Vacation rentals in Hillsborough

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Top-rated vacation rentals in Hillsborough

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Top guest favorite

The exterior of Boulder House is presented, showcasing a modern black facade with large windows. A spacious deck is visible, furnished with two chaise lounges and chairs. Surrounding boulders and colorful fall foliage create a natural and inviting environment.

Cabin in Stoddard

4.98 out of 5 average rating, 103 reviews

Boulder House - Extraordinary Luxury in the Woods!

From its unique interior wall of huge boulders to the soaring post and beam construction, Boulder House is bolder in every way. It's a rare combination of peace, solitude, and luxury in a beautiful and secluded setting within the 250-acre Lakefalls estate. The very private deck overlooks "Chandler Meadow" and 11,000 acres of conserved land and water, with stunning views from the sunken tub and outdoor shower. The interior appointments and amenities provide extraordinary comfort and aesthetics.

Guest favorite

The entrance features a dark door with multiple window panes, topped by a white overhang. The pathway is lined with wooden railings, partially covered in snow. A bright red shovel rests against the wall, indicating winter conditions.

Cottage in Newbury

4.96 out of 5 average rating, 429 reviews

Tranquil Getaway-Dartmouth Lake Sunapee Region

Tranquil, private, cozy home with a beautiful view on a historic country road. Very close and easy access to many activities and services. Including skiing/adventure park at Mt. Sunapee- 6mi; Pats Peak ski area:-12mi; snowmobile trails right outside the door; many hiking/snowshoeing trails just steps outside the door or just a short drive. There are several lakes in the area with public access including the biggest, Lake Sunapee. A lovely, relaxing and beautiful place to stay any time of year.

Top guest favorite

Guest suite in Deering

4.99 out of 5 average rating, 283 reviews

Elegant Lodging in the Woods ~Privacy & Comfort!

Looking for a peaceful getaway? As Superhosts with 5 years of 5-star reviews, we offer a smoke free, private guest suite perfect for couples or solo travelers. Nestled in the quiet countryside near Pat's Peak, Crotched Mtn., Mt. Sunapee, skiing, hiking, golfing & lakes. Convenient location to the seacoast. Enjoy the beauty of rural New England, unwind in comfort, and experience hospitality at its finest. Super clean! Private locked entrance. FREE onsite parking. Only 75 minutes from Boston.

Guest favorite

Cabin in Henniker

4.96 out of 5 average rating, 138 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!

Top guest favorite

The rustic cabin is surrounded by lush greenery and vibrant flower gardens. A spacious porch extends from the front, supported by wooden columns. Sunlight filters through the trees, creating dappled patterns on the lawn. The inviting entrance reflects a serene woodland setting.

Cabin in Bradford

4.98 out of 5 average rating, 389 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

Guest favorite

An outdoor kitchen area is positioned under a wooden pavilion with a sloped roof. Warm lights hang above, illuminating the space. Metal grills, pots, and utensils are visible, alongside a round table with green chairs. The surrounding greenery adds a natural backdrop.

Home in Henniker

4.93 out of 5 average rating, 168 reviews

The Farmhouse at Sweetwater

Welcome to Sweetwater Farm in Henniker . 2 minutes from pats peak mountain and close to many other ski areas!Our familypurchased the Historical Farmhouse (est 1750)in 2006 and recently decided to share it with others. The newly renovated 2 BR farmhouse sleeps 4-5 people. You'll have access to the grounds, including 1000 ft of frontage on the Tooky River (great for swimming, kayaking and fishing).Our guests can also purchase our USDA certified beef and farm fresh eggs to enjoy during your stay

Guest favorite

A serene view of Highland Lake is captured from above, showcasing calm waters framed by lush greenery. The shoreline features boats moored along wooden docks, with distant mountains under a bright blue sky dotted with clouds.

Cabin in Stoddard

4.83 out of 5 average rating, 131 reviews

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!

