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Holiday houses in Greenfield

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Quick stats about holiday rentals in Greenfield

  • Total holiday rentals

    Explore 30 holiday rentals in Greenfield

  • Nightly prices starting at

    Greenfield holiday rentals start at $85 NZD per night before taxes and fees

  • Verified guest reviews

    Over 4,480 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Greenfield holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Greenfield rentals

  • 4.9 Average rating

    Greenfield stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated holiday rentals in Greenfield

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

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Guest favourite
A bright living space features large windows, allowing natural light to fill the room. A comfortable sofa sits beside a wooden coffee table, with visible mountain views outside. A round dining table is surrounded by wooden chairs, enhancing the room's spacious feel.
Apartment in Shelburne Falls
4.92 out of 5 average rating, 321 reviews

Sunny, soaring 2-level downtown loft, scenic views

Walk to everything from this sunny, spacious 2-level, newly renovated 3rd-floor loft in downtown Shelburne Falls, right by the Bridge of Flowers. Cathedral ceiling, giant windows with views of mountains & river. Open upstairs queen bed space. Comfy pull-out queen bed downstairs. Washer/dryer. Well-equipped kitchen w/ dishwasher. Brand-new tiled shower. Fast Internet, two smart TVs, and a 15,000 BTU air conditioner that cools the big space in minutes. 15-minute drive to Berkshire East ski resort.

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Top Guest favourite
The exterior of the country home is showcased, depicting a two-story structure with a welcoming porch. Lush green grass surrounds the house, and vibrant flowers bloom along a stone pathway, enhancing the natural beauty of the tranquil setting.
Home in Shelburne Falls
5 out of 5 average rating, 121 reviews

Charming Brookside Artisan Home

Relax, work & play in this peaceful country home built by a renowned furnituremaker and filled with handmade furniture and art. Explore the countryside, listen to the babbling brook & visit the many local family farms. There is a large firepit and plenty of outdoor activities at your doorstep, including biking, hiking, and x-country skiing. Come get away from it all while being only 10 minutes to Greenfield and the quaint village of Shelburne Falls. Easy 30 minute drive to the five college area.

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Guest favourite
A bright living space is surrounded by floor-to-ceiling windows, offering views of vibrant foliage and serene waterways. A small wooden table is positioned on a natural wood floor, highlighting the connection to the outdoor landscape. Warm sunlight filters through the trees, creating a calm ambiance.
Home in Guilford
4.95 out of 5 average rating, 151 reviews

Vermont Mirror House

Escape to our stunning glass house nestled in the Vermont forest. This modern retreat offers breathtaking 360-degree views of lush wilderness and beautiful waterways. Unwind in the hot tub, warm up by the cozy fireplace, or rejuvenate in the sauna. Floor-to-ceiling windows bring nature indoors! Perfect for romantic getaways, small families or simply work away from work with fiber wifi. Experience tranquility during all seasons in this one-of-a-kind hideaway. Book now for an unforgettable escape!

LocationValueDecor

Top Guest favourite
A cozy studio bedroom features a spacious bed draped with a striped quilt, complemented by a decorative rug. Natural light enters through a window adorned with soft curtains. An art piece hangs above the bed, with a small table and two chairs accommodated nearby.
Guest suite in Greenfield
4.95 out of 5 average rating, 242 reviews

Pristine Oasis with Private Bath

Our studio space (250 sq ft) is separate from the main house and located on the outskirts of Greenfield MA. The location provides easy access to downtown, restaurants, shopping areas and Interstate 91. Modern decor, tiled artsy bathroom, lots of garden art, and sweeping views of Berkshire foothills make this a great choice for foliage season, summer recreation and choice winter skiing. One Queen bed. Our house is 90 miles west of Boston, 60 miles north of Hartford and a 3-hour drive to Canada.

