The best deals on hotels near Theodore Herberg Middle 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 Theodore Herberg Middle School
501 Pomeroy Ave Pittsfield, MA 1201

Berkshire Inn

150 West Housatonic St Pittsfield, Massachusetts

The short drive from Berkshire Inn to Theodore Herberg Middle School in Pittsfield means the commute is always efficient before the stay unfolds.

Guests at Berkshire Inn may encounter straightforward check-in, vending machines, and parking access for practical daily routines. Rooms may provide compact seating, curated décor, and in-room coffee, helping travelers maintain comfort and routine while away. Shared spaces may present breakfast areas, vending machines, and modest lobbies that emphasize reliable convenience for travelers.

A stay may include Wi-Fi, vending access, laundry rooms, and compact breakfast service, aligning simplicity with daily travel routines.

  Call (855) 234-5074 to book with an agent.
  2.6 miles from Theodore Herberg Middle School

Starting at

$145.99

per night

Read Reviews View Amenities View All Rooms

Hotel on North

297 North Street Pittsfield, Massachusetts

For visitors to Pittsfield, Hotel on North is a simple drive from Theodore Herberg Middle School, a choice that supports a stress-free travel plan.

Hotel on North often greets arrivals with curated interiors, cozy seating, and complimentary coffee or tea for a relaxed boutique welcome. Guest rooms typically present artisanal touches, plush bedding, and curated minibars for a refined and boutique-oriented stay. Amenities may include stylish cocktail bars, locally inspired dining, and curated lounges that highlight a boutique guest experience.

Accommodations often present Wi-Fi, bike rentals, self-serve markets, and laundry facilities, ensuring flexibility across boutique visits.

  Call (855) 235-0725 to book with an agent.
  2.6 miles from Theodore Herberg Middle School

Starting at

$342.99

per night

Read Reviews View Amenities View All Rooms

Holiday Inn & Suites Pittsfield-Berkshires by IHG

One West Street Pittsfield, Massachusetts

Theodore Herberg Middle School is a quick drive from Holiday Inn & Suites Pittsfield-Berkshires by IHG, a detail that allows for a thought-free and simple part of the day.

Reception at Holiday Inn & Suites sits prominently in view, creating orientation clarity for first-time and repeat guests alike. All guest rooms contain plush beds, blackout curtains, and quiet HVAC systems, ensuring travelers achieve restorative rest consistently. Lobby seating clusters arranged with long tables, charging hubs, and lounge chairs support orientation clarity and comfortable waits.

Connectivity with Wi-Fi, complimentary breakfast, and pools combines with laundry and fitness, balancing recreation with routines.

  Call (855) 233-7850 to book with an agent.
  2.6 miles from Theodore Herberg Middle School

Starting at

$159.99

per night

Read Reviews View Amenities View All Rooms

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield, Massachusetts

The hotel's location is defined by its predictable commute to Theodore Herberg Middle School, which is a short drive away, making travel a non-issue.

At Berkshire Mountain Lodge, arrivals may feature boutique furnishings, personalized greetings, and complimentary refreshments in the lobby. Accommodations may include stylish interiors, premium linens, and bathrooms with boutique finishes that emphasize comfort. Shared spaces often feature farm-to-table restaurants, artisanal cafés, and eclectic lounges that reflect boutique individuality.

A visit may highlight complimentary Wi-Fi, artisanal breakfast, EV charging, and laundry service, supporting consistency for travelers.

  Call (855) 239-4019 to book with an agent.
  3.4 miles from Theodore Herberg Middle School

Starting at

$151.99

per night

Read Reviews View Amenities View All Rooms

Best Western Plus Berkshire Hills Inn & Suites

1350 West Housatonic St Pittsfield, Massachusetts

From Best Western Plus Berkshire Hills Inn & Suites, the fast drive to Theodore Herberg Middle School takes just minutes to save valuable time, making travel easy.

Best Western posts concise maps and QR guides by the desk, converting common questions into routes for dining, transit, and nearby essentials. All guest rooms keep closets, drawers, hooks, and luggage racks within reach, preventing clutter and speeding repacks on back-to-back days. Kids zones or game rooms, where offered, add low-stakes play areas, helping families decompress without leaving common spaces.

