Best Holiday rentals and Airbnb offers in Greenfield, MA
9.8 51 reviews
Greenfield, MA
29/07 – 01/09
£131/nightTotal: £4454 (34 )
Flowers & Falls Spot House
1 2
apartment , Buckland
This two-bedroom apartment in Buckland is situated just 15 kilometres from Berkshire East Mountain Resort, overlooking the Salmon Falls and Bridge of Flowers. The apartment has been given excellent ratings for location, cleanliness and user experience. The apartment offers a comfortable stay for up to six guests, with one bathroom and a fully equipped kitchen. Guests can enjoy a private garden, parking, air conditioning and breathtaking views from the outdoor deck.
Greenfield, MA
25/07 – 27/07
£403/nightTotal: £806 (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.
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 3 reviews
Greenfield, MA
25/07 – 27/07
£143/nightTotal: £286 (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
£154/nightTotal: £770 (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.
10 81 reviews
Greenfield, MA
25/07 – 27/07
£166/nightTotal: £332 (2 )
Lovely Greenfield Apartment
1 3
apartment , Greenfield Town
This two-bedroom flat is situated in a residential neighbourhood, just 1.6 kilometres from Greenfield town centre and 800 metres from Baystate Franklin Medical Center. The property has received excellent ratings for its cleanliness, location, and user experience. The flat is equipped with a kitchen, a bathroom, and a private balcony, comfortably accommodating up to three guests. The apartment offers modern amenities such as air conditioning, a dishwasher, a microwave, and a fridge, making it a great choice for families and travellers looking for a comfortable stay.
10 301 reviews
Greenfield, MA
25/07 – 27/07
£225/nightTotal: £450 (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.
Greenfield, MA
25/07 – 27/07
£320/nightTotal: £640 (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.
9.8 7 reviews
Greenfield, MA
25/07 – 27/07
£187/nightTotal: £374 (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.
9.7 30 reviews
Greenfield, MA
29/07 – 01/09
£166/nightTotal: £5644 (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.
9.7 488 reviews
Greenfield, MA
25/07 – 27/07
£250/nightTotal: £500 (2 )
Sunny Downtown 2br, Near Bridge Of Flowers
1 3
apartment , Shelburne
This two-bedroom flat is located on the main street of Shelburne Falls, just a short walk from the Glacial Potholes and the Bridge of Flowers, offering easy access to the village's shops, restaurants, and cafes. The property has received excellent ratings for its location, cleanliness, and overall experience. The flat is spacious and can accommodate up to six guests. It features a modern kitchen with a fridge and microwave, a newly-remodelled bathroom with a shower and washer-dryer, and a comfortable living area with a queen-sized sofa bed. Guests can enjoy the street views, explore the surrounding area, and relax in the artistic ambiance of the flat.
Explore Holiday Rentals for Families in Greenfield, MA
Choosing a holiday rental built for families in Greenfield, MA means city attractions are close by for a much smoother trip.
9.7 22 reviews
Greenfield, MA
15/07 – 20/07
£348/nightTotal: £1740 (5 )
The Mountain House
4 2
apartment , Gill
This 4-bedroom family home sits atop Mount Pisgah, just 3.2 kilometres from the Mohawk Trail and 8 kilometres from Greenfield, offering stunning views and a tranquil setting in the heart of the Berkshire Hills. The property boasts excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay. The house is spacious and comfortably accommodates up to 8 guests, with a full kitchen, dining room, family room, and a nursery with a twin bed. Guests can enjoy a private garden, parking, and access to the entire first and second floors, sunroom, breezeway, and attached garage, making it ideal for families and groups seeking a secluded escape in the beautiful surroundings.
9.9 209 reviews
Greenfield, MA
27/06 – 30/06
£211/nightTotal: £633 (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.
Greenfield, MA
15/07 – 20/07
£220/nightTotal: £1100 (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.
9.7 6 reviews
Greenfield, MA
25/07 – 27/07
£194/nightTotal: £388 (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.
Choose the Right Self-Catering Holiday Rentals with Free Parking in Greenfield, MA
A car park at your holiday rental in Greenfield, MA means exploring the city centre is easy every day with no extra faff. Find your perfect stay.
