As local travel experts, we know what travelers are looking for when it comes to finding the perfect accommodations for their next trip. To compile our lists, we scour the internet to find properties with excellent ratings and reviews, desirable amenities, nearby attractions, and that something special that makes a destination worthy of traveling for.

Between places for camping and glamping, inns, and Airbnbs, there is no shortage of interesting accommodations in Massachusetts. Add a historical element to the mix, and you can stay somewhere quite unforgettable. Located in the historic small town of Chester, you’ll find a glamping accommodation that’s sure to be unlike anywhere else you’ve ever spent the night. And if you love trains, then you’ll love sleeping in this authentic Vintage Caboose Rental.

The small community of Chester is located in the Berkshires foothills close to Springfield. Points of interest here include the Chester-Blandford State Forest, Keystone Arch Bridges Trail, and the Chester Railway Station.
glampinghub.com
If you enjoy trains, the historic Chester Railway Station & Museum, housed inside an 1862 Western Railroad station, is a must-visit.
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On the museum's property, there's also a piece of railroad history here that you can rent for the night and have a glamping adventure.
glampinghub.com

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This authentic 1919 vintage railway caboose has been renovated and offers rustic accommodations for up to four guests. Inside you'll find wooden bunks with leather cushions and a desk. Outdoors is a lawn and you'll have access to a grill and picnic table.
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Just a quick walk away are the restrooms and, if you need a shower, there are shower facilities you can use at a nearby campground just two miles away.
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The main track for the CSX railroad runs right by the caboose, so you'll be in the heart of the action as trains rumble by. It's quite the immersive experience!
glampinghub.com
While staying in Chester, you'll have convenient access to plenty of trails and the Keystone Arch Bridges, another piece of Chester's rail history. Not only are the arch bridges gorgeous architectural marvels but were once a part of the country's first railroad that passed over a mountain.
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So, how would you like to spend the night in a vintage caboose in rural Massachusetts? If you’ve been to Chester and have stayed here, please tell us about the experience in the comments. For more information and to book your stay, visit Glamping Hub and the Chester Railway Station website.

Do you know of a fascinating place to stay in Massachusetts you’d like to share with us? Let us know by using our nomination form.

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