Between fitness rooms, pools where available, Wi-Fi, and lounge seating, travelers match workouts and resets to the day’s pace without detours.

  Call (855) 233-7850 to book with an agent.
  3.9 miles from Theodore Herberg Middle School

Starting at

$143.99

per night

Read Reviews View Amenities View All Rooms

Hilton Garden Inn Lenox Pittsfield

1032 South Street Pittsfield, Massachusetts

Because Hilton Garden Inn Lenox Pittsfield keeps Theodore Herberg Middle School an uncomplicated drive, guests can choose to begin their day with a simple commute.

Lounge areas adjacent to bars at Hilton Garden Inn create visible social hubs, encouraging relaxed conversation before guests move on. Each suite provides microwaves, refrigerators, and dining counters, letting guests prepare meals or snacks with ease during longer visits. Meeting rooms with projectors, flexible layouts, and Wi-Fi connectivity provide collaborative environments that enhance productivity.

Complimentary internet, breakfast buffets, indoor pools, event spaces, and valet parking ensure consistency for group or solo visits.

  Call (855) 236-8982 to book with an agent.
  6.1 miles from Theodore Herberg Middle School

Starting at

$227.99

per night

Read Reviews View Amenities View All Rooms

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

1055 South Street Pittsfield, Massachusetts

The journey from Holiday Inn Express & Suites Pittsfield - Berkshires by IHG to Theodore Herberg Middle School is a simple drive, an advantage that contributes to a hassle-free visit.

Concierge-style reception at Holiday Inn Express ensures orientation clarity, offering travelers confidence in their arrival process. Guest rooms are equipped with flat-screen HDTVs, sofa chairs, and outlets, providing relaxation and utility for diverse needs. Breakfast areas offering hot selections, pastries, and cereals provide travelers with consistent clarity in starting daily routines.

Business centers, hot breakfast, and Wi-Fi align with self-parking and pet policies, providing clarity for business and family trips.

  Call (855) 239-5277 to book with an agent.
  6.1 miles from Theodore Herberg Middle School

Starting at

$227.99

per night

Read Reviews View Amenities View All Rooms

The Yankee Trademark Collection by Wyndham

461 Pittsfield Rd Lenox, Massachusetts

The guest's journey from The Yankee Trademark Collection by Wyndham in Pittsfield to Theodore Herberg Middle School is an simple drive, enhancing the feeling of a well-chosen location.

Lobby spaces at Trademark Collection hotels are often designed for social connection, with comfortable arrangements that encourage guests to linger. Rooms with accessibility features ensure that all guests have a comfortable and safe stay, with amenities designed for ease of use. The hotel restaurant often includes a private dining area for small groups, allowing for more intimate celebrations or business dinners.

To accommodate diverse itineraries, a blend of a fitness center, meeting rooms, pet-friendly policies, and a hotel bar is available.

  Call (855) 234-7135 to book with an agent.
  6.5 miles from Theodore Herberg Middle School

Starting at

$171.99

per night

Read Reviews View Amenities View All Rooms

FairBridge Inn Express

16 Cheshire Road Pittsfield, Massachusetts

The hotel offers a direct run to Theodore Herberg Middle School, keeping the commute uncomplicated for guests.

FairBridge Inn Express typically offers arrivals with front desk service, modest lobby seating, and on-site parking to ease guest transitions. Each guest room often highlights plush bedding, blackout curtains, and climate control, promoting restful and consistent overnight stays. Public areas often include vending access, compact breakfast corners, and laundry facilities that maintain consistency for guest needs.

Accommodations often present Wi-Fi, guest laundry, modest breakfast, and parking, maintaining practical routines for visiting guests.

  Call (855) 235-0725 to book with an agent.
  6.6 miles from Theodore Herberg Middle School

Starting at

$89.99

per night

Read Reviews View Amenities View All Rooms

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox, Massachusetts

For guests in Pittsfield, Howard Johnson by Wyndham Lenox keeps Theodore Herberg Middle School a simple cross-town drive, a spot that supports an efficient itinerary.

