Vintage 1919 Wooden Caboose in Historic Small Town in Massachusetts

Chester, Massachusetts (United States) view map
1 unit
4 guest capacity
1 night minimum stay

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Description of Glamping Units

This 1919 wooden caboose is located right next to the CSX main railroad line in Chester, Massachussetts—perfect for a New England getaway! Guests can experience railway life from the 1930s from this caboose, which features wooden bunks with leather cushions for sleeping accommodations for up to four guests.

Outside, the caboose has an outdoor picnic table and a barbecue grill on the lawn. Guests have access to the bathrooms in the station, and shower facilities are two miles away at the nearby Walker Island Campground.

While staying here, guests can learn more about the historical railroad and see some historic railroad artifacts and the very first stone arch bridges in the United States! With an abandoned quarry nearby, home to the only standing wooden derrick in New England, guests will loose themselves in the rich history of the area. Read More

Accommodation Amenities

  • Barbecue
  • Electricity
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This wooden caboose provides a bathhouse for all guests that stay in the caboose. It also offers an extra kitchen caboose for rent so that families can make their own food. There is also a banquet room available to rent for large events.

  • Shared bathroom
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  • Couples
  • Events
  • Family-friendly
  • Groups
  • Weddings
  • Location + Surroundings

    This glamping site located in Chester has a small town feel to it, but is still bursting with character. Chester is a historically listed town in Massachusetts which offers unique festivals and wonderful shops. The location is also settled near a hiking trail where guests can witness the beautiful New England fall foliage. Take a trip to Keystone Arches Trail for the day, or Chester-Blandford State Forest for some scenic hikes. Guests will love a stay at this wooden caboose nestled in the countryside and surrounded by history. Read More


    There is a catering service available to guests if they book for a specific event.


    • Dining
    • Fishing
    • Hiking
    • Sightseeing
    • Walking

    The historic area has so many great shops and things to see. Take a walk to the famous railroad station, old jails, and the many unique art galleries. Around this glamping site guests can hike through one of the largest road-free forests in Massachusetts and see some old railroad artefacts. Along the path guests will discover the first ever keystone arch railroad bridges built in America! Staying in the caboose itself is certainly an experience, but by walking around the are guests will learn the history of the old railroad systems. There is also great fishing near by, and hiking opportunities.

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    Cancellation policy

    • You will receive a full refund if you cancel at least 7 days prior to check-in.
    • You will be charged for one full night’s stay plus 50% of the cost of the rest of the stay if you cancel within 7 days of check-in.
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    Additional Information

    There is a discount for all guests that stay more than one night. This site also holds events for guests looking for a unique and fun experience.

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