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Pittsfield, MA accommodations
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288 Lodgings in Pittsfield, MA

Search Lodgings near the Old Town in Pittsfield, MA

Choosing central accommodation in downtown Pittsfield, MA maximizes your time, putting popular museums, historic districts, and local restaurants within walking distance.

Hawksnest: Quiet 2br Apt, Heart Of The Berkshires - Pittsfield, MA
9.7 194 reviews

Hawksnest: Quiet 2br Apt, Heart Of The Berkshires

apartment, Pittsfield
This renovated Pittsfield apartment, conveniently located off Highway 7, provides easy access to Berkshire attractions like Kripalu Center for Yoga & Health, Lenox, and Tanglewood (all within 15 minutes).
The 2-bedroom, 1-bathroom rental offers a private entrance, a screened porch, shared backyard access, and accommodates up to 4 guests with amenities including air conditioning, free internet, and parking.
Spacious Historic Home In The Berkshires! - Pittsfield, MA
9.8 19 reviews

Spacious Historic Home In The Berkshires!

apartment, Pittsfield
This Pittsfield vacation home offers convenient access to the Colonial Theatre, Berkshire Athenaeum, and Berkshire Museum, all within a 10-minute walk, and is less than a mile from the Housatonic River and Barrington Stage Company.
This 3,300-square-foot house features seven bedrooms, two bathrooms, accommodates nine guests, and includes a fully equipped kitchen, fireplace, in-house washer, private garden, balcony, and parking.
Newly Renovated, And Spacious Great For Family - Pittsfield, MA
9.4 96 reviews

Newly Renovated, And Spacious Great For Family

apartment, Pittsfield
This one-bedroom apartment is situated in downtown Pittsfield, just minutes from the Berkshire Museum and the vibrant restaurants and shops of North Street.
The apartment is newly renovated with modern furniture and appliances, including a private parking spot, a jacuzzi, and access control on all doors for added security.
Spacious 2 Bedroom Downtown Very Nice Area! - Pittsfield, MA
9.6 55 reviews

Spacious 2 Bedroom Downtown Very Nice Area!

apartment, Pittsfield
This Pittsfield apartment rental is centrally located, a 5-minute walk from downtown's main street, offering easy access to numerous cafes, restaurants, shops, and a movie theater.
The two-bedroom, one-bathroom unit comfortably sleeps four guests and includes amenities such as air conditioning, internet, and parking.

Choose the Right Family Lodgings in Pittsfield, MA

These family-friendly lodgings in Pittsfield, MA offer plenty of room and keep city attractions within easy reach; find the perfect fit for your group.

Lakefront Home In The Heart Of The Berkshires - Pittsfield, MA
10 112 reviews

Lakefront Home In The Heart Of The Berkshires

apartment, Pittsfield
This lakefront home is located near Pittsfield, Massachusetts, within a 20-minute drive of Jiminy Peak ski resort and Tanglewood, and a 10-minute drive from the Berkshire Museum. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
The spacious 4-bedroom, 4-bathroom dwelling offers ample room for up to 10 guests. Enjoy stunning lake views, a private balcony, multiple living areas, three decks, a patio with a fire pit, and access to a garden, a Jacuzzi, and parking.
Hearts Desire Is Your Private Escape. - Pittsfield, MA
10 108 reviews

Hearts Desire Is Your Private Escape.

apartment, Lanesborough
This lakefront vacation home is located in Lanesborough, Massachusetts, just 6 miles from Mount Greylock State Reservation, Mount Greylock State Reservation Visitor Center, and Jiminy Peak Mountain Resort.
This 3-bedroom house, comfortably accommodating up to 6 guests, features a fully equipped kitchen, a fireplace, a spa tub, a garden, and a terrace, perfect for enjoying stunning lake views and relaxing after a day of exploring the area.
Cozy Pittsfield Gem W/ Deck, Gazebo & Fireplace! - Pittsfield, MA
10 2 reviews

Cozy Pittsfield Gem W/ Deck, Gazebo & Fireplace!

apartment, Pittsfield
This 3-bedroom, 3-bathroom Pittsfield apartment offers convenient access to outdoor recreation, located 8 miles from Bousquet Mountain Ski Area and 12 miles from Jiminy Peak Mountain Resort, with Ashuwillticook Rail Trail just 1 mile away and Pittsfield State Forest 8 miles distant.
This family-friendly residence accommodates up to 10 guests with a fully equipped kitchen, fireplace, Smart TV, in-unit washer/dryer, and outdoor spaces including a deck, balcony, and gazebo, plus a main-level bedroom and bathroom ideal for guests with mobility considerations.
Cozy Bungalow In Se Pittsfield - Pittsfield, MA
9.9 30 reviews

Cozy Bungalow In Se Pittsfield

apartment, Pittsfield
This Pittsfield apartment is located just 5 minutes from Bousquet Ski Mountain and 20 minutes from Jiminy Peak, offering easy access to outdoor activities in the Berkshires. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
The rental is a single-floor home with space for 5 guests. It features a fully equipped kitchen, a private garden, a deck and an enclosed porch, and a grill for cookouts, making it ideal for entertaining friends and family.

