
Holiday houses in Greenfield
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Top-rated holiday rentals in Greenfield
Guests agree: these stays are highly rated for location, cleanliness and more.

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.

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.

Modern farmhouse close to Montague Retreat Center
This is a fully restored 1880 farmhouse five min. from Montague Retreat Center, 20 min. from Amherst and 25 min. to Northampton. Our house has modern amenities: radiant concrete floors, high end appliances/countertops, a steam shower and 7 ft, radiant heated copper bath tub. Lots of light, open spaces, cathedral ceilings and an outdoor playset for kids. The house is set on 3/4 of an acre with lots of beautiful gardens and is located near Montague Center, where there are restaurants and shops.

Peaceful Blossoms Victorian Home
This is a furnished home in Greenfield MA. It’s great for Deerfield Academy, Eaglebrook School, Northfield Mount Hermon, and Stonleigh-Burnham families. We’re close to Berkshire East, Yankee Candle, and Magic Wings. 3 bedrooms sleep up to 5, 2 baths. Circa 1890, our home has a modern kitchen, comfy couches, and an eclectic antique-heavy decor. The period layout with all bedrooms upstairs and the antique decor may not make our home ideal for people with mobility challenges or young children.

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.

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!

Mountain Retreat close to Northampton & Amherst!
Come have this mountain top home situated on 150 secluded acres in beautiful historic Williamsburg all to yourselves!! If you want privacy within 10-20 minutes from Northampton, Hadley, and Amherst, then this cabin is perfect. Within walking distance, you will have access to trail systems for either your hiking or biking endeavors. You can stay and enjoy the peaceful nature of our home, sit on the massive deck while you gaze upon breathtaking views of the Pioneer Valley, or venture out.

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.

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.

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.

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.

Mohawk Trail View/ private apt. no cleaning Fee
Small, cozy private Apt is located in West Greenfield in a quiet, safe neighborhood. Guests have own private driveway and entrance. There are 2 TV’s, one in living room & bedroom. High speed internet. Queen size bed & desk. Apt. Is 2 min's to Rt. 2, Mohawk Trail, Rt. 91, Supermarket, Restaurants & GCC. Less than 5 min's to Greenfield Center. <10 minutes to Deerfield Academy, Bement, Stonleigh. Berkshire East Resort Ski Area 24 minutes
Popular amenities for Greenfield holiday rentals
Other great holiday rentals in Greenfield

Bridge of flowers cottage

Spacious, Sunny* Woodland Retreat

Serene South Deerfield Retreat

The Mountain House

Magical, Rural Getaway in the Berkshires

Peaceful forest cottage getaway

Sunderland house - 5 College area

Frimpong's Two Bedroom Apartment
When is the best time to visit Greenfield?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $175 NZD | $173 NZD | $173 NZD | $175 NZD | $190 NZD | $189 NZD | $177 NZD | $190 NZD | $192 NZD | $194 NZD | $194 NZD | $185 NZD |
| Avg. temp | -5°C | -4°C | 1°C | 8°C | 14°C | 18°C | 21°C | 20°C | 16°C | 9°C | 4°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.
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 $84 NZD per night before taxes and fees

Verified guest reviews
Over 4,220 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!
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