Entire home

Vintage Caboose Rental in Historic Small Town near Springfield, Massachusetts

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Exterior
Miscellaneous
Bathroom
Property grounds
A small, enclosed shower area with a showerhead, a handheld showerhead, and a towel rack.

Reviews

10 out of 10
Exceptional
1 bedroom1 bathroomSleeps 4

Popular amenities

  • Pet-friendly
  • Air-conditioning
  • Barbecue
  • Internet access
  • Barbecue
  • Bathtub

Explore the area

View map
Chester, MA
  • Place, Chester Town Hall
    ‪5 min walk‬
  • Place, Jacob's Pillow
    ‪18 min drive‬
  • Place, Naismith Memorial Basketball Hall of Fame
    ‪42 min drive‬
  • Airport, Westfield, MA (BAF-Barnes Municipal)
    ‪34 min drive‬

Rooms & beds

1 bedroom (sleeps 4)

Bedroom 2

4 Single Beds

1 bathroom

Bathroom 1

Bathtub or shower

About this property

Vintage Caboose Rental in Historic Small Town near Springfield, Massachusetts

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 a fully-accessible shower in the Station next to the bathrooms.



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 a fully-accessible shower in the Station next to the bathrooms. 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.

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House Rules

Flexible check-in available (contact host in advance of arrival)
Flexible check-out available (contact host to arrange)
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Children

Children allowed: ages 3–17
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Events

Events allowed
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Pets

Pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Property Registration Number C1536453363
Property # 5110309vb
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Parties and events are allowed on site
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property

About the area

Chester

Located in Chester, this holiday home is in the city centre and on a river. Chester Town Hall and Jacob's Pillow are cultural highlights, and some of the area's activities can be experienced at Blandford Ski Area and Otis Ridge. Becket Arts Center and Ashintully Gardens are also worth visiting. Take the opportunity to explore the area for outdoor excitement like hiking.
Map
Chester, MA

What's nearby

  • Chester Town Hall - 5 min walk - 0.5 km
  • Jacob's Pillow - 18 min drive - 16.5 km
  • Big E - 41 min drive - 54.3 km
  • Tanglewood Music Center - 41 min drive - 44.5 km
  • Naismith Memorial Basketball Hall of Fame - 42 min drive - 60.3 km

Getting around

  • Pittsfield Station - 41 min drive
  • Westfield, MA (BAF-Barnes Municipal) - 38 min drive

Restaurants

  • ‪Comfort Kitchen & Bar - ‬11 min drive
  • ‪The Bridge Store - ‬11 min drive
  • ‪Papa Bob's - ‬8 min drive
  • ‪Chester Village Market - ‬8 min walk
  • ‪Bluenote Cafe - ‬3 min walk

Frequently asked questions

Is Vintage Caboose Rental in Historic Small Town near Springfield, Massachusetts pet-friendly?

Yes, pets are allowed at this property.

How much does it cost to stay at Vintage Caboose Rental in Historic Small Town near Springfield, Massachusetts?

As of 13 June 2026, prices found for a 1-night stay for 2 adults at Vintage Caboose Rental in Historic Small Town near Springfield, Massachusetts on 16 June 2026 start from NZ$172, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Where is Vintage Caboose Rental in Historic Small Town near Springfield, Massachusetts located?

Located in the heart of Chester, this holiday home is 0.4 mi (0.6 km) from Chester Town Hall and within 6 miles (10 km) of Becket Land Trust Historic Quarry and Chester Center Historic District. Huntington Town Hall and Huntington Public Library are also within 9 miles (15 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 2 out of 2 reviews
Rating 8 - Good. 0 out of 2 reviews
Rating 6 - Okay. 0 out of 2 reviews
Rating 4 - Poor. 0 out of 2 reviews
Rating 2 - Terrible. 0 out of 2 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

JULIE M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Dave is truly awesome and we will absolutely be back! This is a historic space and a great glamping experience :)
Stayed 1 night in Apr 2026
Verified

10/10 Excellent

Armaan D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Dave is an amazing host and extremely friendly. We got to experience the outdoors in quite an extraordinary fashion while living in a caboose. The space is perfect for setting up camp and had clean bathrooms with warm water. We appreciated having a space heater in the caboose. Staying here felt being taken back in time and enjoyed our time learning about the history pf the railroad. Very pet friendly also.
Stayed 1 night in May 2026

About the host

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