Vacation Rentals in Charlestown, MA: Compare 10+ Sites & Save

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  4.  Massachusetts

  5.  Boston
  6.  Charlestown

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2307 Best Vacation Rentals in Charlestown (Starting from $210)

Charlestown Gem
Charlestown Gem
Apartment
Boston, MA, USA
0.3k from Charlestown center

Apartments, Accommodations, Pet-friendly, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$292
Average price / night
Check Availability
Boston Condo with Free Parking
Boston Condo with Free Parking
Apartment
Boston, MA, 02129, United States
0.1k from Charlestown center

AC, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking

1 Bedroom4 Guests
New to Booking
$373
Average price / night
Check Availability
Cozy N End 1BR steps from Harborwalk BOS-446
Cozy N End 1BR steps from Harborwalk BOS-446
Apartment
Boston, MA, USA
1.3k from Charlestown center

Apartments, Accommodations, Pet-friendly, Lodgings, Vacation rentals, Places to stay

1 Bedroom2 Guests
New to Booking
$235
Average price / night
Check Availability
Luxury Boston Brownstone!
Luxury Boston Brownstone!
House
Boston, MA, 02129, United States
0.3k from Charlestown center

AC, Dryer, Free Parking, Heater, Internet, Laundry, No Smoking, Patio, Washer

4 Bedrooms8 Guests
New to Booking
$2270
Average price / night
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2 Bedroom Condo Cambridge
2 Bedroom Condo Cambridge
Apartment
Cambridge, MA, USA
1.3k from Charlestown center

Apartments, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Places to stay, Family, Condos

2 Bedrooms5 Guests
New to Booking
$492
Average price / night
Check Availability
Historic Boston apartment with private garden/patio
Historic Boston apartment with private garden/patio
Apartment
Boston, MA, 02129, United States
0.6k from Charlestown center

AC, Heater, Internet, No Smoking

1 Bedroom2 Guests
10.0

Exceptional

2 reviews

$367
Average price / night
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Central 3 Bed 1 Bath in Historic Building
Central 3 Bed 1 Bath in Historic Building
Apartment
Boston, MA, USA
1.4k from Charlestown center

Apartments, Accommodations, Lodgings, Places to stay

3 Bedrooms6 Guests
6.7

Good

6 reviews

$763
Average price / night
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Historic Home At Freedom Trail
Historic Home At Freedom Trail
Apartment
Boston, MA, 02129, United States
0.6k from Charlestown center

AC, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking, Patio, TV

1 Bedroom4 Guests
10.0

Exceptional

184 reviews

$347
Average price / night
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North End Apt close to TD Garden Walk to Downtown
North End Apt close to TD Garden Walk to Downtown
Apartment
Boston, MA, USA
1.4k from Charlestown center

Apartments, Accommodations, Lodgings, Places to stay

4 Bedrooms12 Guests
New to Booking
$897
Average price / night
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Great location, Longterm or short term rental in Charlestown
Great location, Longterm or short term rental in Charlestown
Apartment
Boston, MA, 02129, United States
0.7k from Charlestown center

Laundry, No Smoking, Washer

1 Bedroom3 Guests
New to Booking
$695
Average price / night
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3BR3Bth Entire House Steps to Downtown & TD Garden
3BR3Bth Entire House Steps to Downtown & TD Garden
House
Boston, MA, USA
1.4k from Charlestown center

Air Conditioner, Internet, Sports/Activities, Guest Services, Fireplace/Heating, Security/Safety, Laundry

3 Bedrooms6 Guests
New to Booking
$975
Average price / night
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\"1855 Grand Mansion In Historical Charlestown\"   6 bed 4.5 bath Renovated 2021
\"1855 Grand Mansion In Historical Charlestown\" 6 bed 4.5 bath Renovated 2021
House
Charlerstown, MA, 02129, United States
0.7k from Charlestown center

AC, Arcade, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater

6 Bedrooms11 Guests
10.0

Exceptional

1 reviews

$2977
Average price / night
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North End Entire House
North End Entire House
House
Boston, MA, USA
1.4k from Charlestown center

Security/Safety, Sports/Activities, Laundry, Air Conditioner, Pet Friendly, Guest Services, Fireplace/Heating

3 Bedrooms6 Guests
New to Booking
$1430
Average price / night
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Historic and Charming Brownstone
Historic and Charming Brownstone
House
Boston, MA, 02129, United States
0.9k from Charlestown center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, No Smoking, Outdoor Space

4 Bedrooms10 Guests
9.8

Exceptional

58 reviews

$1618
Average price / night
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Club Quarters Boston
Club Quarters Boston
Apartment
Cambridge, MA, USA
1.5k from Charlestown center

