The best deals on hotels near Osceola Park 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 Osceola Park
Osceola St Pittsfield, MA 1201

Berkshire Inn

150 West Housatonic St Pittsfield, Massachusetts

A key time-saving feature of Berkshire Inn in Pittsfield is the easy drive to Osceola Park, leaving more room in the schedule for other activities.

Arrivals at Berkshire Inn may feature modest reception areas, self-serve coffee, and parking options to support guest convenience. Guest rooms often include tasteful interiors, climate control, and plush bedding, creating a consistent and comfortable overnight setting. Facilities may present vending corners, compact breakfast areas, and laundry rooms that sustain practical routines in budget settings.

Guests may enjoy Wi-Fi, modest breakfast, parking, and laundry support, giving visitors a reliable base during budget-friendly stays.

  Call (855) 236-8982 to book with an agent.
  2.1 miles from Osceola Park

Starting at

$145.99

per night

Read Reviews View Amenities View All Rooms

Best Western Plus Berkshire Hills Inn & Suites

1350 West Housatonic St Pittsfield, Massachusetts

This convenient drive to Osceola Park from Best Western Plus Berkshire Hills Inn & Suites is a key feature, because it makes the stay both simple and enjoyable.

Best Western arranges sofa clusters, standing ledges, and café tables near outlets, creating quick huddle points while plans and messages settle. Every guest room maintains ample outlets at beds and desks, so phones, tablets, and laptops recharge while maps and routes refresh. Guest laundries supply washers, dryers, and folding counters, simplifying refresh cycles for clothing and gear during extended itineraries.

From breakfast areas, Wi-Fi, printers, and ride guidance, mornings convert plans into action while routes and confirmations finalize quickly.

  Call (855) 234-7135 to book with an agent.
  2.2 miles from Osceola Park

Starting at

$266.99

per night

Read Reviews View Amenities View All Rooms

Holiday Inn & Suites Pittsfield-Berkshires by IHG

One West Street Pittsfield, Massachusetts

This convenient location keeps Osceola Park just a short drive from Holiday Inn & Suites Pittsfield-Berkshires by IHG, ensuring a simple start.

Holiday Inn & Suites supports loyalty recognition with digital check-in via the IHG app, letting frequent travelers bypass reception lines. Suites come with sofa beds, large TVs, and expanded layouts, offering families dependable flexibility and comfort across stays. Business lounges designed with Wi-Fi, workstations, and comfortable seating make it simple for professionals to stay on top of work.

Complimentary breakfast, Wi-Fi, and fitness centers pair with indoor pools and laundry, covering daily convenience effectively.

  Call (855) 239-4019 to book with an agent.
  2.7 miles from Osceola Park

Starting at

$274.99

per night

Read Reviews View Amenities View All Rooms

Hotel on North

297 North Street Pittsfield, Massachusetts

When visiting Osceola Park in Pittsfield, the drive from Hotel on North is a short drive, allowing for a quick return to the hotel for rest.

Hotel on North often provides arrivals with boutique reception, curated décor, and complimentary refreshments for visiting guests. Accommodations typically highlight stylish décor, artisanal details, and spa-style bathrooms for a boutique-oriented guest retreat. Amenities typically include stylish cocktail bars, cozy lounges, and artisanal cafés that highlight boutique character and flair.

Accommodations may include Wi-Fi, bike rentals, laundry facilities, and artisanal breakfast, supporting consistency across boutique visits.

  Call (855) 233-0132 to book with an agent.
  3.1 miles from Osceola Park

Starting at

$383.99

per night

Read Reviews View Amenities View All Rooms

Hilton Garden Inn Lenox Pittsfield

1032 South Street Pittsfield, Massachusetts

The hotel's spot a straightforward hop from Osceola Park gives Hilton Garden Inn Lenox Pittsfield guests a simple way to engage with their surroundings.