Howard Johnson arrival zones commonly include vending machines, ensuring cold drinks are within reach while rooms are readied near reception. Each guest room typically offers a safe at select sites plus a desk and Wi-Fi, keeping documents secure while you work nearby. Breakfast rooms handle flow with tray drop points, juice dispensers, and coffee stations, so early starts stay orderly under time.

Between Wi-Fi, breakfast, business services, and laundry, practical needs coordinate smoothly so attention stays on the itinerary.

  Call (855) 235-6136 to book with an agent.
  6.6 miles from Theodore Herberg Middle School

Starting at

$115.99

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 Theodore Herberg Middle School within easy reach, guests can enjoy a moment of fresh air before their day begins.

Hampton Inn receptions with sofa clusters give families intuitive regrouping points, allowing them to pause comfortably on arrival. Each suite includes sofa beds, televisions, and lounge tables, creating comfortable zones where families can relax or dine together. Breakfast rooms with hot buffets, pastries, and self-serve coffee provide dependable clarity, helping mornings start smoothly every day.

Complimentary breakfast bags, outdoor pools, self-parking, Wi-Fi, and fitness facilities keep travel routines efficient and dependable.

  Call (855) 235-6136 to book with an agent.
  6.8 miles from Theodore Herberg Middle School

Starting at

$242.99

per night

Read Reviews View Amenities View All Rooms

Days Inn by Wyndham Lenox MA

194 Pittsfield Road Lenox, Massachusetts

The hotel's location is ideal for straightforward travel, with Theodore Herberg Middle School an easy drive away, allowing for predictable travel times.

Elevator banks at Days Inn are placed within a short line of sight from the desk, shrinking learning curves for newcomers on day one. Every guest room lists an HDTV with easy inputs so streaming sticks connect quickly over stable in-room Wi-Fi during stays. Wayfinding pairs icon signage with room-range boards at elevator banks, making first walks direct to markets, restrooms, and meeting rooms.

Parking, clear signage, and Wi-Fi with a lobby nook keep map checks and returns to the car efficient from early to late.

  Call (855) 239-4019 to book with an agent.
  8.3 miles from Theodore Herberg Middle School

Starting at

$232.99

per night

Read Reviews View Amenities View All Rooms

Element Lenox Berkshires

130 PITTSFIELD ROAD Lenox, Massachusetts

When a trip to Pittsfield involves multiple stops, Element Lenox Berkshires's location an easy drive from Theodore Herberg Middle School is a practical asset.

Complimentary Wi-Fi across Element ensures predictable connectivity, showing attentiveness to routines that guests depend on every visit. Every suite integrates eco-conscious design, natural light, and modern finishes, giving travelers calming surroundings that ease extended stays. Fitness rooms highlight cardio gear, weights, and yoga mats, letting wellness-focused guests sustain healthy balance even while traveling.

Complimentary Wi-Fi, Rise breakfast with healthy items, Motion fitness centers, and saline pools combine to keep routines predictable and balanced.

  Call (855) 233-0132 to book with an agent.
  8.8 miles from Theodore Herberg Middle School

Starting at

$379.99

per night

Read Reviews View Amenities View All Rooms

Courtyard by Marriott Lenox Berkshires

70 Pittsfield Rd Lenox, Massachusetts

The journey from Courtyard by Marriott Lenox Berkshires to Theodore Herberg Middle School is an uncomplicated drive, a benefit that contributes to a hassle-free visit.

Courtyard frames reception with clean, modern finishes, delivering a first impression that feels organized and consistently on-brand. Each guest room offers ergonomic desks, strong Wi-Fi, and USB outlets, letting professionals balance productivity with convenience. Guests enjoying the indoor pool find loungers, towel service, and calm lighting, cues that reinforce dependable relaxation daily.

Guests enjoy pet-friendly rooms, indoor pools, parking options, and Wi-Fi, reliable amenities that keep travel simple and balanced.

  Call (855) 239-5277 to book with an agent.
  9.2 miles from Theodore Herberg Middle School

Starting at

$379.99

per night

Read Reviews View Amenities View All Rooms

The Springs Motel

94 U.S. 7 New Ashford, Massachusetts

Because The Springs Motel is a sensible base, guests can appreciate a low-key journey before their day begins.