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Top Guest favourite
An open living area features a dining table surrounded by wooden chairs. A comfortable sofa sits near a coffee table, with an air conditioning unit and a television mounted on the wall. Wooden beams adorn the ceiling, contributing to a cozy atmosphere.
Cottage in Bernardston
4.87 out of 5 average rating, 365 reviews

Cozy, Quiet Cottage on Country rd 2 mil from I-91

Our quite and comfy home is conveniently located less than 2 miles from I-91, but a 1/4 mile down a country road giving you lots of privacy. The cottage is less than a mile from Crump 'N Fox Golf; 2 miles from Northfield Mount Hermon; 10 minutes from Greenfield & Stoneleigh Burnham; 15 min to Brattleboro, Deerfield Academy, Bement & Eaglebrook; 20 min to UMass, Amherst & Northampton; 30 minutes to Keene NH & Shelburne Falls and 45 min to the Basketball Hall of fame in Springfield & Mt Snow VT.

LocationValueQuiet

Top Guest favourite
Tiny home in Wilmington
4.99 out of 5 average rating, 395 reviews

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

LocationFamilyQuiet

Guest favourite
A well-lit guest suite features a queen-sized bed with quality linens, positioned against a wall. A cozy day bed offers additional sleeping space. A round table and chairs complement the room, while large windows allow natural light to fill the space. A patterned area rug adds warmth.
Guest suite in Montague
4.91 out of 5 average rating, 257 reviews

Great Falls Private Suite

Our lovingly designed guest suite is situated 17 miles from the UMass Amherst Campus, 8.2 miles from Northfield Mount Hermon. We are between downtown Turners Falls and Greenfield. If you're looking for a private and bright suite with beautiful natural light and a modern bohemian feel this is the space for you! Please note that there is a kitchenette but not a full kitchen. Turners Falls is one of 5 villages in the town of Montague. It's a vibrant, diverse area that runs along the CT River.

ValueLocationDecor

Top Guest favourite
The bright studio features a cozy sleeping area with a spacious bed, a comfortable yellow armchair, and two plush couches. A coffee table sits in the center, with large windows allowing natural light and views of greenery. A television is mounted on the wall.
Apartment in Shelburne Falls
4.97 out of 5 average rating, 649 reviews

In town, newly renovated studio with private deck

Come explore our unique area and stay in a renovated, light filled studio with private entrance, secluded deck , kitchenette and bath located in the quaint New England village of Shelburne Falls.We are within easy walking distance to numerous shops, candlepin bowling, Glacial potholes, tennis/basketball courts, Bridge of Flowers, eateries/restaurants, Pothole pictures, groceries, playgrounds, hiking & swimming areas, a natural food store and art galleries.Close to Berkshire East and Zoar!

ValueFamilyKitchen

Top Guest favourite
A gravel driveway leads to a two-story house set in a green, open space. Lush shrubs and trees surround the structure, providing a natural, inviting environment. A sign for 'Railroad St.' is visible, indicating the property's location.
Place to stay in Bernardston
4.96 out of 5 average rating, 400 reviews

Unique Private Studio w/Queen bed on second floor

Second floor studio with keyless entry and large eat in kitchen in quiet, rural, residential area. Outdoor yard space for guest use. 15 min. walk to country store, bakery, 2 pizza shops, gas station with Dunkins, library, and Post Office. Easy access to Rt 91 and Rt 2. Eight min drive to Greenfield, 15 to Brattleboro, 20 to Northampton. Close to Northfield Mt Hermon, Stoneleigh Burnham, Deerfield Academy and Thomas Aquinas College. Close to VT and NH and 30-90 minutes to many ski slopes.

ValueFamilyBathroom

Top Guest favourite
The exterior of a red cottage-style home is shown, featuring a covered porch and a wooden deck that extends into a lush green yard. Surrounding trees and bushes create a natural landscape, with a bright sky and white clouds overhead.
Guest suite in Greenfield
4.99 out of 5 average rating, 236 reviews

Historic Greenfield Home: Cozy Private Guest Suite

Bright comfortable guest suite just blocks from lively downtown, yet quiet, private, and easy to park. The suite has one bedroom, one living room, and one private bath; firm queen size mattress, crisp clean linens, Apple TV ready for your Netflix login, excellent high-speed wireless, private deck, and coffee bar stocked with coffee, tea, & snacks. You'll park in the rear of the house, and enjoy total privacy with your own entrance with key-code; come and go as you please.

