Charlestown holiday rentals

We found 67 holiday rentals — enter your dates for availability
Discover a selection of 8 homes and other holiday rentals in Charlestown that are perfect for your trip. Whether you're staying in a holiday rental with family, friends or just your furry companion, you'll have the amenities that you expect and more, which might include parking and a fireplace. You'll be sure to find a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

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Why visit Charlestown

  • Historic landmarks: Explore notable sites such as the Bunker Hill Monument and the Charlestown Navy Yard, steeped in American history.
  • Scenic waterfront: Enjoy picturesque views along the harbour, perfect for leisurely strolls and cultural insights.
  • Vibrant local charm: Wander through charming streets and modern squares that blend historical character with contemporary life.
  • Family-friendly atmosphere: Experience a welcoming neighbourhood ideal for visitors of all ages.
  • Cultural immersion: Discover the rich heritage and lively local eateries that encapsulate the spirit of Charlestown.

Popular types of accommodation around Charlestown

Welcome to Charlestown, a charming neighbourhood in Boston, Massachusetts, brimming with history and character. Visitors can explore iconic landmarks such as the Bunker Hill Monument and the USS Constitution. For your stay, you'll find a variety of popular holiday rentals including private homes, cosy apartments, and inviting condos, ensuring a friendly and comfortable experience. With numerous accommodations available, you're sure to find the perfect place to relax after a day of discovering this vibrant community.

  • Private Holiday Homes: A top choice for visitors, these spacious and fully equipped homes offer a comfortable and private stay in Charlestown.
  • Apartments: Ideal for those seeking a blend of convenience and comfort, apartments provide a homely atmosphere with essential amenities.
  • Condos: Offering modern living spaces, condos are a popular option for travellers wanting a stylish and community-oriented environment.
  • Cottages: For a quaint and charming experience, cottages present a delightful escape that evokes a sense of nostalgia.
  • House Boats: Experience a unique stay on the water with house boats, perfect for those looking to enjoy a different perspective of Charlestown.**

Top attractions near Charlestown

Charlestown, Boston, Massachusetts, is a vibrant neighbourhood perfect for families and culture enthusiasts alike. Visitors can explore urban parks, charming streets, and modern squares that showcase the area's rich history and lively atmosphere. Enjoy a leisurely stroll through its scenic spots, which offer a delightful blend of city charm and cultural experiences that cater to all ages, ensuring a memorable holiday in this historic part of Boston.

  • Fenway Park: Experience the historic sports stadium with its rich cultural and sporting atmosphere, even though it is 5km away from Charlestown.
  • Boston Common: Enjoy the urban park's city charm and family-friendly outdoor vibes, located 3km from Charlestown.
  • Copley Square: Revel in the modern square's vibrant city ambience, situated 3km from Charlestown.

Things to do recommended for couples

Discover a charming escapade in Charlestown, Boston, where you can enjoy hand-in-hand walks along the scenic harbour and savour intimate dinners in cosy local eateries, creating memories that last a lifetime.

Things to do recommended for families

Families visiting Charlestown can explore the historic USS Constitution, embark on a harbour cruise, and enjoy interactive exhibits at the USS Constitution Museum, ensuring a delightful local experience for all ages.

Things to do recommended for groups

Explore the historic Charlestown Navy Yard and visit the USS Constitution, or enjoy a leisurely stroll along the Freedom Trail. For a unique experience, consider a group sailing tour in Boston Harbour to take in the stunning skyline and waterfront views.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Charlestown

Whether you're travelling with a group, as a family, with your pets, or seeking longer stays, be sure to apply the appropriate filters. Here are some Stayz booking tips for you.

  • Traveling to Charlestown with a group: Consider how many bedrooms you require, along with facilities like a fully equipped kitchen or outdoor space for a group get-together. Happily, on Stayz you can apply filters to search for all these features and many more.
  • Traveling to Charlestown with young kids: Travelling with young children can present its own set of challenges. It’s important to prioritise their comfort and safety, including access to suitable amenities like a private swimming pool. Additionally, it’s wise to think about your closeness to attractions that are family-friendly.
  • Taking your pets with you to Charlestown: For many, a family holiday isn't complete without their four-legged companion. If you relate to this, then have a look at Stayz properties that welcome pets. Most pet-friendly accommodations provide feeding bowls and beds so that everyone can feel at home.
  • Planning for a long term stay visiting Charlestown: If you're seeking holiday lets with special offers for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. You might also consider including a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay near Charlestown

Charlestown, a historic neighbourhood in Boston, offers a captivating blend of culture and family-friendly attractions. Visitors can explore iconic landmarks such as the Charlestown Navy Yard and the Bunker Hill Monument, while enjoying the scenic views along the waterfront. The area’s rich history is complemented by vibrant local eateries and friendly locals, creating an inviting atmosphere for all travellers. Whether you're wandering its charming streets or learning about its past, Charlestown promises a memorable experience.