At The Springs Motel, arrivals may feature vending machines, exterior entries, and modest desk service that create consistent clarity. Accommodations often present compact desks, microwaves, and cable TV, reflecting functional clarity across guest routines daily. Facilities often provide vending machines, compact breakfast rooms, and modest lobbies that sustain practical guest support daily.

Guests may encounter Wi-Fi, ice machines, parking, and coin laundry, supporting clear routines during overnight budget-friendly visits.

  Call (855) 234-5074 to book with an agent.
  15.0 miles from Theodore Herberg Middle School

Starting at

$286.99

per night

Read Reviews View Amenities View All Rooms

The Black Swan Lee - Lenox Ascend Hotel Collection

435 Laurel St Lee, Massachusetts

The journey from The Black Swan Lee - Lenox Ascend Hotel Collection to Theodore Herberg Middle School is an easy regional drive, an asset that adds flexibility to any itinerary.

Upon entry, Ascend lobby art and wayfinding help first-time guests recognize the brand and locate reception without extra searching. Suites offer a living area, a dedicated desk, a mini-fridge and blackout curtains so families and business guests maintain routines with ease. The lobby offers seating clusters, charging hubs and a small market to help guests regroup, charge devices and grab snacks.

With free Wi-Fi, grab-and-go breakfast, meeting rooms, fitness facilities, guest laundry and on-site parking, stays support daily rhythms.

  Call (855) 234-5074 to book with an agent.
  15.6 miles from Theodore Herberg Middle School

Starting at

$309.00

per night

Read Reviews View Amenities View All Rooms

Sunset Inn

150 Housatonic Street Lee, Massachusetts

The journey from Sunset Inn to Theodore Herberg Middle School is an easy regional drive, a perk that adds flexibility to any itinerary.

Arrivals at Sunset Inn may highlight a no-frills reception, available parking, and vending services that reflect budget practicality. Guest rooms typically include hardwood accents, premium linens, and streaming-enabled TVs, supporting both comfort and in-room activity. Facilities may feature modest lobbies, breakfast rooms, and vending machines that create practical points of connection during stays.

A visit may feature Wi-Fi, vending machines, parking, and laundry facilities, reflecting the reliable ease of budget accommodations.

  Call (855) 235-6136 to book with an agent.
  18.0 miles from Theodore Herberg Middle School

Starting at

$150.99

per night

Read Reviews View Amenities View All Rooms

Quality Inn

170 Housatonic Street Lee, Massachusetts

Because Quality Inn is a sensible base, guests can enjoy a low-key journey before their day begins.

Quality Inn entry layouts usually include bench seating and luggage racks so early arrivals can stage bags and explore unencumbered once rooms are ready. Rooms place clear pathways from door to desk to bed, reducing friction for late arrivals and making departures less stressful and faster. Pool decks position loungers, shade elements, and towel pickup near shallow sections so families and guests enjoy easy recovery periods.

With extended gym hours at many addresses, guests can squeeze in workouts before early departures or after long meeting days easily.

  Call (855) 239-4019 to book with an agent.
  18.1 miles from Theodore Herberg Middle School

Starting at

$119.99

per night

Read Reviews View Amenities View All Rooms

Econo Lodge Lee - Great Barrington

980 Pleasant Street Lee, Massachusetts

From the lobby of Econo Lodge Lee - Great Barrington, Theodore Herberg Middle School is within driving reach to start the day right.

With a modest footprint, Econo lobbies keep pathways wide for rolling luggage, helping arrivals move from curb to elevator without bottlenecks. Each guest room supplies a microwave, a refrigerator, a work desk and complimentary Wi-Fi so guests can manage meals and emails easily. Meeting rooms provide natural light, whiteboards and temperature controls to keep focus steady during brief presentations or workshops.

With free Wi-Fi, a hot breakfast buffet, meeting rooms, an on-site gym at some locations, guest laundry and EV charging, short trips feel less stressful.

  Call (855) 239-5277 to book with an agent.
  20.3 miles from Theodore Herberg Middle School

Starting at

$99.99

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

In Pittsfield, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG provides a practical base, keeping Theodore Herberg Middle School an easy regional drive away for guests.

