Pittsfield, the largest city in Massachusetts, offers limitless things to see and do for travelers. It is an excellent destination to explore the rich history, savor delicacies in gourmet restaurants, and indulge in outdoor adventure activities. The town boasts some of the finest attractions in the regions, from state forests and ski lodges to museums. Berkshire Museum, for example, brings visitors together for a unique educational and innovative experience. The museum has collections from all continents. Outdoorsy tourists will love racing along the slopes of Bousquet Ski Area for an exciting adventure. Pittsfield State Forest is another wonderful option for your outdoor adventure. If you are planning to visit the city soon and in pursuit of homey accommodation, try out any one of these top Airbnb vacation rentals in Pittsfield, 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 March 07, 2024.
1. Family-friendly property with a kids' play area (from USD 200)
Have a wonderful time in this abode, where comfort, relaxation, and family fun come together, and pets are welcome. Spend quality time watching shows on a 55-inch high-definition TV equipped with Fire TV and standard cable. You’ll love the travel crib and clamp-on table seat high chair, making the little ones’ mealtime and bedtime a breeze. There’s no shortage of entertainment here, with toys and a kids’ play area in the basement.
WiFi lets you stay connected online and productive no matter where your adventures take you. Freshen up in the bathtub after a long day of exploration. Enjoy the covered seating area under the back porch, the perfect spot to enjoy a meal or read a book while living in peaceful surroundings. Gather around the backyard fire pit while sharing stories with family and friends.
Top guest reviews
Amenities & Room:
soft and comfortable - all mattresses were new and perfectthis home was so comfortable for a family of 7 4 adults and 3 young tweensthe dining room sat all of us to dine together and play gamesCleanliness:
clean well decorated and great communicationwe really liked this airbnb it was very clean and comfortable and had a modern yet cozy feelexcellent hosts very nice and clean house in a great locationthe home is clean and comfortable and communication with hosts was excellentRead more reviewsLocation:
the location was perfect for usperfect place to stay for our get away to the berkshiresa lovely berkshires home perfect for a little suburbs getaway and still close to everything you could wantquiet neighborhood with a nice park at the end of the roadit was a good location for exploring pittsfield and doing some day hikes
2. Serene and beautiful home
Stay in this beautiful house in a serene neighborhood surrounded by lush greeneries. You’ll feel right at home among the natural plant decorations that adorn the space. There is a 43-inch flat-screen TV equipped with Disney+ and Netflix, perfect for a night in with your favorite movies and shows. For a bit of old-fashioned fun, board games will keep you entertained for hours on end.
There is fast WiFi, making communicating with loved ones during your stay easy. When you’re ready to unwind, soak in the bathtub for a relaxing end to your day. With free parking on the premises, you can explore the area without the stress of finding a parking spot after returning home. Enjoy the large backyard hill, perfect for picnics or relaxing in the sun.
Pittsfield, Massachusetts, United States
12.34 km (7.7 mi) from Jiminy Peak Mountain ResortSuperhostAccommodates: 7
Top guest reviews
Amenities & Room:
our mattress was extremely comfortablewe recommend that the owners check out why the wifi was slowthe beds were very comfortablethe bathroom was large and beautifulthe bathroom and kitchen are perfect and all rooms are well appointedCleanliness:
house was great clean and comfortablecomfy beds clean home and great locationbeautifully appointed clean and stocked with everything you needthe house was sparkling clean and very well equippedthe hosts provided terrific communication and the place was honestly spotlessHost:
hosts were very responsivevery friendly and helpful hoststhe host has introduced us to a great farm nearby where we found the best tomatoestanya thank you for hosting us we enjoyed the house so muchgreat location and house and the hosts are very communicative and helpfulRead more reviewsLocation:
perfect location in the berkshiresgreat place fairly close to everything we wanted to dohydrangia house is a lovely place in a terrific location for access to the berkshiresthis beautiful home is so close to so many amazing placesall in all a wonderful place to get away
3. Apartment with great views (from USD 70)
Situated in the heart of the city, this four-person apartment in Pittsfield is set on a building’s third floor. It has its own private entrance of its own and offers excellent views. Homey and well-appointed, you will be close to nature, restaurants, shopping centers, skiing areas, and other entertainment options. Although the apartment is set off Highway 7, it offers peace and tranquility. The property features two well-furnished bedrooms and one-and-a-half bathrooms with updated amenities for a hassle-free stay.
