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.

Shelburne Falls Combined Rental - Greenfield, MA
10 4 reviews

Shelburne Falls Combined Rental

apartment, Shelburne
This four-bedroom, two-bathroom house in Shelburne Falls, Massachusetts, sleeps eight and is ideally located for exploring the town's attractions, including the Bridge of Flowers (distance unspecified).
The property boasts a fully equipped kitchen with fridge, freezer, microwave, and dishwasher, offering comfortable family accommodation with ample space.
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.
The Mountain House - Greenfield, MA
9.6 27 reviews

The Mountain House

apartment, Gill
This 4-bedroom family home sits atop Mount Pisgah, just 3.2 kilometres from the Mohawk Trail and 8 kilometres from Greenfield, offering stunning views and a tranquil setting in the heart of the Berkshire Hills. The property boasts excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The house is spacious and comfortably accommodates up to 8 guests, with a full kitchen, dining room, family room, and a nursery with a twin bed. Guests can enjoy a private garden, parking, and access to the entire first and second floors, sunroom, breezeway, and attached garage, making it ideal for families and groups seeking a secluded escape in the beautiful surroundings.
Cozy Mountain Retreat-25 Secluded Acres-beautiful Foliage Views!   Dog Friendly! - Greenfield, MA
9.8 125 reviews

Cozy Mountain Retreat-25 Secluded Acres-beautiful Foliage Views! Dog Friendly!

cabin, Halifax
This Halifax mountain property is located within 15km of Jacksonville Pond, Harriman Reservoir, Deerfield River, The Ledge, and Honora Winery, offering easy access to outdoor activities and sightseeing.
This 186 square metre house sleeps eight guests in three bedrooms and two bathrooms, boasting a fully equipped kitchen, jacuzzi, spa, terrace, garden, parking, and free Wi-Fi.

Best Greenfield, MA holiday rentals with parking

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.
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.
Frimpong's Two Bedroom Apartment - Greenfield, MA
9.5 87 reviews

Frimpong's Two Bedroom Apartment

apartment, Montague
This basement flat is located in the Lake Pleasant neighbourhood of Montague, just a two-minute walk from the lake and within easy reach of neighbouring towns like Greenfield, Sunderland, and Northampton. The apartment consistently receives excellent ratings for its cleanliness, location, and overall experience.
The self-catering flat has two bedrooms and one bathroom, comfortably accommodating up to three guests. The property offers a private entrance, a kitchenette, a modern and fully furnished interior, a TV with Wi-Fi access, air conditioning, and parking.
Charming 2bdrm Farmhouse Apartment With Pond Views - Greenfield, MA
10 5 reviews

Charming 2bdrm Farmhouse Apartment With Pond Views

apartment, Shelburne
This apartment is located a short distance from Shelburne's farm stands, restaurants, breweries, and shops, providing easy access to outdoor pursuits.
This private two-bedroom dwelling accommodates up to four guests and features mid-century contemporary farmhouse styling, air conditioning, internet, and a kitchen, with serene pond views from a covered porch.

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.

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.
Mountaintop Views, Near Private Schools, Ski/golf - Greenfield, MA
10 38 reviews

Mountaintop Views, Near Private Schools, Ski/golf

apartment, Leyden
This secluded Leyden, Massachusetts chalet, situated 3.2km north of Greenfield and under 14.5km from Deerfield, its Academy, Eaglebrook School, and The Bement School, offers stunning mountaintop views and easy access to the Green River.
The 325m² newly renovated property boasts four bedrooms, three bathrooms, sleeping up to twelve guests, and features a large deck with a fire pit, a spacious kitchen, and an upcoming eight-person hot tub (completion end of November 2024); extensive trails are perfect for hiking and ATV riding.
The Nest
In Shelburne Falls - Greenfield, MA
No reviews

The Nest In Shelburne Falls

apartment, Shelburne
This two-bedroom flat offers a private, secluded retreat in the hills of Shelburne Falls, located within the scenic Berkshires, providing easy access to hiking, cycling, and kayaking opportunities, as well as local shops and restaurants.
This accommodation, suitable for up to three guests, features air conditioning, a kitchen with a fridge, internet, and parking, with the added benefit of a garden and the allowance of pets, making it an ideal base for exploring the area.
Apartment In Scenic Shelburne Falls - Greenfield, MA
10 25 reviews

Apartment In Scenic Shelburne Falls

apartment, Shelburne
This charming apartment is situated in a quiet historic neighbourhood in Shelburne Falls, just off Route 2 and within walking distance of the village's dining and shopping options. The apartment has received excellent ratings for its cleanliness, location, and overall user experience.
The apartment has a private entrance and features a spacious bedroom with a king-size bed and a full bathroom, accommodating up to two guests. Guests can enjoy a range of amenities, including a fully equipped kitchen, air conditioning, a garden, a fitness centre, and parking, as well as explore the surrounding area's outdoor activities like skiing, biking, rafting, and hiking.
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