Vintage Caboose Rental in Historic Small Town near Springfield, Massachusetts

Chester, Massachusetts (United States)

Vintage Caboose Rental in Historic Small Town near Springfield, Massachusetts

1 unit
4 guest capacity
Shared Bathroom
No pets allowed
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Hosted by Dave
  • Verified Host
  • Joined in 2014
  • Response rate: 100%
  • Response time: Within 1 day
  • More than 50 bookings

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  • Kid-friendly
  • Private Barbecue
This 1919 wooden caboose is located right next to the CSX main railroad line in Chester, Massachusetts, just an hour from Springfield—perfect for a New England getaway! Guests can experience railway life from the 1930s from this caboose, which features wooden bunks with leather cushions and it can accommodate up to four guests.

Outside, the caboose has an outdoor picnic table and a barbecue grill on the lawn. Glampers can enjoy some rustic, al fresco dining to add to the aesthetic of this unique glamping experience. 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 historic 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 lose themselves in the rich history of the area.


  • Twin/Single bed
  • Linens and pillows
  • Electricity
  • Wi-Fi/Internet
  • Bathroom
  • Desk
  • Private Barbecue
Guests have access to restrooms, just a short walk from the accommodation, and there are shower facilities two miles at a nearby campground. There is also an extra kitchen caboose for rent so that guests can make their own food. The property boasts a banquet hall for events. Should guests require additional sleeping space, they are welcome to set up tents on the lawn next to the caboose.

Guest Services

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

Location + Surroundings

  • Forest
  • River, stream or creek
Local services
  • Town/City
  • Train station
  • Museums
  • Shopping
This glamping site located in Chester, less than an hour's drive from Springfield, Massachusetts, 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 conveniently 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.

Bradley International Airport in Hartford, Connecticut, is the nearest international airport, less than 40 miles from Chester.


  • Hiking
  • Fishing
  • Wildlife watching
  • Biking

The historic area has so many great shops and things to see. Guests can enjoy a walk to the famous railroad station, old jails, and the many unique art galleries in Chester. Around this glamping site, guests can hike through one of the largest road-free forests in Massachusetts and see some old railroad artifacts. 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 area, guests will learn the history of the old railroad systems. There is also great fishing near by and hiking opportunities.

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Accommodation Rules

  • Check-in: Flexible
  • Check-out: Flexible
  • Infants allowed Under 2 years old
  • Children allowed 2-12 years old
  • No Pets allowed
  • No smoking
  • No parties
  • Events allowed
  • Some spaces are shared

Cancellation policy

Free cancellation up to 7 days
Moderate: You will receive a full refund if you cancel at least 7 days prior to check-in.

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.

Glampers will need to bring pillows and blankets as the hosts do not supply them.

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