Top guest reviews
Amenities & Room:
loved the enclosed balcony and well-furnished kitchenwifi did cut in and out a bit but overall was a great experiencethe space has everything you need to feel comfortablethe apartment is beautiful well-equipped in the kitchen and bathroomthe space was private very comfortable and was the perfect winter getaway for usCleanliness:
clean and modern appointmentsclean warm and spaciousthe place was very clean and hospitablevery clean and tidy with a well stocked kitchenthis apartment is clean and nicely furnished and comfortableHost:
the hosts were excellenthosts were quick to respond and helpful when we had questionsthe directions were easy and convenient and the hosts are very graciousthe hosts were always quick to respond and helpfulbraden and andy are great hosts with a lovely spaceRead more reviewsLocation:
a perfect location for being able to walk to downtown activitiesperfect convenient location in pittsfield to stayit's an older neighborhood having big grand houses close to each otherbranden & andy’s place is really cuteit was quiet private and located fairly close to the interesting downtown of pittsfield
4. Spacious and lovely house by the lake (from USD 389)
Come and enjoy your vacation in this spacious gorgeous house with your friends and family. The property is nestled between two lovely lakes and boasts fantastic views. This custom-built property can sleep up to 16 guests and features 8 well-appointed bedrooms, 3 full bathrooms, and 2 fully equipped kitchens. One of the best things to do in Pittsfield while staying in this abode is to visit Lake Onota, just a short walk from the property, where you can indulge in outdoor activities such as picnicking, fishing, boating, and swimming. The other lake is called Pontoosuc and is only a quick ride away.
Top guest reviews
Amenities & Room:
this is a huge place with many beds two kitchens and all the amenities you needit was great having two kitchen areas it allowed guests to split off into different areasbeds were comfy loved having two kitchensthere was plenty of space for everyone and had a bonus of two kitchenstwo kitchens make cooking easyCleanliness:
props for good communication cleanliness and comforthouse per se is very clean and spacious well maintainedthe house was very clean and we'll supplied with everything we needed like paper products linens towels etcclean neat & large enough to hold an extended familythe house was huge clean and had such a great assortment of roomsHost:
margaret was very responsive to any of my questions and was a wonderful hostmargaret was very helpful and kindthe host was extremely helpful and accommodating and the area is absolutely beautifulthe place was perfect to host our group's retreat for the weekendmargaret was easy to work with and friendlyRead more reviewsLocation:
the house was close to two lakes which provided opportunity for daytime activitythe location is great; very secluded and a good getaway location for a gathering with the familythe location is great walking distance to onota lake and a 15 min drive to mount greylockthe location is very good it has 15-20 minutes driving to any food market or either skiingwe had a great time at this location
5. Cute tiny cottage (from USD 190)
Quiet and peaceful, this cute tiny bungalow rental in Pittsfield is suitable for up to six persons and offers views of Richmond Pond. You will be able to enjoy amazing sunrises from this cottage. There are two bedrooms with three squishy beds and a modern bathroom. The property is a 15 to 20-minute drive from attractions such as Norman Rockwell Museum, Shaker Village, and Tanglewood. Come here for a comfortable stay and return home with a bagful of happy memories.
