The best deals on hotels near Pittsfield High School in Pittsfield, MA.

Access unmatched hotel rates and frequent flash deals on rooms.

Save up to 70% when booking as a group. Select 9+ rooms to get started.

Top 24 Hotels Near Pittsfield High School
300 East St Pittsfield, MA 1201



Berkshire Inn

150 West Housatonic St Pittsfield, Massachusetts

This practical drive to Pittsfield High School is a key feature of Berkshire Inn, as it allows for a smooth and simple commute.

Arrivals at Berkshire Inn may present a simple reception, self-serve coffee, and accessible parking configured for routine travel. Each guest room typically offers climate control, hardwood accents, and in-room coffee stations, adding convenience to daily guest routines. Shared spaces often feature vending areas, laundry facilities, and compact lobbies that reinforce practical guest routines each day.

Accommodations often highlight Wi-Fi, laundry facilities, vending corners, and parking, sustaining functional routines across stays.

  Call (855) 234-7135 to book with an agent.
  2.6 miles from Pittsfield High School

Starting at

$87.99

per night

Read Reviews View Amenities View All Rooms

Hotel on North

297 North Street Pittsfield, Massachusetts

This easy drive to Pittsfield High School from Hotel on North helps guests to feel oriented and comfortable in the Pittsfield area.

Hotel on North often presents arrivals with locally inspired décor, complimentary refreshments, and warm boutique-style greetings. Accommodations may present eclectic décor, curated minibars, and plush bedding that highlight a refined boutique experience. Facilities often provide co-working corners, artisanal cafés, and eclectic décor that emphasize boutique orientation and creativity.

A visit often highlights complimentary Wi-Fi, bike storage, family breakfast, and laundry access, supporting daily routines seamlessly.

  Call (855) 235-6136 to book with an agent.
  2.6 miles from Pittsfield High School

Starting at

$143.99

per night

Read Reviews View Amenities View All Rooms

Holiday Inn & Suites Pittsfield-Berkshires by IHG

One West Street Pittsfield, Massachusetts

Pittsfield High School is a simple drive from Holiday Inn & Suites Pittsfield-Berkshires by IHG, a detail that makes the hotel a practical and well-positioned base.

Reception spaces at Holiday Inn & Suites are consistently staffed and brightly lit, ensuring arrivals remain smooth across locations. Guest rooms highlight branded bath products, walk-in showers, and towels, refreshing travelers consistently across every property. Bars located in lobby spaces offer cocktails, snacks, and casual seating, giving guests natural hubs for relaxed evening downtime.

Free Wi-Fi, complimentary breakfast, and pools connect with business centers and parking, balancing relaxation with work routines.

  Call (855) 234-7135 to book with an agent.
  2.6 miles from Pittsfield High School

Starting at

$116.99

per night

Read Reviews View Amenities View All Rooms

Best Western Plus Berkshire Hills Inn & Suites

1350 West Housatonic St Pittsfield, Massachusetts

The hotel's sensible location ensures Pittsfield High School is a straightforward drive away, underscoring its suitability for car-based travel.

Where lounge access applies, Best Western directs eligible guests to quiet seating and light refreshments, clearly marked as a members-only space. All guest rooms keep closets, drawers, and luggage racks in reach, preventing clutter and making repacks faster on back-to-back days. Fire pits or patio clusters at some properties invite brief evening meetups, adding warmth to quick conversations before rest.

Between courtyard seating where present, Wi-Fi, dining options, and parking, short meetups and meal breaks fit tightly scheduled itineraries.

  Call (855) 236-8982 to book with an agent.
  3.9 miles from Pittsfield High School

Starting at

$77.99

per night

Read Reviews View Amenities View All Rooms

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield, Massachusetts

This uncomplicated drive to Pittsfield High School helps Berkshire Mountain Lodge guests get grounded in the local Pittsfield environment without a long journey.

At Berkshire Mountain Lodge, guests are often welcomed with curated furnishings, artisanal details, and staff providing personal attention. Rooms often include artisanal design touches, premium bedding, and boutique bathrooms for a polished and stylish impression. Amenities may include stylish dining venues, curated cocktail bars, and cozy lounges that create a refined boutique impression.