Hilton Garden Inn receptions feature mobile check-in and Digital Key tools, reducing wait times while recognizing loyalty guests reliably. All guest rooms offer premium toiletries, bright vanities, and rainfall showers, supporting guests with daily routines that feel refreshing. Meeting areas with projectors, whiteboards, and reliable Wi-Fi offer functional environments that support productivity and group work.

Fitness centers, complimentary internet, breakfast buffets, outdoor pools, and pet-friendly policies cover flexible guest requirements.

  Call (855) 234-2997 to book with an agent.
  4.2 miles from Osceola Park

Starting at

$302.99

per night

Read Reviews View Amenities View All Rooms

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

1055 South Street Pittsfield, Massachusetts

Because Holiday Inn Express & Suites Pittsfield - Berkshires by IHG is an easy drive from Osceola Park, guests can simply transition to the next part of their day.

Complimentary breakfast stations at Holiday Inn Express are located near lobbies, offering predictability that starts each day clearly. All guest rooms offer flat-screen TVs, ergonomic chairs, and outlets, creating setups that balance comfort with everyday utility. Breakfast spaces including hot selections, pastries, and cereals help families achieve day-start clarity during busy travel mornings.

Pet-friendly policies, Wi-Fi, and complimentary breakfast connect with parking and laundry, easing routines for family travelers.

  Call (855) 234-2997 to book with an agent.
  4.3 miles from Osceola Park

Starting at

$304.99

per night

Read Reviews View Amenities View All Rooms

The Yankee Trademark Collection by Wyndham

461 Pittsfield Rd Lenox, Massachusetts

The hotel's location is a key link to Osceola Park, which is a straightforward hop away, contributing to a well-planned visit.

The arrival experience at a Trademark Collection hotel is intentionally distinct, offering a refreshing alternative to chain hotel uniformity. Guest rooms include modern bathrooms with quality bath amenities, ensuring a refreshing start or a relaxing end to any day's activities. Business centers with 24-hour access give travelers the flexibility to print documents or prepare for meetings on their own schedule.

With a restaurant for meals, a bar for drinks, a pool for leisure, and a business center for tasks, a balanced itinerary is easy to keep.

  Call (855) 236-8982 to book with an agent.
  4.6 miles from Osceola Park

Starting at

$339.99

per night

Read Reviews View Amenities View All Rooms

Wagon Wheel Inn

484 Pittsfield Rd Lenox, Massachusetts

The quick drive from Wagon Wheel Inn to Osceola Park in Pittsfield makes the connection between the two uncomplicated and fast.

Wagon Wheel Inn often provides quick arrivals with a simple front desk, vending access, and on-site parking for easy travel support. Standard guest rooms may include hardwood floors, modest seating, and in-room coffee stations that add to the balance of each stay. Shared spaces often include modest lobbies, vending machines, and laundry access that help maintain reliable daily guest functions.

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

  Call (855) 239-4019 to book with an agent.
  4.6 miles from Osceola Park

Starting at

$79.00

per night

Read Reviews View Amenities View All Rooms

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox, Massachusetts

In Pittsfield, Howard Johnson by Wyndham Lenox has a well-connected location to Osceola Park, letting guests move at their own pace before their stay begins.

Howard Johnson lobbies commonly pair seating near reception with vending access, letting companions regroup while keys are prepared. All guest rooms provide air conditioning and a flat-screen TV alongside a mini-fridge, supporting easy cooldowns and simple downtime. Meeting spaces scale from single rooms to small suites with dividers, making ad-hoc sessions or celebrations straightforward to stage.

For families, free breakfast, pools, and pet-friendly options at select locations combine with Wi-Fi to keep days flexible and low-stress.

  Call (855) 234-2997 to book with an agent.
  4.7 miles from Osceola Park

Starting at

$164.99

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 is a quick drive from Osceola Park, guests can decide on the travel method that best suits their needs.

Digital Key features at Hampton Inn receptions provide loyalty recognition, helping frequent guests bypass wait times with seamless access. Each suite provides ergonomic desks, Wi-Fi access, and multiple charging hubs, helping travelers stay productive in reliable work settings. Lobby lounges with coffee service, sofa clusters, and regional décor foster relaxed atmospheres that encourage guest connection.

