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195 Lodgings in Pittsfield, MA
9.5 37 reviews
Pittsfield, MA
10/13 – 10/18
$186/nighttotal: $930 (5 )
Spacious 2 Bedroom Downtown Very Nice Area!
1 3
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.
9.9 28 reviews
Pittsfield, MA
09/06 – 09/13
$232/nighttotal: $1624 (7 )
Cozy Bungalow In Se Pittsfield
1 2
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.
10 18 reviews
Pittsfield, MA
09/06 – 09/13
$279/nighttotal: $1953 (7 )
Beautiful & Serene Getaway
1 2
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.
9.9 93 reviews
Pittsfield, MA
10/13 – 10/18
$370/nighttotal: $1850 (5 )
Lake/mountain View Getaway
1 3
apartment , Pittsfield
This Pittsfield home, ideally located near Pontoosuc Lake, offers stunning views of the lake and Mount Greylock, with easy walking access to a public beach and boat rentals. The two-bedroom, two-bathroom house sleeps seven guests comfortably, boasting a fully equipped kitchen (fridge, freezer, microwave, dishwasher), a spacious living room, and a variety of sleeping arrangements including a king bed, twin-over-full bunk bed, and queen sofa bed, perfect for families or groups visiting the Berkshires.
10 65 reviews
Pittsfield, MA
09/03 – 09/06
$237/nighttotal: $711 (3 )
Comfy Quaint Tavern
1 2
apartment , Pittsfield
This one-bedroom apartment is located in the southeast section of Pittsfield, a residential neighborhood within walking distance of restaurants and a seasonal ice cream shop. The apartment has received excellent ratings for cleanliness and user experience, along with a very good rating for location. The apartment features a queen-size bed in the bedroom and a queen-size pull-out couch in the living room, comfortably accommodating up to three guests. Guests can enjoy modern amenities like a full kitchen, air conditioning, and off-street parking, as well as a unique 12-foot bar with 5 stools for relaxation and socializing.
8.8 8 reviews
Pittsfield, MA
07/01 – 07/31
$228/nighttotal: $6840 (30 )
1st Floor Mountain View Suite Ski On/off At Jiminy- Fully Redone Decor
1 1
apartment , Hancock
This Hancock slopeside condo is located within two miles of Jiminy Peak Mountain Resort, the Alpine Super Slide, and the Mountain Coaster, offering convenient access to area attractions. This 500-square-foot apartment features two bedrooms, one bathroom, sleeps four, and includes a fully equipped kitchen, in-unit entertainment, and access to an indoor pool, fitness center, and jacuzzi.
9.8 8 reviews
Pittsfield, MA
09/03 – 09/06
$499/nighttotal: $1497 (3 )
House W/ View In The Berkshires.
1 2
apartment , 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.
9.8 14 reviews
Pittsfield, MA
09/03 – 09/06
$642/nighttotal: $1926 (3 )
Spacious Historic Home In The Berkshires!
5 2
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.
9.9 210 reviews
Pittsfield, MA
09/06 – 09/13
$277/nighttotal: $1939 (7 )
Cantabile Life In The Berkshires
1 2
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.
Pittsfield, MA
08/21 – 08/24
$723/nighttotal: $2169 (3 )
New Built - Split Level House In The Berkshires
1 6
apartment , Lanesborough
This 3-bedroom, 3-bathroom Lanesborough rental is a newly built house offering 8 guests a peaceful retreat, located just a 3-minute walk to Pontoosuc Lake and a short drive from Jiminy Peak and downtown Pittsfield. This pet-friendly home features air conditioning, internet, a kitchen, and parking with EV charging, serving as an ideal base for exploring the Berkshires' numerous outdoor activities and cultural attractions.
Pittsfield, MA
10/13 – 10/18
$297/nighttotal: $1485 (5 )
Cozy Cottage In The Berkshires
1 3
apartment , Pittsfield
This one-bedroom condo in Pittsfield is located near the Berkshire Museum and Lichtenstein Center for the Arts, with Guido's Marketplace and Lee Premium Outlets approximately 2 miles away. This accommodation offers free internet, air conditioning, a PC, a TV with a home theater system, an in-unit washer/dryer, a mobile dishwasher, and a complimentary coffee bar, comfortably sleeping up to 4 guests.
9.9 35 reviews
Pittsfield, MA
09/03 – 09/06
$593/nighttotal: $1779 (3 )
The Guest House At Cottage Farm
3 2
apartment , Pittsfield
This Pittsfield, MA house rental boasts 2,300 square feet of space and is located on 12 private acres, minutes from Tanglewood, Barrington Stage Company, and other Berkshire attractions. The three-bedroom, three-bathroom home features a fully remodeled kitchen, open floor plan, outdoor BBQ area, and accommodates up to six guests with free on-site 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.
