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Greenfield, MA accommodations
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27 Lodgings in Greenfield, MA

Our Favorite Family-Friendly Accommodations in Greenfield, MA

Family vacations in Greenfield, MA work best when your lodging offers ample space and puts city attractions within easy reach.

The Jelly Mill-a Peaceful River Retreat - Greenfield, MA
9.9 209 reviews
Greenfield, MA
06/27 – 06/30
$283/nighttotal: $849 (3 )

The Jelly Mill-a Peaceful River Retreat

3 2
apartment , Guilford
This 3-bedroom cottage is located in Guilford, Vermont, just a 20-minute drive from Brattleboro, offering easy access to groceries, restaurants, and gas stations. The cottage consistently receives excellent ratings for its location, cleanliness, and overall user experience.
This 1,300 square foot home comfortably accommodates up to 6 guests. Enjoy a fully equipped kitchen, outdoor spaces with a private yard and patio, and entertainment options like a Roku device, board games, and access to the entire house, including a converted garage patio with a dining table and dart board.
Montague Meadows - Space For The Whole Family - Greenfield, MA
10 23 reviews
Greenfield, MA
07/25 – 07/27
$812/nighttotal: $1624 (2 )

Montague Meadows - Space For The Whole Family

1 3
apartment , Montague
This spacious Montague, Massachusetts house is a short walk from a new playground, a 10-minute walk from the Book Mill, and a 5-minute walk from a village store; UMass Amherst is a 15-minute drive away.
This pet-friendly home features four bedrooms, two bathrooms, a full kitchen with dishwasher, air conditioning, a two-car garage, a backyard patio and deck, and accommodates up to eight guests with baby gear provided.
Private Bed With En-suite Bathroom Marigold Room - Greenfield, MA
Greenfield, MA
08/23 – 09/02
$185/nighttotal: $1850 (10 )

Private Bed With En-suite Bathroom Marigold Room

1 2
apartment , Shelburne
This Shelburne Falls apartment offers a prime central location, steps from the Bridge of Flowers and Deerfield River, and within walking distance of the Charlemont Historical Society and Museum.
This family-friendly dwelling features air conditioning, a refrigerator, microwave, on-site parking, and a dedicated workspace, providing comfortable amenities for your stay.
Summit Retreat:2br/2bath Rustic Beauty + Yoga Room - Greenfield, MA
10 7 reviews
Greenfield, MA
06/23 – 07/05
$434/nighttotal: $5208 (12 )

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

1 4
cabin , Shelburne
Summit Retreat, a two-bedroom cabin in Shelburne, Massachusetts, boasts a hilltop location offering expansive views of the Deerfield and Connecticut River valleys, the Seven Sisters mountain range, and Skinner House on Mount Holyoke.
This Western Massachusetts getaway sleeps four, features a family office/kid zone, yoga room, two bathrooms (one with a deep soaking tub), Boxco cabinets, modern appliances, a private patio, and is ideal for cross-country skiing and exploring nearby Williamsburg.

Best Greenfield, MA lodging with a pool

Among the 27 accommodations in Greenfield, MA, here are the 1 best ones with a pool

Peaceful Cabin In The Woods And Near The Mountains - Greenfield, MA
10 10 reviews
Greenfield, MA
08/23 – 09/02
$286/nighttotal: $2860 (10 )

Peaceful Cabin In The Woods And Near The Mountains

3 2
cabin , Halifax
This charming Vermont cabin is located just 15 minutes from Wilmington and 30 minutes from Mount Snow or Berkshire East, offering easy access to the region's outdoor activities and ski resorts. It's a peaceful escape in the countryside, perfect for those seeking a quiet retreat. The cabin has received excellent ratings from previous guests, so you can be sure of a comfortable stay.
The 1050-square-foot cabin can accommodate up to 6 guests and has three bedrooms and two bathrooms. It features modern amenities like a smart TV, stainless steel appliances, and a laundry facility, making it a perfect choice for families or groups of friends.

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Best Greenfield, MA accommodation with a garden

The Mountain House - Greenfield, MA
9.7 22 reviews
Greenfield, MA
09/07 – 09/11
$608/nighttotal: $2432 (4 )

The Mountain House

4 4
apartment , Gill
This family home sits on Mount Pisgah in Gill, Massachusetts, offering a secluded escape in the woods just two miles from the scenic Mohawk Trail. The home has earned excellent ratings for its cleanliness, location, and overall experience, making it a great option for families or groups. This spacious house has four bedrooms and two bathrooms, comfortably accommodating up to eight guests. The home features a fully equipped kitchen with a fridge, freezer, and dishwasher, a private garden, parking, and internet access, ensuring a comfortable and enjoyable stay.
Peaceful Forest Retreat - Greenfield, MA
10 20 reviews
Greenfield, MA
07/25 – 07/27
$394/nighttotal: $788 (2 )

