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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 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.
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
This Pittsfield apartment is located near Tanglewood Music Center, Colonial Theater, Herman Melville's Arrowhead, and Hancock Shaker Village.
This one-bedroom, one-bathroom unit accommodates up to four guests and features a king bed, a sofa bed, air conditioning, and internet.
Spacious Historic Home In The Berkshires! - Pittsfield, MA
9.7 22 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.

Best Pittsfield, MA vacation rentals with air conditioning

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.
Beautiful Waterfront Home With Deep Water Dock On Onota Lake. Huge Covered Deck. - Pittsfield, MA
9.6 89 reviews

Beautiful Waterfront Home With Deep Water Dock On Onota Lake. Huge Covered Deck.

apartment, Pittsfield
This waterfront vacation home on Onota Lake in Pittsfield offers direct access to water sports and is located within 3 miles of Tanglewood Music Center, Crane Museum of Papermaking, and Colonial Theater, with Bousquet Ski Area just 2 miles away.
This 1800 square foot house features 3 bedrooms, 2 bathrooms, sleeps 10, and includes a modern kitchen with a fridge, microwave, and dishwasher, plus a private dock and a large covered deck for outdoor enjoyment.
Attractive Condo In The Berkshires. - Pittsfield, MA
9.7 40 reviews

Attractive Condo In The Berkshires.

apartment, Pittsfield
This Pittsfield apartment is conveniently located near the river and its canoe launch, making it an ideal choice for those seeking outdoor activities and a peaceful setting. The apartment consistently receives excellent ratings for its cleanliness, location, and overall user experience.
The apartment comfortably accommodates up to six guests with its three bedrooms and one bathroom. Amenities include a fully equipped kitchen, laundry facilities, a private garage, and a garden, ensuring a comfortable and convenient stay.
Large Open Floor Plan. Private Yet Close To Everything. Lovely Meadow Views - Pittsfield, MA
10 2 reviews

Large Open Floor Plan. Private Yet Close To Everything. Lovely Meadow Views

apartment, Pittsfield
This six-bedroom, four-bathroom Pittsfield rental is located a 5-minute walk from Canoe Meadows Wildlife Sanctuary and a 2-minute drive from the Housatonic River.
This spacious vacation home accommodates up to 14 guests and features air conditioning, Wi-Fi, a fully equipped kitchen with a dishwasher and microwave, and on-site parking, offering convenient access to the Berkshire Museum and Bousquet Ski Area.

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.

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.
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.
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.
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.

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.

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.
Lakefront Home On Ponstoosuc Lake, The Berkshires - Pittsfield, MA
10 25 reviews

Lakefront Home On Ponstoosuc Lake, The Berkshires

apartment, Lanesborough
This Lanesborough lake house boasts a prime Pontoosuc Lake location, offering 120 feet of private shoreline and proximity to Mount Greylock State Reservation (within 20 minutes).
The 2,600-square-foot home features three bedrooms, two bathrooms, sleeps eight, and includes a private dock, Weber grill, Roku TVs, and is near miniature golf, a driving range, and Krispy Kreme.
Beautiful Lenox Home, 3 Mi To Shakespeare & Co! - Pittsfield, MA
9.3 112 reviews

Beautiful Lenox Home, 3 Mi To Shakespeare & Co!

house, Lenox
This Lenox home is located just a short drive from Cranwell Spa & Golf Club, Tanglewood Musical Center, and the Norman Rockwell Museum, offering easy access to all that Lenox has to offer. The property has received excellent ratings for cleanliness, location, and overall user experience. This 3-bedroom home comfortably accommodates up to 6 guests in its 2,450 square feet of living space. Amenities include a fully equipped kitchen, air conditioning, a garden, a spa, parking, and free Wi-Fi.
House W/ View In The Berkshires. - Pittsfield, MA
9.6 9 reviews

House W/ View In The Berkshires.

house, Pittsfield
This vacation rental is located in the Berkshires, within a 30-minute drive of attractions like Tanglewood, The Mount, Naumkeag, MassMoca, Clark, and Hancock Village, offering easy access to the area's cultural and historical sites. The surrounding area is peaceful and tranquil, providing a welcome escape from the hustle and bustle of city life.
The home has an open-plan layout with expansive glass doors that connect the indoor and outdoor spaces and can accommodate up to 7 guests. Amenities include a fully equipped kitchen, a private garden, a wrap-around deck with stunning views, and a bonus den in the basement.

Best Pittsfield, MA vacation rentals with parking

Berkshire Lakefront Home W/pool-100%renovated - Pittsfield, MA
10 119 reviews

Berkshire Lakefront Home W/pool-100%renovated

apartment, Pittsfield
Cozy Escape To The Berkshires - Pittsfield, MA
10 3 reviews

Cozy Escape To The Berkshires

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

Modern Gem In The Heart Of Berkshires

apartment, Pittsfield
Cheerful 3 Bedroom House Abutting State Forest - Pittsfield, MA
No reviews

Cheerful 3 Bedroom House Abutting State Forest

house, Lenox

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.

Charming Apartment In Central Pittsfield - Pittsfield, MA
9.2 82 reviews

Charming Apartment In Central Pittsfield

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.

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

Lenox Grand Colonial With Pool By Evergreen Home

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

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

apartment, Richmond
3 Bedroom Home W/ Lake And Mountain Views Near Skiing, And Cultural Attractions! - Pittsfield, MA
8.4 9 reviews

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

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

Pine & Paddle | Pond Access Kayaks

apartment, Richmond

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.

Berkshire Mountain Lodge - Pittsfield, MA
8.9 1716 reviews

Berkshire Mountain Lodge

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

The Oliver Wendell Holmes Guesthouse @ Holmesdale

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.

Hearts Desire Is Your Private Escape. - Pittsfield, MA
10 108 reviews

Hearts Desire Is Your Private Escape.

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

Beautiful Lake-view Getaway!

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

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

apartment, Richmond
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