On-site markets, complimentary Wi-Fi, hot breakfast bags, fitness studios, and laundry facilities provide dependable routines for travelers.

  Call (855) 235-6136 to book with an agent.
  4.8 miles from Osceola Park

Starting at

$459.99

per night

Read Reviews View Amenities View All Rooms

Element Lenox Berkshires

130 PITTSFIELD ROAD Lenox, Massachusetts

Osceola Park is within easy reach of Element Lenox Berkshires, a convenience that allows the hotel to serve as an easy-to-navigate base.

Free Wi-Fi and accessible charging stations in Element’s lobbies provide dependable continuity for digital routines from the very beginning. Every suite delivers spacious layouts, natural light, and eco-conscious finishes, giving travelers balance and comfort for longer stays. Outdoor patios with seating, grills, and shaded tables create dependable spaces for both connection and relaxation during longer guest stays.

Guests enjoy Rise breakfast, Motion gyms, saline pool access, and free Wi-Fi, creating dependable amenities that sustain clarity and wellness.

  Call (855) 234-7135 to book with an agent.
  6.8 miles from Osceola Park

Starting at

$479.99

per night

Read Reviews View Amenities View All Rooms

Courtyard by Marriott Lenox Berkshires

70 Pittsfield Rd Lenox, Massachusetts

Upon leaving Courtyard by Marriott Lenox Berkshires, Osceola Park is an easy drive with an easy commute, simplifying your visit from the start.

Courtyard’s lobby tables and work pods provide light privacy, letting travelers confirm plans or messages before moving upstairs. Each guest room features ergonomic desks, streaming TVs, and bedside outlets, providing comfort and productivity without compromise. The 24/7 Market offering snacks, drinks, and frozen meals ensures consistent convenience and access to essentials at all hours.

Guests enjoy 24/7 markets, indoor pools, free Wi-Fi, and parking, practical amenities that make routines seamless and dependable.

  Call (855) 235-0725 to book with an agent.
  7.2 miles from Osceola Park

Starting at

$539.99

per night

Read Reviews View Amenities View All Rooms

FairBridge Inn Express

16 Cheshire Road Pittsfield, Massachusetts

For visitors to Pittsfield, FairBridge Inn Express keeps Osceola Park within easy reach, a detail that supports a stress-free travel plan.

At FairBridge Inn Express, arrivals may include a basic reception, complimentary parking, and modest lobby seating for guest convenience. Accommodations often highlight comfortable bedding, Wi-Fi, and compact work surfaces, providing guests with simple and functional routines. Facilities may highlight compact business areas, vending corners, and breakfast rooms that reinforce balance during travel routines.

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

  Call (855) 234-5074 to book with an agent.
  7.6 miles from Osceola Park

Starting at

$89.99

per night

Read Reviews View Amenities View All Rooms

The Whitlock

16 Church St Lenox, Massachusetts

Guests at The Whitlock can enjoy Osceola Park being a direct run as a defining feature of a well-located stay.

Guests at The Whitlock may encounter straightforward check-in, vending machines, and parking access for practical daily routines. Rooms may include premium linens, rainfall showers, and hardwood floors that contribute to a practical yet stylish environment for rest. Shared spaces typically provide breakfast counters, vending access, and guest laundries that create straightforward travel support.

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

  Call (855) 239-4019 to book with an agent.
  9.5 miles from Osceola Park

Starting at

$567.99

per night

Read Reviews View Amenities View All Rooms

Apple Tree Inn

10 Richmond Mountain Rd Lenox, Massachusetts

Osceola Park is within driving reach from Apple Tree Inn, a detail that makes the hotel a practical and well-positioned base.

At Apple Tree Inn, arrivals may showcase eclectic interiors, boutique-style check-in, and staff providing personalized service. Rooms may include curated furnishings, premium linens, and boutique bathrooms that create a polished and personalized impression. Shared spaces may highlight intimate dining rooms, curated lounges, and co-working areas that reflect boutique individuality.

