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

Montague Meadows - Space For The Whole Family - Greenfield, MA
10 23 reviews
Greenfield, MA
25/07 – 27/07
$1135/nighttotal: $2270 (2 )

Montague Meadows - Space For The Whole Family

1 3
apartment , Montague
This spacious four-bedroom house in Montague, Massachusetts is a short walk (under 1.6km) from a new playground, the historic Book Mill (with café, art gallery, and record shop), and a village store, and is within a 24km drive of UMass Amherst and Smith College.
The pet-friendly property, sleeping eight, boasts a fully equipped kitchen (fridge, freezer, microwave, dishwasher), air conditioning, a garden with patio and deck, high-speed Wi-Fi, smart TVs, ample parking including a two-car garage, and baby equipment (pack-n-play, high chair, booster seats).
The Jelly Mill-a Peaceful River Retreat - Greenfield, MA
9.9 209 reviews
Greenfield, MA
27/06 – 30/06
$396/nighttotal: $1188 (3 )

The Jelly Mill-a Peaceful River Retreat

3 2
apartment , Guilford
This 3-bedroom cottage is situated on a quiet dirt road in Guilford, Vermont, just 20 kilometres from Brattleboro, where you'll find shops, restaurants and petrol stations. It has received excellent ratings for its location, cleanliness and overall experience.
The 121-square-metre property can comfortably accommodate up to 6 guests. The cottage boasts a fully equipped kitchen, a private garden with a picnic table and barbecue, a converted garage with a patio, a Roku device for streaming, and a selection of books and games, ensuring plenty of entertainment options.
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.
Rose Room  Victorian Home  Queen Bed  Private Bath - Greenfield, MA
Greenfield, MA
15/07 – 20/07
$289/nighttotal: $1445 (5 )

Rose Room Victorian Home Queen Bed Private Bath

1 2
apartment , Shelburne
This one-bedroom flat in Shelburne Falls offers a prime location, situated just 300 metres from the main street and the Bridge of Flowers, with convenient access to the White Barn Studio and Charlemont Historical Society and Museum.
This family-friendly apartment, accommodating up to two guests, features air conditioning, a private bathroom, a balcony, and is within easy reach of local entertainment options such as the Shelburne Falls Bowling Alley.

Best Greenfield, MA vacation rentals with parking

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.
Revitalized Firehouse Retreat In Downtown Shelburne Falls. Walk To Everything! - Greenfield, MA
10 5 reviews
Greenfield, MA
15/07 – 20/07
$644/nighttotal: $3220 (5 )

Revitalized Firehouse Retreat In Downtown Shelburne Falls. Walk To Everything!

2 2
apartment , Buckland
This flat in Shelburne Falls offers industrial-chic accommodation, a short walk from downtown and close to the Bridge of Flowers and G. William Pitt House.
This 60-square-metre dwelling sleeps four guests across two bedrooms, featuring a king-size bed in one and a queen-size bed with 14-foot ceilings in the other, alongside a fully equipped kitchen with a microwave and dishwasher, air conditioning, keyless entry, and two dedicated parking spaces.
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.
Romantic 1-bedroom Retreat In Downtown Shelburne Fallswalk To Everything - Greenfield, MA
10 4 reviews
Greenfield, MA
15/07 – 20/07
$548/nighttotal: $2740 (5 )

Romantic 1-bedroom Retreat In Downtown Shelburne Fallswalk To Everything

1 2
apartment , Buckland
This one-bedroom flat is located in downtown Shelburne Falls, a short walk from the Bridge of Flowers and Glacial Potholes, within a renovated historic firehouse.
This 51 square meter apartment accommodates two guests and features a fully equipped kitchen, a king-size bed, and an in-unit washer/dryer, with skiing and mountain biking available at Berkshire East Mountain Resort.

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

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

Wood Turtle Woods - Greenfield, MA
10 34 reviews
Greenfield, MA
29/07 – 01/09
$338/nighttotal: $11492 (34 )

Wood Turtle Woods

1 2
farm , Conway
Wood Turtle Woods, a converted barn in Western Massachusetts, offers a tranquil escape 40km from Northampton, Greenfield, and Berkshire East Mountain Resort.
This one-bedroom property sleeps four, boasting two bathrooms, a fully equipped kitchen including a freezer, microwave, and dishwasher, plus Wi-Fi, air conditioning, parking, and a garden; nearby activities include hiking, cross-country skiing, and exploring local breweries.
Rustic Beauty: 2-bedroom House In Serene Shelburne Falls - Greenfield, MA
Greenfield, MA
25/07 – 27/07
$758/nighttotal: $1516 (2 )

Rustic Beauty: 2-bedroom House In Serene Shelburne Falls

2 3
apartment , Shelburne
This 2-bedroom, 2-bathroom apartment in Shelburne offers expansive valley views towards the Seven Sisters range, located just 5 minutes from the I-91 and close to local landmarks such as Old Greenfield Village and the Bridge of Flowers.
This property accommodates up to 4 guests and features a well-equipped kitchen, a dedicated Family Office with a crib, a Yoga Room, and a main bathroom with a deep soaking tub, all set within spacious outdoor areas perfect for recreation.
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.
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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