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Vintage Caboose Rental in Historic Small Town near Springfield, Massachusetts

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Exterior
Miscellaneous
Bathroom
Property grounds
Bathroom

Reviews

8.6 out of 10
Excellent
1 bedroom1 bathroomSleeps 4

Popular amenities

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

Explore the area

View in a map
Chester, MA
  • Place, Chester Town Hall
    ‪5 min walk‬
  • Place, Jacob's Pillow
    ‪16 min drive‬
  • Place, Tanglewood Music Center
    ‪39 min drive‬
  • Airport, Hartford, CT (BDL-Bradley Intl.)
    ‪65 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.



Please note that this property does not provide linens, bedding, or towels. Most guests bring sleeping bags.
Our prices include all fees. No hidden fees.

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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
This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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

About the area

Chester

Located in Chester, Vintage Caboose Rental in Historic Small Town near Springfield, Massachusetts 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/biking trails.
Map
Chester, MA

What's nearby

  • Chester Town Hall - 5 min walk - 0.5 km
  • Jacob's Pillow - 16 min drive - 16.5 km
  • Tanglewood Music Center - 39 min drive - 43.8 km
  • MGM Springfield - 41 min drive - 60.0 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
  • ‪Papa Bob's - ‬8 min drive
  • ‪Bluenote Cafe - ‬3 min walk
  • ‪Carm’s Restaurant - Charlies Garage - ‬8 min walk
  • ‪Chester Village Market - ‬8 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.

Reviews

8.6

Excellent

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. 3 out of 4 reviews
Rating 8 - Good. 0 out of 4 reviews
Rating 6 - Okay. 0 out of 4 reviews
Rating 4 - Poor. 1 out of 4 reviews
Rating 2 - Terrible. 0 out of 4 reviews

8.6/10

Cleanliness

10/10

Check-in

10/10

Communication

9.6/10

Location

8.0/10

Listing accuracy

Reviews

Verified review

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 review

10/10 Excellent

Jenny K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The caboose is a fun twist on a camping trip! Amenities are just as described - a lot like camping with an air-conditioned shelter that has electricity and wifi and a private bathroom and shower. There was interesting historical stuff everywhere you looked, and Dave was really nice and helpful - and super informative about the site and the area. Thanks!
Stayed 2 nights in Jul 2026
Response from VrboOwner on 30 Jul 2026
Hi Jenny: Thanks for the nice review. It was great having you. Sorry the weather didn't cooperate. Best, Dave for the caboose
Verified review

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
Verified review

4/10 Poor

Suzanne Z.

Liked: Check-in, communication, location
Disliked: Cleanliness, listing accuracy
Lovely host. Interesting small historical museum to peruse. Extremely rough accommodations in the caboose. Live freight train passes through multiple times throughout the night.
Stayed 1 night in Jul 2026
Response from VrboOwner on 5 Aug 2026
I'm sorry, Suzanne; We have pictures showing how close the trains are. Most of our guests, including any 'regulars', think that's the best part. They see it as an immersive history exhibit. Best regards, Dave for the caboose

About the host

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