Top guest reviews
Amenities & Room:
wifi works perfectwifi worked greateasy stay beds and furniture were very comfythe house accommodated 5 comfortably and had great coffee and wifi plus fire tvthe kitchen has all necessary tools to prepare a nice mealCleanliness:
clean and sweet placethe lakehouse itself was incredibly clean and comfortableit is clean comfortable and well-equippedextremely clean and well kept with lots of thoughtful touchesclean home near a beautiful lakeHost:
)the hosts were very friendly and we appreciate their hospitalitythe hosts were friendly and communicative-they also left delicious pastries and cider for usdave and vicki are gracious generous and thoughtful hostsvicki is very responsive and always ready to helpalways a quick response from dave and vicki and super helpful( above and beyond what you would expect)Read more reviewsLocation:
close to water in easy to walk neighborhoodthe location of dave & vicki's house is greatthe location was great and the neighborhood was very peacefultheir lake house is beautifully located in a quiet settingvery nice to walk around the neighborhood and the kayaks were great
6. h-century guest cottage with modern amenities (from USD 249)
Ideal for a maximum of four guests, this well-appointed two-storey cottage can assure you of a peaceful and relaxed stay. You can easily access Tanglewood as well as other attractions such as fine-dining restaurants and skiing areas while staying here. The property is loaded with a string of modern facilities and amenities so that you don’t have to compromise on the quality of your stay. Although it was built in the 19th century, it has been remodeled to meet the requirements of modern travelers.
Top guest reviews
Amenities & Room:
really appreciated the extremely quiet and effective split ac along with the luxury showerwe were able to do some work at the breakfast table and enjoyed great wififirst all of the reviews that you read about the comfort of the bed are 100% accuratethe 2-level house is beautifully renovated with a lovely kitchen complete with high quality appliancesmichael provides floaties so we could relax read listen to music while in the poolCleanliness:
first the place is extremely clean and updatedthe bed was super-comfortable and the unit was very clean and comfortablethe house was clean and comfortable as well as interestingly designed within a historical buildingeverything was very clean and the cottage is all new and modernHost:
beautiful property and accomadations and great hostsour hosts were so welcoming and the adjacent pool was just terrificmichael is a great host super helpful and prompt in any questions we might havemichael was a gracious host and replied promptly to any questionsboth michael and his son were great hosts and made our stay very relaxingRead more reviewsLocation:
the location was perfectideal location to hit all the area has to offerthe location as far as a headquarters for the area is perfectwe would definitely come back and recommend this place to others
7. Quiet country cottage near attractions
Surrounded by lush green woods, this quiet country cottage is a stone’s throw away from attractions such as Barrington Stage Theater, Tanglewood, and Ski areas of Pittsfield, Massachusetts. The cottage was constructed more than 100 years ago, yet offers you all the modern amenities needed for a comfortable stay. Cozy and clean, it boasts two nicely done rooms and a bathroom with modern fittings. The accommodation is ideal for outdoor activities such as cross-country skiing and hiking. It is also close to conveniences such as restaurants and a convenience store.
Pittsfield, Massachusetts, United States
12.91 km (8.1 mi) from Jiminy Peak Mountain ResortAccommodates: 4
Top guest reviews
Amenities & Room:
very cozy good wifi and disney channel a plusthe cottage is rustic (with some nice artistic touches) and has all the necessary amenities for a comfortable staypauls place is a cozy cottage with a lot of natural light and beautiful viewsclean and easy instructions on how to use ac heat wifi tv etcvery cozy space great for fall viewsCleanliness:
very clean and usefulcomfortable beds and very cleanthe house was clean and well equipedpaul’s place was amazing it was as advertised very clean and cozyit was beautifully clean easy parking and easy check-in/outHost:
paul was very helpfulpaul was also very accommodating and responsive whenever i had questionspaul and lainey were very kind and helpfulpaul was a great host - communicative accommodating and friendlypaul was so incredibly kindRead more reviewsLocation:
close to all the local attractionsthis was in a beautiful and convenient location to the attractions in the areagreat cozy spot close enough to shopping but still feels private and quietsuper close to town and a very laid back atmospherenice place to stay in a great location
8. Beautiful lakefront home (from USD 400)
You can stay only a few feet from the water when you book this lovely lakefront home with a host of updated amenities. Boat rentals are available at a nearby marina so you can enjoy a leisure boat ride with your companions. The cabin offers accommodation for a maximum of 12 guests ideal for a large family or a group of friends. It is located in proximity to restaurants, cultural offerings of Berkshire, and skiing areas. The brand new kitchen is fully equipped so that you can prepare your meals anytime.