9.8 7 reviews
Pittsfield, MA
07/01 – 07/31
$228/nighttotal: $6840 (30 )
Game Night Suite At Jiminy Peak Ski Onoff Sleeps 4
1 1
apartment , Hancock
This Hancock, MA apartment is located at the base of Jiminy Peak Mountain Resort, minutes from Lanesboro, Pittsfield, and North Adams, offering easy access to both mountain activities and local attractions. This 500-square-foot condo features a gamer-themed design, a king bed and queen pull-out sofa sleeping four, a fully equipped kitchenette with an air fryer and Keurig, and access to Jiminy Peak's amenities including a heated pool and hot tubs.
9.9 77 reviews
Pittsfield, MA
08/21 – 08/24
$381/nighttotal: $1143 (3 )
Cozy Cottage In Berkshires: Minutes To Jiminy Peak
4 6
apartment , Lanesborough
This Lanesborough apartment is located in a quiet residential neighborhood at the top of a hill, just 1 mile from the Ashuwillticook Rail Trail and less than a mile from Elle Day Spa. The 4-bedroom home can accommodate up to 6 guests and offers a spacious backyard with a fire pit, a cozy sunken sunroom with a fireplace, and mountain views.
8.0 21 reviews
Pittsfield, MA
07/01 – 07/31
$184/nighttotal: $5520 (30 )
Wow-new Ski Onoff Suite By Pool Sleeps 4 Jiminy Pk
1 1
apartment , Hancock
This Hancock, MA apartment offers convenient access to Jiminy Peak, approximately 20 miles from both Tanglewood and Cranwell Spa & Golf Club. This 500-square-foot unit features one bedroom, one bathroom, sleeps four, and includes a fully equipped kitchen, in-unit laundry, free Wi-Fi, and access to a swimming pool, jacuzzi, and fitness center.
9.8 43 reviews
Pittsfield, MA
10/13 – 10/18
$392/nighttotal: $1960 (5 )
3 Bedroom , 2 Bath, Beautifully Appointed Home
3 3
apartment , Pittsfield
This Pittsfield home is conveniently located near popular attractions like Tanglewood, the Norman Rockwell Museum, and Mass MOCA, making it a great base for exploring the city. The home has received excellent ratings for its location, cleanliness, and overall experience. This 3-bedroom, 2-bathroom house comfortably accommodates up to 6 guests. Amenities include a fully equipped kitchen, air conditioning, a garden, and a fitness center, ensuring a comfortable and enjoyable stay.
Best Pittsfield, MA lodging with a pool
Among the 195 accommodations in Pittsfield, MA, here are the 4 best ones with a pool
10 3 reviews
Pittsfield, MA
07/03 – 07/06
$373/nighttotal: $1119 (3 )
Escape To The Heart Of Jiminy Peak: Country Inn Condo With Full Kitchen, 2 Bths
1 2
apartment , Hancock
This ski-in/ski-out condo at Jiminy Peak Resort in Hancock, Massachusetts offers direct access to 45 slopes. The spacious one-bedroom unit features two bathrooms, a fully equipped kitchen with microwave and dishwasher, and accommodates up to four guests, boasting resort amenities including a pool, jacuzzi, and fitness center.
Pittsfield, MA
09/06 – 09/13
$1712/nighttotal: $11984 (7 )
Elegant 6-br Berkshires Estate 10 Min To Bousquet
6 2
apartment , Pittsfield
This spacious 7800 sq ft vacation home in Pittsfield offers 6 bedrooms and 6 bathrooms, accommodating up to 14 guests, and is located a 4-minute drive from the Colonial Theater and Berkshire Museum. Enjoy amenities such as a shared swimming pool, hot tub, private garden, patio, barbecue, fireplace, foosball, and billiards, with Wi-Fi and air conditioning provided.
Pittsfield, MA
07/01 – 07/31
$622/nighttotal: $18660 (30 )
Available February 17-21 2025. Sleep 8 - 2-bed Apt On Jiminy Peak. Ski In/out!
3 1
apartment , Hancock
This ski-in/ski-out condo is located at the base of Jiminy Peak Mountain Resort in Hancock, Massachusetts, offering easy access to downhill skiing, snowboarding, and the mountain coaster. This three-bedroom, two-bathroom unit sleeps eight comfortably with a king bed, two doubles, and a queen sleeper sofa, and includes a full kitchen, two flat-screen TVs, and access to resort amenities such as indoor/outdoor pools, hot tubs, a sauna, tennis courts, and a game room.
9.8 12 reviews
Pittsfield, MA
07/01 – 07/31
$181/nighttotal: $5430 (30 )
Mountain View Jiminy Peak Ski On Off Sleeps 4
1 1
apartment , Hancock
This one-bedroom suite is located at the base of Jiminy Peak Mountain in Hancock, Massachusetts, providing direct access to Jiminy Peak Mountain Resort and its amenities. The 500-square-foot condo features a king bed, queen pull-out sofa, full kitchen with dishwasher and microwave, and on-site access to a heated pool, hot tub, and fitness center; it comfortably sleeps four guests and offers proximity to the Jiminy Peak Mountain Resort Adventure Park.
