10 Best Airbnb Vacation Rentals In Greenfield, Massachusetts - Updated 2024

Rae Marielle
Rae Marielle 
Updated
| 5 min read

Located in Franklin County, Massachusetts, Greenfield is a laid-back city that is known for its growing commerce and entertainment hubs. Whether you’re here for work or fun, you should take some time to check out its different shops and restaurants. There are also multiple venues and spaces scattered around the city for musical acts, exhibits, and all sorts of performance art. Since Greenfield can be found in the Pioneer Valley, it’s surrounded by towering trees and hiking trails. If you’re lucky, you might catch a glimpse of wildlife in their natural habitat. The best part about Greenfield is that despite its streets bustling with people and activities, its residential neighborhoods are pretty peaceful. There’s no better way to end your day than coming home to a room where you can unwind in peace. So if you’re dropping by Greenfield any time soon, scroll through this list of the top Airbnb vacation rentals in Greenfield, Massachusetts.

We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on February 06, 2024.

1. Antique home with private patio (from USD 195)

This old-timey house will guarantee you an unforgettable vacation. As soon as you enter, you’ll discover antique pieces scattered around the place, giving it a nostalgic feel. When snow starts to fall, you can play by the yard or huddle up in the cozy living room. The private patio has an assortment of fruits and flowers, making it the perfect spot to hang out during spring and summer. Regardless of the season, you’ll definitely have a great time right here.

Stayed at this property?
Greenfield, Massachusetts, United States
9.48 km (5.9 mi) from Magic Wings Butterfly Conservatory
162 reviews   Superhost Wifi Available
ENTIRE HOME 4 Beds 5 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 5

Top guest reviews
Amenities & Room:
very comfortable furniture and furnishings
wifi worked great
the modern appliances in the kitchen and washer/dryer were nice bonuses
the house was more charming and cozy than the photos captured
the house is utterly charming with an updated kitchen modern appliances and good bathrooms
Cleanliness:
spotless and clean
very clean and comfortable
a beautifully clean home and aesthetically wonderful
lovely turn of the century spacious house completely updated clean and gorgeously furnished
super clean well equipped kitchen bathroom and laundry room
Host:
host is super hospitable
wonderful spot and wonderful host
our host met us at check-in accommodated our requests and was a very gracious
beautiful home and a great host
carolyn is a wonderful host
Location:
an easy walk to downtown
nice location in greenfield mass
the location was very convenient and close to great restaurants in greenfield
beautiful old house within walking distance to main street
walking distance to a number of great places downtown
Read more reviews

2. Luxurious villa with eat-in kitchen

Live like royalty inside this large manor near downtown. The spacious eat-in kitchen is just the right size to accommodate a large family of eight. This is the chance to bond over preparing and eating food. You can also enjoy your meals at the dining room during formal or special occasions. The villa has a three-season porch connected to the living room, giving everyone additional room to play or lounge around. If you’re planning to stay in Greenfield with the family for a few weeks or a couple of months, then you might want to check out this stunning villa.

Stayed at this property?
Greenfield, Massachusetts, United States
8.19 km (5.1 mi) from Magic Wings Butterfly Conservatory
65 reviews   Wifi Available
ENTIRE HOME 5 Beds 10 Guests 5 Bedrooms 3 Bathrooms

Accommodates: 10

Top guest reviews
Amenities & Room:
it was about the best stocked kitchen of any air bnb we have ever stayed in
fit 5 adults and 2 children with room to spare
lots of comfortable common areas for visiting eating lounging
tastefully decorated very comfortable and much larger that it looks from the posted pictures
multiple comfortable spaces in and out of the house for gathering/hanging out
Cleanliness:
the house was clean and comfortable
every room was spotless and warmly furnished
martina's place is clean well stocked and beautiful
awesome home very clean and neat
it was very clean beds were comfortable and there was plenty of room
Host:
martina was the perfect host
martina is a super host
martina was a warm and friendly host
martina is a wonderful host who was very responsive to our questions
martina was an excellent host highly recommend
Location:
the location is perfect two
a lovely house right in greenfield village and close to deerfield
wonderful location close to restaurants and activities
perfect location - close/easy to walk to town but in a quiet residential neighborhood
great location—can walk to downtown greenfield as well as to a nice walking trail
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3. Spotless bungalow with two bedrooms (from USD 125)

Don’t miss out on the opportunity to have this entire bungalow to yourself when you visit the charming town of Greenfield. It has two bedrooms that you can divide among your family or friends. Each bedroom has a soft mattress, guaranteeing a peaceful sleep at night. If you have children with you, you won’t have to worry about any of them getting harmed in any way because the bungalow has been designed to be open and uncluttered. Try out the different nearby restaurants or cook yourself a delicious meal in the kitchen.

