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Pittsfield, MA vacation rentals
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Best Vacation rentals and Airbnb offers in Pittsfield, MA

Search Vacation Rentals near the Old Town in Pittsfield, MA

These downtown Pittsfield, MA vacation rentals put you near top restaurants, sights, and transit. Enjoy the heart of the city action.

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

Spacious Historic Home In The Berkshires!

house, Pittsfield
This five-bedroom Pittsfield vacation home is conveniently located 7.6 miles from Tanglewood and 7.8 miles from the Cranwell Spa & Golf Club, offering easy access to area attractions.
The 3,300-square-foot property boasts a fully equipped kitchen, in-house laundry, a fireplace, and accommodates up to 17 guests, perfect for large families or groups visiting the Berkshires.
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.

Best Pittsfield, MA vacation rentals with air conditioning

Bb's Central Berkshire Home - Pittsfield, MA
9.9 97 reviews

Bb's Central Berkshire Home

apartment, Pittsfield
This Pittsfield house, situated on a quiet cul-de-sac near walking trails and a park with a playground, offers easy access to Lenox and Lee (15 minutes), Great Barrington (30 minutes), Mass MoCA, Mount Greylock State Reservation, The Clark Art Institute, and Jiminy Peak Ski Resort (30-45 minutes).
The remodeled two-story home features three bedrooms, two bathrooms, sleeps up to ten guests, includes a finished basement with a pull-out sofa and kids' play area, and provides a backyard with a BBQ and fire pit.
Lakefront Cottage W/ Dock & Kayaks - Pittsfield, MA
9.8 10 reviews

Lakefront Cottage W/ Dock & Kayaks

apartment, Lanesborough
This lakefront cottage in Lanesborough offers direct lake access and is located 5 miles from Barrington Stage Company and the Ashuwillticook Rail Trail.
This 2-bedroom, 1-bathroom apartment accommodates up to 8 guests with 6 beds and features a fully equipped kitchen, fireplace, high-speed WiFi, a deck with lake views, and a firepit, with Jiminy Peak 10 miles away and Tanglewood 13 miles away.
Beautiful Victorian Apartment On Bartlett Ave - Pittsfield, MA
9.0 2 reviews

Beautiful Victorian Apartment On Bartlett Ave

apartment, Pittsfield
This 3rd-floor penthouse, located on a quiet street in Pittsfield, offers convenient access to North Street's dining, shopping, and cultural attractions, and is a short drive to Tanglewood.
This 3-bedroom, 1-bathroom condo accommodates up to 6 guests and features original stained-glass windows, a rooftop deck, a stone terrace, and an open-plan living and kitchen area.
Marie's Place - Pittsfield, MA
9.8 324 reviews

Marie's Place

apartment, Pittsfield
This apartment is located in Pittsfield, just a short drive from the city's cultural attractions like the Berkshire Museum, Colonial Theater, and Barrington Stage Company. It has excellent user, location, and cleanliness ratings, making it a great choice for travelers. The apartment is fully furnished and comfortably accommodates up to four guests. You'll enjoy convenient on-site laundry facilities, off-street parking, and access to the yard and parking area, making your stay hassle-free.

Frequently Asked Questions about vacation rentals in Pittsfield, MA

  • What should a first-time visitor not miss in Pittsfield, MA?

    You should definitely check out the Berkshire Museum for a unique blend of art, science, and history. Also, a visit to the historic Colonial Theatre is a must for any first-timer, and you can't miss the stunning views from the top of Mount Greylock, the highest point in Massachusetts.
  • What are the best Airbnb and vacation rentals in Pittsfield, MA?

    Berkshire Mountain Lodge, Honeysuckle Rose Cottage and Dancing Horse Lodge are the most popular Airbnb and vacation rentals in Pittsfield, MA among travelers.

  • Which neighborhood in Pittsfield, MA should you consider for a vacation rental?

