Compare Vacation Rentals & Airbnb in Greenfield, MA

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Greenfield, MA vacation rentals
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20 Rentals and Airbnb in Greenfield, MA

Best family friendly Greenfield, MA vacation rentals

Among the 20 accommodations in Greenfield, MA, here are the 4 best family friendly rentals

The Mountain House - Greenfield, MA
9.7 22 reviews
Greenfield, MA
15/07 – 20/07
$653/nighttotal: $3265 (5 )

The Mountain House

4 2
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.
Rose Wisteria 4 Guests 2 Bedrooms-full+queen Beds - Greenfield, MA
Greenfield, MA
15/07 – 20/07
$411/nighttotal: $2055 (5 )

Rose Wisteria 4 Guests 2 Bedrooms-full+queen Beds

2 2
apartment , Shelburne
This two-bedroom flat in Shelburne Falls offers convenient access to local attractions, situated within walking distance of Glacial Potholes, Shelburne Falls, and the Bridge of Flowers, with free on-site parking.
This pet-friendly accommodation provides air conditioning and a fully equipped kitchen for up to four guests, with on-site kayaking activities and proximity to cultural sites such as the White Barn Studio and Charlemont Historical Society and Museum.
On-the-river Retreat - Greenfield, MA
9.7 6 reviews
Greenfield, MA
25/07 – 27/07
$363/nighttotal: $726 (2 )

On-the-river Retreat

1 3
apartment , Buckland
This apartment in Shelburne Falls village offers direct riverside access, ideal for swimming, canoeing, and kayaking, and is a short walk to the Bridge of Flowers and local amenities including restaurants and shops.
This family-friendly flat sleeps up to six guests and features air conditioning, a kitchenette with a fridge, freezer, and microwave, a garden, and an outdoor patio with a firepit, with Berkshire East ski resort just a short drive away.
Summit Retreat:2br/2bath Rustic Beauty + Yoga Room - Greenfield, MA
10 7 reviews
Greenfield, MA
25/07 – 27/07
$734/nighttotal: $1468 (2 )

Summit Retreat:2br/2bath Rustic Beauty + Yoga Room

1 3
cabin , Shelburne
Summit Retreat, a self-catering lodge above the Deerfield and Connecticut River valleys in western Massachusetts, boasts expansive valley views and proximity to the Seven Sisters mountain range and Mount Holyoke's Skinner House.
This two-bedroom, two-bathroom property sleeps four, offering a fully equipped kitchen (fridge, freezer, microwave, dishwasher), a dedicated children's area, a yoga room, and outdoor space ideal for picnics and cross-country skiing, with abundant wildlife viewing opportunities.

Best Greenfield, MA vacation rentals with parking

Rustic-chic Cottage W/ Yard & Grill - Near Hiking! - Greenfield, MA
9.7 35 reviews
Greenfield, MA
27/06 – 30/06
$281/nighttotal: $843 (3 )

Rustic-chic Cottage W/ Yard & Grill - Near Hiking!

2 2
house , Northfield
The Rustic-Chic Cottage is located in Northfield, just 39 kilometres from both Amherst College and the Beneski Museum of Natural History, making it a great base for exploring the area. The cottage has received excellent ratings for user experience, location, and cleanliness.
This 2-bedroom cottage sleeps 2 guests and offers 125 square metres of living space. The cottage is fully equipped with a kitchen, air conditioning, free Wi-Fi, a garden, and free bikes, plus it has a patio with river views and is close to hiking trails.
Deck, Mountain Views: Colorful Retreat In Vernon! - Greenfield, MA
10 5 reviews
Greenfield, MA
25/07 – 27/07
$340/nighttotal: $680 (2 )

Deck, Mountain Views: Colorful Retreat In Vernon!

2 3
apartment , Vernon
This Vernon apartment, situated 16 kilometres from Fort Dummer State Park, offers easy access to Santa's Land USA (40 kilometres) and Molly Stark State Park (42 kilometres).
The 156-square-metre property boasts a spacious two-bedroom layout, sleeping up to 11 guests, and includes a fully equipped kitchen, free Wi-Fi, parking, and air conditioning.
Private Suite With A Sweet View. Spacious, Close To Town, Dog Friendly - Greenfield, MA
9.9 98 reviews
Greenfield, MA
25/07 – 27/07
$430/nighttotal: $860 (2 )

Private Suite With A Sweet View. Spacious, Close To Town, Dog Friendly

2 3
apartment , Shelburne
The Kiva Suite is a spacious studio apartment located just two miles from the charming village of Shelburne Falls, nestled in the picturesque Berkshires. This property has received excellent ratings for its location, cleanliness, and overall experience, making it an ideal choice for travellers seeking a peaceful and comfortable stay.
The suite spans 279 square metres and offers a private entrance, a large open plan layout, and a private garden. Guests can enjoy a range of amenities including a fully equipped kitchen, a private bathroom, air conditioning, and a comfortable sleeping area. The studio is also dog-friendly, perfect for those travelling with their furry companions.
Charming 1-br Apartment In Conway, Wifi/ac - Greenfield, MA
10 3 reviews
Greenfield, MA
25/07 – 27/07
$267/nighttotal: $534 (2 )

Charming 1-br Apartment In Conway, Wifi/ac

1 3
apartment , Conway
This spacious one-bedroom apartment in Conway, Massachusetts, is situated in a historic Victorian mansion dating back to the 1880s, a 16-kilometre drive from I-91 and approximately 32-40 kilometres from Greenfield, Amherst, Northampton, and Berkshire East.
The self-catering flat, sleeping up to six guests, boasts vintage features including marble fireplaces, high ceilings, and a unique ‘wildscaped’ yard with a pond; laundry facilities are available by arrangement, and high-speed internet access is provided.