Guests may encounter Wi-Fi, boutique breakfast, laundry facilities, and yoga mats, ensuring boutique routines remain consistent.

  Call (855) 236-8982 to book with an agent.
  5.6 miles from Pittsfield High School

Starting at

$88.99

per night

Read Reviews View Amenities View All Rooms

Hilton Garden Inn Lenox Pittsfield

1032 South Street Pittsfield, Massachusetts

Pittsfield High School is within easy reach of Hilton Garden Inn Lenox Pittsfield, a convenience that ensures the journey there is as simple as the stay itself.

Digital Key access in Hilton Garden Inn receptions signals loyalty recognition, allowing frequent travelers to streamline their arrival routines. Every guest room offers televisions, sofa seating, and streaming options, allowing guests to unwind with entertainment after long days. Business corners with copy machines, Wi-Fi, and desk seating give guests dependable access to tools that make work efficient.

Complimentary Wi-Fi, hot breakfast, outdoor pools, self-parking, and laundry services provide ease that supports extended guest stays.

  Call (855) 234-5074 to book with an agent.
  6.1 miles from Pittsfield High School

Starting at

$142.99

per night

Read Reviews View Amenities View All Rooms

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

1055 South Street Pittsfield, Massachusetts

The uncomplicated drive from Holiday Inn Express & Suites Pittsfield - Berkshires by IHG to Pittsfield High School in Pittsfield ensures guests have a pleasant option for their daily travel.

Holiday Inn Express lobbies feature open layouts and bright décor, producing arrival clarity that feels consistent across properties. Each guest room includes plush mattresses, blackout shades, and quiet HVAC systems, making restorative rest simple and consistent. Fitness rooms containing treadmills, ellipticals, and weights give travelers reliable facilities to preserve healthy daily habits.

Business centers, Wi-Fi, and pet policies combine with breakfast and laundry, supporting productivity and family comfort together.

  Call (855) 234-7135 to book with an agent.
  6.1 miles from Pittsfield High School

Starting at

$149.00

per night

Read Reviews View Amenities View All Rooms

The Yankee Trademark Collection by Wyndham

461 Pittsfield Rd Lenox, Massachusetts

When plans in Pittsfield are spread out, Pittsfield High School is a simple drive from The Yankee Trademark Collection by Wyndham, letting guests arrive relaxed and on schedule.

Bell services at select Trademark Collection locations add a layer of convenience, assisting with luggage so guests can settle in faster. An in-room workspace with an ergonomic chair supports longer periods of productivity, making it easier to meet deadlines while on the road. Versatile meeting spaces with high-speed internet ensure that presentations and collaborative work can proceed smoothly and professionally.

The hotel's amenities, including a restaurant, a fitness center, a bar, and event spaces, are designed to enhance any travel agenda.

  Call (855) 233-7850 to book with an agent.
  6.5 miles from Pittsfield High School

Starting at

$108.99

per night

Read Reviews View Amenities View All Rooms

FairBridge Inn Express

16 Cheshire Road Pittsfield, Massachusetts

From FairBridge Inn Express, Pittsfield High School is a direct run, a detail that makes for an uncomplicated start to the day.

FairBridge Inn Express often provides an uncomplicated desk experience, on-site parking, and a compact lobby aimed at keeping wait times low. Guest rooms often feature tasteful interiors, plush bedding, and Wi-Fi, creating a reliable foundation for comfortable overnight stays. Facilities typically include modest breakfast corners, vending machines, and seating zones that provide consistent ease for visitors.

A visit may provide Wi-Fi, continental breakfast, vending areas, and guest laundry, reinforcing simple travel support for all visitors.

  Call (855) 235-6136 to book with an agent.
  6.6 miles from Pittsfield High School

Starting at

$89.99

per night

Read Reviews View Amenities View All Rooms

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox, Massachusetts

This easy commute to Pittsfield High School permits Howard Johnson by Wyndham Lenox to be a convenient anchor before the on-site experience starts.