Balcony/Terrace, Smoking, Parking, Wheelchair Accessible, Child Friendly, Pool, Internet

4 Bedrooms8 Guests
7.0

Good

3 reviews

$756
Average price / night
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Prima North End 2brm
Prima North End 2brm
Apartment
Boston, MA, 02113, United States
1.1k from Charlestown center

AC, Heater, Internet, Laundry, No Smoking

2 Bedrooms6 Guests
8.8

Fabulous

5 reviews

$486
Average price / night
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Entire Apt Near Wharf
Entire Apt Near Wharf
Apartment
Boston, MA, USA
1.5k from Charlestown center

Apartments, Cheap, Accommodations, Pet-friendly, Lodgings, Places to stay, Family

1 Bedroom2 Guests
9.8

Exceptional

4 reviews

$250
Average price / night
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Lux 2nd floor 3brm/1bath
Lux 2nd floor 3brm/1bath
Apartment
Boston, MA, 02113, United States
1.1k from Charlestown center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

3 Bedrooms6 Guests
9.6

Exceptional

9 reviews

$839
Average price / night
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Boston Family Friendly Suite
Boston Family Friendly Suite
Apartment
Cambridge, MA, USA
1.5k from Charlestown center

Apartments, Accommodations, Pools, Pet-friendly, Lodgings, Places to stay, Family

3 Bedrooms7 Guests
New to Booking
$607
Average price / night
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3-bedroom family friendly house in historic and convenient Charlestown
3-bedroom family friendly house in historic and convenient Charlestown
House
Boston, MA, 02129, United States
1.1k from Charlestown center

AC, Crib, Dryer, Fireplace, Heater, Internet, Kitchen, Laundry, No Smoking

3 Bedrooms5 Guests
New to Booking
$323
Average price / night
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3 bedroom cambridge lux escape
3 bedroom cambridge lux escape
Apartment
Cambridge, MA, USA
1.5k from Charlestown center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay

3 Bedrooms6 Guests
9.0

Fabulous

1 reviews

$647
Average price / night
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Primo North End Studio
Primo North End Studio
Apartment
Boston, MA, 02113, United States
1.3k from Charlestown center

AC, Dryer, Heater, Internet, Kitchen, Laundry, No Smoking, TV, Washer

1 Bedroom2 Guests
9.2

Superb

13 reviews

$425
Average price / night
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Lux 3 Bedroom Apartment Boston
Lux 3 Bedroom Apartment Boston
Apartment
Cambridge, MA, USA
1.5k from Charlestown center

Apartments, Accommodations, Pet-friendly, Lodgings, Places to stay

3 Bedrooms7 Guests
New to Booking
$586
Average price / night
Check Availability
3brm/1bath North End Gem
3brm/1bath North End Gem
Apartment
Boston, MA, 02113, United States
1.3k from Charlestown center

AC, Dryer, Heater, Internet, Kitchen, Laundry, No Smoking

3 Bedrooms6 Guests
9.2

Superb

31 reviews

$890
Average price / night
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2-bedroom apart in Cambridge with balcony Garage parking
2-bedroom apart in Cambridge with balcony Garage parking
Apartment
Cambridge, MA, 02141, United States
1.3k from Charlestown center

AC, Balcony, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Laundry, Microwave

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$664
Average price / night
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Modern 1BR steps to Mass General Hospital, TD Garden, Esplanade with Pool/Gym
Modern 1BR steps to Mass General Hospital, TD Garden, Esplanade with Pool/Gym
Apartment
Boston, MA, 02114, United States
1.3k from Charlestown center

AC, Dryer, Fitness Equipment, Heater, Internet, Laundry, Living Area, No Smoking, Washer

1 Bedroom3 Guests
New to Booking
$210
Average price / night
Check Availability
Ideal North End 1brm Central To Everything
Ideal North End 1brm Central To Everything
Apartment
Boston, MA, 02113, United States
1.3k from Charlestown center

AC, Crib, Extra Bed, Internet, Kitchen, Microwave, No Smoking, Outdoor Space, TV

1 Bedroom4 Guests
9.6

Exceptional

40 reviews

$475
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Charlestown.

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Frequently Asked Questions

You can explore 2307 verified vacation rentals in Charlestown. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Charlestown vary depending on the season, property size, and location. Rates typically start from around $210 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Charlestown include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Charlestown welcome pets. Currently, 55 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Charlestown often include amenities such as Fireplace/Heating, Wellness Facilities, and Internet. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.