Holiday rentals in Greenfield

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Top-rated holiday rentals in Greenfield

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Guest favourite
A historic two-story house with yellow siding is surrounded by greenery. A spacious front porch with white railings invites relaxation. Pink roses bloom in the foreground, framing the home's welcoming façade and enhancing the charm of the village setting.
Home in Hancock
4.94 out of 5 average rating, 108 reviews

Large Home in Peaceful Historical Village

We are located in the Monadnock region, 25 minutes from Keene NH in the quaint historical village of Hancock. The house is located on Main Street within minutes walking distance to the John Hancock Inn, the Hancock Market, Fiddleheads Café and the Town Beach. Our home was built in 1807 and has many of the features and uniqueness associated with a 219 year old home. The Monadnock area offers many outdoor activities including golfing, fishing, skiing, hiking, biking or just relaxing on the porch.

Top guest favourite
An inviting open living space showcases warm brick walls and original timber beams. A spacious seating area features a brown leather couch and wooden coffee table, while a grand piano occupies one corner. Large windows with serene views of the outdoors offer natural light.
Loft in Peterborough
5 out of 5 average rating, 230 reviews

Peaceful Mill with Waterfall - Top 1% 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 remote workspace

Top guest favourite
The exterior of a cozy guest suite is depicted, adorned with twinkling lights on a wintery day. A wooden staircase leads to the entrance, framed by a gently snow-covered landscape. Trees in the front yard are wrapped in warm lights, adding a touch of charm.
Guest suite in Deering
4.99 out of 5 average rating, 318 reviews

Elegant Lodging in the Woods ~Privacy & Comfort!

Looking for a relaxing escape? As Superhosts with 6 years of 5-star reviews, we warmly welcome you to our smoke-free, private guest suite. Perfect for couples or solo travelers seeking comfort & tranquility. Tucked away in the peaceful countryside near Pat's Peak & Crotched Mountain, our location offers convenient access to skiing, hiking, golfing, scenic lakes, and the charm of rural New England. Enjoy the comfort of serene surroundings & experience genuine hospitality. 75 minutes from Boston.

Top guest favourite
Guest house in New Ipswich
4.95 out of 5 average rating, 403 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)

Guest favourite
A cascading waterfall flows over natural rocks, surrounded by lush greenery. Delicate pink flowers in the foreground enhance the serene setting, where the sound of rushing water and natural beauty create a peaceful atmosphere.
Guest house in Wilton
4.94 out of 5 average rating, 673 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
A comfortable sofa is positioned near a window with sheer curtains, allowing natural light to illuminate the space. A decorative pillow with text is placed on the sofa, while a glass of wine rests on a wooden table outside, visible through the window.
Cabin in Winchendon
4.96 out of 5 average rating, 103 reviews

The little house on Mirror Pond

Escape to our fully renovated tiny pond house on the serene Mirror Pond. Perfect for up to 4 guests, enjoy swimming, kayaking, or floating on tubes. Unwind by the fire pit, barbecue on the deck, or cozy up by the fireplace (our apologize but it is currently not working) with board games on cooler days. With great WiFi, it’s also ideal for a peaceful work retreat. Whether you're here to relax, or get some work done, this tranquil hideaway offers the perfect blend of adventure and relaxation.

Top guest favourite
The studio features a spacious bed with white linens, accented by decorative throw pillows. A vibrant piece of art adorns the wall above the bed. A modern vanity area with a sink is visible, along with natural light filtering through windows that offer views of the surrounding woods.
Guest suite in Milford
5 out of 5 average rating, 162 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 CVS. Whatever brings you…business, skiing, hiking, antiques, a family celebration or a romantic weekend away…we are looking forward to hosting you!

Top guest favourite
Home in Antrim
4.99 out of 5 average rating, 221 reviews

Relaxing Hot Tub Getaway

The ultimate experience for couples & families 5-10min from hiking trails & ski resorts A Mile from Gregg Lake Beach ALL YEAR PRIVATE/SECLUDED HOT TUB Grill, Hammock, Gym equipment XBox Series S, Life Size Janga, Yahtzee, Darts, Corn Hole, ping pong table, mini pool table Luxury KING PURPLE Brand Mattresses in every bedroom for the best nights rest with individual mini splits for optimal comfort Fully stocked kitchen High speed WiFi, house on 2 private acres

Guest favourite
The exterior of a cozy house is illuminated by warm lights during twilight. Snow blankets the ground and roof, while bare trees stand around the property. The entrance features a welcoming glow, suggesting a comfortable atmosphere inside.
Home in Greenfield
4.93 out of 5 average rating, 177 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.

Superhost
A well-lit studio features a king-sized bed with navy blue and white bedding, accompanied by bedside tables with lamps. A kitchenette is visible in the background, equipped with modern appliances and gray cabinetry. Exposed wooden beams add character to the space.
Flat in Manchester
4.87 out of 5 average rating, 121 reviews

Unit 320: the Press Box - Premium King Bed!

This king-sized unit is a home run! Cheeky and nostalgic, it features New England sports memorabilia, unique art, and even a mini putting green, as well as amenities like the equipped kitchenette, full bathroom, and a Bedgear Performance Bed with adjustable settings to lift your head and feet to ensure you’re comfortable while enjoying your favorite sport in HD with a soundbar. The Factory is pleased to be able to welcome visitors from all around the world!

Top guest favourite
A private deck features a hot tub beside a wooden seating area with four chairs arranged around a fire pit. A blue umbrella provides shade, while cozy bathrobes hang on the fence, inviting relaxation in the natural surroundings.
Guest suite in New Boston
4.99 out of 5 average rating, 221 reviews

Private Suite with Hot Tub

#BarnQuiltHouse Cozy, private guest suite with hot tub in the wooded hills of a quaint New Hampshire farming town. Residential neighborhood, centrally located in Southern New Hampshire. 20+/-min to Concord, Manchester Airport, St. Anselms College, New England College, Pat's Peak, Crotched Mountain. Head north to the lakes region, west to Mt. Sunapee, or south to visit Boston..all within an hour and half drive. May the peace of the wilderness be with you.

Top guest favourite
A welcoming sleeping area features a queen bed dressed in navy bedding, complemented by two bedside lamps. A decorative pillow adds an accent to the bed. Textured area rugs are placed on the hardwood floor, enhancing the cozy atmosphere of the room.
Guest suite in Greenfield
4.96 out of 5 average rating, 157 reviews

Welcome to Merry Hill!

Take a break and unwind at Merry Hill - a peaceful wooded oasis. Merry Hill is located in Greenfield, NH about 10 minutes away from Crotched Mountain for skiing and hiking. We are mid-point between Keene and Manchester. Your private, separate entrance guest suite includes: • Queen Bed with 14” Memory Foam Mattress • Full Bathroom with Tub and Shower • Complimentary Shampoo, Conditioner & Body Wash • Mini-Fridge with Coffee / Tea Station

Popular amenities for Greenfield holiday rentals