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Greenfield, MA vacation rentals
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Best Vacation rentals and Airbnb offers in Greenfield, MA

Our Favorite Family-Friendly Vacation Rentals in Greenfield, MA

Booking a family-oriented vacation rental in Greenfield, MA keeps you close to top city attractions for a stress-free getaway.

Gorgeous Timber Frame Home In Ashfield - 4 Bedrooms, 3 Bathrooms And Sauna - Greenfield, MA
9.6 8 reviews
Greenfield, MA
07/15 – 07/20
$617/nighttotal: $3085 (5 )

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

4 2
farm , Ashfield
This Ashfield farm, a secluded timber frame home in the western Massachusetts hills, is a 20-minute drive from Berkshire East Ski Resort and near the Bridge of Flowers.
This 4-bedroom, 3-bathroom accommodation sleeps up to 9 guests and features an open floor plan with a historic farm sink kitchen, a wrap-around porch with a gas grill and outdoor bed, on-site trails, and a wood-burning sauna with a pond plunge.
Modern Farmhouse Close To Montague Retreat Center - Greenfield, MA
9.9 194 reviews
Greenfield, MA
07/25 – 07/27
$543/nighttotal: $1086 (2 )

Modern Farmhouse Close To Montague Retreat Center

1 3
apartment , Montague
This restored 1880 farmhouse is located in picturesque Montague, MA, just 5 minutes from Montague Retreat Center, 20 minutes from Amherst, and 25 minutes from Northampton. With excellent user, location, and cleanliness ratings, this apartment is a great choice for travelers visiting Montague.
The apartment has 3 bedrooms, 2 bathrooms, and can accommodate up to 8 guests. It features modern amenities with radiant concrete floors, high-end appliances/countertops, cathedral ceilings, and an outdoor wooden playset. Guests can also enjoy activities such as playing board games, using the outdoor playset, or relaxing in the steam shower or 7-foot radiant heated copper bathtub.
Private Suite With A Sweet View. Spacious, Close To Town, Dog Friendly - Greenfield, MA
9.9 98 reviews
Greenfield, MA
07/25 – 07/27
$308/nighttotal: $616 (2 )

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

2 3
apartment , Shelburne
This studio is located just 2 miles from Shelburne Falls village, offering easy access to restaurants, shops, and the famous Bridge of Flowers. It's also conveniently located near Berkshire East, a four-season resort, and the Audubon Society Wildlife Sanctuary & High Ledges. The studio has received excellent ratings for location, cleanliness, and overall experience.
This spacious studio features a large open floor plan with a private entrance and a private bathroom, covering 1000 square feet. Enjoy amenities like a private terrace, a garden, and a cozy sleeping alcove with a queen bed. You can also take advantage of the radiant heated floors, air conditioning, and access to outdoor activities like swimming, hiking, and exploring the nearby Glacial Potholes.
Family Home | Flexible Layout | Walkable Town - Greenfield, MA
9.7 98 reviews
Greenfield, MA
07/15 – 07/20
$324/nighttotal: $1620 (5 )

Family Home | Flexible Layout | Walkable Town

1 2
apartment , Greenfield Town
This Greenfield, Massachusetts home is centrally located on a main street, yet offers privacy, being near Deerfield Academy, Northfield Mount Hermon, and the Five Colleges, with easy access to farmers' markets, coffee shops, and restaurants.
This four-bedroom, one-bathroom house comfortably sleeps five guests and features a private balcony with a hammock, a Goshen stone patio, and high-end amenities including a dishwasher and air conditioning.

Best Greenfield, MA vacation rentals with parking

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.
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.
Charming 1-br Apartment In Conway, Wifi/ac - Greenfield, MA
10 3 reviews
Greenfield, MA
07/25 – 07/27
$191/nighttotal: $382 (2 )

Charming 1-br Apartment In Conway, Wifi/ac

1 3
apartment , Conway
This spacious one-bedroom apartment in Conway, Massachusetts, is a 10-minute drive from I-91 and within 20-25 minutes of Greenfield, Amherst, Northampton, and Berkshire East, offering easy access to cultural attractions like the Double Edge Theatre and Three Sisters Sanctuary.
The unit, located in a historic Victorian mansion built in the 1880s, sleeps six guests and features a fully equipped kitchen, private porch, shared outdoor spaces, on-site laundry, and a cannabis-friendly environment (tobacco prohibited), along with vintage details such as marble fireplaces and high ceilings.
Rose Wisteria 4 Guests 2 Bedrooms-full+queen Beds - Greenfield, MA
Greenfield, MA
07/15 – 07/20
$294/nighttotal: $1470 (5 )

Rose Wisteria 4 Guests 2 Bedrooms-full+queen Beds

2 2
apartment , Shelburne
This pet-friendly 2-bedroom, 1-bathroom apartment in Shelburne Falls is located within walking distance of Glacial Potholes, Shelburne Falls, and the Bridge of Flowers, offering convenient access to local attractions.
This accommodation features air conditioning, on-site parking, internet, and a refrigerator, with kayaking available nearby for guests.