Superhost

A serene winter landscape is depicted, featuring a cabin surrounded by a snowy expanse. Snow-covered trees create a tranquil scene, while a blanket of white covers the ground, adding to the peaceful atmosphere. The sky appears overcast, contributing to the muted tones.

Home in Antrim

4.8 out of 5 average rating, 130 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!

Guest favorite

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, 192 reviews

Birchwood at Stonehenge

Totally private self-contained quaint and private in-law studio in private home in Henniker, New Hampshire, walk to Pat’s Peak Ski Area, near New England College. Sleeps 2-3 people with 1 Queen and 1 single bed. Walkout basement with own entrance, separate bedroom, kitchenette, bathroom, and patio with outdoor gas grill. Nice yard in wooded area, rivers, lakes and mountains with four season recreational activities nearby. Suitable for 2-3 people. No pets, no smoking, no drugs.

Guest favorite

A serene waterfront scene is captured, showcasing calm, reflective waters framed by lush greenery. A cozy seating area with striped cushions is positioned nearby, inviting relaxation. In the distance, a family enjoys time on the water while the sun filters through the trees.

Chalet in Antrim

4.93 out of 5 average rating, 103 reviews

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

My year-round A-Frame cabin is 30 min to Mount Sunapee, 20 min to Crotched, and 15 min to Pat's Peak! It’s on a small 32-acre pond in New Hampshire. It is truly heaven on earth. There is over 100 feet of direct waterfront. There is a 6 foot main dock, and a small fishing dock off to the side. The fishing on our pond gets rave reviews! Most people catch and release, but please follow NH fishing laws: 16+ needs a license. The property sits on 1/3 of an acre, on a sloped hill.

Top guest favorite

A stone fire pit is surrounded by several green Adirondack chairs, with a small table nearby. The lake is visible in the background, and a floating dock can be seen across the water. Trees frame the scene, under a clear blue sky.

Cottage in Weare

4.94 out of 5 average rating, 285 reviews

Seasonal lake side cottage

Cottage comes with the use of two kayak's, a canoe, two stand up paddle boards, hammock and outside fire place to roast s'mores. (Please do not use fireplace until dusk). Refrigerator & freezer, microwave, keurig, toaster, basic pots and pans, outside grill,a clean lake with swimming area. Tv/DVD player & DVD’s(no cable), WiFi. We supply towels,linens & beach towels. Friendly neighbors on either side of cottage. A perfect relaxing, unplugged weekend getaway.

Guest favorite

A loft bedroom within an A-frame structure displays a spacious bed with a white comforter and decorative pillows. A patterned rug is placed beneath the bed, and large windows frame scenic views. Soft, natural light filters through the space, enhancing the cozy atmosphere.

Chalet in Stoddard

4.95 out of 5 average rating, 263 reviews

Highland Haus AFrame Lake Access Vintage 70s Charm

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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Popular amenities for Hillsborough vacation rentals

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Other great vacation rentals in Hillsborough

Top guest favorite

A compact bathroom features a stand-up shower with a rustic shower curtain and a marble tile enclosure. A small sink and toilet are positioned against the wooden wall. Natural light filters in, highlighting the warm wooden tones of the cabin.

Cabin in Lempster

5 out of 5 average rating, 31 reviews

Welcome to Strol-in Cabin 1

ChrisRating, 5 stars2 weeks ago

It was a very peaceful place to stay. Away from everyone, close enough to do stuff and get the essentials. About 15-20 minutes to find food or shopping for essentials. Went to a few fishing spots otherwise chilled at our well stocked cabin with a fire. Was hoping to check in early and offered for check in at 11am. Thought that’s was great if our host. Definitely recommend as a starting point to go fishing, hiking or hit mount sunapee. Thanks to our host for making our night out memorable

Guest favorite

A wooden bridge spans a clear stream, connecting areas of lush greenery. Smooth stones are partially submerged in the water, creating a peaceful natural setting. Sunlight filters through the leaves, enhancing the serene atmosphere of the woodland.

