Best Holiday rentals and Airbnb offers in Greenfield, MA
9.6 8 reviews
Greenfield, MA
15/07 – 20/07
SG$794/nighttotal: SG$3970 (5 )
Gorgeous Timber Frame Home In Ashfield - 4 Bedrooms, 3 Bathrooms And Sauna
4 2
farm , Ashfield
This farmstead is situated in Shelburne Falls, western Massachusetts, approximately 32 kilometres from Berkshire East Ski Resort and near the Bridge of Flowers. This property accommodates up to nine guests across four bedrooms and three bathrooms, featuring a pool table, a wood-burning sauna with a cold plunge pond, and immediate access to hiking and biking trails.
10 301 reviews
Greenfield, MA
25/07 – 27/07
SG$388/nighttotal: SG$776 (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.
9.8 208 reviews
Greenfield, MA
25/07 – 27/07
SG$404/nighttotal: SG$808 (2 )
Peaceful Blossoms Victorian Home
3 3
apartment , Greenfield Town
This three-bedroom flat is situated in Greenfield, Massachusetts, just a short distance from popular attractions like Berkshire East, Yankee Candle, and Magic Wings. The surrounding area offers a charming New England setting, perfect for exploring the region's natural beauty and cultural landmarks. This property has consistently received excellent ratings for its cleanliness, location, and overall guest experience. The spacious apartment comfortably accommodates up to five guests and features a fully equipped kitchen with a fridge, microwave oven, and dishwasher. Guests can enjoy the convenience of a private garden, parking, and internet access, making it an ideal choice for families or groups of friends looking for a comfortable and well-equipped home away from home.
10 4 reviews
Greenfield, MA
15/07 – 20/07
SG$504/nighttotal: SG$2520 (5 )
Romantic 1-bedroom Retreat In Downtown Shelburne Fallswalk To Everything
1 2
apartment , Buckland
This one-bedroom flat is located in downtown Shelburne Falls, a short walk from the Bridge of Flowers and Glacial Potholes, within a renovated historic firehouse. This 51 square meter apartment accommodates two guests and features a fully equipped kitchen, a king-size bed, and an in-unit washer/dryer, with skiing and mountain biking available at Berkshire East Mountain Resort.
9.8 7 reviews
Greenfield, MA
25/07 – 27/07
SG$322/nighttotal: SG$644 (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.
9.5 79 reviews
Greenfield, MA
25/07 – 27/07
SG$220/nighttotal: SG$440 (2 )
Frimpong's Two Bedroom Apartment
1 3
apartment , Montague
This basement flat is located in the Lake Pleasant neighbourhood of Montague, just a two-minute walk from the lake and within easy reach of neighbouring towns like Greenfield, Sunderland, and Northampton. The apartment consistently receives excellent ratings for its cleanliness, location, and overall experience. The self-catering flat has two bedrooms and one bathroom, comfortably accommodating up to three guests. The property offers a private entrance, a kitchenette, a modern and fully furnished interior, a TV with Wi-Fi access, air conditioning, and parking.
9.7 6 reviews
Greenfield, MA
25/07 – 27/07
SG$334/nighttotal: SG$668 (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.
10 67 reviews
Greenfield, MA
25/07 – 27/07
SG$262/nighttotal: SG$524 (2 )
Spacious, Sunny* Woodland Retreat
1 3
apartment , Conway
This charming apartment is located in a renovated Victorian mansion on a street named after the family who built it in the 1880s, just 16 kilometres from I-91 and 32 kilometres from Greenfield. The property is also within a 40 kilometre radius of Amherst, Northampton, and Berkshire East Resort. The apartment has one bedroom with a queen bed, a queen futon couch, and a full sleeper sofa in the living room, making it suitable for up to six guests. Guests can enjoy a spacious and sunny apartment with a vintage Atari, a digital projector for playing Pong on the living room wall, a "wildscaped" yard with a small pond, and access to a local resident-only town pond/beach during the summer.
9.8 25 reviews
Greenfield, MA
25/07 – 27/07
SG$569/nighttotal: SG$1138 (2 )
Revitalized Firehouse Retreat In Charming Downtown
1 3
apartment , Buckland
This Buckland apartment, situated in a renovated Shelburne Falls fire station a short walk from the town centre, offers a unique stay near the shops and restaurants of Shelburne Falls. The two-bedroom, one-bathroom flat sleeps four, includes a fully equipped kitchen with dishwasher, in-unit laundry, air conditioning, and two designated parking spaces, plus additional free overnight public parking nearby.
9.6 57 reviews
Greenfield, MA
29/07 – 01/09
SG$238/nighttotal: SG$8092 (34 )
Two Geese Cottage, Private Home For Getaways!
1 2
cabin , Montague
The Two Geese Cottage, a delightful countryside retreat near Montague, offers a tranquil escape beside a flowing river, its precise location within the town unspecified. This single-bedroom cottage sleeps four, boasting a kitchen with fridge, freezer, and microwave, air conditioning, a garden, parking, and excellent guest reviews; nearby attractions in Montague are not specified, but the peaceful riverside setting promises relaxation.
9.9 98 reviews
Greenfield, MA
25/07 – 27/07
SG$341/nighttotal: SG$682 (2 )
Private Suite With A Sweet View. Spacious, Close To Town, Dog Friendly
1 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.
9.7 30 reviews
Greenfield, MA
29/07 – 01/09
SG$286/nighttotal: SG$9724 (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.
Best family friendly Greenfield, MA holiday rentals
Among the 20 accommodations in Greenfield, MA, here are the 4 best family friendly rentals
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.
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, 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.
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
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.
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.
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.
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?
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?
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?
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
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.
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
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.
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.
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.
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.