Holiday Rentals in Greenfield, MA

20 available vacation rental offers

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Greenfield, MA holiday rentals
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Best Holiday rentals and Airbnb offers 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

Rose Wisteria 4 Guests 2 Bedrooms-full+queen Beds - Greenfield, MA
Greenfield, MA
15/07 – 20/07
SG$378/nighttotal: SG$1890 (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.
Rose Room  Victorian Home  Queen Bed  Private Bath - Greenfield, MA
Greenfield, MA
15/07 – 20/07
SG$266/nighttotal: SG$1330 (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.
Summit Retreat:2br/2bath Rustic Beauty + Yoga Room - Greenfield, MA
10 7 reviews
Greenfield, MA
25/07 – 27/07
SG$675/nighttotal: SG$1350 (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.
Family Home | Flexible Layout | Walkable Town - Greenfield, MA
9.7 98 reviews
Greenfield, MA
15/07 – 20/07
SG$417/nighttotal: SG$2085 (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).

Best Greenfield, MA holiday rentals with parking

The Jelly Mill-a Peaceful River Retreat - Greenfield, MA
9.9 209 reviews
Greenfield, MA
27/06 – 30/06
SG$364/nighttotal: SG$1092 (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.
Revitalized Firehouse Retreat In Downtown Shelburne Falls. Walk To Everything! - Greenfield, MA
10 5 reviews
Greenfield, MA
15/07 – 20/07
SG$592/nighttotal: SG$2960 (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.
Charming 1-br Apartment In Conway, Wifi/ac - Greenfield, MA
10 3 reviews
Greenfield, MA
25/07 – 27/07
SG$246/nighttotal: SG$492 (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
SG$364/nighttotal: SG$1820 (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.

Frequently asked questions about holiday 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 in the spring or autumn. The weather is pleasant during these seasons, and there are fewer crowds than during the summer. You might find better deals if you book outside of peak season.
  • What are the best Airbnb and vacation rentals in Greenfield, MA?

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

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

    There are plenty of budget-friendly activities in Greenfield. You can take a walk or cycle along the Greenfield Bike Path, visit the Greenfield Public Library, or explore the Greenfield Common. The Greenfield Farmers Market is another great option for a budget-friendly day out.
  • 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?

    Greenfield has some great restaurants serving local dishes. The Greenfield Diner is a classic spot for American diner fare, and The Greenfield Restaurant is a great option for a more formal meal. For a taste of local cuisine, try The Greenfield Tavern, which serves up New England classics.
  • 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 walking or cycling routes in Greenfield, MA?

    The Greenfield Bike Path is a great option for both walking and cycling. It runs for several miles along the Connecticut River, offering beautiful views of the surrounding area. The Greenfield Common is also a popular spot for walking, and there are several hiking trails in the nearby Greenfield State Park.
  • Are there pet-friendly attractions in Greenfield, MA?

    There are a few pet-friendly attractions in Greenfield. The Greenfield Common is a great place to take your dog for a walk, and the Greenfield Farmers Market is also pet-friendly. The Greenfield State Park has hiking trails that are suitable for dogs on a leash.
  • What are the top sports attractions and facilities in Greenfield, MA?

    Greenfield does not have any major sports attractions or facilities. However, there are a few local sports teams, such as the Greenfield High School football team, and the Greenfield Recreation Department offers a variety of sports programs for people of all ages.

Destinations nearby

Best Greenfield, MA holiday rentals with a balcony

Vikings Villages Resort - Greenfield, MA
Greenfield, MA
15/07 – 20/07
SG$364/nighttotal: SG$1820 (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
SG$246/nighttotal: SG$492 (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

Garden Falls - Greenfield, MA
Greenfield, MA
25/07 – 27/07
SG$694/nighttotal: SG$1388 (2 )

Garden Falls

1 3
apartment , Shelburne
This charming three-bedroom house is situated in the historic village of Shelburne Falls, just a short walk from the famous Bridge of Flowers and a range of shops, restaurants, and recreational areas. The village is known for its picturesque setting and lively atmosphere, with plenty to offer visitors of all ages.
The house can comfortably accommodate up to six guests and features a fully equipped kitchen, a private patio, and free parking. Guests can enjoy a range of amenities including air conditioning, Wi-Fi, and a washing machine, as well as close proximity to outdoor activities like skiing, hiking, and swimming.
Wood Turtle Woods - Greenfield, MA
10 34 reviews
Greenfield, MA
29/07 – 01/09
SG$311/nighttotal: SG$10574 (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.
Cozy Country House In Conway - Greenfield, MA
Greenfield, MA
25/07 – 27/07
SG$551/nighttotal: SG$1102 (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.
1850s Grist Mill - Greenfield, MA
9.0 2 reviews
Greenfield, MA
29/07 – 01/09
SG$275/nighttotal: SG$9350 (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.
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