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) 239-5277 to book with an agent.
  2.1 miles from Osceola Park

Starting at

$89.99

per night

Read Reviews View Amenities View All Rooms

Best Western Plus Berkshire Hills Inn & Suites

1350 West Housatonic St Pittsfield, Massachusetts

From the moment you arrive at Best Western Plus Berkshire Hills Inn & Suites, Osceola Park is a simple drive, making for an easy start.

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) 239-5277 to book with an agent.
  2.2 miles from Osceola Park

Starting at

$77.99

per night

Read Reviews View Amenities View All Rooms

Holiday Inn & Suites Pittsfield-Berkshires by IHG

One West Street Pittsfield, Massachusetts

The journey from Holiday Inn & Suites Pittsfield-Berkshires by IHG to Osceola Park is a simple drive, a benefit that contributes to a cohesive and convenient visit.

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

$116.99

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) 234-7135 to book with an agent.
  3.1 miles from Osceola Park

Starting at

$155.99

per night

Read Reviews View Amenities View All Rooms

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield, Massachusetts

The guest's journey from Berkshire Mountain Lodge in Pittsfield to Osceola Park is a quick drive, enhancing the sense of being in a convenient location.

At Berkshire Mountain Lodge, 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) 235-0725 to book with an agent.
  3.8 miles from Osceola Park

Starting at

$86.99

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 drive 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) 239-5277 to book with an agent.
  4.2 miles from Osceola Park

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

At Holiday Inn Express & Suites Pittsfield - Berkshires by IHG, being a quick drive from Osceola Park is a central aspect that enhances the freedom of the guest.

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) 233-7850 to book with an agent.
  4.3 miles from Osceola Park

Starting at

$149.00

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 drive 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) 233-7850 to book with an agent.
  4.6 miles from Osceola Park

Starting at

$96.99

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) 239-4019 to book with an agent.
  4.7 miles from Osceola Park

Starting at

$76.99

per night

Read Reviews View Amenities View All Rooms

Hampton Inn & Suites Berkshires-Lenox

445 Pittsfield Rd Lenox, Massachusetts

This accessible drive to Osceola Park allows Hampton Inn & Suites Berkshires-Lenox to offer a convenient and well-integrated lodging experience.

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) 236-8982 to book with an agent.
  4.8 miles from Osceola Park

Starting at

$147.99

per night

Read Reviews View Amenities View All Rooms

Berkshires Untold

194 Pittsfield Rd Lenox, Massachusetts

A notable advantage of Berkshires Untold in Pittsfield is the simple drive to Osceola Park, making the hotel a strategic hub for a multi-purpose visit.

Guests at Berkshires Untold may encounter cozy seating, artisanal décor, and complimentary refreshments for a boutique welcome. Guest rooms often feature artisanal décor, plush bedding, and curated minibars that contribute to a boutique-focused guest stay. Facilities often present artisanal cafés, stylish bars, and eclectic lounges that emphasize boutique-style orientation and design.

Guests may enjoy Wi-Fi, boutique breakfast, laundry access, and pet allowances, reinforcing boutique practicality during extended stays.

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

Starting at

$125.10

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.

FairBridge Inn Express 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) 234-2997 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.

At The Whitlock, 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) 239-5277 to book with an agent.
  9.5 miles from Osceola Park

Starting at

$131.99

per night

Read Reviews View Amenities View All Rooms

The Black Swan Lee - Lenox an Ascend Collection Hotel

435 Laurel St Lee, Massachusetts

Osceola Park is within driving reach from The Black Swan Lee - Lenox an Ascend Collection Hotel, a design that offers a simple way to get there.

Arrivals at The Black Swan Lee - Lenox an Ascend Collection Hotel typically include a polished reception, attentive concierge guidance, and refined seating in the lobby area. Accommodations may include polished décor, premium bedding, and minibars that contribute to a refined and comfortable guest experience. Facilities may provide elegant lounges, upscale restaurants, and wellness services that contribute to a sophisticated impression.

Accommodations may include premium bedding, fitness centers, stylish lounges, and Wi-Fi, blending relaxation with productivity needs.

