
Holiday houses in Hillsborough
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Top-rated holiday rentals in Hillsborough
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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!
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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
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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!
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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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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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Lewis Hill Farm
Come and stay in our historic 16th century home located in the Lake Sunapee Region with views of Bald Sunapee Mountain. Centrally located between the area's best lakes and mountains, convenient to area attractions, and outdoor activities, it is an hour and twenty minutes outside of Boston with easy access to snowmobiling, skiing, hiking, swimming, kayaking, and golfing. The residence is in the renovated attached barn with beams dating back to 1824. It highlights an open floor concept.
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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!
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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.
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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.
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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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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.
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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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Popular amenities for Hillsborough holiday rentals
Other great holiday rentals in Hillsborough

New Hampshire Chalet-Cabin
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*Amazing Mountain Views* log cabin w/ pool+firepit
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Stone Pond Farm. Restored farmhouse, country life.
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Breezy Hill
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Lakeside Retreat 4BR/2BA- 2hrs from Boston
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The 1799 Farmhouse at the base of Pat's Peak
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Water view, 2 min to public beach, king beds
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Peaceful Lakefront Escape With a Porch and Kayaks!
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Destinations to explore
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- White Mountain National Forest
- Okemo Mountain Resort
- Squam Lake
- Weirs Beach
- Canobie Lake Park
- Pats Peak Ski Area
- Monadnock State Park
- Magic Mountain Ski Resort
- Snhu Arena
- Dartmouth College
- Tenney Mountain Resort
- Gunstock Mountain Resort
- Ragged Mountain Resort
- Bear Brook State Park
- Mount Monadnock
- Squam Lakes Natural Science Center
- Mount Sunapee Resort
- Montshire Museum of Science
- Ellacoya State Park
- Camp Plymouth State Park
- Quechee Gorge
- Plymouth State University
- New Hampshire Motor Speedway
- Jamaica State Park





