Holiday rentals in Bennington

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Top-rated holiday rentals in Bennington

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Top guest favourite

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.

Top guest favourite

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.

Superhost

Tiny home in Bennington

4.91 out of 5 average rating, 247 reviews

Swim, Hike, Boat, Hot tub + Waterfront Tiny House

Waterfront oasis. Relax in fully equipped Tiny House with wifi, cable tv, bath & shower tucked in a private wooded setting overlooking a small waterfall in nature's paradise on Powder Mill Pond and Contoocook River. Hike, Swim, Fish, Kayak, Canoe, Paddle boat. Private fire pit. Hot tub. Eclectic dining, 4 golf courses, shops, breweries, skiing all nearby. Just outside of Peterborough in Southern New Hampshire, only 1.5 hours from Boston or 2.25 hrs. from Hartford in legendary Monadnock Region.

Top guest favourite

Guest house in New Ipswich

4.95 out of 5 average rating, 358 reviews

"The Porch" Your cozy home away from home!

Welcome to The Porch! Ready for a mini vacation, or just a place to hang out, or work from? You are most welcome here! . This cozy cabin is very flexible and user friendly! It is private to only your group! The downstairs with all it offers, is for one or two person stays. The upstairs becomes available if you enter 3 or more people. This building is in the backyard of our home, as in photos on our Airbnb site, Other info is listed there also! Info book is in room! Welcome! (no pets)

Top guest favourite

Guest house in Wilton

4.95 out of 5 average rating, 644 reviews

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.

Top guest favourite

Cabin in Harrisville

4.96 out of 5 average rating, 181 reviews

Trailside Cottage in charming Harrisville, NH

Hike, bike, cross-country, snowshoe, or just inhale/exhale and enjoy the peace and quiet of a classic New England escape. Welcome to Trailside Cottage, a charming getaway in Harrisville, NH. Recently converted into a cozy space for two. It sits alongside one of the many trails in the Harrisville area, and is accessible to all of the amenities in the Monadnock Region. Our small farm is next door which means you might hear the sounds of country life including our donkey who brays at times!

Top guest favourite

Loft in Peterborough

4.99 out of 5 average rating, 175 reviews

Peaceful Mill on the Water - Home Away from Home

Immerse in tranquility at our serene mill retreat in Southern NH. This historic space, adorned with original timber, rustic brickwork, and lofty 11 ft ceilings, offers a spacious 2,650 sq ft sanctuary. Relax in the soaking tub, or savor the calming waterfall views from the deck. Conveniently near downtown, but distant enough for undisturbed peace. Welcome to your soothing retreat for rest and rejuvenation. A remote worker's dream office with high speed connectivity and dedicated workspace.

Superhost

Home in Antrim

4.8 out of 5 average rating, 131 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 favourite

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 favourite

Loft in Peterborough

4.96 out of 5 average rating, 290 reviews

1850 Waterfall Mill-Loft Style Chic

IMMACULATE COUNTRY HOME W/ FAST WiFi in fresh air New Hampshire. Snuggled in on a quiet street, yet steps away from DOWNTOWN, two "Mini Whole Food" markets! State-of-the-art gourmet kitchen fleshed out with organic spices, wares for entertaining, and other luxuries such as a rReverse Osmosis drinking faucet. Stunning sunlit water views and soothing water sounds! Beautiful antique furnishings and marble finishes add to the unique beauty of this New England home.

Guest favourite

Home in Greenfield

4.94 out of 5 average rating, 155 reviews

Charming House on 7 Acres in Rural New Hampshire

This magical place has been our home away from home for twenty years and we are excited to share it with you. We hope you'll experience the same time-out-of-time feeling we get when sitting out on the deck in the early morning or looking up on a moonless night as the Milky Way snakes its way across the dark sky. The house sits on seven mostly wooded acres that abut a scenic beaver pond. The property is located on a quiet unpaved road in rural New Hampshire.

Guest favourite

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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Other great holiday rentals in Bennington

Cabin in Dunbarton

5 out of 5 average rating, 4 reviews

Waterfront-2/1- Cozy Cottage -Adventure & Romance

MarinaRating, 5 stars6 days ago

Our stay at the lakefront cottage was fantastic! The place was clean and welcoming. We enjoyed the fully stocked kitchen and the sitting areas. But most of all we loved the outdoors. The lake was perfect for paddle-boarding, and there were wonderful trails nearby in the walking distance. Watching beautiful sunsets over the lake made our trip magical. Nico is a gracious host, responsive, genuine, and welcoming. He went out of his way to make sure the kids and I had everything we needed.

Guest favourite

Home in New Boston

5 out of 5 average rating, 6 reviews

Woods'n ’Wetlands

Michael,AlanRating, 5 stars1 week ago

We enjoyed our stay… Quiet, peaceful setting.

Top guest favourite

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 favourite

Home in Bradford

5 out of 5 average rating, 51 reviews

Ski Sunapee or Pat’s Peak Look To The Mountain

DalbertRating, 5 stars1 month ago

Absolutely incredible experience! From the moment we arrived, it was clear that this place was something special. The property was immaculate—clean, beautifully decorated, and thoughtfully stocked with everything we could possibly need for a comfortable stay. Every detail, from the cozy bedding to the pristine kitchen, was perfection and made our trip unforgettable. Judith went above and beyond in every way, and clearly thought of everything a guest would need to feel right at home. She is also very responsive and easy to communicate with Without question, this property sets the gold standard for all Airbnb rentals. If every Airbnb were like this one, hotel chains would be out of business. We can’t recommend it highly enough and will absolutely be back. Mahalo you for an exceptional stay and A Hui Hou!

Guest favourite

Private room in Troy

4.9 out of 5 average rating, 101 reviews

9 MLS to downtown Keene . quiet, comfortable clean

CollinRating, 5 stars2 weeks ago

Lovely place, with a kind host. This was the perfect place to rest and clean up after a long bike ride to NH.

Guest favourite

Guest house in Hancock

4.93 out of 5 average rating, 127 reviews

Hancock large studio apt sleeps 4 Monadnock Region

KeithRating, 5 stars8 months ago

Beautiful, comfortable, and quiet. Very restful. Very private. The porch is a little oasis where you can enjoy your coffee, listen to the birds, and watch the deer in the forest. Its a lot of space for 2 people.

Superhost