A visit often highlights complimentary Wi-Fi, laundry service, self-serve markets, and yoga mats, creating flexibility for guest routines.

  Call (855) 235-6136 to book with an agent.
  10.1 miles from Osceola Park

Starting at

$390.99

per night

Read Reviews View Amenities View All Rooms

The Black Swan Lee - Lenox Ascend Hotel Collection

435 Laurel St Lee, Massachusetts

Upon leaving The Black Swan Lee - Lenox Ascend Hotel Collection, Osceola Park is within driving reach for a stress-free trip, simplifying your visit.

Upon arrival, Ascend lobbies often include a grab-and-go market and coffee station, letting guests pick essentials before heading upstairs. Suites offer a living area, a dedicated desk, a mini-fridge and blackout curtains so families and business guests maintain routines with ease. Conference spaces offer projector hookups, breakout tables and flexible seating to support hybrid meetings and workshops efficiently.

With free Wi-Fi, hot breakfast, meeting rooms, fitness equipment, vending and accessible parking, travel days feel more manageable and calm.

  Call (855) 239-5277 to book with an agent.
  13.6 miles from Osceola Park

Starting at

$349.00

per night

Read Reviews View Amenities View All Rooms

Berkshire Travelodge

12703 Rte 22 Austerlitz, New York

Osceola Park is a simple commute from Berkshire Travelodge, a plan that ensures the pre-event journey is always a calm one.

Travelodge features complimentary breakfast stations adjacent to the lobby, providing clarity and dependability for morning routines. Each guest room presents comfortable bedding, blackout drapes, and quiet HVAC systems, promoting restorative sleep every night. Pools featuring loungers, towels, and umbrellas give travelers dependable leisure areas that balance rest with family recreation.

Free Wi-Fi, laundry service, and breakfast options pair with parking and vending, supporting consistent clarity across stays.

  Call (855) 236-8982 to book with an agent.
  14.9 miles from Osceola Park

Starting at

$139.99

per night

Read Reviews View Amenities View All Rooms

Sunset Inn

150 Housatonic Street Lee, Massachusetts

The benefit of using Sunset Inn as a practical base renders it into a great anchor point before the main experience.

Sunset Inn typically offers arrivals with front desk service, modest lobby seating, and on-site parking to ease guest transitions. Each guest room typically provides climate control, compact seating, and in-room coffee, reinforcing comfort and daily travel routines. Public areas may include modest lobbies, vending machines, and laundry access, reflecting the functional focus of budget properties.

Guests may encounter Wi-Fi, continental breakfast, vending access, and laundry spaces, supporting consistent routines while traveling.

  Call (855) 234-5074 to book with an agent.
  16.0 miles from Osceola Park

Starting at

$175.99

per night

Read Reviews View Amenities View All Rooms

Quality Inn

170 Housatonic Street Lee, Massachusetts

As a practical base, Quality Inn is a central element that allows for a more dynamic daily rhythm.

Quality Inn arrival cues—lighting, signage, staff presence, and seating—combine to create a tidy, dependable first impression on arrival. Guest rooms pair microwaves, mini-fridges, and single-serve coffee makers so quick meals and meds remain convenient without leaving the room. Business centers supply computers, printers, and reliable Wi-Fi, enabling last-minute printing, boarding passes, and quick prep on site.

With dependable Wi-Fi and full breakfast service at many locations, mornings remain compact so guests can head to meetings or travel without delay.

  Call (855) 239-5277 to book with an agent.
  16.2 miles from Osceola Park

Starting at

$208.99

per night

Read Reviews View Amenities View All Rooms

Econo Lodge Lee - Great Barrington

980 Pleasant Street Lee, Massachusetts

In the Pittsfield region, Econo Lodge Lee - Great Barrington's role as a practical base lets guests commute easily to Osceola Park before their stay.