Stayed at this property?
Greenfield, Massachusetts, United States
11.01 km (6.9 mi) from Magic Wings Butterfly Conservatory
66 reviews   Wifi Available
ENTIRE HOME 2 Beds 4 Guests 2 Bedrooms 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
my hosts went the extra step to make me feel comfortable with thoughtful touches like tea/coffee and toiletries
the bed linens were particularly comfortable and there were lots of fluffy towels
both bedrooms are super comfortable and so are the living room and dining room
Cleanliness:
bright and clean as advertised
house was very clean and comfortable
very clean and easy to locate
darry + kristi’s place is a convenient clean easy spot
very comfortable and clean
Host:
communication with the hosts was clear and we appreciated the helpful information they provided about the surrounding areas
darry and kristi are awesome hosts
wonderful place to spend a few days or a week darry and kristi were great hosts
hosts were great with communication and made some gracious accommodations to make our stay easier
communication was prompt and easy and they provided helpful tips about restaurants in the area
Location:
the house is in a great location; a short drive to downtown and many restaurants
what a lovely house to stay at we were close to the wedding we were attending
what a lovely place to stay while on a holiday vacation
the central air conditioning was an added bonus as we stayed on a muggy summer weekend
a really great place to stay
Read more reviews

4. Warm and sunny suite with free parking (from USD 136)

Greenfield is an exciting and interesting city with tons of activities and buildings to explore. However, there’s no better feeling than retiring to a quiet home at the end of the day. This suite is positioned a few blocks away from the busy downtown, close enough to get there easily but far enough from the urban noise and people. This bright suite is an intimate lodging, good for two people. There’s a private deck at the back, where the sunlight hits just right, making it an excellent spot for reading or drinking tea. A parking space near the entrance is provided for your vehicle. Play and rest all you want in Greenfield.

Stayed at this property?
Greenfield, Massachusetts, United States
8.69 km (5.4 mi) from Magic Wings Butterfly Conservatory
154 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 1 Bed 3 Guests 1 Bedroom 1 Bathroom

Accommodates: 3

Top guest reviews
Amenities & Room:
the outdoor space with tables and chairs was private and relaxing
very comfortable and cozy furnishings
the bed and bedding are amazing
highly recommend such a good spot and has outdoor patio and plenty of room inside
the place is beautifully decorated and the bed super comfy
Cleanliness:
very clean and great locatio
shower and bathroom are modern and clean and perfect
everything was very clean organized and easily accessible
comfortable clean and convenient to town
very cozy well appointed super clean and private
Host:
excellent hosts just perfect
our hosts were very easy to reach
great hosts and they gave us awesome recommendations
hosts were super accommodating and thoughtful in everything they provide for their guests
molly and matthew were good hosts
Location:
great location perfect for 2 guests
such a sweet place in a really cute town
molly and matthew’s place was the perfect getaway very quiet and private but close enough to walk anywhere
a cozy yet modern space great location near downtown greenfield
what an amazing place to stay amazing location right in town and absolutely adorable
Read more reviews

5. Stylish studio with backyard garden (from USD 65)

Look no further because this chic studio room is the getaway that you’ve been waiting for. You’ll find it by the outskirts of Greenfield near various attractions. Take a 20-minute ride to Berkshire East, where you can go skiing, mountain biking, hiking, and try other outdoor activities. It’s also just an hour away from Okemo Mountain Resort and Mount Snow, two of the best skiing resorts in Vermont. There’s a mini kitchen for preparing quick drinks and snacks, but if you want a full meal, eating at restaurants and diners is recommended. Stroll around the garden and take Instagram-worthy photos with the mini sculptures littered along the backyard. Don’t forget to step outside at night and admire the beautiful night sky accompanied by twinkling stars.

