudy sky.
Home in Antrim
4.77 out of 5 average rating, 184 reviews

Quiet House in the Woods

Relax with the whole family at this peaceful place to stay. - Gregg Lake 5 mins away (Swim, Volleyball, Swings, Boat Docks) - Great hiking trails (Monadnock & Miller State Park) - Ski in the winter (Crotched Mountain 20 mins away, Pats Peak 30 mins away) - Small town: Mom & Pop shops/restaurants, Antique stores - 2 Decks: Out door dining & sitting areas This is not an investment property, this is my home. Please be respectful of the property. Thank you! Hope you enjoy your stay!

Top Guest favourite
The historic brick mill building features a traditional facade with multiple windows, partially obscured by morning fog. A green metal roof accents the structure. Vintage cars are parked in front, adding charm to the exterior view along the road.
Home in Antrim
5.0 out of 5 average rating, 44 reviews

Milling about in history!

Stay for a few nights in the historic Goodell Handle Shop. Relax in the comfort and unique character of this 1851 brick mill building originally part of the Goodell Mills. Two large bedrooms and a cozy room with pullout couch provide you with welcome rest after a day spent in the beautiful Monadnock region. Freshly renovated, the space offers an excellent location walkable to many of Antrim’s quaint amenities like Edmund’s Hardware, Tuttle Library, and Rick and Diane’s restaurant.

Guest favourite
A welcoming home is surrounded by vibrant autumn foliage, with orange and yellow leaves highlighting the entrance. Stairs lead up to the door, which is adorned with a wreath, while a path is flanked by well-maintained landscaping. A lantern stands near the driveway.
Home in Hillsboro
4.89 out of 5 average rating, 97 reviews

Cozy Lakeside Getaway

Spacious home with a modern rustic vibe and tons of natural light. Enjoy a fire pit, game room with a pool table and a full kitchen. Just a few minute walk to a peaceful private lake with multiple sand beaches, and minutes from Pats Peak ski resort! House surrounded by nature and woods, close to hikes and a local brewery and perfect for leaf peeping in fall! The house has all you need including a swing set at the backyard, it’s perfect for family and friends gathering.

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

Top Guest favourite
Home in Hillsboro
5.0 out of 5 average rating, 23 reviews

Four Season Lake House Retreat

This is a place to find relaxation and fun. My place is good for couples, solo adventurers, and small families, and those who enjoy water sports such as swimming, fishing, paddle boating, kayaking, and rowing in the warmer weather. In the winter there skiing, snow shoeing, and ice fishing nearby. The spring is fishing season. Most of our guest book for a week in the summer. The fall, winter and spring season all have beauty, enchanting experiences.

Top Guest favourite
Two white Adirondack chairs are positioned on a grassy area, offering a view of rolling hills and a cloudy sky in the distance. Lush trees frame the scene, creating a peaceful outdoor space ideal for relaxation.
Home in Bradford
5.0 out of 5 average rating, 74 reviews

Ski Sunapee/Pat’s Peak Swimming/Hiking/Mt Views

Come and stay in rural New Hampshire in this peaceful home. You will not want to leave this mountain top setting once you experience the stunning views from the farmer’s porch and all of the main rooms, but if you do, there is a ten minute drive to Bradford’s restaurants, cafe, and convenience store with gas. For skiing, Mt. Sunapee is 30 minutes away, and Pat’s Peak is just 20 minutes away. Trail access is within walking distance.

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