Discover a selection of 1,000 vacation rentals in Pittsfield, MA that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $117 per night, and houses and condos are popular options for a stay in Pittsfield. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Pittsfield
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Destination guide

Explore the lakeside setting in Pittsfield

Take a vacation to Pittsfield and enjoy the area's entertainment, theater scene and opera. This city's baseball games, museums and biking draw many visitors. With a vacation rental, you get a home away from home—many rentals offer full kitchens and outdoor grills for some home cooking.

Things to do

Activities and attractions in Pittsfield

Do you want to find attractions to see while you're in town? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Pittsfield a fun place to get away. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • Bousquet Ski Area (2.6 mi / 4.3 km)
  • Cranwell Golf Club (7.3 mi / 11.8 km)
  • Jiminy Peak Mountain Resort (7.6 mi / 12.3 km)
  • Furnace Brook Winery at Hilltop Orchards (7.6 mi / 12.3 km)
  • Kennedy Park (4.9 mi / 7.9 km)
  • Hoffman's Pottery (10.2 mi / 16.3 km)
Natural features

Exploring the natural landscape of Pittsfield

Whether you're looking for adventure or just want to appreciate the scenery, Pittsfield is a great place to get outside. Here are some of the area’s noteworthy natural features, all within 30 miles (48.2 km) of the city center:

  • Mount Greylock State Reservation Visitor Center (7.6 mi / 12.2 km)
  • The Mount (7.9 mi / 12.8 km)
  • October Mountain State Forest (8.9 mi / 14.3 km)
  • Naumkeag (11.4 mi / 18.4 km)
  • Mount Greylock (13.8 mi / 22.2 km)
  • Savoy Mountain State Forest (16.7 mi / 26.8 km)
How to get there

Transportation options to and around Pittsfield

Fly into Albany Intl. Airport (ALB), the closest airport, located 34.9 mi (56.2 km) from the city center. If you're unable to find a flight that fits your schedule, you can also fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is 2.5 mi (4 km) away.

If you'd rather travel by train, make your way to Pittsfield Intermodal Transportation Center or Pittsfield Station to see more of the city.

What are the top vacation rentals in or near Pittsfield?

Whether you're after a cozy escape for you and your sweetheart or someplace roomy to fit the family, you'll find some top vacation rentals in and around Pittsfield. Here are a couple to get you started:

  • Make use of amenities including a smart TV and golf at "Close To Skiing Beautiful +family Friendly". Situated around 25 miles from Pittsfield, this quality property has 4 bedrooms and is a hit with guests.
  • Another excellent choice is "4br/3bath Lakefront/ski House In Berkshires. Fully Fitted Kitchen. Hi Speed Wifi", which is around 20 miles from Pittsfield. Offering 4 bedrooms, a bicycle and a garden, it has everything you need to keep you comfortable and content.

For even more great options, use the search bar at the top of the page to find the perfect Pittsfield vacation rental for you.

Can I find log cabins to rent in or near Pittsfield?

Whether you want to spend your trip chasing outdoor adventure or reconnecting with your crew, we've got gorgeous log cabins where you can do both. Pack your suitcase and check out these favorites in and around Pittsfield:

  • "Water Front Log Cabin Next To Tanglewood": At this cabin, you'll be perfectly placed to participate in some of the fantastic outdoor activities this area has on offer, including fishing and ice skating.
  • "Cozy Log Cabin Adjacent To Beartown Forest": Spend your break enjoying all the conveniences of this log cabin. When it's time for some fresh air, snowmobiling and golf are some awesome things to do.

What are the top-rated vacation rentals for weekend getaways in or near Pittsfield?

Get away from the hustle and bustle of everyday life at one of our weekend getaways in or near Pittsfield. Whether you'd like to catch up with pals or spend time with your love, we'll have something to suit your needs. These are some of our top-rated options:

  • "Elterwater - - Your Lakefront Oasis" is around 25 miles south of Pittsfield and an ideal place to recharge your batteries. You'll like the useful amenities here, including free toiletries and a stovetop.
  • "Swiss Chalet Style Timber Frame Home In Berkshires With All Modern Conveniences" is another popular option to consider. It's located about 12 miles to the east of Pittsfield and comes with cable/satellite TV services, ski-in/ski-out facilities and more.

Can I find studio apartments for rent in and around Pittsfield?

Absolutely. If you'd like a small but stylish stay, you can't go past a studio apartment. These compact properties exude charm and are often conveniently placed in the center of town. We recommend the following options in or near Pittsfield:

  • Get away on your own or take a few friends to "Cabin - A - Frame In Sherwood Forest". You'll have loads of amenities to take advantage of, including pet-friendly services and coffee and tea making facilities.
  • Another great option is "Available For Healthcare And Long Term Stays Welcome 3 Miles From Hospital". Don't let it's compact size fool you — this comfortable apartment is filled with convenient amenities like off-street parking options, a restaurant dining guide and plenty more.

