Charlestown vacation rentals

We found vacation rentals — enter your dates for availability

Discover a selection of 12 homes, 11 apartments, and other vacation rentals in Charlestown that are perfect for your trip. Whether you're staying in a vacation rental with your kids or with friends, you'll find the amenities you need and want, including parking and a TV. You'll be sure to find a rental for everyone's needs, including options that are accessible or non-smoking.
  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value

Find out more about Charlestown

Find out more about Charlestown

Why visit Charlestown

  1. Rich History: Explore Charlestown's historic streets and iconic landmarks, immersing yourself in its storied past.
  2. Waterfront Views: Enjoy stunning scenic views along the waterfront, perfect for leisurely strolls and photography.
  3. Family-Friendly Activities: Discover a variety of attractions and parks tailored for family enjoyment.
  4. Charming Neighbourhoods: Wander through charming neighbourhoods, experiencing local culture and community vibes.
  5. Comfortable Accommodations: Choose from a range of vacation rentals, ensuring a comfortable and convenient stay.

Popular types of accommodation around Charlestown

Planning a getaway to Charlestown? The excitement begins with selecting your perfect accommodation! Discover a range of popular vacation rentals, including houses, apartments, and condos. Whether you're searching for Charlestown apartments, holiday rentals, or apartment rentals, you'll find a variety of options that offer comfort and convenience. Enjoy your stay in this charming destination with transparency and savings at the forefront!

  • Houses: The top choice for visitors to Charlestown, offering a spacious and comfortable environment for families or groups.
  • Apartments: Second in popularity, these rentals provide a convenient and flexible option for those seeking a home-like atmosphere.
  • Condos: A stylish and modern accommodation option, perfect for those wanting amenities and a community feel.
  • Cottages: A charming and quaint choice, ideal for a relaxing getaway with a touch of rustic charm.
  • House Boats: For a unique experience, consider staying on a houseboat, offering a memorable view of the waterfront.**

Top attractions around Charlestown

Charlestown offers a delightful mix of city-themed, family-friendly, and business-oriented experiences. Visitors can explore a variety of attractions, including historic colleges and universities, urban parks, and event venues. With a focus on culture and family experiences, Charlestown is the perfect destination for travellers seeking a rich blend of history and urban charm.

  1. Fenway Park: A historic sports stadium, Fenway Park is renowned for its rich baseball culture and vibrant atmosphere. Home to the Boston Red Sox, it offers fans an authentic sports experience just 4.8km from Charlestown.
  2. TD Garden: Located only 1.3km away, TD Garden is a premier event venue that hosts exciting sports events and concerts. Its modern design and business vibes make it a hub for entertainment and corporate gatherings.
  3. Boston Common: A beautiful urban park located 3.2km from Charlestown, Boston Common is perfect for families and outdoor enthusiasts. With its lush greenery and city vibes, it’s a great spot for leisurely strolls and picnics.

Things to do recommended for couples

Experience romance in Charlestown! Enjoy live music at the House of Blues, embrace adventure at the Courageous Sailing Center, or indulge in a performance at the Jose Mateo Ballet Theatre. Each offers a unique vibe, perfect for couples seeking a memorable getaway.

Things to do recommended for families

Your family will have a blast at LEGOLAND® Discovery Center, only 3.2km away, filled with adventure and fun. Don’t miss the Charles Hayden Planetarium, just 1.4km away, for an entertaining experience, and cheer on your favourite teams at Agganis Arena, 6.4km away!

Things to do recommended for groups

Groups visiting Charlestown can explore the vibrant Faneuil Hall Marketplace for shopping and entertainment, enjoy a show at the historic Orpheum Theater, and experience local flavours at the Boston Public Market, all within a short distance from your location.

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

If you're planning a trip with friends, family, pets, or seeking extended stays, it's essential to prioritize your preferences when filtering options. Here are some helpful Vrbo booking tips for you.

  • Traveling to Charlestown with a group: Think about how many bedrooms you'll require, as well as features like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Charlestown with young kids: Travelling with young children can present its own set of challenges. It's important to prioritize their comfort and safety, along with suitable amenities, like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Charlestown: For many, a family vacation isn’t truly complete without their furry companion. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Charlestown: If you're seeking vacation rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay around Charlestown

Charlestown, Boston, offers a captivating blend of history and family-friendly activities. Visitors can explore the historic streets, enjoy scenic views of the waterfront, and discover charming neighbourhoods nearby. The area's vibrant atmosphere is perfect for those seeking an urban adventure or a relaxed family vacation. Don't miss the chance to visit the iconic sites, enjoy local eateries, and perhaps even find your dream home in this delightful neighbourhood.