Arriving late, guests at many Econo properties find a staffed 24-hour front desk available for dependable key pickup and assistance. Suites provide a separate sitting area, a sizeable desk, a refrigerator and a microwave to let families spread out and plan easily. Guest laundries offer washers, dryers and folding surfaces plus detergent vending at many properties so longer stays can refresh wardrobes easily.

Free Wi-Fi, free breakfast, meeting space, fitness facilities at some locations, laundry and a market keep short stays organized and useful.

  Call (855) 235-6136 to book with an agent.
  18.2 miles from Osceola Park

Starting at

$149.99

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

Within the region, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG serves as a practical base, keeping Osceola Park a simple commute.

Bright finishes and open layouts in Holiday Inn & Suites lobbies create welcoming first impressions that remain consistent worldwide. Guest rooms include plush beds, blackout curtains, and digital thermostats, making nightly rest consistent and reliable. Meeting rooms furnished with AV equipment, adjustable lighting, and breakout spaces create flexibility for varied professional uses.

Meeting spaces, breakfast service, and Wi-Fi connect with business lounges and pools, keeping professional trips balanced and clear.

  Call (855) 233-7850 to book with an agent.
  18.7 miles from Osceola Park

Starting at

$373.99

per night

Read Reviews View Amenities View All Rooms

Travelodge by Wyndham Great Barrington Berkshires

400 Stockbridge Rd Great Barrington, Massachusetts

Because Travelodge by Wyndham Great Barrington Berkshires is a convenient base, guests can utilize a low-key journey before their day begins.

Communal seating areas in Travelodge lobbies offer versatile spaces for conversation, regrouping, or casual planning between guests. All guest rooms include ergonomic desks, supportive chairs, and Wi-Fi, helping professionals maintain productivity on the go. Lobby spaces decorated with murals, seating clusters, and bright finishes provide clarity for orientation and social interaction.

Pet-friendly policies, Wi-Fi, and breakfast counters connect with laundry and vending, simplifying routines for traveling families.

  Call (855) 233-0132 to book with an agent.
  24.0 miles from Osceola Park
Read Reviews View Amenities View All Rooms

Holiday Inn Express Hotel & Suites Great Barrington by IHG

415 Stockbridge Rd Great Barrington, Massachusetts

The uncomplicated regional drive from Holiday Inn Express Hotel & Suites Great Barrington by IHG to Osceola Park in Pittsfield makes the connection between the two easy and fast.

Holiday Inn Express lobby seating areas include charging hubs, giving guests practical comfort while waiting or regrouping with others. Guest rooms are arranged with branded bath amenities, showers, and towels, refreshing travelers and sustaining daily routines. Fitness facilities offering cardio machines, weights, and stretching areas make it convenient to keep exercise routines consistent.

Business lounges, meeting rooms, and Wi-Fi align with breakfast and pools, ensuring balance between productivity and relaxation.

  Call (855) 234-7135 to book with an agent.
  25.9 miles from Osceola Park

Starting at

$377.99

per night

Read Reviews View Amenities View All Rooms

Fairfield Inn & Suites by Marriott Great Barrington Lenox / Berkshires

249 Stockbridge Rd Great Barrington, Massachusetts

The hotel's regional location is a strategic choice, serving as a convenient base with Osceola Park within driving reach.

Fairfield Inn keeps charging hubs and USB-equipped tables visible from reception, enabling quick top-ups while you check-in or plan the day. All guest rooms feature plush bedding, blackout drapes, and quiet HVAC, ensuring restful conditions that help travelers feel refreshed each morning. Business areas supply ergonomic chairs, printers, and reliable computers, allowing continuity of tasks and reducing stress for professionals.

Free Wi-Fi, hot breakfast, self-parking, and fitness centers combine to simplify stays, helping travelers maintain clarity and balanced routines.

  Call (855) 239-5277 to book with an agent.
  26.5 miles from Osceola Park

Starting at

$538.99

per night

Read Reviews View Amenities View All Rooms