At the desk, Howard Johnson staff can point guests to shuttle pickups where available, clarifying transfers before keys are in hand. Each guest room’s mini-fridge keeps drinks cold while the microwave handles quick heat-ups, minimizing errands between activities and meals. Outdoor pool decks position umbrellas, towel stations, and shade cabanas, encouraging short sun breaks while energy rebounds gently.

From breakfast and Wi-Fi to a fitness room and indoor pool, mornings launch clearly and evenings wind down without extra errands.

  Call (855) 233-7850 to book with an agent.
  6.6 miles from Pittsfield High School

Starting at

$76.99

per night

Read Reviews View Amenities View All Rooms

Berkshires Untold

194 Pittsfield Rd Lenox, Massachusetts

The simple drive from Berkshires Untold to Pittsfield High School in Pittsfield makes the connection between the two simple and fast.

Guests at Berkshires Untold may encounter eclectic décor, complimentary lobby coffee, and boutique-style reception experiences. Guest rooms may feature stylish interiors, curated furnishings, and premium linens that underscore boutique sophistication. Shared spaces typically highlight art installations, artisanal cafés, and small dining rooms that reflect boutique-style creativity.

A stay may include Wi-Fi, EV charging, artisanal snacks, and laundry support, reinforcing boutique practicality for modern travel.

  Call (855) 239-5277 to book with an agent.
  8.3 miles from Pittsfield High School

Starting at

$125.10

per night

Read Reviews View Amenities View All Rooms

Courtyard by Marriott Lenox Berkshires

70 Pittsfield Rd Lenox, Massachusetts

Pittsfield High School is a simple cross-town drive of Courtyard by Marriott Lenox Berkshires, a convenience that ensures the journey there is as simple as the stay itself.

Courtyard highlights its Bistro in the lobby, signaling convenience with food and beverage options that simplify daily routines. Every suite delivers rainfall showers, plush robes, and stocked toiletries, refreshing travelers and reinforcing daily consistency. At the meeting spaces, ergonomic seating, projectors, and AV support provide convenience and productivity for all types of events.

Amenities include business spaces, Starbucks® service, outdoor pools, and valet parking, dependable options that simplify stays daily.

  Call (855) 233-7850 to book with an agent.
  9.2 miles from Pittsfield High School

Starting at

$182.99

per night

Read Reviews View Amenities View All Rooms

Hampton Inn & Suites Berkshires-Lenox

445 Pittsfield Rd Lenox, Massachusetts

Because Hampton Inn & Suites Berkshires-Lenox keeps Pittsfield High School within easy reach, guests can decide on the travel method that best suits their needs.

Curated design touches in Hampton Inn receptions reinforce polished identity, ensuring first impressions remain dependable and clear. Each suite offers sofa beds, televisions, and armchairs, allowing families to relax together in practical and comfortable spaces. Lobby lounges with 24/7 coffee, sofa clusters, and bright lighting create welcoming areas where guests can relax or socialize casually.

Complimentary Wi-Fi, pet-friendly options, fitness facilities, laundry service, and breakfast buffets give travelers consistency and care.

  Call (855) 239-5277 to book with an agent.
  6.8 miles from Pittsfield High School

Starting at

$180.99

per night

Read Reviews View Amenities View All Rooms

The Springs Motel

94 U.S. 7 New Ashford, Massachusetts

This practical base from The Springs Motel helps guests to feel oriented and comfortable in the Pittsfield area.

At The Springs Motel, arrivals may feature modest front desks, vending machines, and direct parking that create straightforward consistency. Each guest room may highlight microwaves, Wi-Fi, and climate control, supporting simple practicality for travelers away from home. Shared spaces may include vending corners, compact lobbies, and laundry rooms that sustain daily consistency in budget accommodations.

Guests may encounter Wi-Fi, pet-friendly options, vending access, and parking, sustaining reliable routines across short overnight stays.

  Call (855) 233-0132 to book with an agent.
  15.0 miles from Pittsfield High School

Starting at

$108.99

per night

Read Reviews View Amenities View All Rooms

The Black Swan Lee - Lenox an Ascend Collection Hotel

435 Laurel St Lee, Massachusetts

Because The Black Swan Lee - Lenox an Ascend Collection Hotel is a convenient base, guests can decide to start their day with a moment of quiet reflection.