  • Downtown Boston: Located a mere mile from Charlestown, Downtown Boston is the bustling core of the city, offering a blend of history, culture, and modern attractions. Visitors are drawn to its vibrant cityscape, where family-friendly activities abound. Explore the renowned shopping malls and centres, or take in a game at the historic sports stadium. The area is also home to many educational institutions and conference venues, making it a hub for both leisure and business travelers.
  • Cambridge: Approximately three miles from Charlestown, Cambridge is a city steeped in academic prestige and cultural richness. Known for its historic college campuses, including Harvard and MIT, it attracts visitors interested in education and innovation. The city boasts a lively shopping scene with various malls and boutique shops, alongside stadiums that host exciting events. Cambridge is perfect for families and culture enthusiasts looking to explore a unique blend of history and modern city life.
  • Thompson Square - Bunker Hill: Just 322m from Charlestown, Thompson Square - Bunker Hill is a vibrant neighbourhood that offers a mix of city vibes and local charm. Ideal for families and business travelers alike, the area features a range of educational facilities and shopping centres. Visitors can enjoy events at the local sports facility stadium and conference venues, making it a dynamic place to experience Boston's community spirit while being close to Charlestown's rich historical backdrop.

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 Vrbo is simple

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Furthermore, booking an extended stay can often lead to significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly platform where you can easily create new travel itineraries, continue from where you paused, or manage your existing plans. You’ll discover your saved or booked properties neatly organized into categories: Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Charlestown?
House boats are the most popular type of vacation rental in Charlestown, according to our data. Even if you’ve got something bigger or smaller in mind, Vrbo has properties in many sizes and shapes. Explore our options to find your ideal fit.
How much does it cost to rent a vacation rental in Charlestown?
Different factors can affect how much you pay for a vacation rental in Charlestown, like the time of year, property type and length of stay. However, all of our vacation homes have one thing in common — amazing value. Just add your travel dates to find your ideal escape.
How much does it cost to rent a beach house in Charlestown?
The average price for a vacation rental close to the beach in Charlestown will depend on when you’ll be there and the type and size of property you’re searching for. You can find prices quickly and easily on Vrbo by entering your preferred travel dates. Then use our filters to choose the number of bedrooms and amenities that you need, like WiFi, air conditioning and a pool.
Are there pet-friendly vacation rentals in Charlestown?
With 20 properties that allow pets, your furry best friend can join in on your Charlestown getaway. Use the filter tool to browse our pet-friendly vacation rentals and find the pawfect pad on Vrbo.
Can I rent a house with a pool in Charlestown?
Tick the “pool” box in our filter tool and you can choose from three houses with private pools in Charlestown on Vrbo. Ball games, gentle soak or noodle joust? How you spend your leisure time is up to you when your Vrbo vacation home comes with a swimming pool.
What are popular rental amenities in Charlestown?
A water view, an ocean view and tennis are rated the most popular rental amenities in Charlestown. Whether you’re planning to travel on your own, with your other half or a group of dear friends, Vrbo will help you find a vacation rental that suits your tastes with all the features you’re looking for.
Are there large group vacation rentals in Charlestown?
Take your pick of two properties in Charlestown that can accommodate 10 or more guests. Whether you’re planning a family trip or a celebration like an anniversary, there’s enough room to get your loved ones together under one roof.
Are there vacation rentals in Charlestown that welcome kids?
With 20 family-friendly vacation rentals to select from in Charlestown, now is the perfect time to introduce your little ones to the magic of travel. Simply check our “Properties good for families” filter to browse stays that come with amenities ideal for traveling families, such as multiple bedrooms, outdoor spaces, bunk beds and entertainment areas.
What are the top attractions for families in Charlestown?
Keep the kids entertained at these fabulous family-friendly attractions in Charlestown:

  • New England Aquarium
  • Museum of Science
  • Boston Tea Party Ship

Are there one-bedroom vacation rentals in Charlestown?
Yes, you can choose from eight one-bedroom rentals in Charlestown. Whether you’re looking for an apartment or a cabin, our one-bedroom rentals are just right if you don’t need loads of space. One of the best parts about having your own place? You won’t ever have to share your adventure with strangers.
Can I find two-bedroom vacation rentals in Charlestown?
Take off with your loved ones and enjoy a relaxing escape in one of the six two-bedroom vacation properties Charlestown has to offer.
Are there vacation rentals with WiFi in Charlestown?
Charlestown has eight vacation rentals with WiFi, so you can stay connected during your vacation. Simply check the “WiFi” box in our handy search filter to find the perfect property. From streaming movies with the family to catching up on social media, these Vrbo homes make it a breeze to go online.
How can I find vacation rentals with air conditioning in Charlestown?
Charlestown has 19 vacation rentals where you’ll be able to kick back in air-conditioned comfort. To book a property on Vrbo that offers this amenity, enter your travel dates and use the handy filters to select the “air conditioning” box.
How old do you have to be to rent a vacation rental in Charlestown?
The minimum age is normally 16, 18 or 21. It can change from property to property on Vrbo, so check the rules of your chosen Charlestown vacation rental before booking your stay.
How long can I rent a vacation rental in Charlestown for?
The amount of time you can rent a Charlestown vacation rental for depends on the property. Just tap in your dates of travel to browse available options offering longer term stays. They include all you require to make your extended vacation more convenient and comfortable, like kitchens and backyards. Some properties may also offer discounted weekly or monthly prices, so you can hang around longer for less.

More Vacation Rentals ideas

People also search for