Cabin in Greenfield

4.88 out of 5 average rating, 32 reviews

Rustic Studio by Woodland Stream

JoshuaRating, 5 stars1 month ago

Our weekend here was so peaceful. Leslie is an exceptional host and provided charming breakfasts in the morning. We hiked the nearby mountain from the cabin and the surrounding area is beautiful. This place is wonderful for anyone looking for some relaxing cabin camping.

Guest favorite

A stone pathway lined with lush green plants leads to a white door framed by natural wood siding. The inviting entrance is enhanced by clear blue skies and tall trees, creating a serene transition from the exterior to the interior.

Apartment in Bradford

4.95 out of 5 average rating, 39 reviews

Cozy Spring Loft

AlisonRating, 5 stars2 weeks ago

Very cozy studio! Had a relaxing time in Bradford and enjoyed the consignment store next door. Great for a quiet weekend getaway.

Top guest favorite

Home in Hillsborough

5 out of 5 average rating, 9 reviews

Very Private Cabin on 12 Acres

SamanthaRating, 5 stars3 weeks ago

Great place, very responsive and great communication, comfy and cozy definitely recommended! it was a wonderful get away.

Top guest favorite

A butterfly with intricate orange and black patterns rests on delicate pink flowers. The background showcases wildflowers and greenery, creating a vibrant natural scene filled with color and life.

Yurt in Henniker

5 out of 5 average rating, 97 reviews

Unique Sunny Yome on Beetle Hill Farm

BumbleRating, 5 stars1 month ago

What an incredible experience! The yurt was beautiful on a lovely property! The stay has everything you need to live comfortably in the yurt for your visit. While it rained for our visit, we enjoyed the serenity of nature and peaceful interior of the yurt, as well as the games and puzzles provided by the host. We cannot wait to return for a longer stay in a warmer month to enjoy all the surrounding area has to offer. There are plenty of state parks, antique stores and local businesses within a short drive, leaving plenty to do, (or not do) while enjoying your stay.

Top guest favorite

Cabin in Washington

5 out of 5 average rating, 21 reviews

Mtn Mtn Cabin. Log home with forever views.

MarianaRating, 5 stars5 months ago

We went with six people, and we had memorable moments at the cabin; it was amazing! The view from the windows is breathtaking. Very cozy!!!

Guest favorite

An aerial view captures a rustic cabin surrounded by dense greenery, situated near a tranquil lake. A fire pit with seating circles its perimeter, providing a cozy gathering space. The trees intertwine with the landscape, enhancing the serene setting under a twilight sky.

Cabin in Washington

4.94 out of 5 average rating, 33 reviews

Lakefront Log Cabin on 2 acres

GuilhermeRating, 5 stars2 weeks ago

Really amazing place, quiet and amazing view the cabin was also amazing

Superhost

A wooden dock extends into calm waters, flanked by lush greenery. A single lounge chair rests on the dock facing the serene lake, surrounded by gentle ripples. Clear blue skies with a few clouds create a tranquil ambiance.

Camper/RV in Henniker

4.92 out of 5 average rating, 24 reviews

Mini Haven RV

ShelbyRating, 5 stars3 weeks ago

The camper was as described, don’t expect anything fancy. The AC worked really well which was great. I expected it to be more private than it was. There were people riding atvs directly behind the camper and you can see and hear the people across from the fire pit. There were so many bugs that it was almost intolerable. If you’re looking for a rustic camping experience but with a toilet and shower this is the place for you. Def pack industrial strength your bug spray! Host was very friendly and helpful.

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Vacation rentals in Hillsborough

Top-rated vacation rentals in Hillsborough

Vacation rentals for every style

Popular amenities for Hillsborough vacation rentals

Other great vacation rentals in Hillsborough

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