Choose from 48 vacation rentals located in Charlestown, Massachusetts. Top filters in Charlestown include Air conditioner, Internet / Wifi, and Kitchen / Kitchenette. Prices range from $94 to $2,600 per night. Our most popular vacation rental types near Charlestown are Hotel and RV.

Top vacation rentals in Charlestown

Property view
5.0
Outstanding(176 Reviews)
Docked boat
 in Boston
\"Travelers' Choice Award\" Green Turtle I Houseboat in Boston Harbor!
2 guests · 1 bath
Pool · Kitchen / Kitchenette · Air conditioner

Looking to create some memories in Charlestown? Look no further than our Docked boat, \"Travelers' Choice Award\" Green Turtle I Houseboat in Boston Harbor! . Enjoy top-rated amenities including Air conditioner, Internet / Wifi and Laundry, and more.

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The Blue Pearl
4.8
Outstanding(154 Reviews)
Docked boat
 in Boston
Houseboat in Boston Harbor Wifi A\/C \/Heat Be rocked to sleep
6 guests · 1 bedroom · 1 bath
Pets allowed · Kitchen / Kitchenette · Air conditioner

The best choice in Charlestown for Docked boat, for $120 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

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Why stay anywhere else when visiting Boston?
4.8
Outstanding(121 Reviews)
Docked boat
 in Boston
Boston Harbor Yacht, AC\/Heat, Walk to North End WiFi
6 guests · 2 bedrooms · 2 baths
Pets allowed · Kitchen / Kitchenette · Air conditioner

Discover the beauty of Charlestown with a stay at Boston Harbor Yacht, AC\/Heat, Walk to North End WiFi, a top rated Docked boat with amenities such as Air conditioner, Internet / Wifi and Laundry, and more.

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Living area
5.0
Outstanding(132 Reviews)
Condo
 in Boston
Historic Home At Freedom Trail
4 guests · 1 bedroom · 1 bath
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Looking for the perfect place to call home during your trip to Charlestown? This Condo offers a comfort and style with top-notch amenities, including Air conditioner, Dishwasher and Internet / Wifi, and more.

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Search by property type

Vacation rentals with air conditioning in Charlestown

Marina
4.8
Outstanding(51 Reviews)
Docked boat
 in Boston
Your Floating Suite in Boston Harbor
3 guests · 1 bedroom · 1 bath
Pets allowed · Kitchen / Kitchenette · Air conditioner

Enjoy the best of Charlestown in our Docked boat, Your Floating Suite in Boston Harbor . A stunning property with amenities including Air conditioner, Internet / Wifi and Pets allowed, and more.

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2015 cherry kitchen with stainless appliances, coffee maker, d/w, laundry
4.8
Outstanding(51 Reviews)
Condo
 in Boston
Historic Charlestown
2 guests · 1 bedroom · 1 bath
Garden · Pool · Pets allowed

This attractive Condo in Charlestown, $335 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

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Property view
4.9
Outstanding(51 Reviews)
House
 in Boston
Victorian Glam Overlooking Charlestown's Main Square
4 guests · 2 bedrooms · 1 bath
Garden · Kitchen / Kitchenette · Air conditioner

Discover the beauty of Charlestown with a stay at Victorian Glam Overlooking Charlestown's Main Square, a top rated House with amenities such as Air conditioner, Dishwasher and Fireplace, and more.

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Property grounds
4.7
Outstanding(56 Reviews)
Docked boat
 in Boston
Charlestown Houseboat Walk to attractions Be rocked to sleep
4 guests · 1 bedroom · 1 bath
Pets allowed · Kitchen / Kitchenette · Air conditioner

This Docked boat in Charlestown, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

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city photo
Charlestown

Charlestown travel guide

Let us help you plan your perfect Charlestown vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Charlestown, and more.

Frequently asked questions

What do I need to know before visiting Charlestown, MA?

Before visiting Charlestown, MA, there are a few things to know. Here are some tips to help you prepare:

  • The best time to visit is in the summer months when the weather is warmer and the days are longer.
  • Be sure to bring comfortable walking shoes, as Charlestown is a very walkable city.
  • The Charlestown Navy Yard is a popular tourist attraction and offers a variety of historical sites to explore.

Charlestown is also home to many great restaurants, shops, and entertainment venues, so be sure to check out the local scene before you leave.

What are the must-visit tourist attractions in Charlestown, MA?