Frequently Asked Questions about accommodations in Pittsfield, MA

  • What are the top attractions and must-see sites in Pittsfield, MA?

    You definitely want to check out the Berkshire Museum, it has a great collection of art and history. The Clark Art Institute is also a must-see, they have an amazing collection of Impressionist and early modern art, and the grounds are beautiful. And don't forget about the Barrington Stage Company, they put on some great shows throughout the year.
  • What are the best accommodations in Pittsfield, MA?

    Among the accommodations in Pittsfield, MA, Hotel On North, Best Western Plus Berkshire Hills Inn & Suites and Hilton Garden Inn Lenox Pittsfield are the most popular ones.

  • Which cultural festivals and seasonal events should visitors attend in Pittsfield, MA?

    The biggest event is the 10 Days of Summer festival in July, it's a great way to experience local music and art. You should also check out the Pittsfield Farmers Market on Saturdays, it's a great place to get fresh produce and local crafts. And if you're in town during the fall, you can't miss the foliage, it's absolutely stunning.
  • What are the best accommodations with a pool in Pittsfield, MA?

  • What are the most convenient modes of transportation within Pittsfield, MA?

    Pittsfield is pretty walkable, especially downtown. You can also take the bus, the Berkshire Regional Transit Authority has routes throughout the city. If you're planning on exploring the surrounding area, renting a car is your best bet.
  • What are the best accommodations with a jacuzzi in Pittsfield, MA?

  • What outdoor activities and adventures are popular in and around Pittsfield, MA?

    There's plenty to do outdoors in Pittsfield. You can hike or bike the Appalachian Trail, go kayaking on Lake Onota, or visit the nearby Mount Greylock State Reservation, the highest point in Massachusetts. You can also check out the Taconic Crest Trail, which runs along the Taconic Mountains.
  • What are the best accommodations for families and kids in Pittsfield, MA?

    The best accommodations for families and kids in Pittsfield, MA are Hotel On North, Best Western Plus Berkshire Hills Inn & Suites and Hilton Garden Inn Lenox Pittsfield.

  • What types of accommodations are available in Pittsfield, MA?

    You can find everything from budget-friendly motels to upscale hotels in Pittsfield. There are also a few bed and breakfasts and vacation rentals available. You can also find some great places to stay in the nearby towns of Lenox and Stockbridge.
  • What are the best pet friendly accommodations in Pittsfield, MA?

    The best pet friendly accommodations in Pittsfield, MA are Hotel On North, Best Western Plus Berkshire Hills Inn & Suites and Hilton Garden Inn Lenox Pittsfield.

  • When is the best time to visit Pittsfield, MA?

    The best time to visit Pittsfield is in the fall, when the leaves change color. It's also a great time to visit in the summer, when the weather is warm and there are lots of outdoor activities to enjoy. You can find some great deals on accommodations during the shoulder seasons, too.
  • What are the best accommodations with parking in Pittsfield, MA?

    Hotel On North, Best Western Plus Berkshire Hills Inn & Suites and Hilton Garden Inn Lenox Pittsfield are the best accommodations with parking in Pittsfield, MA.

  • What local dishes and culinary experiences are a must-try in Pittsfield, MA?

    You have to try the Berkshire pork. It's a local specialty, and there are plenty of restaurants in Pittsfield that serve it. You should also check out the local breweries, they're making some really great craft beers. You can also find some great Italian food in Pittsfield, it's a popular cuisine here.
  • In which part of Pittsfield, MA should you consider renting accommodation?

    Downtown Pittsfield is a good choice, it's close to all the action and has a good selection of restaurants and shops. If you're looking for something quieter, you might want to consider staying in the nearby town of Lenox, which is known for its beautiful scenery and charming shops.

Popular destinations

Best Pittsfield, MA accommodation with a kitchen

Dancing Horse Lodge - Pittsfield, MA
9.7 375 reviews

Dancing Horse Lodge

apartment, Pittsfield
This vacation rental is located in the mountains, just a short drive from Pittsfield's cultural attractions like the Colonial Theater, Berkshire Museum, and Housatonic River. The house has earned excellent ratings for its cleanliness, location, and overall experience.
The home has 3 bedrooms and 1 bathroom, comfortably accommodating up to 6 guests. Enjoy amenities like a fully equipped kitchen, a garden, and a relaxing mountain setting.
Hidden Oasis In The Mountains By Evergreen Home - Pittsfield, MA
9.9 170 reviews

Hidden Oasis In The Mountains By Evergreen Home

apartment, Pittsfield
This Berkshire County colonial-style home sits atop a hill overlooking October Mountain, seven minutes from Bousquet Mountain Ski Area, seven minutes from Lenox, and nine minutes from Pittsfield.
This 3,600-square-foot house features five bedrooms, three bathrooms, and accommodates up to ten guests, boasting a hot tub, home gym, pool table, and proximity to hiking, skiing, and golfing.
Cozy Escape To The Berkshires - Pittsfield, MA
10 3 reviews