  • Boston: Boston, the capital city of Massachusetts, offers a rich tapestry of history and culture. As the birthplace of the American Revolution, it boasts numerous historic sites and landmarks, including the iconic Freedom Trail. Travellers flock to Boston for its vibrant atmosphere, characterised by a mix of educational institutions, shopping centres, and entertainment venues. The city is home to renowned sports stadiums and event conference venues, making it an ideal destination for families and those seeking a city-themed experience. With a plethora of museums, theatres, and parks, Boston provides a diverse range of activities for visitors of all ages.
  • Downtown Boston: Located 2km from Charlestown, Downtown Boston is the bustling heart of the city. This neighbourhood is a hub for business and leisure, offering a plethora of shopping centres and urban parks. Visitors can enjoy a lively atmosphere filled with dining options, street performances, and cultural events. Downtown Boston is also home to significant landmarks, including historic sports stadiums and event conference venues, making it a popular destination for families and those on business trips. The area is well-connected, ensuring a convenient travel experience for exploring the wider city.
  • Cambridge: Situated 5km from Charlestown, Cambridge is renowned for its prestigious universities and rich intellectual heritage. This vibrant city attracts those seeking a mix of family-friendly activities and business opportunities. Visitors can explore historic college campuses, art galleries, and bookshops that contribute to its unique charm. Cambridge's shopping centres and local eateries invite you to indulge in a delightful culinary experience. The proximity to Boston makes Cambridge an appealing option for those looking to enjoy a city-themed adventure while immersing themselves in its academic and cultural offerings.

Best time to go to Charlestown

If you're planning a trip to Charlestown, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April and June to July, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January30.0°F (-1.1°C)Light RainMostly SunnyAverageSlightly Low
February31.5°F (-0.3°C)Light RainMostly CloudyAverageSlightly Low
March37.9°F (3.3°C)Light RainMostly SunnyAverageSlightly Low
April48.2°F (9.0°C)Light RainMostly SunnySlightly HighAverage
May58.5°F (14.7°C)Light RainMostly SunnyAverageAverage
June66.6°F (19.2°C)Light RainMostly SunnySlightly HighSlightly High
July73.6°F (23.1°C)Light RainMostly SunnySlightly HighSlightly High
August72.7°F (22.6°C)Light RainMostly SunnyAverageSlightly High
September65.7°F (18.7°C)Light RainMostly SunnyAverageAverage
October55.6°F (13.1°C)Light RainMostly SunnySlightly LowAverage
November44.4°F (6.9°C)Light RainMostly SunnySlightly LowAverage
December36.3°F (2.4°C)Light RainMostly SunnySlightly LowAverage

Booking with Stayz is simple

Looking to save on your next break? Consider being flexible with your travel dates as prices can vary. Moreover, booking a longer stay can often result in significant savings. To find the ideal Stayz property that suits your budget, simply use our filters to search by price, location, and type of holiday rental.

Stayz Trips: Planning made easy

Stayz’s Trip Board provides a space to create new journeys, continue planning, or review and organise your bookings. Properties you’ve saved or reserved are now categorised into Potential, Upcoming, or Current Trips. To explore the Trip Boards, please visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

When is the best time to visit Charlestown for a holiday rental?
The best time to book a holiday rental in Charlestown is during the vibrant peak season, which runs from May to July. This period is particularly popular among travellers eager to experience the rich history and cultural offerings of the area, with July being the most sought-after month. Visitors can experience firsthand outdoor activities, such as exploring the picturesque waterfront and enjoying the numerous events and festivals that come alive during the summer.With average temperatures ranging from the mid-teens to low 30s Celsius, the warm weather makes it ideal for strolling through the charming streets, visiting historical sites like the USS Constitution, and enjoying the nearby parks. The atmosphere is filled with excitement, as both locals and tourists engage in outdoor activities and make the most of the long summer days.For those looking for a more budget-friendly option, visiting in November can be a great choice. This quieter month offers a chance to explore Charlestown's historic charm without the summer crowds, while still enjoying the beauty of the season. You can take leisurely walks along the waterfront and appreciate the changing colours of autumn foliage.Ultimately, the best time to visit Charlestown depends on your preference for lively summer festivities or the tranquil ambiance of the shoulder season.
What are the top attractions in Charlestown, Massachusetts, United States of America?
In Charlestown, Massachusetts, visitors can explore a range of historic and cultural attractions. The USS Constitution, the oldest commissioned warship afloat in the world, is a major draw, located in the Charlestown Navy Yard. Nearby, the Bunker Hill Monument offers a significant piece of American history, commemorating the first major battle of the Revolutionary War, and provides stunning views from the top of its 294 steps.The charming streets of Charlestown are dotted with beautiful brick row houses, and the neighbourhood's proximity to the Boston waterfront enhances its appeal. The picturesque Charlestown Harbour is superb for leisurely walks along the waterfront, while the nearby Warren Tavern, one of the oldest pubs in Massachusetts, provides a taste of local cuisine and history.For those interested in green spaces, the scenic parks along the waterfront offer a tranquil environment for relaxation and picnics.
Are all fees included in the Charlestown holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Charlestown holiday homes with parking?
Stayz offers a wide selection of holiday homes in Charlestown with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Charlestown holiday homes?
You can find great discounts on holiday homes in Charlestown on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Charlestown holiday home booking on Stayz?
To find Charlestown holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Charlestown?
A long-stay holiday home in Charlestown is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Charlestown holiday home?
Book your Charlestown holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Charlestown?
Prices for holiday homes in Charlestown vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Charlestown to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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