Charlestown holiday homes

We found 69 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.
  • 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, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why visit Charlestown

  • Historic charm: Stroll through storied streets adorned with rich history and cultural landmarks.
  • Urban green spaces: Relax in modern parks and vibrant public squares that offer a peaceful retreat.
  • Family-friendly attractions: Enjoy numerous local experiences perfect for a city break with the whanau.
  • Contemporary vibe: Immerse yourself in the lively streets and modern urban energy of Charlestown.
  • Cultural blend: Experience a unique mix of historical legacy and modern city life in this iconic neighbourhood.

Top attractions near Charlestown

Discover Charlestown in Boston, Massachusetts, a vibrant neighbourhood perfect for a cultural and family city break. Enjoy the urban parks, lively streets, and modern squares that reflect its rich history and contemporary vibe. With plenty of attractions and local experiences to explore, Charlestown offers an authentic taste of city life, ensuring a memorable holiday experience for every traveller from New Zealand.

  • Newbury Street: Enjoy the lively city vibes on this street, offering trendy boutiques and cafés, though it is 3km away from Charlestown.
  • The Freedom Trail: Discover rich cultural heritage along this historic path, located 483m from Charlestown, perfect for history enthusiasts.
  • Old North Church: Step into the past with this historic church exuding cultural significance, situated 1km from Charlestown.

Things to do recommended for couples

For a romantic escape in Charlestown, take a leisurely stroll along the picturesque waterfront, marvel at the historic architecture, and enjoy a sunset picnic at the Bunker Hill Monument. Don't miss a cozy dinner at a local eatery, where you can savour delectable cuisine together.

Things to do recommended for families

Families will enjoy exploring the historic USS Constitution and the charming Bunker Hill Monument in Charlestown, Boston, with plenty of local treats and scenic harbour views to delight children and adults alike.

Things to do recommended for groups

Group travellers in Charlestown, Boston can explore historic sites like the USS Constitution and take a harbour cruise, enjoying local pubs and waterfront eateries for a true Kiwi experience in the heart of the USA.

*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 journeying as a group, with family, accompanied by your furry mates or planning extended stays, be sure to filter your search using the appropriate criteria. Here are some Vrbo booking tips to guide you.

  • Traveling to Charlestown with a group: Think about how many bedrooms you'll require, as well as features like a full kitchen or outdoor areas for group get-togethers. Thankfully, you can easily filter for these options and many more on Vrbo.
  • Traveling to Charlestown with young kids: Travelling with young children can present some challenges. It's important to prioritise 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 holiday isn’t complete without their furry companion in tow. If that sounds like you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly options include feeding bowls and beds, ensuring everyone feels right at home.
  • Planning for a long term stay visiting Charlestown: If you’re in search of holiday rentals offering great deals 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 amenities like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Charlestown

Charlestown in Boston offers a rich tapestry of history, culture, and family-friendly attractions. Wander through its storied streets, explore historic landmarks, and soak in the urban charm of this well-loved neighbourhood. Perfect for a city-themed holiday, Charlestown invites you to experience its unique blend of historical vibes and modern energy, making it an ideal base for your New Zealand adventure in the heart of Boston.

  • Boston: As one of the oldest cities in the United States, Boston is rich in history and culture, making it a must-visit destination for any traveller. Located within close proximity to Charlestown, Boston offers a vibrant urban environment brimming with educational institutions, shopping malls, and music venues. Explore iconic landmarks such as the historic sports stadium and various conference centres that host events throughout the year. Whether you're keen on delving into the city's storied past or enjoying modern attractions, Boston provides a dynamic experience for families and culture enthusiasts alike.
  • Cambridge: Just 5km from Charlestown, Cambridge is renowned for its academic atmosphere, thanks to its prestigious universities. This city is ideal for those seeking a blend of education and leisure, with numerous shopping centres and cultural venues to explore. Visitors can admire the architecture of historic colleges while enjoying a variety of local eateries and shops. Cambridge is also home to significant landmarks like historic sports stadiums and event venues, making it a vibrant locale for family and business-themed experiences.
  • Back Bay: Located a mere 3km from Charlestown, Back Bay is a charming neighbourhood known for its stunning Victorian brownstones and upscale shopping. This area attracts visitors with its blend of cultural attractions, urban parks, and educational institutions. Stroll through the picturesque streets, relax in one of the local parks, or discover the historic college universities in the vicinity. Back Bay is perfect for families and culture lovers, offering a delightful mix of leisure and exploration opportunities.

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.

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

Booking with Vrbo is a breeze

Looking to get the best value for your next adventure? Think about keeping your travel dates flexible, as rates can vary. Also, booking a longer stay often leads to significant savings. To help you find the perfect Vrbo property within your budget, use our filters to narrow down options by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s innovative Trip Board offers you a dedicated space to plan new adventures, pick up where you left off, or organise your travel plans. Your previously saved or booked properties are now neatly categorised as Potential, Upcoming, or Current Trips. To get started with Trip Boards, visit: https://www.bookabach.co.nz/trips

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of holiday home accommodation in Charlestown?
House boats are the most popular type of holiday home in Charlestown, according to our data. Even if you've got something bigger or smaller in mind, Bookabach has properties in many sizes and shapes. Explore our options to find your ideal fit.
How much does it cost to rent a holiday home in Charlestown?
Different factors can affect how much you pay for a holiday home in Charlestown, like the time of year, property type and length of stay. However, all of our holiday 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 holiday home 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 Bookabach 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 holiday homes 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 holiday homes and find the pawfect pad on Bookabach.
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 Bookabach. Ball games, gentle soak or noodle joust? How you spend your leisure time is up to you when your Bookabach holiday home comes with a swimming pool.
What are popular home amenities in Charlestown?
A water view, an ocean view and tennis are rated the most popular home amenities in Charlestown. Whether you're planning to travel on your own, with your other half or a group of dear friends, Bookabach will help you find a holiday home that suits your tastes with all the features you're looking for.
Are there large group holiday homes 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 holiday homes in Charlestown that welcome kids?
With 20 family-friendly holiday homes 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 travelling 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 holiday homes in Charlestown?
Yes, you can choose from eight one-bedroom homes in Charlestown. Whether you're looking for an apartment or a cabin, our one-bedroom homes 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 holiday homes in Charlestown?
Take off with your loved ones and enjoy a relaxing escape in one of the six two-bedroom holiday properties Charlestown has to offer.
Are there holiday homes with WiFi in Charlestown?
Charlestown has eight holiday homes with WiFi, so you can stay connected during your holiday. 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 Bookabach homes make it a breeze to go online.
How can I find holiday homes with air conditioning in Charlestown?
Charlestown has 19 holiday homes where you'll be able to kick back in air-conditioned comfort. To book a property on Bookabach 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 holiday home in Charlestown?
The minimum age is normally 16, 18 or 21. It can change from property to property on Bookabach, so check the rules of your chosen Charlestown holiday home before booking your stay.
How long can I rent a holiday home in Charlestown for?
The amount of time you can rent a Charlestown holiday home 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 holiday 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.