LocationValueNearby

Top Guest favourite
A modern kitchen features white cabinetry and a spacious countertop. A white refrigerator and stove are positioned along one wall, while a round dining table set for two is placed in the foreground. Natural light brightens the room from an unseen window.
Apartment in Greenfield
4.96 out of 5 average rating, 121 reviews

Cozy one bedroom apartment

This is a beautiful one bedroom apartment located on the first floor that was recently remodeled. The stylish place is perfect for 2 people. It has a good size kitchen and a porch in the back. Located on a quiet and safe street yet close local restaurants and coffee shops. Easy hikes with great views like Poet Seat Tower and Highland Park. Also close to Deerfield Academy, Northfield Mount Hermon, The Bement School, Eaglebrook Schoool and Stonleigh-Burnham School.

ValueLocationHeating

Top Guest favourite
A spacious, two-story dark wooden building is nestled among trees, showcasing a welcoming entrance with a large front porch. Lush green grass surrounds the structure, enhancing its serene setting. Bright blue skies and scattered clouds further complement the inviting atmosphere.
Apartment in Conway
4.96 out of 5 average rating, 218 reviews

A Country Retreat-Enhanced Studio Apartment

Welcome to our lovely apartment, located in the beautiful, quiet Western MA hill-town of Conway. This is our second time as Airbnb hosts, having hosted almost 150 reservations and achieved Superhost status there. We built again and downsized but included this spacious studio apartment with a bedroom alcove. Wooded and quiet yet just 3 miles from the charming tourist town of Shelburne Falls, and not far off RT91 and the cities of Amherst, Northampton and Greenfield.

FamilyLocationTV

Popular amenities for Greenfield holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Greenfield's top sights

Mesa Verde

14 locals recommend

Highland Park

7 locals recommend

Whitney Hill Antiques

5 locals recommend

Other great holiday rentals in Greenfield

Top Guest favourite
Home in Charlemont
4.98 out of 5 average rating, 40 reviews

Stone Ridge Cottage

LocationFamilyDecor

Guest favourite
A bright bedroom is showcased, featuring a spacious bed with white bedding. Natural light streams through a large window dressed with sheer curtains. Two framed botanical prints are displayed on the wall, enhancing the room's simple aesthetic. A light fixture stands beside the bed, providing soft illumination.
Apartment in Greenfield
4.97 out of 5 average rating, 35 reviews

Light-filled 3-br on park

LocationFamilyKitchen

Top Guest favourite
An open living area is highlighted by large windows that allow natural light to fill the space, which features a dark sofa and a wooden coffee table. A small plant sits on the floor, adding a touch of greenery to the room.
Cottage in Ashfield
4.96 out of 5 average rating, 380 reviews

hope house

FamilyValueBeach

Guest favourite
Cabin in New Salem
4.95 out of 5 average rating, 19 reviews

Rustic cabin with A/C at historic orchard & cidery

LocationFamilyOutdoor spaces

Guest favourite
A living room features a comfortable love seat and a rocking chair, both placed on hardwood flooring. Light floods the space through two windows, accentuating the soft green walls. An air conditioning unit is positioned near the window for climate control.
Apartment in Greenfield
4.89 out of 5 average rating, 63 reviews

1st fl, 2-bed apt, accessible, easy access to HWYs

FamilyLocationGetting around

Top Guest favourite
A spacious deck overlooks a vibrant sunset, with an expansive view of rolling hills and trees under a partially cloudy sky. The area is enclosed by modern railing, and the deck's surface provides ample space for relaxation or gatherings.
Home in Leyden
5 out of 5 average rating, 38 reviews

Mountaintop Views, near Private Schools, ski/golf

FamilyLocationIndoor spaces

Guest favourite
Apartment in Greenfield
4.94 out of 5 average rating, 35 reviews

Treetop Haven

FamilyLocationCheck-in

Top Guest favourite
Apartment in Shelburne Falls
5 out of 5 average rating, 93 reviews

Falcon's Nest | hot tub | scenic views |

ValueFamilyIndoor spaces

When is the best time to visit Greenfield?

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Avg. price$177 NZD$175 NZD$175 NZD$197 NZD$189 NZD$177 NZD$178 NZD$192 NZD$194 NZD$195 NZD$195 NZD$187 NZD
Avg. temp-5°C-4°C1°C8°C14°C18°C21°C20°C16°C9°C4°C-2°C

Frequently Asked Questions

  • What are the best places to stay in Greenfield?

