Charlestown Vacation Rentals

Compare Vacation Rentals & Rent By Owner Homes in Charlestown, Boston, Massachusetts, USA

10.0 (227 Reviews)
1 Bedroom 2 Guests
From US $374 per night
9.1 (11 Reviews)
2 Bedrooms 6 Guests
10.0 (168 Reviews)
1 Bedroom 4 Guests
From US $293 per night
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New
1 Bedroom 4 Guests
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8.6 (790 Reviews)
192 Bedrooms 45 Guests
9.8 (73 Reviews)
1 Bedroom 6 Guests
From US $491 per night
9.8 (63 Reviews)
1 Bedroom 2 Guests
9.8 (43 Reviews)
1 Bedroom 2 Guests
From US $458 per night
9.8 (7 Reviews)
1 Bedroom 3 Guests
9.6 (132 Reviews)
2 Bedrooms 6 Guests
From US $382 per night
9.6 (57 Reviews)
1 Bedroom 3 Guests
8.0 (1 Review)
2 Bedrooms 6 Guests
New
2 Bedrooms 5 Guests

About Charlestown Vacation Rentals

With more than 49 Charlestown vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Charlestown.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Charlestown, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Charlestown. Places to stay near Charlestown are 713.27 ft² on average, with prices averaging US $573 a night.

RentByOwner makes it easy and safe to find and compare vacation rentals in Charlestown with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Charlestown Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Charlestown?

How many Rentbyowner vacation rentals are available in Charlestown?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 49 in the Charlestown area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Charlestown. 

Nearby Neighborhood (2)

Neighborhood Property Count
Thompson Square - Bunker Hill Vacation Rentals in Boston, Massachusetts 37
Medford Street - The Neck Vacation Rentals in Boston, Massachusetts 3009