Top guest reviews
Amenities & Room:
large deck overlooking lake with lots of amenities -- central ac strong wi-fi 3 bathrooms grill kayaksit was so peaceful sitting on the comfortable couch while watching the beautiful lake viewthe view from the living room overlooking the lake is outstandingvery comfortable for our group of 10Cleanliness:
jay’s house is beautiful modern and extremely cleanhouse was perfect lots of room clean and comfortablethis is a lovely clean well-appointed home on a beautiful spot on the lakethe house was clean all the details were communicated perfectly and it was a totally awesome weekendbedrooms and bathrooms are cleanHost:
host and property manager were very responsivethe owner and the lake house manager were a great host and very responsivejay and the house manager were very helpful and gave us everything we neededjay is a great host check-in is easy and the house was sparkling cleanRead more reviewsLocation:
place was great and lake front location was just perfect for a quick getaway with our family and kids
9. Beautifully renovated farmhouse (from USD 101)
Stay close to a string of conveniences such as a hospital, a pharmacy, and a shopping center by booking this lovely renovated farmhouse fit for two guests. Although the farmhouse was built in 1850, it has undergone a complete renovation so that you will not miss any essential facilities. A modern fully furnished kitchenette will help you cook as you please. Enjoy free parking space for your vehicle just outside the door. The host also provides a barbecue facility for your enjoyment.
Top guest reviews
Amenities & Room:
it was cozy and a minutes walk to great coffee and breakfastour stay at duane’s place was great the apartment was a perfect size for two peopleCleanliness:
nice and cleanthe apartment was clean quiet and comfortablecomfortable and clean place with everything you needan extremely clean and quiet space for relaxationsqueaky clean newly renovated space lots of roomHost:
duane and sheila are also wonderful hostsduane and sheila were great hosts and were wonderful to chat withduane and sheila were great hostsduane and sheila are great hoststhe hosts are accessible if needed and were willing to help as neededRead more reviewsLocation:
close to many restaurants (walking distance) as well as centrally located for area attractions and day tripseasy walk to good places to eat in pittsfieldwe had a lovely stay and would absolutely choose their place againperfectly renovated flat in the rear of a house very closed to the main streeta great place to stay
10. Cozy studio for two (from USD 53)
The studio is ideal for any person who is planning to relax and rejuvenate after a hectic week of work. It is also a haven for hikers and can accommodate two guests at a time. Although the property is not set in the best of localities, it is still comfortable and homey and offers picturesque scenery around without breaking the bank. The locality is safe and close to several attractions in Berkshire. The property is perfect either for a long-term stay or for a short visit.
Top guest reviews
Amenities & Room:
it had what you’d expect like wifi tv kitchen washer/drier etcfull electric reclining leather couch xbox 360 2 flatscreens (1 smart tv) etc) the bed area and couch are nice and comfortable with two tvs (i never used)there’s a washer/drier a good tv with streaming and an xbox and a kitchenthe water bottles and breakfast food is a nice little touch as wellCleanliness:
it was very clean and tidyit’s decently clean but the shower just doesn’t really feel clean to methe apartment itself was very clean and felt extremely secureit’s quiet clean and warmclean nice atmosphere and a lot is provided forHost:
david was s a very kind hostdavid is a great hostdavid was so helpful and played the perfect hosta great host and a great placelovely spot with a super thoughtful host and a great valueRead more reviewsLocation:
great space in a convenient locationgreat location everything we needed was 30 minutes or lessgreat place to stay close to everything great valuegreat place to stay great value close to everythingperfect for location near downtown pittsfield and very spacious
11. Beautiful private room in villa (from USD 100)
Situated in a quiet neighborhood, this century-old cottage is rich with history. The owners have renovated it carefully so that it retains its original old-world charm. Perfect for two guests, it comes with a nicely done bedroom and one attached private bathroom. The room is spacious and cozy while a big private yard can be accessed for relaxing and reading books. It is a bed and breakfast property in Pittsfield where you can start your day with delicious food every morning and use the kitchen to whip up a quick meal.
