Vacation Rentals in Greenfield, MA

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Greenfield, MA holiday rentals
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39 Holiday rentals and Airbnb in Greenfield, MA

Top-Rated Family-Friendly Holiday Rentals in Greenfield, MA

Ensure a relaxed, stress-free stay with plenty of room to move at family holiday rentals in Greenfield, MA.

Spacious 5br W/ Hot Tub & Games - Greenfield, MA
9.9 274 reviews

Spacious 5br W/ Hot Tub & Games

apartment, Colrain
This family-friendly property is located in Colrain, within a 5km radius of Arthur A. Smith Covered Bridge, G. William Pitt House and Collection, and White Barn Studio. It has received excellent ratings for its cleanliness, location, and overall user experience.
This 5-bedroom home spans 186 square metres and offers a range of amenities, including a fully equipped kitchen, a Jacuzzi, a terrace, and a garden. Guests can enjoy outdoor grilling, relax in the spa tub, and explore the nearby Deerfield River and High Ledges Wildlife Sanctuary.
Spacious & Cozy Ground Floor 2/3 Bed Private Suite - Greenfield, MA
9.5 12 reviews

Spacious & Cozy Ground Floor 2/3 Bed Private Suite

apartment, Shelburne
This Shelburne Falls apartment, a five-minute walk (0.8 km) from the town centre, offers easy access to Shelburne Falls' shops and restaurants.
Sleeping six guests comfortably, this three-bedroom, one-bathroom flat boasts a spacious layout including a living room, dining room, sunroom, well-equipped kitchen, and private south-facing garden with off-street parking.
Cozy Home With Relaxing Views - Greenfield, MA
9.8 32 reviews

Cozy Home With Relaxing Views

apartment, Northfield
This Northfield, Massachusetts house is minutes from I-91, 5 minutes from Mount Hermon School, and within a 20-40 minute drive (approximately 32-64 km) of Brattleboro, Greenfield, Amherst, and Northampton, offering easy access to local attractions and the Connecticut River.
Sleeping six guests across three bedrooms and one bathroom, this self-catering property boasts a fully equipped kitchen, garden, parking, high-speed internet, central heating and fans, and enjoys mountain views of the Old Mount Hermon Campus.
The 1770 House - Greenfield, MA
9.8 143 reviews

The 1770 House

apartment, Colrain
This 1770 farmhouse is located in Colrain, Massachusetts, just a short drive from the Green River Valley and offering stunning views of Vermont. The property enjoys excellent ratings for location, cleanliness, and overall user experience.
This spacious country home sleeps up to 14 guests and offers a chef's kitchen, a large dining room with a huge hearth, a living room with original charm, and a double-decker deck with stunning views. The amenities include a private swimming pool and spa, an indoor cedar hot tub, high-speed internet, and a selection of toys for all ages.

Best Greenfield, MA holiday rentals with parking

Charming Country-chic 1br In Greenfield  King Bed, Rain Shower, Near Berkshires - Greenfield, MA
9.6 9 reviews

Charming Country-chic 1br In Greenfield King Bed, Rain Shower, Near Berkshires

apartment, Greenfield Town
This one-bedroom flat in Greenfield, Massachusetts, offers direct access to downtown dining, the historic Shea Theatre, and the People's Pint brewery, with the Mohawk Trail and Berkshires accessible within 20 kilometres.
This serviced apartment accommodates up to four guests and includes a fully equipped kitchen, a king-size bed, an in-unit washer/dryer, and private off-street parking, with contactless check-in available through a key-coded entry.
Treetop Haven - Greenfield, MA
9.8 44 reviews

Treetop Haven

apartment, Greenfield Town
This one-bedroom flat is located a few blocks from Greenfield town centre, atop a hill within a historic Victorian mansion, offering a tranquil escape.
Guests can enjoy a secluded setting with access to a zen garden, meditation bench, and trails leading to Highland Park and the Connecticut River, with an internet connection and air conditioning provided.
Sunny, Spacious Downtown Luxury Loft, Scenic Views - Greenfield, MA
9.0 2 reviews

Sunny, Spacious Downtown Luxury Loft, Scenic Views

apartment, Shelburne
This newly renovated 3rd-floor loft apartment is located in Shelburne Falls, a short walk from the Bridge of Flowers, offering mountain and river views.
This spacious, two-level apartment sleeps up to four guests, featuring a queen bed, a pull-out queen bed, a fully equipped kitchen with a dishwasher, in-unit laundry, and is a 15-minute drive from Berkshire East ski resort.
Spacious & Cozy Ground Floor 2/3 Bed Private Suite - Greenfield, MA
9.6 5 reviews

Spacious & Cozy Ground Floor 2/3 Bed Private Suite

apartment, Shelburne
This four-bedroom apartment in Shelburne Falls, Buckland, offers convenient access to local attractions such as the Bridge of Flowers and G. William Pitt House, though precise distances aren't specified.
The self-catering property sleeps six guests across one twin bed, one queen bed, a sofa bed, and a futon, and includes two bathrooms, fast Wi-Fi, air conditioning, and a fully equipped kitchen.

