Discover a selection of 29 vacation rentals in Greenfield that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including gardens and backyards and swimming pools. Prices start at $85 per night, and condos and houses are popular options for a stay in Greenfield. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Greenfield
Destination guide

Why people love visiting lively Greenfield

Take a vacation to Greenfield and enjoy the area's live music, festivals and culture. Travelers to this romantic city praise the shopping, cafés and riverfront. Many of our vacation rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.


Activities and attractions in and around Greenfield

Do you want to discover attractions to visit in the city? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Greenfield a one-of-a-kind vacation spot. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Hawley Bog Preserve (14.4 mi / 23.2 km)
  • Berkshire East Ski Resort (14.5 mi / 23.3 km)
  • Honora Winery (18.1 mi / 29.2 km)
  • Madame Sherri Forest (19.6 mi / 31.5 km)
  • Brattleboro Country Club (19.7 mi / 31.8 km)
Natural features

Exploring the natural features in Greenfield

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Greenfield is a great place to spend some time outside. Here are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city center:

  • Magic Wings Butterfly Conservatory (5.4 mi / 8.7 km)
  • Conway Town Park (7.4 mi / 11.9 km)
  • Hawley Bog Preserve (14.4 mi / 23.2 km)
  • Fort Dummer State Park (16.5 mi / 26.5 km)
  • Mohawk Trail State Forest (18.1 mi / 29.1 km)
  • Jacksonville Pond (18.4 mi / 29.6 km)
How to get there

Traveling to and around Greenfield

The nearest airport is in Westfield, MA (BAF-Barnes Municipal), located 29.6 mi (47.7 km) from the city center. If you can't find a flight that's convenient for your trip, you might consider flying into Hartford, CT (BDL-Bradley Intl.), which is 45.7 mi (73.5 km) away.

If you prefer train travel, the main station is Greenfield Station.

How many vacation rentals are available around Greenfield?

Our 2021 property listings offer a large selection of 29 vacation rentals around Greenfield. From 7 condo and apartment rentals to 17 house rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.