Can I find short term rentals in or near Pittsfield?

Whether you're in search of a studio apartment for you and your other half or a townhouse big enough for the whole family, there's no shortage of short-term rentals in and around Pittsfield. These properties are an ideal base for a whirlwind visit:

  • For a wonderful night or two away, settle in at "The Playhouse: 7, 000 Square Feet Of Berkshires Modern Luxury And History". It's close to the center of Pittsfield, along with lots of things to put on your itinerary.
  • Alternatively, spend a couple of nights at "Bargain Rates After Late Cancellation". This centrally located property makes exploring the sights easy.

What are the best romantic weekend getaways in or near Pittsfield?

Nothing says "I love you" quite like planning a romantic weekend together. If you're longing to spend a couple of nights away with your sweetie, we've got some romantic getaways in and around Pittsfield that will get your heart racing:

  • Put on some soft tunes and chill together at "Close To Skiing Beautiful +family Friendly". Around 25 miles from Pittsfield, this property has all you need for a couple's weekend away, including a fireplace and skiing facilities.
  • Alternatively, spend your mini break enjoying each other's company at "4br/3bath Lakefront/ski House In Berkshires. Fully Fitted Kitchen. Hi Speed Wifi", around 20 miles from Pittsfield. A firepit and outdoor furniture will help set the scene for romance.

What are the best houses for rent with a pool in or near Pittsfield?

Nothing says fun and frivolity like a pool. Dig out your inflatable unicorn and browse these rental houses in or near Pittsfield that come with this vacation perk:

  • Treat your crew to an unforgettable stay at "4br/3bath Lakefront/ski House In Berkshires. Fully Fitted Kitchen. Hi Speed Wifi". There's a lot to love about this escape besides its pool, such as a TV and childrens activities.
  • "General Williams Estate House Lenox" is the type of place you go to leave the everyday behind and make the most of your surroundings, starting with its inviting pool. A pool table and on-site watersports are also on hand to make your stay comfortable and convenient.

Pittsfield has a humid continental climate, with average summertime temperatures ranging between 55 ºF and 75 ºF. But you don't have to wait until summertime to visit. Take a look at the search bar at the top of the page and adjust the filters to find the ideal Pittsfield vacation rental and plan your escape for whenever you like.

What are the best large family vacation rentals in or near Pittsfield?

Nana and Pawpaw, Great-Uncle Andre ... You can put them on your guest list when you escape to a large family vacation rental in or near Pittsfield. Get everyone you adore under the one roof at one of these spacious properties:

  • Make your visit one you won't forget at "88 Acres Of Beauty In The Berkshires". This escape has 4 bedrooms, caters to 9 guests and features a range of amenities, including a dining table and pet-friendly facilities. It's around 25 miles south of Pittsfield.
  • "4br/3bath Lakefront/ski House In Berkshires. Fully Fitted Kitchen. Hi Speed Wifi", around 20 miles to the southeast of central Pittsfield, was made for family vacations. As many as 10 of your favorite people can fit into this sought-after rental which offers 4 bedrooms, a kitchen, childrens activities and more.

We know it's tempting, but don't spend your entire vacay kicking back indoors. Get out and see some nearby family-friendly attractions, starting with Tannery Falls.

Can I find family cabin rentals in or near Pittsfield?

Escape the busyness of life and treat the ones you love to a different sort of vacation. Stay in one of these family cabins in or near Pittsfield and get the camping experience — but with all the creature comforts!

  • "Cabin - A - Frame In Sherwood Forest" - This sought-after getaway offers outdoor furniture and a barbecue grill and is located around 12 miles southeast of the center of Pittsfield.
  • "Quiet Comfortable Cabin 5 Min. Walk To Swimming And Boating" - This property is another favorite with families and is around 17 miles southeast of Pittsfield. Offering towels, a microwave oven and more, it'll get everyone's tick of approval.

For more options, use the search bar at the top of the page and adjust the filters to find the Pittsfield vacation rental that's perfect for your needs.

What are the best large houses to rent with indoor pools in or near Pittsfield?

Go for a dip anytime you want when you book one of our large rental houses with an indoor pool. Slip on your swimsuit and check out these escapes in or near Pittsfield that feature this fancy perk:

  • With 5 bedrooms sleeping up to 10 people, "Private, Mountain Retreat With Indoor Pool And Fantastic Westward Mountain Views" is the perfect place to enjoy some downtime with your favorite people. Make use of this getaway's range of amenities, including a sauna and a swimming pool.
  • Another attractive property is "Equipped Villa With Access To Pools". With 3 bedrooms accommodating up to 8 people, you can invite your entire crew to stay, hang out and swim. A swimming pool and a sauna are other amenities your guests can make use of here.

For more options, use the search bar at the top of the page and adjust the filters to find the Pittsfield vacation rental that's perfect for your needs.