Vacation rentals in Greenfield

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Top-rated vacation rentals in Greenfield

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Top guest favorite

Farm stay in Mont Vernon

5 out of 5 average rating, 16 reviews

Zen Haven Farm Dog Paradise! A True Zen Escape!

WendyRating, 5 stars2 months ago

We could not have found a better place to stay while having renovations done at our own home. We packed up our gaggle of golden retrievers and one beagle and felt welcomed the moment we stepped into the house. There were treats for the dogs, blankets to put on the couch, verrrry comfortable twin-sized memory foam dog beds and endless amounts of toys for our pups to enjoy. There was also a treat station as well as lickit mats and doggie painting to keep these retrievers happy and busy. This house is so dog friendly. It’s a perfect balance of a beautiful home for the humans that is also perfect for the dogs. The furniture was comfortable, the kitchen large and well-stocked with necessities, such as paper towels, dish soap, dishes, pots and pans and that stove…. Beautiful! The bed was very comfortable and cozy. If the dogs hadn’t wanted to get up so early, we may have slept part of the day away. Having the availability to do laundry was also very helpful. We truly enjoyed our stay!

Guest favorite

The cottage is situated on the lakeshore, featuring a two-tier deck lined with outdoor furniture. Colorful kayaks and paddleboards are visible beside the water. The warm glow of the setting sun casts a gentle light on the lush green trees surrounding the property.

Home in Westminster

4.9 out of 5 average rating, 181 reviews

Lakefront, view of ski mtn, fireplace, sauna

EdwardRating, 5 stars2 weeks ago

Really liked the ocation right on the water and great size for us (two adults and 2 kids under 10). It was a quick trip and didnt spend as much time in Tyler's place as we wanted (since we were diving around a bunch visiting family and friends). But would certainly stay again next time we visit the area.

Top guest favorite

The rustic cabin is surrounded by lush greenery and vibrant flower gardens. A spacious porch extends from the front, supported by wooden columns. Sunlight filters through the trees, creating dappled patterns on the lawn. The inviting entrance reflects a serene woodland setting.

Cabin in Bradford

4.98 out of 5 average rating, 384 reviews

Deer Valley Retreat, Lovely Log Cabin

MeganRating, 5 stars3 weeks ago

My husband and I had a very relaxing weekend away. The cabin was cozy, especially the beds and seating by the fireplace. Alecia made us feel welcome and comfortable with all the features of the house. She was very responsive and paid a lot of attention to detail. While visiting the cabin I was able to go for a long run (plenty of hills!) and eat at some delicious local restaurants. We look forward to an opportunity when we can come back.

Superhost

Cottage in Westford

4.92 out of 5 average rating, 37 reviews

Beach & pond cottage ! Westford MA and Boston!

MelanieRating, 5 stars6 months ago

We had an absolute blast on our girls getaway weekend!! The cottage and community were amazing, exactly what we were hoping for and Doug couldn't have been nicer or more helpful. He was always available by text or phone. The cottage was clean, nicely equipped, and a great location!! We will definitely be renting this cottage again on our next trip!!! Thanks for having us... we loved every minute!! 🧙🧙🧙

Guest favorite

A waterfront home is surrounded by lush greenery, featuring a large deck with multiple seating areas. A small blue paddleboat is visible on the lake, alongside a spacious dock equipped with Adirondack chairs. A calm, reflective water surface complements the serene environment.

Cottage in Croydon

5 out of 5 average rating, 10 reviews

Charming Lakefront cottage with beautiful views

AmeliaRating, 5 stars6 months ago

If you are looking for an idyllic lake house experience, this is it! We could have spent our entire trip just sitting on the porches—upstairs, downstairs, one screened-in porch, and the lovely dock. We used the kayaks and the paddle boat multiple times. The house was perfect for us because we are a close family of three, but if you need privacy from other guests, this wouldn’t be the ideal house as one bedroom opens into the other. The beds are soft and comfortable as is the sofa. Paula and Tim were extremely responsive and helpful. We would absolutely return to this house. It was difficult to leave the gorgeous leaves.

Guest favorite

Home in Harrisville

4.9 out of 5 average rating, 10 reviews

Harrisville Lake House - A Tranquil Get-Away

JudyRating, 5 stars7 months ago

I’m grateful that Peggy and Harry were willing to rent to us at the last minute. Our family needed a quiet respite to be together during a difficult time of loss. The solitude of the lake and woods was calming and we had plenty of room to be together. I only wish we could have stayed longer!

Guest favorite

A sandy beach area borders the calm waters of Big Island Pond, with colorful beach chairs arranged in a welcoming fashion. Swimmers enjoy the water, and paddleboards are visible in the background, framed by lush greenery and a clear blue sky.

Cottage in Hampstead

4.95 out of 5 average rating, 40 reviews

3 Bedroom Lakefront Cottage on Family Campground.

ClaudiaRating, 5 stars6 months ago

Thank you so much for letting us stay at ur cottage. We were there for a wedding & it was great to be able to fit all of our family into one place. It was quiet and serene. The area was beautiful! Thank you for the s’mores kit—we made s’mores almost every night in the fire pit.

Superhost

Large windows provide a clear view of the tranquil lake, reflecting the surrounding greenery. The interior space includes light-colored flooring, with ceiling fans above enhancing air circulation. A wooden staircase leads down to the water's edge, completing the serene lakeside atmosphere.

