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Vintage Caboose Rental in Historic Small Town near Springfield, Massachusetts

Chester, Massachusetts (United States of America)

Vintage Caboose Rental in Historic Small Town near Springfield, Massachusetts

Accommodation verified by Glamping Hub
4.5 38 Reviews

"Dave was an absolutely wonderful and kind host! The area of Cheater is picturesque: beautiful mountains surrounding the entire town with many calming…"

Chris Helminski, guest in Feb. 16, 2021.
Private Caboose
4 guests
Entire Caboose
Pets allowed

Go glamping this weekend in a vintage caboose near Springfield, MA!

This 1919 wooden vintage 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 vintage 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.

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 vintage caboose.

Features and services

  • Wi-Fi/Internet
  • barbecue Private Barbecue
  • Desk
  • Electricity
  • Bathroom
  • single-bed Twin/Single bed
  • River, stream or creek
  • Forest
  • Town/City

COVID-19 Actions

All guest areas are wiped down before each new arrival. Host checks temperature before greeting guests. All state regulations regarding the pandemic are posted in the caboose.

Hosted by Dave
90% positive feedback

  • Response rate: 100%
  • Response time: Within 1 day
  • Joined in 2014
  • More than 100 bookings

units 1 accommodation in Glamping Hub

Have a question? Contact Dave

4.5 - 38 Reviews

Accommodation rules

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

Be kind to the environment and take care of the surroundings.

Cancellation policy

Free cancellation up to 24 hours
Flexible: You will receive a full refund if you cancel 24 hours or more prior to check-in.

Location and surroundings

Chester, Massachusetts (United States of America)

Detailed location provided after booking

  • Forest
  • River, stream or creek
  • Town/City


  • Hiking
  • Biking
  • Fishing
  • Wildlife watching

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.