    If you want to be close to the action, the downtown area is great. If you prefer a quieter stay, the historic and charming Morningside neighborhood is a good choice. Both offer a variety of rental options.
  • What are the most popular Airbnbs in Pittsfield, MA?

    Among the Airbnbs in Pittsfield, MA, Honeysuckle Rose Cottage, Dancing Horse Lodge and Marie's Place are the most popular ones.

  • What are the top family-friendly attractions in Pittsfield, MA?

    The Berkshire Museum is a great option, especially for kids interested in dinosaurs and natural history. The Hancock Shaker Village is another great choice, with lots of interactive exhibits and activities for families. And don't forget about the Pittsfield Farmers Market, which runs every Saturday from May to October.
  • What are the best vacation rentals with a pool in Pittsfield, MA?

    Berkshire Mountain Lodge, The Nest At Birdland and *Berkshire's Sweet Spot-close To Ski/spa Open are the best vacation rentals with a pool in Pittsfield, MA.

  • When is the best time to book a vacation rental in Pittsfield, MA?

    The best time to book a vacation rental in Pittsfield depends on what you're looking for. If you want to experience the lively summer festivals, book in July or August. If you prefer quieter and more affordable options, consider booking in the spring or fall.
  • What are the best rentals for families and kids in Pittsfield, MA?

    The best rentals for families and kids in Pittsfield, MA are Berkshire Mountain Lodge, Marie's Place and Heart Of The Berkshires.

  • What events or festivals should visitors check out in and around Pittsfield, MA?

    The annual Tanglewood Music Festival, held in nearby Lenox, is a must-see for music lovers. The Pittsfield Farmers Market is a great way to experience local culture and enjoy fresh produce. And if you're here in September, don't miss the Berkshire International Film Festival.
  • What are the best rentals or Airbnbs with a jacuzzi in Pittsfield, MA?

  • What are the best budget-friendly activities in Pittsfield, MA?

    The Pittsfield Public Library offers free events and programs throughout the year. The Pittsfield State Forest is a great place for hiking and enjoying nature, and it's free to enter. And don't forget about the beautiful views from the top of Mount Greylock - it's free to hike up the mountain!
  • What are the best restaurants with local dishes in Pittsfield, MA?

    For a taste of classic New England, try the Red Lion Inn, which has been serving up delicious food since the 18th century. If you're looking for something a little more modern, check out the downtown restaurant scene, where you'll find a variety of options, including the popular The Porches.
  • What are the best walking or cycling routes in Pittsfield, MA?

    The Pittsfield Greenway is a great option for both walking and cycling, offering scenic views of the city and the surrounding Berkshire Hills. The Taconic Crest Trail is a popular hiking destination, offering stunning views of the surrounding mountains.
  • Are there pet-friendly attractions in Pittsfield, MA?

    Yes, there are many pet-friendly attractions in Pittsfield. The Pittsfield State Forest is a great place to take your dog for a walk or hike, and many restaurants in the downtown area have outdoor seating that is pet-friendly.
  • What are the benefits of choosing a vacation rental in Pittsfield, MA?

    Vacation rentals offer more space and privacy than hotels, and they often come with kitchens, making it easier to cook your own meals. They can also be a more affordable option, especially for families or groups.
  • What are the top sports attractions and facilities in Pittsfield, MA?

    The city has a great sports scene, including the Wahconah Park, home to the Pittsfield Suns, a collegiate summer baseball team. The city also has several parks and recreation centers, including the Pittsfield YMCA, which offers a variety of fitness classes and programs.

Popular destinations

Find the Best Vacation Rentals with Balconies in Pittsfield, MA

Enjoy your own private terrace with city skyline views at these vacation rentals in Pittsfield, MA.