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?
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?
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 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?
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.
Destinations nearby
Best Pittsfield, MA accommodation with a garden
10 33 reviews
Pittsfield, MA
10/13 – 10/18
$271/nighttotal: $1355 (5 )
Lenox Retreat Near Tanglewood W/ Rescued Donkeys
1 3
apartment , Lenox
This Lenox apartment, a renovated 1770s stagecoach stop, is located near Tanglewood and other Berkshire attractions. The two-bedroom unit, sleeping up to five guests, features a kitchenette, garden access, on-site mini donkeys (scheduling required), and provides paper goods for convenient stays.
Pittsfield, MA
07/01 – 07/31
$367/nighttotal: $11010 (30 )
Berkshires/lenox
1 1
apartment , Lenox
This Lenox apartment is situated in an 1840 Victorian home, a short distance from the Bousquet Ski Area and other attractions like Butternut. The charming Berkshires setting offers a peaceful retreat for travelers seeking a unique experience. This cozy, one-bedroom unit features a private entrance and fenced patio area. The apartment offers amenities including a full kitchen, a swimming pool, a garden, parking, and free laundry facilities, making it ideal for couples seeking a comfortable and convenient stay.
9.6 100 reviews
Pittsfield, MA
09/06 – 09/13
$576/nighttotal: $4032 (7 )
The Oliver Wendell Holmes Guesthouse @ Holmesdale
1 2
apartment , Pittsfield
Historic Holmesdale Cottage is situated on 16 acres of a private estate on the Pittsfield/Lenox border, offering tranquility amidst the Berkshires. With excellent user, location, and cleanliness ratings, this one-bedroom, one-bathroom cottage accommodates up to four guests, featuring a king-size bed and a spiral staircase. Guests enjoy access to a pool, tennis court, and reflecting pond, along with modern conveniences like central AC/heat, high-end appliances, and a king-size iComfort mattress with luxury linens. The cottage retains original details like wood floors and a fireplace, while offering stunning views of the Berkshire mountains.
9.7 80 reviews
Pittsfield, MA
09/06 – 09/13
$393/nighttotal: $2751 (7 )
Berkshire's Sweet Spot 2-pool And Spa
3 2
apartment , Pittsfield
This Pittsfield duplex is conveniently located in central Berkshire County, within walking distance of downtown Pittsfield, Tanglewood, and the Mahaiwe Performing Arts Center. The apartment has received excellent ratings for location, cleanliness, and overall user experience. The home features three bedrooms and a queen-sized sofa bed, comfortably sleeping up to eight guests. Enjoy a private backyard with a seasonal pool, a year-round hot tub, a fully equipped kitchen, and modern amenities like smart TVs.
Neighborhoods and points of interest in Pittsfield, MA
Best Pittsfield, MA accommodation with a kitchen
10 8 reviews
Pittsfield, MA
07/01 – 07/31
$51/nighttotal: $1530 (30 )
Your Glamping Getaway
1 1
glamping , East Nassau
This refurbished RV glamping site is located on a 75-acre property in East Nassau, offering a rural retreat with access to local natural beauty. Accommodating up to 4 guests, this glamping experience features a full gas range oven, refrigerator, toilet with shower, a cold spring-fed pool, and a gas grill, all set within expansive grounds perfect for nature observation.
9.4 92 reviews
Pittsfield, MA
09/06 – 09/13
$101/nighttotal: $707 (7 )
Newly Renovated, And Spacious Great For Family
1 2
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.
9.6 5 reviews
Pittsfield, MA
07/01 – 07/31
$228/nighttotal: $6840 (30 )
Mountain View Suite At Jiminy Peak - Ski On Off - Near Elevator, Pool, And Lobby
1 1
apartment , Hancock
This Hancock, Massachusetts apartment is located at the base of Jiminy Peak Mountain Resort, offering easy access to Lanesboro, Pittsfield, and North Adams. The 500-square-foot suite features two bedrooms, one bathroom, and sleeps four, boasting a fully equipped kitchenette with modern appliances, a heated outdoor pool, hot tubs, and access to Jiminy Peak's year-round activities.
10 3 reviews
Pittsfield, MA
07/01 – 07/31
$184/nighttotal: $5520 (30 )
Must See Cabin Suite Jiminy Sleeps 4- Mountainview
1 1
apartment , Hancock
This Hancock, Massachusetts condo is located directly on Jiminy Peak Mountain, providing ski-in/ski-out access in winter and immediate access to hiking trails in summer, plus proximity to Jiminy Peak Mountain Resort's Adventure Park. The fully renovated one-bedroom suite sleeps four with a king bed, queen sofa bed, kitchenette (including a Keurig), two TVs, and access to Jiminy Peak's year-round heated pool, hot tubs, and fitness center.