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, spring and fall. The weather is still pleasant, but the crowds are smaller and the prices are lower. You can also find great deals on vacation rentals during the winter months, but be aware that some attractions may be closed.
  • 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 events or festivals should visitors check out in and around Greenfield, MA?

    Greenfield's annual Greenfield Jazz Festival is a popular event, and the Greenfield Farmers Market is a great place to sample local produce. If you're visiting in the fall, the Greenfield Apple Festival is a must-see event.
  • 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 budget-friendly activities in Greenfield, MA?

    Greenfield has a lot to offer visitors on a budget. You can enjoy a picnic at the Greenfield Common, stroll through the Greenfield Center, or take a hike on the Greenfield Montague Trail. For a unique experience, check out the Greenfield Historical Society Museum's free admission days.
  • 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?

    Greenfield has a lot of pet-friendly attractions, including the Greenfield Common, the Montague City Park, and the Greenfield Historical Society Museum. You can also find pet-friendly restaurants and shops throughout the town.
  • What are the benefits of choosing a vacation rental in Greenfield, MA?

    Vacation rentals offer a lot of benefits over hotels, including more space, more privacy, and often a more affordable price. You'll also have access to a kitchen, so you can save money by cooking some of your own meals.
  • What are the top sports attractions and facilities in Greenfield, MA?

    Greenfield has a few great sports facilities, including the Greenfield High School Athletics Complex, which has a track, a football field, and a baseball field. For a more casual experience, check out the Greenfield Recreation Department's community center. They offer a variety of sports programs and activities.

Destinations nearby

Find the Best Vacation Rentals with Balconies in Greenfield, MA

Enjoy a Greenfield, MA vacation rental with a balcony and stunning city skyline views for a truly memorable stay.

Vikings Villages Resort - Greenfield, MA
Greenfield, MA
07/15 – 07/20
$283/nighttotal: $1415 (5 )

Vikings Villages Resort

1 2
resort , Guilford
The Vikings Villages Resort in Guilford offers a self-contained experience, located 18 miles from the city center.
This resort provides complimentary Wi-Fi, air conditioning, a terrace, a garden, and on-site parking, with an elevator for accessibility and a picnic area for guest enjoyment.

Top Dog-Friendly Vacation Rentals in Greenfield, MA

Discover dog-friendly vacation rentals in Greenfield, MA situated perfectly for city walks and nearby dog parks.

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.
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.
Cozy Home With Relaxing Views - Greenfield, MA
9.7 30 reviews
Greenfield, MA
07/29 – 09/01
$222/nighttotal: $7548 (34 )

Cozy Home With Relaxing Views

1 2
apartment , Northfield
This Northfield apartment is located in a peaceful countryside setting, surrounded by scenic mountain views and rolling fields. It has excellent user, location, and cleanliness ratings.
The apartment has 3 bedrooms, 1 bathroom, and can accommodate up to 6 guests. It features a fully equipped kitchen, comfortable amenities such as central heat and high-speed internet, and on-site parking and laundry facilities. Guests can enjoy scenic views, proximity to local attractions, and a tranquil ambiance.
Cozy, Quiet Cottage On Country Rd 2 Mil From I-91 - Greenfield, MA
9.7 352 reviews
Greenfield, MA
07/25 – 07/27
$192/nighttotal: $384 (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 2 miles from I-91, and within easy driving distance of attractions like Crump 'N Fox Golf, Northfield Mount Hermon, Greenfield, and Brattleboro. The cottage boasts excellent ratings for user experience, location, and cleanliness.
This cozy retreat features a spacious open floor plan, comfortably accommodating up to 4 guests. Enjoy a fully equipped kitchen, a large yard, hiking trails, cable TV, Wi-Fi, a washer and dryer, and access to a peaceful field perfect for outdoor activities.
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