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.
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.
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.
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!
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.
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.
Getting away from it all doesn’t have to mean jetting across the globe. There are plenty of places right here in the Bay State that can help you feel a million miles away from the everyday. The perfect way to unwind is with a getaway at one of these amazing cabins in Massachusetts. The following 14 cabin rentals in Massachusetts all offer beautiful natural surroundings and next-level amenities. Which one of the following best cabins in Massachusetts is your next staycation destination?
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Affordable Cabins in Massachusetts
Enjoy the best of the Bay State without breaking the bank when you check into one of these adorable *and* affordable cabins in Massachusetts:
This Charming Historic Cottage comes highly rated and is the perfect blend of historic charm and modern luxury. Built in 1832 as a one-room schoolhouse – a function it served until 1950 -- this charming and historic building has been given new life as a guest house - since 1998. Perfect for couples or even small families, this cabin is located just a stone's throw from Mt. Greylock.
Size: This two-bedroom, one-bathroom sleeps up to four guests.
Price: $90/night.
Amenities: This eclectic cabin features a private backyard, a washer/dryer, books, a gaming console, a full kitchen, and lake access.
Ratings: 5/5.
The Nerd Preservation Sanctuary is one of the most unique cabin getaways in Massachusetts. Toutedn by the owner as a "nerdscapist, geekmantic country home," you can expect the unexpected here. Adorning the walls is art from the MA Museum of Bad Art and there are "bad sculptures" throughout the space as well. If you love artsy, eclectic places, this one is hard to beat! The cabin is also close to Tanglewood, Butternut, and Jacob's Pillow as well as five lakes.
Size: This studio with one bathroom sleeps up to two guests.
Price: $100/night.
Amenities: Queen bed, electricity, water, mini fridge, outhouse, and an outdoor shower.
Ratings: 4.9/5.
The Artsy Pine Cabin in the Woods is a tiny rustic abode in the woods where you'll be surrounded by nature and, therefore, experience peace, quiet, and privacy. Warwick State Forest surrounds the property where the owners also live. This unique getaway is perhaps one of the cutest cozy cabins in the state!
This luxury beachfront cabin in West Yarmouth is truly one-of-a-kind. A family-owned cabin for 70 years, this well-appointed rental has a robust array of modern amenities while retaining the charm of Old Cape Cod. Sleeping up to nine, this is a great getaway for a large family or even multiple families!
Size: The Barn can accommodate five guests and has three bathrooms.
Price: $322/night.
Amenities: This well-appointed cabin features a gas fireplace stove, a full kitchen, hot tub, and a solar-heated saltwater pool.
Ratings: 4.86/5.
The 1740 Barn is unlike any other cabin in the Bay State. Located in Barnstable, Massachusetts, The Barn was built in 1740 and is packed with cozy charm. While the inside is pure luxury, the outside is even better. With a hot tub, expansive courtyard, and on-site wellness studio with private yoga and massage sessions, it doesn't get more luxurious than this!
Size: This 950 sq. ft. cabin has three bedrooms and one bathroom.
Price: $400/night.
Amenities: Guests have access to the numerous amenities at Summer Village, including pools, a hot tub, beach, full-service restaurant, and bar.
Ratings: 4.8/5.
This cozy cabin is part of the Summer Village resort community, offering a great rental option for those looking for resort-level amenities in a cozy cabin package. In addition to the amenities offered at the resort, the cabin itself has a kitchen, outdoor deck, and a lovely patio.
This charming cabin is peak romantic vibes, with high-end appliances, smart technology, and an immaculately designed space. It's also located approximately a mile from both Edgartown and a mile from South Beach, though with its amazing digs, you might just decide to cozy up and never leave!
Size: This cottage has two bedrooms and one bathroom and can accommodate up to five guests.
Price: $229/night.
Amenities: This lakefront cottage has several non-motorized watercraft you can use during your stay as well as a private beach.
Ratings: 5/5.
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If you've ever wanted the seclusion that only comes with a private beach, then Breezy Point is for you. This incredible rustic cabin sits on the shores of Winnekeag Lake in Ashburnham, and it's as relaxing as it is picturesque. As one of the best cabin getaways in Massachusetts, staying here is a must.
Massachusetts might not be a huge state, but there are plenty of places to "get lost" in the wondrous wilds of MA. If you're seeking R&R, these secluded cabins in Massachusetts are a great place to get it!
Size: This pet-friendly can sleep 10 guests and has four bathrooms.
Price: $250/night.
Amenities: Pet-friendly, hot tub, secluded location, full kitchen, smart technology, en suite bathrooms, a deck with an outdoor fire, gas grill, and dining table.
Ratings: 5/5.
Known as Waldtreff, this large cabin in Becket is the perfect place for a large family getaway or a couple’s retreat with space to spare. The cabin is situated on a 60-acre private lot and is just a few minutes away from nearby Becket beach. The master bathroom features a full soaking tub, while another full bathroom offers a Jacuzzi and sauna.
