Accommodation verified by Glamping Hub

Vintage Caboose Rental in Historic Small Town near Springfield, Massachusetts

4.5 60 Reviews

"Everything was as expected. Very comfortable and great place to stay. Hiking options were great and local food choices were very nice. Dave was …"

Charles, guest in Dec. 17, 2023.
Entire Caboose
Pets allowed

Caboose • 4 guests • Bathroom

About this place

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.

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

Features and services

  • Pets allowed

  • Wi-Fi/Internet

  • Hiking

  • River, stream or creek

  • Fishing

  • Forest

  • Wildlife watching

  • barbecue

    Private Barbecue

  • Bathroom

View all

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.

Property reviews

4.5 - 60 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.

CHESTER RAILWAY STATION, a museum where the Glamping Caboose is kept, was named a National Historic Landmark on January 13, 2022. The Secretary of the Interior identifies nationally significant places that best represent the American experience. Landmark designation encourages the preservation of places that have exceptional value for illustrating the history of the United States, for the inspiration and benefit of all Americans. This designation was also afforded to the Keystone Arches, an early series of stone railroad bridges highlighted in a nearby hiking trail enjoyed by many of our Glamping guests.

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

Cancellation policy: Flexible

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50% refund available if cancelled before [date].

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50% refund available if cancelled before [date].

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Location and surroundings

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Chester, Massachusetts (United States of America)

Detailed location provided after booking

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

Activities near Chester, MA

  • Hiking

  • Biking on-site

  • Fishing on-site

  • Wildlife watching on-site

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.