Frequently asked questions about holiday rentals in Greenfield, MA

  • Which neighborhood in Greenfield, MA should you consider for a vacation rental?

    The area around the Greenfield Green is a good choice for a vacation rental. It's close to the heart of town, with easy access to shops, restaurants, and the beautiful Greenfield Common.
  • What are the best Airbnb and holiday rentals in Greenfield, MA?

    Mohawk Trail View/ Private Apt - No Cleaning Fee, The Cozy Treetop Apartment and Lovely 2nd Floor Apartment are among the best Airbnb and holiday rentals in Greenfield, MA.

  • When is the best time to book a vacation rental in Greenfield, MA?

    Greenfield is a lovely place to visit year-round, but if you're looking for the best weather, aim for the summer months. You'll also find plenty of events and festivals happening during the summer.
  • What are the most popular Airbnbs in Greenfield, MA?

    Among the Airbnbs in Greenfield, MA, Mohawk Trail View/ Private Apt - No Cleaning Fee, The Cozy Treetop Apartment and Lovely 2nd Floor Apartment are the most popular ones.

  • What events or festivals should visitors check out in and around Greenfield, MA?

    The Greenfield Summer Concert Series is a great way to enjoy live music outdoors. The annual Greenfield Farmers Market is also a popular event, offering fresh produce and local crafts.
  • What are the best rentals for families and kids in Greenfield, MA?

    The best rentals for families and kids in Greenfield, MA are Lovely 2nd Floor Apartment, Cozy Farmhouse Apartment and Treehouse Retreat.

  • What are the best budget-friendly activities in Greenfield, MA?

    A walk or bike ride along the Montague Greenway is a great way to enjoy the outdoors without spending any money. The Greenfield Public Library is also free to visit and has a variety of events and programs.
  • What are the best restaurants with local dishes in Greenfield, MA?

    The Restaurant at the Greenfield Hotel is a great place to try local cuisine. They have a seasonal menu that features fresh, local ingredients. The Greenfield Market is also a great place to find local food.
  • What are the best walking or cycling routes in Greenfield, MA?

    The Montague Greenway is a beautiful and easy bike path that runs along the Connecticut River. The Greenfield Common is also a great place to take a walk or run.
  • Are there pet-friendly attractions in Greenfield, MA?

    The Greenfield Common is a great place to take your dog for a walk. Many of the local shops and restaurants are also pet-friendly.
  • What are the benefits of choosing a vacation rental in Greenfield, MA?

    Vacation rentals offer more space and privacy than a hotel. They're also often located in more convenient locations, closer to the attractions that you want to see.
  • What are the top sports attractions and facilities in Greenfield, MA?

    Greenfield has a great sports scene. There's a Greenfield Recreation Department that offers a variety of programs and activities. The Greenfield High School has a great athletic program. And the Greenfield Community College is home to the Greenfield Community College Hawks athletic teams.

Popular destinations

Popular Holiday Rentals with a Terrace in Greenfield, MA

Catch the morning breeze and watch the local world go by from holiday rentals featuring an outdoor balcony in Greenfield, MA.

Light-filled Treetop Apartment Close To Downtown Greenfield And Highland Park - Greenfield, MA
10 12 reviews

Light-filled Treetop Apartment Close To Downtown Greenfield And Highland Park

apartment, Greenfield Town
This one-bedroom flat is located within a historic Victorian mansion in Greenfield, just a few blocks from the town centre, offering a secluded natural retreat surrounded by mature pines and close to the Connecticut River trails.
This pet-friendly apartment accommodates up to four guests and features a microwave, dishwasher, air conditioning, a private terrace or balcony, and access to a zen garden, with nearby attractions including Griswold Wildlife Sanctuary and Richardson's Candy Kitchen.

Popular Dog-Friendly Holiday Rentals in Greenfield, MA

Let your dog stretch their legs and explore a new neighborhood alongside you at pet-friendly holiday rentals in Greenfield, MA.

Shelburne Falls House In Village - Greenfield, MA
10 4 reviews

Shelburne Falls House In Village

apartment, Shelburne
This immaculate Victorian house in Shelburne Falls offers a peaceful retreat, a short walk from the village centre with its shops, restaurants, and bowling alley.
The three-bedroom property, sleeping six, features an open-plan kitchen-family room, a dining room, and a private back deck with a barbecue, plus garage storage for sports equipment; nearby activities include skiing, cycling, and rafting.
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