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Vintage Caboose Rental in Historic Small Town near Springfield, Massachusetts

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Interior
Property grounds
Exterior
Miscellaneous
Miscellaneous

Reviews

8.8 out of 10
Excellent

Popular amenities

  • Barbecue grill
  • Air-conditioning
  • Pet-friendly
  • Fireplace
  • Non-smoking

Explore the area

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

Rooms & beds

1 bedroom (sleeps 4)

Bedroom

4 Single Beds

1 bathroom

Shared Bathroom

Bathtub or shower · Toilet

Spaces

Number of living rooms

Add dates for prices

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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.
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 - 60.6 km
  • Naismith Memorial Basketball Hall of Fame - 42 min drive - 61.0 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
  • ‪Classic Pizza - ‬3 min walk
  • ‪The Bridge Store - ‬11 min drive

Frequently asked questions

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

Yes, pets are allowed at this property.

What time is check-in at Vintage Caboose Rental in Historic Small Town near Springfield, Massachusetts?

Check-in begins at noon.

What time is check-out at Vintage Caboose Rental in Historic Small Town near Springfield, Massachusetts?

Checkout is at noon.

Reviews

8.8

Excellent

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 4 out of 5 reviews
Rating 8 - Good. 0 out of 5 reviews
Rating 6 - Okay. 0 out of 5 reviews
Rating 4 - Poor. 1 out of 5 reviews
Rating 2 - Terrible. 0 out of 5 reviews

8.8/10

Cleanliness

10/10

Check-in

10/10

Communication

9.6/10

Location

8.4/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

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

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful, unique experience. The train going by was pretty humbling. Love the preservation of history in this charming landscape.
Stayed 1 night in Sep 2026
Response from VrboOwner on 14 Sept 2026
Thanks so much, Jess. It was great having you. Hope to see you again sometime. Best, Dave for the caboose
Verified review

10/10 Excellent

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

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

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
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