    Downtown Greenfield is frequently suggested for easy access to restaurants, cafes, and shops, while quieter neighborhoods around public parks also have relaxing stays. Look for accommodations with unique local touches such as historic architecture or garden views.

  • What are the best things to do in Greenfield with kids?

    Families often explore playgrounds, splash pads, or hiking trails in Greenfield’s parks. The local library and community center sometimes host storytime sessions or craft workshops popular with children.

  • What are some of the best things to do in Greenfield?

    Visit public parks, browse indie shops around the downtown area, and explore art galleries or community theaters. Outdoor enthusiasts often head to nearby hiking trails or rivers for relaxing walks and kayaking opportunities.

  • How is the weather in Greenfield?

    Greenfield has cold winters around 13–32°F (-11–0°C), while summers reach 57–81°F (14–27°C) with more rainfall in July and August. Spring and fall bring moderate temperatures and colorful seasonal changes, so layers are helpful year-round.

  • When is the best time to visit Greenfield?

    May through October is often recommended for pleasant weather and outdoor events. Late spring shows blooming landscapes, while early fall is known for colorful foliage and harvest season festivities.

  • What are the best places to visit in Greenfield?

    Explore Greenfield’s historic downtown, enjoy park spaces like Energy Park, and learn at the local history museum. The town also has access to scenic outdoor areas, community arts spaces, and farmers’ markets, making it easy to soak in its local character.

  • What are some hiking trails in Greenfield?

    Explore forested paths in areas like Rocky Mountain Park, traverse trails with river views, or try woodland routes around Poet’s Seat Tower. These trails provide options for both relaxed walks and more challenging climbs.

  • What are some family activities we can do in Greenfield?

    Families can visit community parks, try hands-on exhibits at local museums, or enjoy public pools in the warmer months. Seasonal fairs and farmers’ markets often include activities for children, crafts, and live music.

  • What are some of the best day trip ideas from Greenfield?

    Explore nearby small towns known for historic architecture and artisan shops, or visit state parks with lakes and mountain trails. Orchard tours, local food tastings, and art centers around the region are frequently suggested for a day out.

  • Are there any pet friendly accommodations available in Greenfield?

    Pet friendly vacation rentals can be found in several Greenfield neighborhoods. Some hosts provide amenities for pets, such as small fenced yards or pet beds, so be sure to check individual listings for details.

  • What are some local tips for visiting Greenfield?

    Chat with local shop owners for recommendations on restaurants and activities, and check neighborhood bulletin boards for upcoming events. Bring comfortable shoes to explore historic streets, and consider visiting during a community fair for a lively local experience.

  • What is Greenfield known for?

    Greenfield is known for its historic downtown, commitment to sustainability, and access to natural beauty throughout the Pioneer Valley. The town attracts visitors with lively arts events, farmers’ markets, and a strong sense of local community.

  • What are the best hidden gems to explore in Greenfield?

    Look for local art installations, independent bookshops, and quiet trails in the forested areas around town. Community gardens and lesser-known parks provide peaceful spots to relax or discover public art.

  • What are the best foods to try in Greenfield?

    Greenfield’s locally rooted cuisine includes farm-fresh produce, regional cheeses, and maple products. Bakeries, coffee shops, and restaurants in town often highlight ingredients from Franklin County farms, complemented by creative New England flavors.

  • What should I bring for a trip to Greenfield?

    Pack layers for variable weather, especially in spring and fall, along with sturdy shoes for exploring parks or trails. A rain jacket is useful year-round, and reusable totes come in handy for farmers’ markets and local shops.

  • What is the nightlife in Greenfield like?

    Greenfield’s nightlife centers on local pubs, cozy music venues, and casual eateries. Community theaters and event spaces may host live performances or open mic nights, with a friendly and laid-back ambiance.

  • What are the most popular events or festivals in Greenfield?

    Greenfield is known for its summer music and food festivals, as well as community fairs that take place in late summer and early fall. Local celebrations often feature live performances, family activities, and regional foods.

  • Are there family friendly vacation rentals in Greenfield?

    Many Greenfield hosts provide family friendly accommodations, including homes with multiple bedrooms and outdoor spaces. Some rentals feature amenities such as cribs, games, or easy access to parks and community spots.

Destinations to explore