Frequently Asked Questions about vacation rentals in Greenfield, MA

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

    The best time to book a vacation rental in Greenfield is during the shoulder seasons, from April to May and September to October. You'll avoid the crowds and get better deals on rentals.
  • What are the best Airbnb and vacation rentals in Greenfield, MA?

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

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

    A walk along the Greenfield Bikeway is a great way to get some exercise and enjoy the scenery. You can also visit the Greenfield Public Library, which offers free events and programs throughout the year.
  • 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 are the best restaurants with local dishes in Greenfield, MA?

    The Greenfield Diner is a classic spot for breakfast and lunch, and they have great American food. For a more upscale dining experience, try The Restaurant at the Hotel Northampton, which offers a seasonal menu with local ingredients.
  • 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.

  • Are there pet-friendly attractions in Greenfield, MA?

    The Greenfield Green is pet-friendly, and there are many dog-walking trails in the area. The Greenfield Farmers Market also welcomes dogs.
  • What are the top sports attractions and facilities in Greenfield, MA?

    Greenfield is home to the Greenfield Community College, which has a variety of athletic facilities, including a gymnasium, swimming pool, and tennis courts. The Greenfield Recreation Department also offers a range of sports programs and activities for all ages.

Destinations nearby

Best Greenfield, MA vacation rentals with a balcony

Charming 1-br Apartment In Conway, Wifi/ac - Greenfield, MA
10 3 reviews
Greenfield, MA
25/07 – 27/07
$267/nighttotal: $534 (2 )

Charming 1-br Apartment In Conway, Wifi/ac

1 3
apartment , Conway
This spacious one-bedroom apartment in Conway, Massachusetts, is situated in a historic Victorian mansion dating back to the 1880s, a 16-kilometre drive from I-91 and approximately 32-40 kilometres from Greenfield, Amherst, Northampton, and Berkshire East.
The self-catering flat, sleeping up to six guests, boasts vintage features including marble fireplaces, high ceilings, and a unique ‘wildscaped’ yard with a pond; laundry facilities are available by arrangement, and high-speed internet access is provided.
Vikings Villages Resort - Greenfield, MA
Greenfield, MA
15/07 – 20/07
$396/nighttotal: $1980 (5 )

Vikings Villages Resort

1 2
resort , Guilford
The Vikings Villages Resort, offering the Vikings Villages Resort package, is situated in Jacksonville, 18 kilometres from Guilford city centre.
This self-contained accommodation provides WiFi, air conditioning, a terrace, garden, parking, and an elevator, with a picnic area for guests' enjoyment.

Best pet friendly Greenfield, MA vacation rentals

Among the 20 accommodations in Greenfield, MA, here are the 4 best pet friendly rentals

Family Home | Flexible Layout | Walkable Town - Greenfield, MA
9.7 98 reviews
Greenfield, MA
15/07 – 20/07
$453/nighttotal: $2265 (5 )

Family Home | Flexible Layout | Walkable Town

1 2
apartment , Greenfield Town
This Greenfield family home, centrally located on a main street yet set back from the road, offers easy access to Deerfield Academy, Northfield Mount Hermon, and the Five Colleges.
The four-bedroom, one-bathroom property sleeps five guests and boasts a private balcony with hammock, Goshen stone patio, and high-end amenities including a dishwasher, microwave, fridge and freezer, plus Wi-Fi and air conditioning; regular professional cleaning is available for longer stays (at extra cost).
Gorgeous Timber Frame Home In Ashfield - 4 Bedrooms, 3 Bathrooms And Sauna - Greenfield, MA
9.6 8 reviews
Greenfield, MA
15/07 – 20/07
$863/nighttotal: $4315 (5 )

Gorgeous Timber Frame Home In Ashfield - 4 Bedrooms, 3 Bathrooms And Sauna

4 2
farm , Ashfield
This farmstead is situated in Shelburne Falls, western Massachusetts, approximately 32 kilometres from Berkshire East Ski Resort and near the Bridge of Flowers.
This property accommodates up to nine guests across four bedrooms and three bathrooms, featuring a pool table, a wood-burning sauna with a cold plunge pond, and immediate access to hiking and biking trails.
Cozy, Quiet Cottage On Country Rd 2 Mil From I-91 - Greenfield, MA
9.7 352 reviews
Greenfield, MA
25/07 – 27/07
$268/nighttotal: $536 (2 )

Cozy, Quiet Cottage On Country Rd 2 Mil From I-91

1 3
apartment , Bernardston
This charming cottage is located just off a quiet country road, less than 3 kilometres from the I-91 highway, offering a peaceful retreat while remaining close to major routes and attractions. The property has received excellent ratings for its cleanliness, location, and overall experience.
The two-bedroom cottage comfortably accommodates up to four guests and has an open floor plan, creating a spacious and airy feel. Guests can enjoy amenities such as a fully equipped kitchen, Wi-Fi, a washer and dryer, and access to a large field and hiking trails.
Shelburne Guest House -The Ranch - Greenfield, MA
10 301 reviews
Greenfield, MA
25/07 – 27/07
$421/nighttotal: $842 (2 )

Shelburne Guest House -The Ranch

1 3
house , Shelburne
This three-bedroom apartment is situated in Shelburne, just 5km from Shelburne Falls Village and 10km from Greenfield Rotary on the I-91, offering a peaceful escape from the hustle and bustle. It has received excellent ratings for location, cleanliness, and overall user experience.
The property features a spacious layout, accommodating up to 6 guests, and is perfect for families. Guests can enjoy a fully equipped kitchen, a large garden with a fire pit, and easy access to nearby attractions like Berkshire East Mountain Resort, hiking trails, and the Bridge of Flowers.
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