Holiday rentals in Greenfield

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Top-rated holiday rentals in Greenfield

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Top guest favourite
Flat in Peterborough
4.93 out of 5 average rating, 210 reviews

Private Apartment with a Mt. view

*We may make special exceptions for a dog. $50.00 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.

Top 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, 689 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.

Guest favourite
Home in Bennington
4.85 out of 5 average rating, 33 reviews

Peaceful Lakefront Escape With a Porch and Kayaks!

Relax on the tranquil shores of Lake Whittemore! Our charming cabin invites you to spend your afternoons paddling with our complimentary kayaks, canoes, and rowboats. After exploring nearby trails, breweries, or ski slopes, enjoy dinner on the screened-in porch, or unwind by the outdoor fireplace. Accommodates six guests with two queen beds and a pull-out couch. Located minutes from the vibrant shops and restaurants of charming Peterborough, this is the perfect nature retreat for any season.

Top guest favourite
The exterior of the cottage showcases a two-car garage, a combination of stone and wood siding, and large windows. A spacious driveway leads up to the home, surrounded by trees and landscaped grounds. The screened-in porch offers a glimpse of outdoor living space.
Home in Greenfield
4.97 out of 5 average rating, 34 reviews

Cozy & Private Retreat-54 Acres

Secluded, yet convenient to so much! This private, romantic and cozy NH getaway at the end of a 1 mile long dirt road is far from the closest house. A great option for couples looking for a privacy of a house, w/out the cost of a big house. Lots of wildlife! Area trails abound- summit Pack Monadnock or simply stroll into the woods to enjoy the sound of spring fed water through the creek's granite boulders. The house is thoughtfully appointed -many new furnishings, linens and amenities.

Top guest favourite
A modern home features a combination of dark siding and natural wood accents, positioned among tall trees. A welcoming porch extends from the entrance, complemented by an American flag. The surrounding area includes a gravel path and vibrant greenery, providing a serene atmosphere.
Home in Jaffrey
4.98 out of 5 average rating, 106 reviews

Willow Falls Home ~Hot tub & Waterfront

Constructed waterfall views are just feet away from you! Not far from Boston, RI or CT, this newly designed home is located at a privately viewed pond, in New England, near Mt. Monadnock! Kick back, relax & listen to the water falling in a screened-in gazebo, or in the outdoor hot tub! Or view it all at the picture windows and enjoy the solitude at this picturesque retreat! Inside you'll find multiple lounging areas, luxurious beds, a fully stocked kitchen and a fun game room.

Top guest favourite
A spacious dining area features a glass-top table surrounded by four chairs, illuminated by a modern light fixture. The vaulted ceiling with exposed wooden beams adds character. A beige sofa is positioned nearby, with large windows allowing natural light to fill the space.
Cottage in Harrisville
4.95 out of 5 average rating, 114 reviews

The Harrisville Ranch - Monadnock Region Getaway!

Located in the heart of the Monadnock Region and surrounded by forests and lakes the Harrisville Ranch is ready to host you! With 4 bedrooms it is great for groups & families visiting the area for hiking, weddings, or just a getaway to a quaint NH village. Mount Monadnock: 5-15 minutes depending on the hiking trail Dublin School: 5 minutes Aldworth Manor & Mayfield Farm Venues: 8 minutes Harrisville Center: 5 minutes Peterborough: 15 minutes Hancock: 15 minutes Keene: 20 minutes

Top guest favourite
A charming two-story building with dark wooden siding is set against a backdrop of vibrant orange foliage from a large tree. Wet pavement reflects the colors of the surroundings, and neighboring buildings contribute to the quaint New England streetscape.
Flat in Peterborough
4.95 out of 5 average rating, 114 reviews

Studio Apt with Full Kitchen

Take a two minute walk over our newly renovated bridge to downtown Peterborough, a beautiful New England town. Thornton Wilder, who wrote the play “Our Town”, describes it as a “good place to live”. Leave your car and walk to amazing restaurants, a healthy food market, a wonderful bookstore, antique shops, a movie theater, clothing stores, historic buildings, a beautiful new library, fun walkways along the river or drive to the many wonderful outings in the Monadnock region.

Top guest favourite
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, 314 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.

Superhost
Home in Antrim
4.98 out of 5 average rating, 248 reviews

HotTub FirePit Games Huge Backyard Family Friendly

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, 187 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 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, 184 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

Guest favourite
A bright living space features a comfortable sofa, a modern electric fireplace, and a television mounted on the wall. Natural light filters through the room, complemented by houseplants and a decorative bowl on a wooden coffee table. The open layout connects to an adjoining area.
Flat in Peterborough
4.91 out of 5 average rating, 129 reviews

Cute, Quiet, Art-Filled Apt.

This above-garage apartment is cozy and comfortable. Perfect getaway! Just 1.5 miles from Peterborough in the beautiful Monadnock region this gem has easy access to trails (backyard) and lakes. Quality linens, tasteful decor, great coffee and a spot to stash all your gear in the breezeway. Guests share main entrance with owners (but separate dwelling) who respect your privacy. Apartment access thru narrow stairs off breezeway.

Popular amenities for Greenfield holiday rentals