Discover a selection of 34 vacation rentals in Greenfield, MA 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 kitchens. Prices start at $81 per night, and condos and studios are popular options for a stay in Greenfield. Either way, you'll find a rental for everyone's needs.
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, MA?

Our 2020 property listings offer a large selection of 34 vacation rentals around Greenfield. From 9 condo and apartment rentals to 10 studio vacation rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent a mountain-view property in Greenfield?

Would you look at that view?! That's what you'll find yourself saying when you travel out to the hills and indulge in a fantastic high-altitude escape. Vrbo has 15 mountain getaway rentals available. Of course, that might not work for the whole group. Luckily, Vrbo has heaps of other choices, including:

  • 12 rural vacation rentals.
  • 11 village vacation rentals.
  • 3 water-view vacation rentals.

Can I rent a house in Greenfield?

If you want to live like a local and don't feel like sharing space with strangers this time round, renting a whole house is the way to go. There are 14 houses currently listed on Vrbo. Prices start from $200 per night. If that doesn't suit your posse's taste, we have a range of other rental options available, such as:

  • Apartment: 6 vacation homes. Prices start from $64 per night.
  • Hotel: 3 vacation homes. Prices start from $119 per night.
  • Farmhouse: 2 vacation homes. Prices start from $300 per night.

Can I stay in Greenfield in a large group?

It can be tough finding the time to relax with friends and family members. A vacation is a wonderful opportunity to come together. If you were hoping to kick back together, Vrbo has places to suit. At the moment, house vacation homes are popular for large groups of travelers here, and we have 3 available on our database. If you're hoping to travel in a larger group, the rental properties that can meet your needs include:

  • Searching for vacation homes that can sleep 6 of you? We have 4 that will be ideal. Prices start from $265 per night.
  • If you've got 10 in your squad, you'll be thrilled to find out that there are 3 vacation homes perfect. Prices start at $250 per night.
  • Seeking properties for rent suitable for 5 guests? You'll be thrilled to know we have 3 that'll be ideal. You can get one from just $295 a night.

So don't fear! When you book with us you can bring along your aunt, your cousins and all your pals to Greenfield.

Where are the cheapest rentals in Greenfield?

Tight hotel rooms are no place to spend your precious vacation moments! Discover our budget-friendly rentals now and ensure everyone has room to move. When it comes to getting your hands on a great deal, the first place you look ought to be Florence. Here, Vrbo has 2 rentals at an average price of $317 a night. Jacksonville is another place to consider. We have 2 rentals here, and the average price is around $491 a night.