Stayed at this property?
Greenfield, Massachusetts, United States
12.24 km (7.7 mi) from Magic Wings Butterfly Conservatory
140 reviews   Superhost Wifi Available
Entire guest suite 1 Bed 2 Guests 0 Bedrooms 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
room was comfortable with microwave fridge coffee clean towels extra soap awesome shower nice ac unit etc
the room is decorated with lots of nice touches and the garden area has outdoor sculptures and art
fridge microwave tea pot and toaster make it possible to prepare a nice continental breakfast
Cleanliness:
extremely clean and comfortable
great place to stay very clean very quiet
great little place to stay very clean
clean great location & great communication
a lovely clean quiet space perfect for a weekend getaway
Host:
hosts were wonderful: warm responsive and provided us with recommendations
jj was an awesome host the place is perfect
this place is truly an oasis the hosts were so kind and helpful
they were incredibly friendly and the town was gorgeous
it’s a lovely and very artfully decorated little space with very friendly and helpful owners
Location:
located in farm/suburban surroundings but close enough to town to get great food with a short drive
a great location for a couple looking for a getaway
jjs place is great close to shops and in the nicer part of town
Read more reviews

6. Breezy apartment with full bathroom (from USD 103)

Find your inner peace inside this serene apartment decorated with wide windows and high ceilings, giving you all the space and air you need to relax and have fun. You’ll have the entire upper floor to yourselves, which you can enter through a private entrance. There’s a bathtub in the bathroom, where you can soak yourself and unwind from all the accumulated stress. To make things even better, you can watch the sunset while lounging on the front porch.

Stayed at this property?
Greenfield, Massachusetts, United States
8.16 km (5.1 mi) from Magic Wings Butterfly Conservatory
64 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 3 Beds 4 Guests 2 Bedrooms 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
it’s easy to find the iron the towels the ironing board the coffee maker the coffee etc
her apartment is spacious comfortable & beautiful with natural wood trim and hardwood floors
the bedding was comfortable
this was a beautiful old house that was warm and cozy on a snowy new england night
very spacious accomodation with an actual kitchen and large comfortable bedrooms
Cleanliness:
the entire unit was clean and well equipped
julie's place is amazing it is very clean and stylish
the space is nicely clean
enjoyed the stay -- julie's place was tidy and clean and she communicated with us clearly
excellent stay clean great suggestions on local restaurants and fresh flowers
Host:
julie is a very kind host
julie is a great host and is very responsive
she was very helpful and accommodating
and julie was a clear communicator and thoughtful host
julie is an amazing host--we felt extraordinarily welcome
Location:
great location walking distance to temple woods close drive to poet's seat
the location is convenient to everything and feels very safe and secure
it’s a great location close to town with surrounding area parks full of nice hiking trails
the location is also great for going into the town or visiting local parks
great place perfect spot close to downtown julie was so helpful
Read more reviews

7. Serene cabin with WiFi (from USD 71)

Relax and replenish your energy inside this quaint cabin for two. It has enough room and amenities to ensure a memorable and hassle-free stay. Have a cup of tea by the window and watch a few birds come and go. Use the WiFi if you have work to attend to.There’s a heater and an air conditioner within the residence, so you can adjust the temperature of the room to whatever suits you best. While everyone’s out and about for the holidays, you can just sit back and relax in this dainty little space.

Stayed at this property?
Greenfield, Massachusetts, United States
9.64 km (6.0 mi) from Magic Wings Butterfly Conservatory
100 reviews   Wifi Available
Private room in guest suite 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
the space is lovely with a bed guaranteed to provide a restful sleep
it was comfortable everything was where needed and she’d put out fresh flowers (from her garden i presume)
when we finally returned to crash just before midnight we experienced a supremely comfortable bed
the room was great for two people
the room was exactly as pictured and was quiet and very comfortable
Cleanliness:
very clean and nicely decorated
clean cozy and comfortable
everything is clean new and comfortable
nice quaint clean space
very clean quiet comfortable space
Host:
pam is a great host
pam was very responsive and a wonderful host
pam was a great host and responded immediately when we had questions
pam was a terrific host
pam's an awesome host
Location:
it's located in a quiet neighborhood with good walking/running trails nearby
it is located is a great quiet neighborhood
a lovely quiet location that is an excellent value
i enjoyed going for walks in the neighborhood and around the college campus close by
pam has a lovely suite in a great location
Read more reviews

8. Whimsical lodging with modern amenities (from USD 274)

Go on a trip to Greenfield without paying for expensive hotels in this unique apartment. Its interior is an aesthetically-pleasing mix of modern and old-fashion design that will make you feel like you’re living in another world. There are three bedrooms that can sleep up to six people in total. The property exudes a vintage vibe, but there are also modern appliances, such as flat-screen television and washing machine, to make your stay easy and convenient The train and bus station is just a five-minute walk away, so you can travel to other places without too much of hassle.

