Holiday Rentals in Greenfield, MA

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Greenfield, MA holiday rentals
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20 Holiday Rentals and Airbnb in Greenfield, MA

Best family friendly Greenfield, MA holiday 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
NZ$1397/nighttotal: NZ$2794 (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).
Charming 1-br Apartment In Conway, Wifi/ac - Greenfield, MA
10 3 reviews
Greenfield, MA
25/07 – 27/07
NZ$329/nighttotal: NZ$658 (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.
Family Home | Flexible Layout | Walkable Town - Greenfield, MA
9.7 98 reviews
Greenfield, MA
15/07 – 20/07
NZ$558/nighttotal: NZ$2790 (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).
The Mountain House - Greenfield, MA
9.7 22 reviews
Greenfield, MA
15/07 – 20/07
NZ$803/nighttotal: NZ$4015 (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.

Best Greenfield, MA holiday rentals with parking

Deck, Mountain Views: Colorful Retreat In Vernon! - Greenfield, MA
9.8 7 reviews
Greenfield, MA
25/07 – 27/07
NZ$431/nighttotal: NZ$862 (2 )

Deck, Mountain Views: Colorful Retreat In Vernon!

2 3
apartment , Vernon
This Vernon holiday home, near the Norcross Wildlife Sanctuary (walking distance) and Satan's Kingdom Wildlife Management Area (a 2km drive), offers convenient access to local attractions including the Latchis Theatre.
The 156 square metre property features two bedrooms, two bathrooms, and sleeps six, boasting a private terrace with a fire pit and barbecue, plus a fully equipped kitchen and air conditioning.
Deck, Mountain Views Colorful Retreat In Vernon! - Greenfield, MA
10 5 reviews
Greenfield, MA
25/07 – 27/07
NZ$418/nighttotal: NZ$836 (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.
Vikings Villages Resort - Greenfield, MA
Greenfield, MA
15/07 – 20/07
NZ$487/nighttotal: NZ$2435 (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.
Revitalized Firehouse Retreat In Downtown Shelburne Falls. Walk To Everything! - Greenfield, MA
10 5 reviews
Greenfield, MA
25/07 – 27/07
NZ$840/nighttotal: NZ$1680 (2 )

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

2 3
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.

Frequently asked questions about holiday rentals in Greenfield, MA

  • What are the benefits of choosing a vacation rental in Greenfield, MA?

    Vacation rentals offer more space and privacy than a hotel room. They can also be a more affordable option, especially if you're travelling with a family or group of friends. You'll also have access to a kitchen, which can save you money on dining out.
  • What are the best Airbnb and holiday rentals in Greenfield, MA?

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

  • What are the top sports attractions and facilities in Greenfield, MA?

    Greenfield has a variety of sports facilities, including the Greenfield Community College Athletic Complex, which features a baseball field, soccer field, and track. The Greenfield Town Common also has a playground and tennis courts. For a more leisurely activity, the Greenfield Greenway is perfect for walking, running, or cycling.
  • 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 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.

Destinations nearby

Best Greenfield, MA holiday rentals with a balcony

Charming 1-br Apartment In Conway, Wifi/ac - Greenfield, MA
10 3 reviews
Greenfield, MA
25/07 – 27/07
NZ$329/nighttotal: NZ$658 (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
NZ$487/nighttotal: NZ$2435 (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 holiday rentals

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

1850s Grist Mill - Greenfield, MA
9.0 2 reviews
Greenfield, MA
29/07 – 01/09
NZ$368/nighttotal: NZ$12512 (34 )

1850s Grist Mill

1 2
apartment , Leverett
This historic Leverett mill, situated beside the Sawmill River in Massachusetts, offers a unique riverside location with a private island accessible via a stone dam.
The property, sleeping up to six guests in one bedroom and two bathrooms, boasts a fully equipped kitchen, outdoor fireplace, and grill, plus a private island picnic area; the 1850s building features 20+ inch floorboards and exposed beams.
Cozy Home With Relaxing Views - Greenfield, MA
9.7 30 reviews
Greenfield, MA
29/07 – 01/09
NZ$382/nighttotal: NZ$12988 (34 )

Cozy Home With Relaxing Views

1 2
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.
Cozy Country House In Conway - Greenfield, MA
Greenfield, MA
25/07 – 27/07
NZ$738/nighttotal: NZ$1476 (2 )

Cozy Country House In Conway

1 3
apartment , Conway
This two-bedroom flat in Conway is located 6.4 kilometres from Treehouse Brewing Company, 9.7 kilometres from Deerfield Academy, and 19.3 kilometres from UMass Amherst.
This residence offers a full kitchen, three televisions, a king and queen bed, two showers, two bathtubs, and an in-unit washer and dryer, comfortably accommodating up to six guests.
Shelburne Falls House In Village - Greenfield, MA
10 4 reviews
Greenfield, MA
25/07 – 27/07
NZ$1031/nighttotal: NZ$2062 (2 )

Shelburne Falls House In Village

1 3
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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