Vintage Caboose Rental in Historic Small Town near Springfield, Massachusetts

Caboose in Chester, MA

4 guests • 1 bedroom • 4 beds • 1 bathroom

4.5
• 69 reviews

Features and services

Beds

  • single-bed

    4 Twin/Single beds

Most popular features

  • Pets allowed

  • Wi-Fi/Internet

  • Heating

  • Hiking

  • River, stream or creek

  • Fishing

  • Air conditioning

  • Forest

  • Wildlife watching

  • barbecue

    Private Barbecue

  • 1 Bathroom

  • Parking

  • Firewood

  • Shower

  • Town/City

  • Biking

Where you will stay

Get in touch to book your luxury camping rental

Chester, Massachusetts

Detailed location provided after booking

Scenic views
  • Forest

  • River, stream or creek

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.
Activities near Chester
  • 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. From mid-June until mid-August, Chester Theatre Co., professional equity guild theatre, is in season and within walking distance from the caboose.

Property reviews

4.5 overall rating
Overall experience
4.5
Cleanliness
4.5
Activities
4.0
Nature surroundings
5.0
Uniqueness
5.0
Comfort
2.5

Things to know

Arrival and departure

  • Check-in: Flexible

  • Check-out: Flexible

House rules

Cancellation policy

Additional info

loading