3 Acres, Mtn Views, Hot Tub, Steps To Winery - Pittsfield, MA
No reviews

3 Acres, Mtn Views, Hot Tub, Steps To Winery

apartment, Richmond
This pet-friendly vacation home in Richmond is located a short walk from Balderdash Cellars and a 3-minute drive from Hancock Shaker Village, offering prime access for outdoor activities like kayaking and motor boating.
This 2740 sq ft apartment features 3 bedrooms, 2 bathrooms, and accommodates up to 6 guests, with amenities including a full kitchen, air conditioning, a jacuzzi, a terrace, a garden, and on-site covered parking.
Dharma Grove - Bask In The Light - Pittsfield, MA
10 1 review

Dharma Grove - Bask In The Light

apartment, Richmond
This 3-bedroom, 2-bathroom Richmond rental is located on 2.5 acres, offering a quiet retreat just 1 minute from Balderdash Cellars and 4 minutes from Hancock Shaker Village.
This 2060 sq ft home accommodates up to 6 guests and features a fully-equipped kitchen, high-speed Wi-Fi, free parking, a garden, terrace, and is dog-friendly.
Pine & Paddle | Pond Access  Kayaks - Pittsfield, MA
No reviews

Pine & Paddle | Pond Access Kayaks

cottage, Richmond
This 2-bedroom, 1-bathroom apartment in Richmond provides a country cottage experience with a private community beach on Richmond Pond, a short walk away, and is near Tanglewood and Bousquet.
This pet-friendly unit accommodates up to 4 guests and features a newly renovated kitchen with a convection oven and induction cooktop, a wood-burning fireplace, a balcony for dining, and access to local attractions like apple picking and hiking trails.
Timpani Corners | Private Pond  Ac - Pittsfield, MA
No reviews

Timpani Corners | Private Pond Ac

cabin, Lenox
This pet-friendly cabin offers a unique waterfront setting on a private quarry pond beside a brook in Lenox, located 9 miles from Tanglewood and The Mount, and 6 miles from Bousquet Mountain Ski Area.
This 820 sq ft retreat accommodates up to 6 guests with 3 bedrooms, a full kitchen, air conditioning, and Wi-Fi, situated on a spacious yard with an outdoor grill, providing easy access to local attractions and a full-time local support team.

Neighborhoods and points of interest in Pittsfield, MA

Our Favorite Family-Friendly Vacation Rentals in Pittsfield, MA

Make family travel to Pittsfield, MA seamless with spacious vacation rentals located just minutes from top city attractions.

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

Lenox Grand Colonial With Pool By Evergreen Home

apartment, Lenox
This Lenox vacation home is situated in a rural setting, two miles from the Housatonic River, Arrowhead Museum, and Herman Melville's Arrowhead.
This 3,020-square-foot house features four bedrooms, three bathrooms, sleeps eight guests, and includes a private pool, fully equipped kitchen, and free Wi-Fi.
Cantabile Life In The Berkshires - Pittsfield, MA
9.9 226 reviews

Cantabile Life In The Berkshires

apartment, Pittsfield
This apartment is located in a quiet, friendly neighborhood in Pittsfield, just minutes from several lakes, mountains, and attractions like Tanglewood and Bousquet Ski Area. It boasts excellent ratings for location, cleanliness, and user satisfaction.
The rental offers three bedrooms and two bathrooms, comfortably accommodating up to six guests. Enjoy the spacious living areas, well-equipped kitchen, and outdoor space, plus family-friendly amenities like games, a piano, and child-friendly equipment.
Cozy & Safe, New One Bedroom Apartment - Pittsfield, MA
9.9 20 reviews

Cozy & Safe, New One Bedroom Apartment

apartment, Pittsfield
This three-bedroom, one-bathroom Pittsfield apartment rental is located in a quiet neighborhood minutes from downtown, offering easy access to shops, restaurants, and a short drive to Tanglewood and Mass MoCA.
The 3-bedroom unit features a spacious kitchen, large living area, in-unit laundry, enclosed backyard with porch and grill, accommodating up to 7 guests and providing a tranquil escape near numerous parks and walking trails.
Lenox Grand Colonial With Pool By Evergreen Home - Pittsfield, MA
10 46 reviews

Lenox Grand Colonial With Pool By Evergreen Home

apartment, Lenox
This spacious Lenox house, located on a quiet cul-de-sac ten minutes from downtown Lenox and Tanglewood, offers convenient access to shops, restaurants, and numerous Berkshire attractions.
The 3000-square-foot, four-bedroom home comfortably sleeps eight, boasting a private pool, extensive backyard, fully equipped kitchen, and in-home entertainment options including a ping pong table, all within a short drive of Mass MoCA, the Red Lion Inn, and various wineries and ski resorts.