Peaceful Forest Retreat

1 3
apartment , Northfield
Escape to a tranquil forest home in Northfield, just 18 minutes from downtown Brattleboro and 6 minutes from Northfield Mount Hermon. This secluded retreat offers a spacious deck and minimalist interior design, perfect for relaxation and unwinding.
With three bedrooms and one bathroom, the home accommodates up to four guests. Enjoy modern amenities like air conditioning, internet, and a fully equipped kitchen. Unwind amidst nature's beauty, explore nearby hiking trails, or simply relax on the deck with a book.
Cozy 'Fiddler's Rest:' Cabin: 11 Miles To Skiing! - Greenfield, MA
10 55 reviews
Greenfield, MA
08/23 – 09/02
$188/nighttotal: $1880 (10 )

Cozy 'Fiddler's Rest:' Cabin: 11 Miles To Skiing!

1 2
cabin , Vernon
This Vernon cabin is located in the mountains, just 9 miles from the Connecticut River, Ashuelot River, and Fort Dummer State Park, offering easy access to outdoor activities and scenic beauty. It has received excellent user ratings.
The 800-square-foot cabin comfortably accommodates four guests in one bedroom and one bathroom. It features a fully equipped kitchen, a garden, a terrace, and a barbecue grill, making it perfect for a relaxing getaway.
1850s Grist Mill - Greenfield, MA
9.0 2 reviews
Greenfield, MA
07/29 – 09/01
$214/nighttotal: $7276 (34 )

1850s Grist Mill

1 2
apartment , Leverett
This historic mill is located in Leverett, Massachusetts, situated on the banks of the Sawmill River, just a short distance from the center of town and close to the scenic Mount Toby. This three-story riverfront home offers 1 bedroom, 2 bathrooms, and can comfortably accommodate up to 6 guests, featuring a private island, a fireplace on the side porch, and a fully equipped kitchen with a dishwasher.

Best Greenfield, MA accommodation with a kitchen

Romantic 1-bedroom Retreat In Downtown Shelburne Fallswalk To Everything - Greenfield, MA
10 4 reviews
Greenfield, MA
07/15 – 07/20
$392/nighttotal: $1960 (5 )

Romantic 1-bedroom Retreat In Downtown Shelburne Fallswalk To Everything

1 2
apartment , Buckland
This apartment is located in the historic Firehouse building in downtown Shelburne Falls, a short walk from the Bridge of Flowers and Glacial Potholes, and near artisan galleries, shops, and eateries.
This 550 square foot unit features one bedroom and one bathroom, accommodates two guests, and offers amenities including a king-size memory foam bed, a fully equipped kitchen with a microwave and dishwasher, air conditioning, in-unit laundry, and parking.
Charming Brookside Artisan Home - Greenfield, MA
10 119 reviews
Greenfield, MA
09/07 – 09/11
$338/nighttotal: $1352 (4 )

Charming Brookside Artisan Home

3 4
apartment , Shelburne
This country home is located near Shelburne Falls, a short drive from Greenfield and the Five College area, offering a peaceful escape in the countryside. The property has consistently received excellent ratings for cleanliness, location, and overall experience.
This three-bedroom house can accommodate up to six guests and features a spacious, open layout, a well-equipped kitchen, and a wraparound porch. Enjoy amenities like a fire pit, a babbling brook, and access to a local farm store, as well as outdoor activities like hiking, biking, and cross-country skiing.
Vikings Villages Resort - Greenfield, MA
9.8 618 reviews
Greenfield, MA
09/07 – 09/11
$446/nighttotal: $1784 (4 )

Vikings Villages Resort

2 4
resort , Guilford
Vikings Villages Resort, a 2-star Guilford inn, offers a peaceful rural setting nine miles from Vermont Marketplace, The Stone Church, and Brattleboro Common, and twelve miles from the Tasha Tudor Museum and Northfield Mount Hermon School.
This lodging boasts free Wi-Fi, free parking, a rooftop terrace with scenic views, a garden, and a cozy lobby fireplace; housekeeping is provided once per stay.
Shelburne Falls House In Village - Greenfield, MA
10 4 reviews
Greenfield, MA
07/25 – 07/27
$600/nighttotal: $1200 (2 )

Shelburne Falls House In Village

1 3
apartment , Shelburne
This 3-bedroom, 1-bathroom Victorian house in Shelburne Falls is a short walk from the village's shops and restaurants.
The 1890 property features a family room, kitchen with dishwasher, a private driveway, garage storage, and a large back deck, comfortably sleeping six guests and offering easy access to Shelburne Falls' amenities and outdoor recreation.
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