Top guest reviews
Amenities & Room:
our room and bath were very comfortablespectacular house and an extremely comfortable bed in the arden roomwe slept peacefully in the comfy king-bedded arden roombreakfast by the fireplace was a real treatsuch a beautiful bed and breakfastCleanliness:
the place was as advertised and very clean and comfortablethe rooms are tastefully decorated clean and roomyprivate bath and everything was cleanthe place is spotless and beautifully decorated as was our room (the arden)i stayed in the arden room and it was clean with comfortable bed and linens and quietHost:
wonderful hosts who care about their guestshosts were a great pleasurethe hosts are knowledgeable and very friendlyken and laurie were great hostshosts were very good about communicatingRead more reviewsLocation:
fantastic location and a really unique propertypeaceful and secluded yet close to the town centrethe property is exquisite the location is walking distance to downtown attractions and restaurantspictures don’t even come close to what edmister feels likeedmister house was great and close to everything tanglewood kripalu etc
12. Spacious colonial-style house
Spacious and comfortable, this colonial-style home is suitable for up to seven guests at a time and enjoys a central location in Berkshires. The property boasts four beautifully decorated bedrooms and two full bathrooms. There is a big front porch where you can relax with a cup of coffee or any of your favorite drinks. The property also has a huge background patio with a couple of barbecue grills and fire pits. A spacious dining table can comfortably seat eight people for a delicious meal. You will be close to Lanesborough, Tanglewood, and several hiking trails while staying here. Other Pittsfield attractions such as Jacobs Pillow, Berkshire Theater Company, and Colonial Theater are also nearby.
Pittsfield, Massachusetts, United States
11.68 km (7.3 mi) from Jiminy Peak Mountain ResortSuperhostAccommodates: 8
Top guest reviews
Amenities & Room:
we loved the huge sofa with large tv screenit was nice that there were multiple places to eat: kitchen formal dining room and tables outsideCleanliness:
house was clean and tidyhouse was very clean and backyard was so enjoyablethe house is large clean and comfortable with 4 bedrooms and 2 bathrooms and a recently updated kitchenthe house was clean and provided us with everything we needed for our stayHost:
the hosts were incredibly quick to respond gave local tips and were very kindhost was very helpful and responsive - answered questions incredibly quickly before booking and during our stayRead more reviewsLocation:
the location is also excellentif you need to travel anywhere it’s also close to highways which is super handythe neighborhood is also quiet and lovely which makes for perfect bonfire nights
Enjoy a home-away-from-home experience in this huge city
During your trip here, don’t miss out on any attractions that can be explored in and around this big city. Check out these Airbnb vacation rentals in Pittsfield, Massachusetts, if you wish to enjoy a home-away-from-home experience. If you want a fun-filled getaway, the best ski resorts are in the Berkshires.
Frequently asked questions about the top Airbnb vacation rentals in Pittsfield, Massachusetts
1. Which Airbnb vacation rentals in Pittsfield have a hot tub?
If you want to stay in Pittsfield, whether for business or leisure, stay at this spacious and lovely house by the lake, where you can ensure that you’ll have a wonderful experience with a hot tub available for your unwinding.
2. Which Airbnb vacation rentals in Pittsfield have parking?
This apartment with great views, this spacious and lovely house by the lake, this quiet country cottage near attractions, and this beautiful private room in the villa all have parking available for their guests’ convenience.
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