Guests at The Black Swan Lee - Lenox an Ascend Collection Hotel often find a sophisticated lobby setting with attentive staff, concierge presence, and upscale finishes. Accommodations often present elegant décor, plush bedding, and in-room espresso machines that may add convenience to the guest experience. Property amenities often provide elegant restaurants, spa-inspired services, and stylish lounges designed for a luxury orientation.

A stay often presents plush bedding, wellness services, fine dining, and Wi-Fi, reflecting a lifestyle of polished comfort and balance.

  Call (855) 233-0132 to book with an agent.
  15.6 miles from Pittsfield High School

Starting at

$95.99

per night

Read Reviews View Amenities View All Rooms

Berkshire Travelodge

12703 Rte 22 Austerlitz, New York

Within the region, Berkshire Travelodge is a convenient base, a fact that offers a sense of connection to Pittsfield High School.

Travelodge lobbies with refreshed décor, murals, or modern finishes contribute to updated identity while retaining functional clarity. All guest rooms contain ergonomic desks, chairs, and Wi-Fi, enabling business travelers to remain productive while away from the office. Vending areas with snacks, bottled drinks, and packaged meals simplify routines, offering convenience for guests at all hours.

Free Wi-Fi, laundry, and breakfast buffets align with parking and vending, giving travelers clarity across both short and long trips.

  Call (855) 234-7135 to book with an agent.
  16.6 miles from Pittsfield High School

Starting at

$74.99

per night

Read Reviews View Amenities View All Rooms

Sunset Inn

150 Housatonic Street Lee, Massachusetts

For guests in the Pittsfield region, Sunset Inn is a practical base, a spot that makes for an unhurried start to the day.

At Sunset Inn, arrivals may feature efficient reception, vending options, and close parking that favor practical guest routines. Accommodations may include rainfall showers, hardwood floors, and compact layouts, reinforcing both practicality and simple comfort. Shared spaces may provide coin-operated laundries, vending access, and compact business areas that help travelers stay productive.

Guests may encounter Wi-Fi, modest breakfast, vending access, and laundry support, helping create reliable balance during overnight stays.

  Call (855) 235-6136 to book with an agent.
  18.0 miles from Pittsfield High School

Starting at

$76.99

per night

Read Reviews View Amenities View All Rooms

Pilgrim Inn

165 Housatonic St Lee, Massachusetts

This convenient base from Pilgrim Inn allows guests to feel more in control of their schedule in the Pittsfield area.

Guests at Pilgrim Inn may encounter a no-nonsense front desk, modest lobby chairs, and parking access for stress-reduced arrivals. Rooms may provide premium bedding, modest seating, and streaming access, giving guests consistent comfort and entertainment options. Facilities often highlight vending machines, modest lobbies, and laundry areas that emphasize simple and reliable daily guest routines.

A stay often includes Wi-Fi, laundry rooms, breakfast counters, and parking, maintaining straightforward guest routines on the road.

  Call (855) 233-7850 to book with an agent.
  18.0 miles from Pittsfield High School

Starting at

$76.99

per night

Read Reviews View Amenities View All Rooms

Quality Inn Lee - Lenox South

170 Housatonic Street Lee, Massachusetts

The benefit of using Quality Inn Lee - Lenox South as a sensible base makes it into a starting point for a day of easy transitions.

Quality Inn positions charging hubs and seating clusters near the desk so companions regroup and charge devices while keys are prepared. Guest rooms combine layered lighting, task lamps, and ergonomic desk chairs so evening work and relaxed reading both fit comfortably. Guest vending corners and market shelves provide batteries, toiletries, and snacks so travelers avoid late-night trips off property during stays.

Between breakfast bars, microwaves, and in-room fridges, quick snacks and early meals are handled efficiently to maintain momentum for busy days.

