Vacation Rentals in Greenfield, MA

20 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • stayz
  • expedia
  • hotelscom
  • tripadvisor
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Greenfield, MA holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

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

On-the-river Retreat - Greenfield, MA
9.7 6 reviews
Greenfield, MA
25/07 – 27/07
A$370/nighttotal: A$740 (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
A$747/nighttotal: A$1494 (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.
Private Suite With A Sweet View. Spacious, Close To Town, Dog Friendly - Greenfield, MA
9.9 98 reviews
Greenfield, MA
25/07 – 27/07
A$438/nighttotal: A$876 (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.
The Jelly Mill-a Peaceful River Retreat - Greenfield, MA
9.9 209 reviews
Greenfield, MA
27/06 – 30/06
A$403/nighttotal: A$1209 (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.

Best Greenfield, MA holiday rentals with parking

Shelburne Falls On Main - Greenfield, MA
Greenfield, MA
25/07 – 27/07
A$301/nighttotal: A$602 (2 )

Shelburne Falls On Main

1 3
apartment , Shelburne
This Shelburne Falls on Main flat is located in Shelburne, approximately 40-46 kilometres from Amherst College, Hampshire College, Beneski Museum of Natural History, East Village Historic District, and Molly Stark State Park.
This one-bedroom apartment accommodates up to seven guests and includes complimentary WiFi, air conditioning, a fully equipped kitchen, and on-site private parking.
Deck, Mountain Views Colorful Retreat In Vernon! - Greenfield, MA
10 5 reviews
Greenfield, MA
25/07 – 27/07
A$346/nighttotal: A$692 (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.
Deck, Mountain Views: Colorful Retreat In Vernon! - Greenfield, MA
9.8 7 reviews
Greenfield, MA
25/07 – 27/07
A$357/nighttotal: A$714 (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.
Rose Wisteria 4 Guests 2 Bedrooms-full+queen Beds - Greenfield, MA
Greenfield, MA
15/07 – 20/07
A$418/nighttotal: A$2090 (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.

Frequently asked questions about holiday rentals in Greenfield, MA

  • Which neighborhood in Greenfield, MA should you consider for a vacation rental?

    The area around the Greenfield Green is a good choice for a vacation rental. It's close to the heart of town, with easy access to shops, restaurants, and the beautiful Greenfield Common.
  • What are the best Airbnb and holiday rentals in Greenfield, MA?

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

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

    Greenfield is a lovely place to visit year-round, but if you're looking for the best weather, aim for the summer months. You'll also find plenty of events and festivals happening during the summer.
  • 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 events or festivals should visitors check out in and around Greenfield, MA?

    The Greenfield Summer Concert Series is a great way to enjoy live music outdoors. The annual Greenfield Farmers Market is also a popular event, offering fresh produce and local crafts.
  • 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.

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

    A walk or bike ride along the Montague Greenway is a great way to enjoy the outdoors without spending any money. The Greenfield Public Library is also free to visit and has a variety of events and programs.
  • What are the best restaurants with local dishes in Greenfield, MA?

    The Restaurant at the Greenfield Hotel is a great place to try local cuisine. They have a seasonal menu that features fresh, local ingredients. The Greenfield Market is also a great place to find local food.
  • What are the best walking or cycling routes in Greenfield, MA?

    The Montague Greenway is a beautiful and easy bike path that runs along the Connecticut River. The Greenfield Common is also a great place to take a walk or run.
  • Are there pet-friendly attractions in Greenfield, MA?

    The Greenfield Common is a great place to take your dog for a walk. Many of the local shops and restaurants are also pet-friendly.
  • What are the benefits of choosing a vacation rental in Greenfield, MA?

    Vacation rentals offer more space and privacy than a hotel. They're also often located in more convenient locations, closer to the attractions that you want to see.
  • What are the top sports attractions and facilities in Greenfield, MA?

    Greenfield has a great sports scene. There's a Greenfield Recreation Department that offers a variety of programs and activities. The Greenfield High School has a great athletic program. And the Greenfield Community College is home to the Greenfield Community College Hawks athletic teams.

Destinations nearby

Best Greenfield, MA holiday rentals with a balcony

Vikings Villages Resort - Greenfield, MA
Greenfield, MA
15/07 – 20/07
A$403/nighttotal: A$2015 (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.
Charming 1-br Apartment In Conway, Wifi/ac - Greenfield, MA
10 3 reviews
Greenfield, MA
25/07 – 27/07
A$272/nighttotal: A$544 (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.

Best pet friendly Greenfield, MA holiday rentals

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

Shelburne Guest House -The Ranch - Greenfield, MA
10 301 reviews
Greenfield, MA
25/07 – 27/07
A$540/nighttotal: A$1080 (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.
Family Home | Flexible Layout | Walkable Town - Greenfield, MA
9.7 98 reviews
Greenfield, MA
15/07 – 20/07
A$461/nighttotal: A$2305 (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).
Cozy, Quiet Cottage On Country Rd 2 Mil From I-91 - Greenfield, MA
9.7 352 reviews
Greenfield, MA
25/07 – 27/07
A$272/nighttotal: A$544 (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.
Rustic Beauty: 2-bedroom House In Serene Shelburne Falls - Greenfield, MA
Greenfield, MA
25/07 – 27/07
A$771/nighttotal: A$1542 (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.
©2026 cozycozy.com