Stayed at this property?
Greenfield, Massachusetts, United States
8.34 km (5.2 mi) from Magic Wings Butterfly Conservatory
20 reviews   Wifi Available
ENTIRE RENTAL UNIT 3 Beds 4 Guests 3 Bedrooms 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
the house is very well decorated with warm and elegant facilities
more than adequate closet space dresser space and comfortable seating areas to relax
Cleanliness:
very clean and comfortable
very clean floors and area rugs
very comfortable beds the whole place was very clean & inviting
it was everything that was described - very clean spacious nicely furnished and well stocked with necessities
very clean with lots of light and the best choice for big family
Host:
linda is a great host
our host was most accommodating in all respects
linda was very communicative and responsive
linda is also very nice and responsive to anything you ask for
it was super clean and comfortable and linda is a lovely host
Location:
really nice spot in a quiet neighborhood of greenfield super close to the center of everything
great house close within walking distance to restaurants and a local coffee shop
linda's apartment is in a great location
this beautiful apartment was a perfect place to stay while visiting family in greenfield
it is walking distance from restaurants and coffee shops which was nice
Read more reviews

9. Spacious tent with outdoor shower

Discover this hidden gem surrounded by enchanting trees and wildlife. Despite being located in an isolated area, it has everything you need to make your experience in the outdoors comfortable and convenient. Watch the stars at night and when it starts to feel chilly, settle down and use the wood-burning stove to keep yourselves warm. There’s an eco-friendly outdoor shower and compost toilet behind the tent to ensure your privacy. Go on a healing holiday and reconnect with nature inside this charming yurt tent.

Stayed at this property?
Greenfield, Massachusetts, United States
14.8 km (9.2 mi) from Magic Wings Butterfly Conservatory
30 reviews   Wifi Available
Yurt 3 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
with a kitchenette toilet and shower clean water and electricity the yurt has everything you need
Cleanliness:
it was super clean comfortable and had everything we needed
the yurt is clean and comfortable
Host:
wendy is a great host
wendy was an extremely kind and friendly host
wendy was a loving host and very easy to communicate with
wendy is a thoughtful and accommodating host
wendy was a wonderful host who offered a wealth of information leading up to our arrival
Location:
perfect location and dwelling for those who love the outdoors
amazing location great place to unwind and clear your head after a day of hiking through fall foliage
it's a nice place to get away and relax
this is a magical place to stay for those who wish to enjoy sustainable living at its best
wendy’s yurt is in a beautiful secluded location perfect for a weekend away from the hubbub and noise
Read more reviews

10. Snug house with wraparound porch

Want to take a break from your busy daily schedules, then book this cozy house in a quiet neighborhood. Spend some time together and catch up in the living room while you keeping yourself warm by the wood-burning stove. You can also have your favorite tea or coffee by the porch while getting some fresh air. Get that healing and life-changing vacation that you need.

Stayed at this property?
Greenfield, Massachusetts, United States
9.76 km (6.1 mi) from Magic Wings Butterfly Conservatory
5 reviews   Wifi Available
ENTIRE HOME 2 Beds 6 Guests 3 Bedrooms 1 Bathrooms

Accommodates: 6

Top guest reviews
Host:
advice to host: make sure your cleaners clean everything in the kitchen and bathroom
Read more reviews

Explore the laid-back city of Greenfield

While Greenfield might not have world-famous attractions, there’s a variety of things you can do here whether you prefer laid-back retreat or thrilling outdoor activities. You can enjoy a meal or two at a local diner and visit a gallery afterwards. You can also go hiking and skiing, if the weather permits. The charm of Greenfield lies in its silence and intimacy. This is the best spot to go to especially when you need a big break from your everyday routine.

Stayed at this property?
Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Rae Marielle is a fiercely independent woman whose longest relationship is with food. She has a Bachelor's degree in Information Technology and a Master's degree in Communication Research....Read more

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