Vacation rentals in Greenfield

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Greenfield

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

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.

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, 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 favorite

A large living area is furnished with a gray sofa, a wooden coffee table, and two armchairs. The carpeted space features neutral wall colors and access to a staircase. A doorway leads to the bedroom area, with a glimpse of the bathroom visible.

Guest suite in Merrimack

4.99 out of 5 average rating, 228 reviews

Guest suite with king bed and private entrance

Come and relax in our spacious one-bedroom basement guest suite that is comfortable and bright. It has a private entrance with off street parking. The suite has a large living area, bedroom with king bed and private bath . The location is an ideal 20 minutes from the Manchester/Boston Regional airport and 10 minutes from the Merrimack Premium Outlets as well as a wide variety of restaurants. Boston, skiing, the beach and the #1 most hiked mountain in the world are all about an hour away.

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, 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!

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

This simple, peaceful studio by our running stream has been used by our family as a song writing space, and a place for quiet reflection. Close to hiking on Ted's Trail and the Wapack Trail on North Pack Monadnock, just up the road. The studio has no electricity, and no running water except the stream for bathing. Outhouse is nearby. Bring your favorite lantern and a couple of flashlights, and anything else you like to have with you when you camp. We love this place--we hope you do too!

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, 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!

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, 130 reviews

4 Br Home for family gatherings, town walkable

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.

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.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Greenfield vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Greenfield

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 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 favorite

An outdoor deck features a large wooden dining table surrounded by comfortable chairs, shaded by a spacious umbrella. The setting is bordered by lush greenery, creating a serene atmosphere for outdoor dining or relaxation.

Home in Peterborough

4.95 out of 5 average rating, 94 reviews

Hazelhurst Vacation House

ERating, 5 stars5 months ago

You walk into Eric’s place and it feels like a home thoughtfully set up so that you can just walk in and be comfortable. It’s an “and, breathe” kind of relaxing, homey place. Eric was super responsive to any & all questions we had. We absolutely loved our time there and look forward to rebooking in the future!

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, 6 reviews

Woods'n ’Wetlands

Michael,AlanRating, 5 stars1 week ago

We enjoyed our stay… Quiet, peaceful setting.

Top guest favorite

Large windows frame the scenic views of the surrounding landscape, allowing natural light to fill the open kitchen and dining area. A white kitchen island is complemented by modern bar stools. Adjacent seating includes a wicker chair and telescope, inviting relaxation and exploration.

Home in Hancock

5 out of 5 average rating, 12 reviews

Meadow House at Powder Mill Pond

Ashley NicoleRating, 5 stars3 months ago

We loved our ski vacation stay at Rebecca’s! The house is beautiful, gorgeous high vaulted ceilings and the view is stunning! It felt welcoming, clean, and comfortable. Our kids also loved the ping-pong table and games!

Guest favorite

A charming white house features a spacious wraparound porch adorned with hanging flower baskets. The entryway is framed by lush greenery and colorful flower beds, while a stone pathway leads to the welcoming entrance. Large windows provide a bright and airy appearance.

Apartment in Peterborough

5 out of 5 average rating, 38 reviews

Idyllic Peterborough Apt. Above TwinElmFarm

JasonRating, 5 stars3 weeks ago

Trish was a fantastic host of a great property! We chose this stay because my mom loves antiques but we all had the best time. Extremely clean and had everything we needed. My mom even said it was her best sleep in years in the big king bed. The location was perfect, a very short drive into town. We definitely will book again if back in town!

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.

Top guest favorite

The cabin's exterior is surrounded by lush trees, highlighting a spacious wooden deck with two chairs and a table. A single door with a decorative handle invites guests inside, while vibrant flowers are displayed in a planter near the entry.

Guesthouse in Nelson

5 out of 5 average rating, 51 reviews

Romantic Mountain View Guest Cabin

EmilyRating, 5 stars4 weeks ago

Place was wonderful exactly as pictured. Hosts left great recommendations for places to see and eat in the area. We had a great time and would come again.

Guest favorite

A spacious screened-in porch is furnished with a light-colored sectional sofa and a glass-topped coffee table. Large windows provide an unobstructed view of the vibrant foliage outside, allowing natural light to fill the area.

Home in Greenfield

5 out of 5 average rating, 5 reviews

Cozy & Private Retreat-54 Acres

VictorRating, 5 stars2 weeks ago

beautiful spacious home, privately secluded in the woods with all the kitchen tools you could need. plenty of seating throughout the house, creating many uniquely catered spaces throughout the home. the 2 office spaces and plenty of closet / shelf space was an appreciated bonus. The kind host even has a few "in case you forgot" items to ensure your stay is peaceful and that you're cared for! They are a responsive, accommodating, and very friendly host. Thank you!

Show all

Vacation rentals in Greenfield

Top-rated vacation rentals in Greenfield

Vacation rentals for every style

Popular amenities for Greenfield vacation rentals

Other great vacation rentals in Greenfield

Destinations to explore