  Call (855) 234-5074 to book with an agent.
  18.1 miles from Pittsfield High School

Starting at

$81.99

per night

Read Reviews View Amenities View All Rooms

The Red Lion Inn

30 Main Street Stockbridge, Massachusetts

For a trip to the area, The Red Lion Inn's location as a sensible base is a fundamental component of the guest journey.

A gracious and enthusiastic greeting from the front desk team at a Red Lion hotel makes every guest feel like a VIP from the start. The spacious bathrooms include premium fixtures and ample counter space, offering a luxurious and refreshing bathing experience. Indoor or outdoor pools provide a year-round opportunity for a refreshing swim, offering a fun and relaxing activity for guests.

A strong set of features like an indoor pool, a hot tub, a fitness center, and a free hot breakfast adds comfort to any journey.

  Call (855) 235-0725 to book with an agent.
  20.0 miles from Pittsfield High School

Starting at

$152.99

per night

Read Reviews View Amenities View All Rooms

Econo Lodge Lee - Great Barrington

980 Pleasant Street Lee, Massachusetts

Guests at Econo Lodge Lee - Great Barrington can appreciate it as a convenient base, a defining feature of a well-located stay.

At some Econo hotels, mobile check-in via the Choice app shortens desk time for eligible reservations so arrivals can head upstairs faster when rooms are ready. Every guest room includes a desk near outlets, a refrigerator, a microwave and free Wi-Fi to keep device charging and snacks within reach. Meeting rooms feature natural light, whiteboards and temperature controls to keep focus steady during short sessions and hybrid calls.

Free Wi-Fi, hot breakfast, meeting space, fitness equipment at some hotels, laundry and parking make travel days less complicated overall.

  Call (855) 233-0132 to book with an agent.
  20.3 miles from Pittsfield High School

Starting at

$64.99

per night

Read Reviews View Amenities View All Rooms

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

190 Meadow Street South Lee, Massachusetts

From Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, the easy regional drive to Pittsfield High School makes it a sensible hub for smart planning for your visit.

Lobby seating clusters at Holiday Inn & Suites include lounge chairs and long tables, supporting both social connection and regrouping. Each guest room includes plush beds, blackout curtains, and digital thermostats, making restful sleep predictable and reliable. Business centers equipped with terminals, printers, and Wi-Fi provide clarity and support for professionals managing quick tasks.

Fitness centers, free breakfast, and Wi-Fi combine with pools and parking, supporting dependable clarity across family travel needs.

  Call (855) 233-7850 to book with an agent.
  20.8 miles from Pittsfield High School

Starting at

$125.00

per night

Read Reviews View Amenities View All Rooms

Chatham Travelodge

598 NY 295 Old Chatham, New York

This practical location allows Chatham Travelodge to serve as a calm starting point before the easy regional drive to Pittsfield High School.

Complimentary coffee service at Travelodge signals brand reliability, offering travelers care details that ease arrival transitions. Guest rooms offer mini-fridges, microwaves, and coffee makers, letting travelers maintain simple routines throughout their visits. Breakfast dining setups with cereals, pastries, and coffee create clarity and consistency, ensuring simple starts for every guest.

Pet accommodations, breakfast dining, and Wi-Fi combine with pools and parking, reinforcing dependable balance for families daily.

  Call (855) 234-2997 to book with an agent.
  23.9 miles from Pittsfield High School

Starting at

$115.99

per night

Read Reviews View Amenities View All Rooms

The Little Lion

506 Stockbridge Road Great Barrington, Massachusetts

This sensible location permits The Little Lion to provide a convenient yet peaceful setting before the easy drive to Pittsfield High School.

The Little Lion often greets guests with warm staff welcomes, artisanal décor, and complimentary refreshments for a boutique entry. Accommodations typically provide unique décor, curated minibars, and spa-style bathrooms for a boutique-style guest orientation. Facilities may showcase eclectic lounges, curated interiors, and cocktail bars for a polished and boutique-forward impression.

Accommodations often showcase Wi-Fi, family dining, laundry services, and bike rentals, aligning routines with boutique hospitality.

  Call (855) 239-4019 to book with an agent.
  24.9 miles from Pittsfield High School

Starting at

$110.99

per night

Read Reviews View Amenities View All Rooms