Vacation rentals in Greenfield

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Top-rated vacation rentals in Greenfield

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Top guest favorite

Guest suite in Deering

4.99 out of 5 average rating, 275 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.

Top guest favorite

A light-filled living area features a cozy sofa covered in white fabric, complemented by two dark throw pillows. To the side, an armchair adds seating, while a large bookshelf filled with books lines the wall. Windows provide a view of the surrounding landscape.

Apartment in Peterborough

4.92 out of 5 average rating, 189 reviews

Private Apartment with a Mt. view

*We may make special exceptions for a dog. $30.00 fee per night. *The water from our well is excellent Comfortable, private apartment in a Mid-Century Modern house with stunning views of Mt. Monadnock and farm. 1 Bedroom with Queen Bed w/AC sleeps 2. NOTE: $50 fee for each bed after main bed. Fully equipped Kitchenette, Huge bathroom & Living room -Queen Hide-a-bed sleeps 2. NOTE: We have internet TV, but no cable. So please remember to bring your sign in information for Netflix and Amazon.

Superhost

Tiny home in Bennington

4.92 out of 5 average rating, 243 reviews

Ski, Hot tub, Hike & MORE at 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

Guest suite in Milford

5 out of 5 average rating, 108 reviews

New England Village Luxury Studio

Kick back and relax in this stylish studio! Our house is in a quiet neighborhood of older homes surrounded by woodlands yet conveniently located downtown, a half mile from our village green (Milford Oval). A short stroll over the river will take you to cafes, restaurants, pubs with live music, post office, library, shops & useful stores such as Rite Aid. Whatever brings you…business, skiing, hiking, antiques, a family gathering or a romantic weekend away…we are looking forward to hosting you!

Top guest favorite

A private deck is featured, surrounded by greenery and trees. A glass-top table is set with four metal-framed chairs and a yellow umbrella for shade. Potted flowers add color to the space, inviting relaxation in the outdoors.

Apartment in Dublin

4.97 out of 5 average rating, 226 reviews

Private Dublin apartment nestled in the woods

Nestled in the quiet woods just north of Mt. Monadnock our cozy one bedroom apartment invites the outdoors in with peeks of the mountain through the trees. Sit out on your private deck and enjoy the view or stroll around the yard and pick a few blueberries in season. We welcome hikers, nature lovers, those visiting friends or family or just wanting to enjoy the area's beautiful scenery and many artistic venues. I like to think of it as a peaceful sanctuary that we'd like to share with you.

Top guest favorite

A serene outdoor seating area features three brightly colored adirondack chairs in pink, yellow, and green, arranged on a stone patio. Surrounded by lush greenery and seasonal foliage, the inviting space offers a peaceful atmosphere for relaxation.

Guesthouse in Wilton

4.95 out of 5 average rating, 640 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 charming wooden cottage is surrounded by trees, featuring a screened-in porch. The exterior showcases warm, natural tones with a combination of shingles and wood paneling. A gravel path leads to the entrance, bordered by vibrant flower beds.

Cabin in Harrisville

4.96 out of 5 average rating, 176 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 comfortable seating area on an outdoor balcony features soft cushions and a wooden table, positioned to overlook a serene body of water surrounded by autumn foliage. The peaceful landscape reflects nature's colors, enhancing the calming ambiance.

Loft in Peterborough

4.99 out of 5 average rating, 167 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.

Guest favorite

The A-frame chalet cabin is surrounded by lush greenery, featuring a striking triangular roof and large front windows. A small porch leads to the entrance, and the nearby structure provides additional amenities. The natural setting offers a sense of seclusion.

Chalet in Stoddard

4.96 out of 5 average rating, 255 reviews

Highland Haus-70s AFrame-short walk to lake/canoe

Cozy 1975 A-frame chalet cabin sleeps 5 with a comfortable living space, two wood stoves, and a full kitchen. Located in the rural community of Stoddard. Enjoy the peace and quiet that this area has to offer. Many local hiking, swimming and fishing nearby. In warmer months, guests will have access to our canoe. It is less than a 2-hour drive from Boston to the Highland Haus! Winter Guests- please note that Shedd Hill rd is very hilly and all-wheel drive or 4-wheel drive is recommended.

Superhost

An outdoor deck features a wooden railing and a pair of striped poufs. A lounge chair is positioned to overlook a tranquil green backyard surrounded by trees, providing a peaceful spot to relax.

Home in Antrim

4.81 out of 5 average rating, 125 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 favorite

A quaint cabin sits amidst lush greenery, framed by tall trees. The blue exterior features a welcoming porch, flanked by blooming white hydrangeas. A well-kept lawn complements the serene landscape, providing a peaceful retreat in a natural setting.

Guesthouse in New Ipswich

4.95 out of 5 average rating, 350 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!

Top guest favorite

A tranquil scene depicts a covered bridge spanning a calm river, surrounded by vibrant autumn foliage reflecting in the water. Mist drifts above the surface, adding a serene quality to the picturesque landscape.

Barn in Hancock

4.94 out of 5 average rating, 126 reviews

4 Bedroom Rustic Home for Special Gatherings

Rustic converted barn 4 bedrooms, big kitchen, dining, living room, 2 level deck, fire pit. Family/friends gatherings are welcome! Big field for dogs & kids to play. Sleeps 8. Good for playing acoustic music, board games, heart to heart conversations and deep sleep. Hancock Harris Center, Norway Pond, Hornberg Brewery, Fiddleheads. Nearby restaurants, art, live music, yoga, fancy shops, swimming, biking, skiing. Location not really suited for loud late night parties.