Vacation rentals in Bennington

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Top-rated vacation rentals in Bennington

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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.

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.

Superhost

A serene view of a calm pond reflects vibrant fall foliage in shades of orange, yellow, and red. A diving board is positioned over the water, with a person standing nearby, framed by the colorful landscape.

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 favorite

A charming cabin features a light blue exterior with a sloped roof and welcoming porch. Surrounded by lush greenery, landscaped flower beds with blooming white hydrangeas and evergreen bushes complement the serene setting. A spacious lawn provides ample outdoor space for relaxation.

Guesthouse 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 favorite

A colorful hammock suspended between two trees invites relaxation. The vibrant stripes of the hammock contrast with the surrounding greenery. Bare feet rest comfortably on its edge, while the red house and lush foliage are visible in the background, creating a peaceful atmosphere.

Guesthouse in Wilton

4.95 out of 5 average rating, 643 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 favorite

A screened porch features four wooden rocking chairs, inviting relaxation. Natural light filters through large windows, displaying the green space outside. The wooden walls and ceiling provide a warm, rustic feel, while a small basket and dining table enhance the cozy atmosphere.

Cabin in Harrisville

4.96 out of 5 average rating, 180 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 favorite

A serene waterfall cascades over a stone edge, providing a soothing soundscape. Surrounded by lush greenery and autumnal trees, the scene offers a tranquil view of nature's beauty. The water flows gently into a calm body below, enhancing the peaceful ambiance of the area.

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

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

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 serene view of a river bordered by lush greenery and colorful autumn foliage. The water reflects vibrant hues of blue and gold, creating a peaceful atmosphere. A wooden railing lines the bank, adorned with seasonal flowers, enhancing the natural beauty of the setting.

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 favorite

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.

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.

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Other great vacation rentals in Bennington

Superhost

A modern coffee machine is positioned on a wooden countertop. The machine features a sleek design with a transparent water reservoir on one side and control dials on the front. The compact unit includes a drip tray and is ready to brew.

Chalet in Hillsboro

4.74 out of 5 average rating, 31 reviews

Modern Cabin with Rustic Touches

MichaelRating, 5 stars2 weeks ago

We were pleasantly surprised on how clean and modernize the place was. We have traveled several times to Hillsboro area to visit with family events and this by far the best place we stayed at.

A calm lake is depicted, reflecting a clear blue sky dotted with white clouds. The surrounding lush green trees create a serene backdrop, enhancing the tranquil atmosphere. A small dock is visible in the foreground, providing access to the water.

Cabin in Dunbarton

5 out of 5 average rating, 4 reviews

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

MarinaRating, 5 stars4 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 favorite

Three product dispensers are mounted on the wall, labeled for shampoo, body wash, and conditioner. The surrounding tiles feature a decorative pattern, while the wall displays a natural stone texture. A gray towel is hung nearby, complementing the neutral tones of the bathroom.

Home in New Boston

5 out of 5 average rating, 5 reviews

Woods'n ’Wetlands

IsaacRating, 5 stars1 week ago

Had a wonderful, tranquil time at Eli's guesthouse! Eli was really easy to communicate with and available if I needed anything. The place was exactly as it was depicted in the photos. I'd recommend some light hiking at Joe English Reservation not too far away (which Eli recommended).

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.

Guest favorite

A sandy beach is shown beside a calm lake, with two docks extending into the water. Trees line the shore, providing shade and a sense of tranquility. Soft clouds drift overhead, and a few individuals are enjoying the water, highlighting a serene outdoor environment.

Home in Hancock

4.94 out of 5 average rating, 93 reviews

Large Home in Peaceful Historical Village

AlexRating, 5 stars3 months ago

Lovely historic home in a super cute area. My only suggestion is that if you’re coming for snowboarding/winter activities, make you come prepared with food because a lot of nearby restaurants and markets shut down due to the weather. I have nothing bad to say about the house, neighborhood, or town, just something worth noting! Very close and convenient to Crotched Mtn.

Guest favorite

Double glass doors open to a private deck, framed by a stone wall and lush greenery. A light area rug is positioned on the floor, contrasting with the neutral wall tone. A lounge chair is visible on the deck, inviting relaxation.

Guesthouse 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.

A panoramic view of a snow-covered landscape is presented, featuring rolling hills and scattered trees. Snow blankets the ground, while distant mountains are visible under a bright blue sky with gentle clouds.

Apartment in Bennington

4.69 out of 5 average rating, 13 reviews

Crotched Mtn. Ski Condo

JenniferRating, 5 stars2 months ago

Great place to stay if you need to crash after a long day of skiing at Crotched Mountain!

Top guest favorite

The spacious kitchenette features reclaimed barn wood cabinetry and modern appliances, including a retro refrigerator. Natural light filters through the window, illuminating the warm wood tones and inviting decor. A small dining area and handmade details can be seen throughout the room.

Farm stay in Jaffrey

5 out of 5 average rating, 53 reviews

Comfy Quarters Suite 2 Saltbox Hideaway

AlyshaRating, 5 stars2 weeks ago

Lori was an amazing host and the suite was adorable. It was a perfect t quiet getaway. Private and comfortable with amazing views and area to be outside and explore. Lori was so responsive and friendly, and even gave me advice on my chickens!! Would definitely recommend to anyone hoping for some peace and quiet!

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Vacation rentals in Bennington

Top-rated vacation rentals in Bennington

Vacation rentals for every style

Popular amenities for Bennington vacation rentals

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