Best Pittsfield, MA vacation rentals with parking

Attractive Condo In The Berkshires. - Pittsfield, MA
9.7 40 reviews

Attractive Condo In The Berkshires.

apartment, Pittsfield
Renovated Pittsfield Colonial By Evergreen Home - Pittsfield, MA
9.9 101 reviews

Renovated Pittsfield Colonial By Evergreen Home

apartment, Pittsfield
Beautiful Blue Studio Downtown 5 Mins To Downtown - Pittsfield, MA
9.2 68 reviews

Beautiful Blue Studio Downtown 5 Mins To Downtown

apartment, Pittsfield
Berkshire Getaway Ranch 3 Acres + Saltwater Pool - Pittsfield, MA
9.8 106 reviews

Berkshire Getaway Ranch 3 Acres + Saltwater Pool

apartment, Pittsfield

Popular Luxury Vacation Rentals in Pittsfield, MA

Elevate your travel experience with a luxury rental in Pittsfield, MA, where high-end design meets a prime location.

Dancing Horse Lodge - Pittsfield, MA
9.7 376 reviews

Dancing Horse Lodge

apartment, Pittsfield

Top Dog-Friendly Vacation Rentals in Pittsfield, MA

Stay in a pet-friendly vacation rental in Pittsfield, MA situated near dog parks and city walks, ensuring a comfortable stay for both you and your pet.

Sunny 1 Bedroom Apartment Spacious Downtown - Pittsfield, MA
8.5 11 reviews

Sunny 1 Bedroom Apartment Spacious Downtown

apartment, Pittsfield
Hidden Oasis In The Mountains By Evergreen Home - Pittsfield, MA
9.9 170 reviews

Hidden Oasis In The Mountains By Evergreen Home

apartment, Pittsfield
Pine & Paddle | Pond Access  Kayaks - Pittsfield, MA
9.8 18 reviews

Pine & Paddle | Pond Access Kayaks

apartment, Richmond
3 Bedroom Home W/ Lake And Mountain Views Near Skiing, And Cultural Attractions! - Pittsfield, MA
8.4 10 reviews

3 Bedroom Home W/ Lake And Mountain Views Near Skiing, And Cultural Attractions!

apartment, Pittsfield

Top-Rated Vacation Rentals with a Pool in Pittsfield, MA

Choose a Pittsfield, MA rental with a pool for a refreshing swim right in the heart of the city.

The Oliver Wendell Holmes Guesthouse @ Holmesdale - Pittsfield, MA
9.6 103 reviews

The Oliver Wendell Holmes Guesthouse @ Holmesdale

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

Lenox Grand Colonial With Pool By Evergreen Home

apartment, Lenox
Lenox Grand Colonial With Pool By Evergreen Home - Pittsfield, MA
10 46 reviews

Lenox Grand Colonial With Pool By Evergreen Home

apartment, Lenox
Berkshire Getaway Ranch 3 Acres + Saltwater Pool - Pittsfield, MA
9.8 106 reviews

Berkshire Getaway Ranch 3 Acres + Saltwater Pool

apartment, Pittsfield

Check Out Vacation Rentals with a Hot Tub in Pittsfield, MA

Unwind after exploring the city with a private hot tub in your own Pittsfield, MA vacation rental.

Beautiful Lake-view Getaway! - Pittsfield, MA
9.9 70 reviews

Beautiful Lake-view Getaway!

apartment, Pittsfield
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