Charlestown, MA is home to some of the most iconic tourist attractions in the United States. Here are some of the must-visit attractions in Charlestown:

  • USS Constitution Museum
  • Bunker Hill Monument
  • Charlestown Navy Yard
  • The Freedom Trail

These attractions are all iconic and educational, and offer visitors a unique glimpse into the history of the city and the country. Visitors to Charlestown should make sure to check out these attractions to get the full experience.

How can I get around in Charlestown, MA?

You can get around Charlestown, MA by:

  • Walking
  • Biking
  • Taking public transportation

Charlestown has many public transportation options, like the MBTA bus and the MBTA Commuter Rail.

Where can I find affordable accommodation in Charlestown, MA?

Charlestown, MA is home to a variety of affordable accommodation options. Here are 4 options for visitors to consider:

  • The Inn at Charlestown: Located in the heart of Charlestown, this inn offers comfortable rooms at a great price.
  • Charlestown Bed and Breakfast: This B&B is situated in a historic building and provides guests with a cozy and inviting atmosphere.
  • The Charlestown Inn: This inn offers a variety of room types and amenities, including free Wi-Fi and a fitness center.
  • Charlestown Hotel and Suites: This hotel offers spacious rooms and suites with modern amenities, including a swimming pool and on-site restaurant.

What is the culture like in Charlestown, MA?

Charlestown, MA is a vibrant community with a unique culture that is deeply rooted in its long history. Here are five aspects of the culture in Charlestown:

  • Friendly Locals: Charlestown is known for its friendly locals who welcome newcomers to the community.
  • Restaurants and Bars: Charlestown is home to a variety of restaurants and bars, offering a range of cuisines to suit all tastes.
  • Historic Sites: Charlestown is filled with historic sites, from the USS Constitution Museum to the Bunker Hill Monument.
  • Sports: Charlestown is home to several sports teams, including the Boston Bruins and the Boston Celtics.
  • Community Events: Charlestown hosts a variety of community events throughout the year, from the Charlestown Arts Festival to the Bunker Hill Day Parade.

Is Charlestown, MA safe to travel to?

Charlestown, MA is a safe place to travel to. Here are some tips to ensure your safety:

  • Be aware of your surroundings.
  • Travel in groups, if possible.
  • Be aware of local laws and customs.

What are the popular shopping destinations in Charlestown, MA?

Charlestown, MA is home to a variety of popular shopping destinations:

  • The Charlestown Navy Yard
  • Charlestown Mall
  • Charlestown Farmers Market

These popular shopping destinations offer a variety of items ranging from fresh produce to unique handcrafted items.

What are the best neighborhoods to visit in Charlestown, MA?

Charlestown, MA is a great place to visit with many exciting neighborhoods to explore. Here are some of the best neighborhoods to visit in Charlestown:

  • Sullivan Square
  • Navy Yard
  • Charlestown Heights
  • Monument Square

Each of these neighborhoods offer something unique and special, from historical sites to delicious restaurants.

Where is Charlestown, MA?

Charlestown, MA is a neighborhood of Boston, located on the Charles River across from downtown Boston. It is one of the oldest neighborhoods in the city, founded in 1628, and is the site of the historic Battle of Bunker Hill. Today, Charlestown is a vibrant community with a mix of historic buildings, modern homes, and a variety of shops and restaurants.

What are the most popular vacation rental amenities in Charlestown, MA?

Charlestown, MA, is an ideal destination for a vacation rental. Here are some of the most popular amenities that vacationers can expect when renting in the area:

  • Fully equipped kitchen
  • High-speed internet access
  • On-site laundry facilities
  • Spacious living areas
  • Outdoor seating areas

These amenities, along with the area's many attractions and activities, make Charlestown an ideal destination for a vacation rental.

What are the top things to do in Charlestown, MA?

Charlestown, MA is a great place to explore. With its rich history, harbor views, and vibrant culture, there is something for everyone. Here are the top things to do in Charlestown:

  • Visit the USS Constitution Museum
  • Explore the Bunker Hill Monument
  • Stroll along the Boston Harborwalk
  • Take a Harbor Cruise

What is the price range for rentals in Charlestown?

Vacation rentals in Charlestown have a price range between $94-$2,600. The average price for rentals in Charlestown is $216 per night.

What are the most popular vacation rental amenities in Charlestown?

  • Air conditioner
  • Internet / Wifi
  • Kitchen / Kitchenette

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