Charlestown holiday homes

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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  • More quality time

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  • 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

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 Bookabach?
Bookabach 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?
Bookabach 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 Bookabach, 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 Bookabach?
To find Charlestown holiday rentals with free cancellation, just use Bookabach'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, Bookabach 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 Bookabach?
Bookabach'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 Bookabach 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. Bookabach offers something for every taste and budget, from affordable homes in Charlestown to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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 Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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 Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach 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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