Size: This 1,800 sq. ft. cabin has three bedrooms and two bathrooms.
Price: $291/night.
Amenities: Galley kitchen, wood stove, beautiful deck with a grill and outdoor seating, master bedroom with an en suite, cozy den with smart technology, video games, and a piano.
Ratings: 4.9/5.
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Escape in the wilds of the Berkshires at this cozy cabin in the woods. Perched just up the hill from Lake Garfield, this cabin, AKA The Hupi House, offers a truly magical view of the lake and mountains for miles beyond, with sunset vistas that will drop your jaw.
Size: This charming cottage can accommodate up to four guests and has one bedroom and one bathroom.
Price: $150/night.
Amenities: Wireless internet, a pool (open June through September), a wood stove, a full kitchen, and a washer and dryer.
Ratings: 4.9/5.
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Overlooking the Westfield River and surrounded by a state forest in Cummington is the newly-renovated Clearing Cottage. This is the ultimate secluded getaway that puts you within arm's reach of nature. Go hiking, biking, or birding just steps away from this charming abode.
Size: This cabin has one bedroom and two bathrooms and can accommodate up to two guests.
Price: $225/night.
Amenities: This 100-year-old cabin features a central fireplace, wood stove, and outdoor Jacuzzi.
Ratings: 4.93/5.
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The Great Barrington Cabin has it all... and then some. If you’re looking for a snug hideaway, this cabin at the foot of Monument Mountain in Great Barrington is it. With enough space for two guests, it’s the perfect couple’s retreat. The Trails to Flag Rock are just a short walk away. Upstairs, you’ll find a small art studio with art supplies included! This rental is perfect for a romantic getaway in MA.
Size: This cabin has four bedrooms and two bathrooms.
Price: $366/night.
Amenities: Modern kitchen, two cozy fireplaces, an outdoor hot tub, and scenic location with a babbling brook make this cabin rental a true hidden gem.
Ratings: 4.94/5.
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There’s nothing like a weekend in the Berkshires, and this rustic cabin is the perfect mountain getaway. Located in Monterey, it’s situated just a few minutes up the road from Lake Garfield. The cabin has four bedrooms and a covered deck overlooking the forest, which is perfect for grilling. The kitchen is also pretty luxurious, featuring all-new appliances and stunning granite countertops. And don’t forget the outdoor hot tub! This place can sleep up to seven and even has three kayaks available for use.
Size: This cabin has two bedrooms plus a loft and one bathroom.
Price: $222/night.
Amenities: An outdoor hot tub, washer and dryer, a full kitchen, a fire pit, and beach access.
Ratings: 5/5.
Need some serenity by a lake? This beautiful cabin with a hot tub is located at Lake Ashmere in Hinsdale, a 287-acre body of water set in the Berkshires. Take a quick 2-minute walk to the lake's beach and launch a kayak or a canoe for some time on the water. When you come back to shore, spend some time with a relaxing soak in the hot tub. After all, you earned it!
Each of these charming cabins is simply perfect for a relaxing getaway in New England. For more information on booking one of the best cabins in Massachusetts with a hot tub, please visit the listing for each spot.
Do you know of any other cozy cabins in Massachusetts with hot tubs? Share your experiences with us in the comments!
If you have ever paid a visit to a historic village such as Old Sturbridge Village or the Plimoth Patuxet Museums, you can probably picture what it was like to live in New England back in the colonial days. But have you ever imagined what it is like to stay the night at an authentic historic property? If this experience is on your bucket list (it is absolutely on mine), a unique opportunity to live like it is 1680 awaits you at the William Haskell House in Gloucester, Massachusetts.
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A stay at the William Haskell House is a true destination experience. While other historic properties have been renovated and modernized, the Haskell House has been delicately preserved and restored. This special home dates back to the 1680s and is one of the oldest houses in the area.
When you step into the Haskell home, you can’t help but be transported back to the 17th century. As you gaze at the exposed wooden beams, brick fireplaces, and plethora of antique furniture, you will definitely feel like you have traveled back to a time when the Haskell family resided here.
The North Ell room of the home is available for overnight stays. The room includes a comfortable queen-sized bed, a little seating area, and a private bathroom (with running water).
Imagine having your breakfast in this historic parlor!
And no need to worry about cooking dinner over an open flame. The home also has a shared modern kitchen and lounge area with an electric stove, dishwasher, coffee maker, and cooking utensils.
Other updated amenities include WiFi, a television, and heating/air conditioning.
A stay at the Haskell House also includes access to the outside patio and firepit. The home is set on over two acres of beautiful land surrounded by a saltwater marsh. Guests can enjoy scenic views, birdwatching, and a sense of serenity on this peaceful property.
Have you spent the night at the William Haskell House? Are there other historic rentals you would recommend staying at? Find out more about booking an unforgettable stay at the William Haskell House. Other historic Massachusetts rentals worth a visit include the 1693 Newcomb Tavern in Sandwich and Brooksong, a renovated 1866 schoolhouse in Dalton.