Greenfield, MA
15/07 – 20/07
£211/nightTotal: £1055 (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 5 reviews
Greenfield, MA
25/07 – 27/07
£181/nightTotal: £362 (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.
9.9 194 reviews
Greenfield, MA
25/07 – 27/07
£405/nightTotal: £810 (2 )
Modern Farmhouse Close To Montague Retreat Center
1 3
apartment , Montague
This restored farmhouse, situated in the picturesque Montague, Massachusetts, is just 8 kilometres from the Montague Retreat Centre and a 32-kilometre drive from Northampton. This spacious property, perfect for families, boasts three bedrooms, two bathrooms, and can comfortably accommodate up to eight guests, featuring modern amenities such as a dishwasher, air conditioning, and a dedicated play area for children.
9.7 35 reviews
Greenfield, MA
27/06 – 30/06
£150/nightTotal: £450 (3 )
Rustic-chic Cottage With Yard And Grill - Near Hiking!
2 2
house , Northfield
The Rustic-Chic Cottage is located in Northfield, just 39 kilometres from both Amherst College and the Beneski Museum of Natural History, making it a great base for exploring the area. The cottage has received excellent ratings for user experience, location, and cleanliness. This 2-bedroom cottage sleeps 2 guests and offers 125 square metres of living space. The cottage is fully equipped with a kitchen, air conditioning, free Wi-Fi, a garden, and free bikes, plus it has a patio with river views and is close to hiking trails.
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 mild, and there are fewer crowds. You can find great deals on rentals during these seasons.
What are the best Airbnb and holiday rentals in Greenfield, MA?
What are the best budget-friendly activities in Greenfield, MA?
A stroll along the Greenfield Bikeway is a great way to enjoy the scenery and get some exercise. The Greenfield Public Library is a free resource with a great collection of books and movies. The Greenfield Community College campus also has a number of free events throughout the year.
What are the most popular Airbnbs in Greenfield, MA?
Are there pet-friendly attractions in Greenfield, MA?
The Greenfield Town Common is a great place to take your dog for a walk. The Greenfield Farmers' Market also allows dogs on leashes. The Greenfield Community College campus is also a great place for a walk with your dog, as it has a number of open spaces and trails.
What are the best rentals for families and kids in Greenfield, MA?
What are the top sports attractions and facilities in Greenfield, MA?
Greenfield is home to the Greenfield High School, which has a number of sports teams, including football, basketball, and soccer. The Greenfield Community College also has a number of sports teams, including baseball, softball, and volleyball. There are also a number of parks and recreation facilities in the area, including the Greenfield Town Common, which has a playground, a basketball court, and a tennis court.
Destinations nearby
Best Self-Catering Holiday Rentals with a Terrace in Greenfield, MA
Enjoying morning coffee with city skyline views is a simple pleasure when staying in these holiday rentals and Airbnbs in Greenfield, MA.
Greenfield, MA
15/07 – 20/07
£211/nightTotal: £1055 (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
£143/nightTotal: £286 (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.
Popular Pet-Friendly Holiday Rentals in Greenfield, MA
Bringing your dog to Greenfield, MA? These holiday rentals are perfectly set up with dog parks nearby and city walks on the doorstep.
10 4 reviews
Greenfield, MA
25/07 – 27/07
£447/nightTotal: £894 (2 )
Shelburne Falls House In Village
1 3
apartment , Shelburne
This immaculate Victorian house in Shelburne Falls offers a peaceful retreat, a short walk from the village centre with its shops, restaurants, and bowling alley. The three-bedroom property, sleeping six, features an open-plan kitchen-family room, a dining room, and a private back deck with a barbecue, plus garage storage for sports equipment; nearby activities include skiing, cycling, and rafting.
10 34 reviews
Greenfield, MA
25/07 – 27/07
£226/nightTotal: £452 (2 )
Wood Turtle Woods
1 3
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
£405/nightTotal: £810 (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.
9.7 98 reviews
Greenfield, MA
15/07 – 20/07
£242/nightTotal: £1210 (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).