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

Starting at

$97.99

per night

Read Reviews View Amenities View All Rooms

Pleasant Valley Motel West Stockbridge

42 Stockbridge Rd West Stockbridge, Massachusetts

The hotel's location is a practical hub, with Osceola Park within driving reach, making trip logistics straightforward.

Arrivals at Pleasant Valley Motel West Stockbridge may highlight vending corners, compact desk service, and exterior parking that reinforce daily guest routines. Each guest room typically includes Wi-Fi, climate control, and compact bathrooms, sustaining functional routines across visits. Facilities often showcase compact lobbies, vending corners, and modest breakfast spaces that reflect straightforward practicality.

A visit may provide Wi-Fi, vending access, exterior parking, and modest breakfast snacks, reflecting budget-friendly practicality daily.

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

Starting at

$60.99

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.

Guests at Sunset Inn 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) 239-5277 to book with an agent.
  16.0 miles from Osceola Park

Starting at

$76.99

per night

Read Reviews View Amenities View All Rooms

Pilgrim Inn

165 Housatonic St Lee, Massachusetts

The journey from Pilgrim Inn to Osceola Park is an easy regional drive, a perk that helps frame a convenient and well-organized stay.

Pilgrim 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) 236-8982 to book with an agent.
  16.1 miles from Osceola Park

Starting at

$75.99

per night

Read Reviews View Amenities View All Rooms

Quality Inn Lee - Lenox South

170 Housatonic Street Lee, Massachusetts

This practical base of operations from Quality Inn Lee - Lenox South lets guests enjoy the Pittsfield region while keeping Osceola Park accessible.

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) 233-7850 to book with an agent.
  16.1 miles from Osceola Park

Starting at

$81.99

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 convenient base, guests can plan on an easy regional drive to Osceola Park.

The Springs Motel often includes exterior entries, vending machines, and modest lobbies that create practical and straightforward arrivals. Accommodations may feature cable TV, mini-fridges, and climate control, ensuring basic consistency for travelers staying overnight. Shared spaces may include vending machines, guest laundries, and modest lobbies that emphasize practical routines for overnight visitors.

Guests may enjoy Wi-Fi, ice dispensers, vending machines, and parking, sustaining reliable routines across budget accommodations.

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

Starting at

$110.99

per night

Read Reviews View Amenities View All Rooms

The Red Lion Inn

30 Main Street Stockbridge, Massachusetts

When staying in the Pittsfield area, the uncomplicated drive from The Red Lion Inn to Osceola Park remains a low-stress start to the day.

The welcoming ambiance of a Red Lion hotel lobby provides a stimulating and immersive welcome that is both chic and unpretentious. Bedrooms are pet-friendly, with plenty of space and durable surfaces to provide a worry-free and comfortable stay for animal guests. The free breakfast is a hallmark of the hotel's hospitality, offering a hearty and convenient start to the day at no additional charge.

Between the fitness center, the indoor pool, the hot tub, and the free breakfast buffet, both wellness and convenience are well-covered.

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

Starting at

$151.99

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) 233-7850 to book with an agent.
  18.2 miles from Osceola Park

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

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) 239-4019 to book with an agent.
  18.7 miles from Osceola Park

Starting at

$121.99

per night

Read Reviews View Amenities View All Rooms

The Little Lion

506 Stockbridge Road Great Barrington, Massachusetts

As a convenient base, The Little Lion is a central element that supports a flexible and relaxed visit.

The Little Lion often greets guests with curated interiors, warm greetings, and boutique reception areas designed for personal attention. Guest rooms may feature eclectic décor, premium bedding, and curated minibars that reflect a stylish boutique orientation. Amenities may provide farm-to-table dining, curated cocktail bars, and cozy seating that reinforce a personalized boutique stay.

A stay may feature complimentary Wi-Fi, bike storage, laundry service, and artisanal snacks, aligning travel with boutique convenience.

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

Starting at

$110.99

per night

Read Reviews View Amenities View All Rooms

Chatham Travelodge

598 NY 295 Old Chatham, New York

Reaching Osceola Park from Chatham Travelodge is an easy regional drive, a trait that weaves simplicity into the guest's daily routine.

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) 233-7850 to book with an agent.
  22.9 miles from Osceola Park

Starting at

$115.99

per night

Read Reviews View Amenities View All Rooms