Cozy Escape To The Berkshires

apartment, Pittsfield
This Southeast Pittsfield rental is situated in a quiet neighborhood perfect for walks, offering convenient access to the Berkshires' museums, music venues, theaters, skiing, and hiking.
This two-bedroom, one-bathroom suite accommodates up to four guests and features a fully stocked kitchen, a king-sized bed, a queen-sized bed, a walk-in shower, an in-unit washer and dryer, keyless entry, and Smart TVs.
Huge Yard W/ Patio, Playset! Berkshires Retreat - Pittsfield, MA
No reviews

Huge Yard W/ Patio, Playset! Berkshires Retreat

house, Pittsfield
This Pittsfield house is located in the Berkshires, 9.9 miles from Cranwell Spa & Golf Club, 11 miles from Tanglewood, and 16 miles from the Norman Rockwell Museum.
This 1540 sq ft home features 3 bedrooms, 2 bathrooms, a full kitchen with a dishwasher and microwave, air conditioning, a terrace, a garden with a playset, and an on-site fitness center, with parking and a guest capacity of 11.

Neighborhoods and points of interest in Pittsfield, MA

Best Pittsfield, MA accommodation with parking

Lake House Onota Lake - Pittsfield, MA
10 2 reviews

Lake House Onota Lake

apartment, Pittsfield
This three-bedroom, two-bathroom lakeside house on Lake Onota in Pittsfield, Massachusetts, is minutes from several ski areas and a 15-minute drive from Tanglewood.
The 8-guest home offers direct lake access for swimming and boating, a fully equipped kitchen, parking, internet, and proximity to numerous outdoor recreational opportunities.
Spacious Historic Home In The Berkshires! - Pittsfield, MA
9.7 21 reviews

Spacious Historic Home In The Berkshires!

apartment, Pittsfield
This 5-bedroom vacation rental is conveniently located just minutes from downtown Pittsfield, a short drive from the Berkshires' beauty and attractions, and only 7 miles from the renowned Tanglewood music venue.
This spacious home features a fully equipped kitchen, a fireplace, a soaker tub, a covered porch, and a backyard, perfect for families or groups of up to 9 guests.
Explore The Berkshires From This Charming Home. - Pittsfield, MA
9.8 32 reviews

Explore The Berkshires From This Charming Home.

apartment, Pittsfield
This centrally located accommodation in Pittsfield offers easy access to various attractions within short driving distances, including ski resorts, charming towns, and cultural attractions. Guests have rated this accommodation as excellent for its cleanliness and location.
The accommodation has 2 bedrooms, 1 bathroom, and can accommodate up to 6 guests. It features a fully equipped kitchen, air conditioning, parking, and access to streaming services. Guests can enjoy the charming towns nearby, visit cultural attractions, attend live music performances at Tanglewood, or go skiing at nearby resorts.
Marie's Place, Unit 1 - Pittsfield, MA
9.9 119 reviews

Marie's Place, Unit 1

apartment, Pittsfield
This Pittsfield apartment is conveniently located just a 7-minute drive from the Bosquet ski area and 28 minutes from Jiminy Peak, making it ideal for winter sports enthusiasts. The apartment enjoys excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
This 3-bedroom rental can accommodate up to 6 guests and features a spacious eat-in kitchen and living room. Enjoy the enclosed front porch or the small outside deck, relax with the provided wet towel basket, and take advantage of the off-street parking for two cars.

Best Pittsfield, MA lodging with a pool

Among the 288 accommodations in Pittsfield, MA, here are the 2 best ones with a pool

Lenox Grand Colonial With Pool By Evergreen Home - Pittsfield, MA
10 45 reviews

Lenox Grand Colonial With Pool By Evergreen Home

apartment, Lenox
Lenox Grand Colonial With Pool By Evergreen Home - Pittsfield, MA
10 3 reviews

Lenox Grand Colonial With Pool By Evergreen Home

apartment, Lenox

Browse 5-Star Accommodations in Pittsfield, MA

Comfort and a prime location define these luxury lodgings in Pittsfield, MA, each hand-selected with your total relaxation in mind.

Extended Stay- Full Kitchen 1br Apartment In Downtown Pittsfield - Pittsfield, MA
10 1 review

Extended Stay- Full Kitchen 1br Apartment In Downtown Pittsfield

apartment, Pittsfield

Top-Rated Pet-Friendly Lodgings in Pittsfield, MA

Traveling with a pet to Pittsfield, MA is effortless when your lodging is equipped with nearby dog parks and city walks right on the doorstep.

Spacious Historic Home In The Berkshires! - Pittsfield, MA
9.0 1 review

Spacious Historic Home In The Berkshires!

house, Pittsfield
Friendly Hills | Passive Home  Ev Charger - Pittsfield, MA
9.8 41 reviews

Friendly Hills | Passive Home Ev Charger

apartment, Hancock
Modern Gem In The Heart Of Berkshires - Pittsfield, MA
9.9 70 reviews

Modern Gem In The Heart Of Berkshires

apartment, Pittsfield
Net Zero Home With Rustic Berkshire Charm - Pittsfield, MA
9.9 133 reviews

Net Zero Home With Rustic Berkshire Charm

apartment, Pittsfield
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