Cottage in Amherst

4.68 out of 5 average rating, 25 reviews

Baboosic Lake

EmilyRating, 5 stars5 months ago

Phil’s place was a great choice for the weekend! Plenty of room for the amount of people we had. Beautiful property right on the water. Spacious living room to hang out in. Everything was clean and tidy. There are also restaurants and things to do nearby! Would recommend.

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Popular amenities for Greenfield vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Greenfield's top sights

Harlow's Pub & Restaurant55 locals recommend

Peterborough Players41 locals recommend

Waterhouse Restaurant34 locals recommend

Mariposa Museum & World Culture Center25 locals recommend

Toadstool Bookshops22 locals recommend

Peterborough Community Theatre20 locals recommend

Other great vacation rentals in Greenfield

Guest favorite

A rustic wooden structure is set against a vibrant blue sky, reflected in the calm waters below. The building features large windows, a clock façade, and a wraparound porch lined with potted plants, surrounded by trees showcasing autumn colors.

Home in Westminster

4.94 out of 5 average rating, 127 reviews

Wachusett Mountain Get-Away

DaeshaRating, 5 stars3 months ago

It was a pleasure staying here ! Everything is clean and the house is such a nice size !

Top guest favorite

Chalet in Hillsboro

4.88 out of 5 average rating, 34 reviews

Summer time family fun at Emerald lake!

CraigRating, 5 stars2 months ago

Myself and 2 daughters loved staying at Rob's house. We went for skiing and it's very convenient to get to the local ski hills. There was plenty of space for the three of us; it was clean, cozy warm and very comfortable. Rob is very personable and responsive; loved chatting with him! We will be going back again this year if we get the chance at another ski weekend. His place is also in a prime spot for summer, something we'll consider if we decide not to do tent camping. Overall 5 stars for us.

Guest favorite

A private deck is seen overlooking a calm body of water, featuring a hot tub surrounded by comfortable seating and an umbrella. Autumnal foliage adds color to the landscape, enhancing the tranquil setting by the water's edge.

Home in Sandown

4.94 out of 5 average rating, 16 reviews

Sunrise Beach Escape

DebraRating, 5 stars1 week ago

This was the perfect location for our family to spend spring break together! The teenagers loved the games and hot tub, and the adults loved sitting on the patio and chit chatting. The beds were all comfortable, and the window air-conditioning units let each room pick their comfortable temperature. There is plenty of space in the kitchen, and the house had a ton of items available! They provided sufficient paper towels, toilet paper, and dishwasher soap (which so many do not) We all enjoyed the pinball enough that we definitely had to get an extra few rolls of quarters for our 5 night trip. We also all don't do well with the Melaluca brand products that the house uses, so we got our own soaps. There are so many great spaces on the property, and we would have spent even more time outdoors if the weather was warmer, but there was SO much to do inside! We all kept commenting how perfect it was for our group of 6 adults, 2 teens, and 2 tweens.

Guest favorite

An outdoor patio area features a stone-paved surface with a seating arrangement of black chairs and a dining table. A grill and hot tub are visible, alongside vibrant green grass. The building showcases a combination of red and white siding with large windows.

Home in Grafton

4.93 out of 5 average rating, 107 reviews

Cozy Home in Village- hot tub, walk to Grafton Inn

PaulRating, 5 stars2 months ago

Truly wonderful home. Spacious and clean. Perfect for two families of four. The jacuzzi is a great perk. Plenty of parking. The town is quaint and lovely with a great deli for early morning coffee on way to ski, also the tavern in town is very historic and has great food and ambiance. Overall I give it five stars and look forward to staying again.

Guest favorite

A stainless steel sink is centered beneath a wall-mounted shelf, featuring a wooden cutting board and a dish rack. The countertop is crafted from marble, and a modern faucet adds functionality to the space. Light beige walls provide a neutral background.

Apartment in Henniker

5 out of 5 average rating, 8 reviews

Henniker Vacation Rental AirBnb 6

KatieRating, 5 stars2 months ago

We had a great stay! The hosts were so kind and communicative. The Airbnb is quite nice, very clean, and close to anything you’d want in Henniker. The town is so charming, and we had a blast skiing Pat’s Peak. We will definitely return!

Superhost

Three white Adirondack chairs are positioned on a grassy area facing a serene pond, with rolling hills visible in the background. The cloud-dotted sky contributes to a calm and inviting setting.

Apartment in Henniker

4.83 out of 5 average rating, 36 reviews

Paradise on the pond

GabrielleRating, 5 stars2 months ago

This is the second year we stayed at Paradise on the Pond, a great spot to access both Pat's Peak and Crotched Mountain Ski resorts. Cynthia was very accommodating of some changes in our schedule due to my upcoming surgery and she provided an extra very comfy blow up bed for a 3rd guest. Thank you Cynthia! Hope to see you again next year!

Superhost

A seating area featuring wooden chairs around a round table is positioned on the deck, overlooking a serene lake surrounded by trees. The clear blue water reflects the greenery, providing a tranquil setting ideal for relaxation.

Home in Barnstead

4.89 out of 5 average rating, 111 reviews

Family lake house with pvt beach, dock

EnriqueRating, 5 stars1 week ago

Had a great stay! The house was clean, cozy, and just steps away from the lake—perfect for a relaxing getaway. The view was beautiful, especially at sunrise. Would definitely come back!

Superhost