Complimentary tea and coffee stations at Holiday Inn & Suites ease the shift from transit, offering travelers simple care touches. Guest rooms come with in-room coffee makers, mini-fridges, and ample outlets, supporting simple routines and everyday convenience. Bars inside Holiday Inn & Suites properties serve cocktails, small plates, and wine, creating premium-feeling areas for connection.

Business centers, free breakfast, and Wi-Fi link with parking and pools, offering clarity and consistency across all guest stays.

  Call (855) 233-7850 to book with an agent.
  20.8 miles from Theodore Herberg Middle School

Starting at

$283.99

per night

Read Reviews View Amenities View All Rooms

Travelodge by Wyndham Great Barrington Berkshires

400 Stockbridge Rd Great Barrington, Massachusetts

This practical function as a base is a key aspect of Travelodge by Wyndham Great Barrington Berkshires, since it facilitates a smooth and easy visit to Theodore Herberg Middle School.

Lobby zones at Travelodge incorporate vending and simple seating, ensuring convenience and predictable arrival comfort for travelers. Each guest room highlights ergonomic desks, Wi-Fi, and outlets, giving professionals practical setups to remain productive easily. Lobby lounges with murals, seating clusters, and natural light create refreshed brand cues and orientation comfort for guests.

Complimentary breakfast, Wi-Fi, and laundry align with vending and parking, delivering consistent clarity for everyday travel routines.

  Call (855) 234-7135 to book with an agent.
  26.1 miles from Theodore Herberg Middle School

Starting at

$144.99

per night

Read Reviews View Amenities View All Rooms

Howard Johnson by Wyndham Williamstown

213 Main St Williamstown, Massachusetts

For a trip to the area, Howard Johnson by Wyndham Williamstown's location as a sensible base is a fundamental element of its practical charm.

At many sites, a 24/7 coffee station near reception at Howard Johnson supports early departures and late check-ins alike for tired travelers. Guest rooms at renovated properties add backlit mirrors and brighter task lighting, improving morning routines and clarity at the sink. Business corners in compact footprints replace full rooms with a PC, printer, and a small worktop by the lobby, keeping essentials covered quickly.

With breakfast service, Wi-Fi, a fitness room, and pool access, both workdays and weekends hold together with fewer moving parts.

  Call (855) 235-6136 to book with an agent.
  27.9 miles from Theodore Herberg Middle School

Starting at

$184.99

per night

Read Reviews View Amenities View All Rooms

Holiday Inn Express Hotel & Suites Great Barrington by IHG

415 Stockbridge Rd Great Barrington, Massachusetts

Upon leaving Holiday Inn Express Hotel & Suites Great Barrington by IHG, Theodore Herberg Middle School is an easy regional drive, simplifying your visit.

Holiday Inn Express coffee and tea service signals care and consistency, giving travelers refreshing touches immediately upon entry. Each guest room supplies branded toiletries, walk-in showers, and soft linens, creating refreshing and consistent daily experiences. Fitness facilities containing cardio machines, weights, and stretching mats help travelers maintain energy and balance on the road.

Complimentary breakfast, fitness centers, and Wi-Fi connect with pools and laundry, keeping travel routines clear and consistent.

  Call (855) 233-0132 to book with an agent.
  28.0 miles from Theodore Herberg Middle School

Starting at

$210.99

per night

Read Reviews View Amenities View All Rooms

Fairfield Inn & Suites by Marriott Williamstown

430 Main St Williamstown, Massachusetts

A defining quality of the Fairfield Inn & Suites by Marriott Williamstown experience is its role as a practical base with Theodore Herberg Middle School within driving reach.

At check-in, Fairfield Inn arranges staff and wayfinding cues to point guests toward seating, market, or business services for smoother arrivals. All guest rooms include desks with ergonomic chairs, complimentary Wi-Fi, and bedside outlets, supporting continuity of routines without friction. Breakfast halls provide eggs, fruit, and oatmeal alongside coffee, letting travelers maintain clarity and dependable habits each morning.

Complimentary Wi-Fi, hot breakfast with eggs and fruit, fitness center access, and indoor pool facilities combine to keep routines dependable daily.

  Call (855) 239-4019 to book with an agent.
  28.2 miles from Theodore Herberg Middle School

Starting at

$329.99

per night

Read Reviews View Amenities View All Rooms