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, 109 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, 243 reviews

Peaceful Mill with Waterfall - 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 remote workspace

Top guest favourite
Cabin in Stoddard
4.97 out of 5 average rating, 238 reviews

Cozy Comfort on 250 Acre Private Estate

If you’re looking for serenity, peace and quiet, you've found it, amidst a 250 acre private estate. On a lake at the end of a mile long driveway (well plowed in the winter) Is Snowshoe Cabin. Built in 1929 as the garage for "Lakefalls Lodge, it's been completed renovated into a luxurious, cozy home with modern amenities. Guests rave about "views of the snowy pond while you’re warm inside" from heated floors and a wood burning stove with free firewood. Spikes provided for wonderful winter walks.

Top guest favourite
Cabin in Bradford
4.98 out of 5 average rating, 428 reviews

Deer Valley Retreat, Lovely Log Cabin

This Lake Sunapee Region cabin retreat is perfect for romantics, artists, writers, outdoor enthusiasts, gardeners, friends, & family. Centrally located between the area's best lakes and mountains, convenient to area attractions, and outdoor activities. Still, the cabin feels like a destination in itself, where you can relax, recharge, and reconnect. Cozy up by the stone fireplace, relax on the porch, see nature, read, listen, play, cook, stargaze, and enjoy just being! M&R license #: 063685

Top guest favourite
A welcoming entrance features a wooden staircase leading up to a small porch adorned with flowers. The home showcases neutral siding, complemented by a flowering tree and a gravel path, set among a verdant wooded landscape.
Guest suite in Deering
4.99 out of 5 average rating, 327 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 private, smoke free 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 scenic lakes, golfing, hiking, skiing and the charm of rural New England. Enjoy the comfort of serene surroundings & experience genuine hospitality. 75 minutes from Boston.

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, 681 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
4.97 out of 5 average rating, 117 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.

Guest favourite
Home in New Boston
4.89 out of 5 average rating, 129 reviews

River's View Cozy Getaway

Secluded, tranquil, woodland retreat. Unique home overlooks river-cathedral ceilings and large windows throughout. Stay cozy indoors by the wood stove or explore acres of conservation land abutting the property. All you need for quiet getaway or ski vacation. Sleeps 6 in winter months; extra bed on sleeping porch overlooking river in warmer months. Master bath has deep soaking jacuzzi tub. Skiing 20 minutes away at Pat's Peak & Crotched Mt. Trails nearby for hiking, snowshoeing & x-country.

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, 102 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.

Guest favourite
Home in Antrim
4.98 out of 5 average rating, 233 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, 183 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
Home in Mont Vernon
4.95 out of 5 average rating, 237 reviews

Private Waterfront • Views, Hot Tub, King Bed

Escape to a modern post-and-beam farmhouse set right on the water, with rustic charm and upscale comfort. Cook in the fully equipped kitchen then unwind in the outdoor hot tub under the stars. Sleep soundly in the king bed after exploring the pond with kayaks, getting active in our gym room or lofted yoga room. Serene views with wildlife visits from deer, beavers, eagles and more. Great location close to hiking, skiing, waterfalls, and great local dining.

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