Family-Friendly Vacation Rentals in Courageous Sailing Center, MA: Compare 10+ Sites & Save

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  6.  Courageous Sailing Center

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749 Best Family Vacation Rentals in Courageous Sailing Center (Starting from $224)

Cozy N End 1BR steps from Harborwalk BOS-446
Cozy N End 1BR steps from Harborwalk BOS-446
Apartment
Boston, MA, USA
0.6k from Courageous Sailing Center center

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

1 Bedroom2 Guests
New to Booking
$235
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 Courageous Sailing Center 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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Entire Apt Near Wharf
Entire Apt Near Wharf
Apartment
Boston, MA, USA
0.7k from Courageous Sailing Center 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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Boston Condo with Free Parking
Boston Condo with Free Parking
Apartment
Boston, MA, 02129, United States
0.8k from Courageous Sailing Center center

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

1 Bedroom4 Guests
New to Booking
$373
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
0.7k from Courageous Sailing Center center

Apartments, Accommodations, Lodgings, Places to stay

4 Bedrooms12 Guests
New to Booking
$897
Average price / night
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4BR Boston Home 5-minute walk to Subway
4BR Boston Home 5-minute walk to Subway
Apartment
Boston, MA, 02113, United States
0.9k from Courageous Sailing Center center

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

4 Bedrooms12 Guests
10.0

Exceptional

3 reviews

$1281
Average price / night
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Luxury Apartments by Hyatus Downtown Boston
Luxury Apartments by Hyatus Downtown Boston
Apartment
Boston, MA, USA
0.7k from Courageous Sailing Center center

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

6 Bedrooms4 Guests
New to Booking
$7650
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, 02113, United States
0.9k from Courageous Sailing Center center

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

3 Bedrooms6 Guests
10.0

Exceptional

8 reviews

$575
Average price / night
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Charlestown Gem
Charlestown Gem
Apartment
Boston, MA, USA
0.7k from Courageous Sailing Center center

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

1 Bedroom4 Guests
New to Booking
$292
Average price / night
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North End Entire House
North End Entire House
Apartment
Boston, MA, 02113, United States
0.9k from Courageous Sailing Center center

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

3 Bedrooms6 Guests
10.0

Exceptional

20 reviews

$518
Average price / night
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Boston Harbor views Modern north end condo FREE PARKING!
Boston Harbor views Modern north end condo FREE PARKING!
Apartment
Boston, MA, USA
0.9k from Courageous Sailing Center center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay, Family, Self-catering, Condos

3 Bedrooms6 Guests
9.3

Superb

12 reviews

$850
Average price / night
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Comfortable 2BR/2BA by MGH, Ideal for Families, River Walk, Gym, Laundry in Unit
Comfortable 2BR/2BA by MGH, Ideal for Families, River Walk, Gym, Laundry in Unit
Apartment
Boston, MA, 02114, United States
1.7k from Courageous Sailing Center center

AC, Barbecue, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

2 Bedrooms5 Guests
8.4

Very Good

7 reviews

$370
Average price / night
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Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino
Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino
House
Chelsea, MA, 02150, United States
1.7k from Courageous Sailing Center center

AC, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms8 Guests
9.4

Superb

102 reviews

$689
Average price / night
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Premier 3BR&2BA • 1700sqft  • Heart of Downtown Boston
Premier 3BR&2BA • 1700sqft • Heart of Downtown Boston
Condo
Boston, MA, 02111, United States
1.9k from Courageous Sailing Center center

AC, Crib, Dryer, Elevator, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms7 Guests
10.0

Exceptional

4 reviews

$1057
Average price / night
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Gorgeous 2 bed best North End location w parking
Gorgeous 2 bed best North End location w parking
Apartment
MA, USA
0.9k from Courageous Sailing Center center

Air Conditioner, Internet, Child Friendly

2 Bedrooms5 Guests
New to Booking
$224
Average price / night
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Modern 3BR Home Near Downtown Boston • Walk to T • Minutes to Logan
Modern 3BR Home Near Downtown Boston • Walk to T • Minutes to Logan
Apartment
Boston, MA, 02128, United States
1.9k from Courageous Sailing Center center

AC, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
New to Booking
$1214
Average price / night
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Beautiful 3BR 3BA Duplex parking Best Location Boston
Beautiful 3BR 3BA Duplex parking Best Location Boston
Apartment
Courageous Sailing Center, Boston, Massachusetts, USA
0.9k from Courageous Sailing Center center

Apartments, Accommodations, Lodgings, Vacation rentals, Places to stay, Self-catering

3 Bedrooms7 Guests
10.0

Exceptional

4 reviews

$981
Average price / night
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The Maverick - Luxurious Apartment - Near Airport/Downtown - Free Parking!
The Maverick - Luxurious Apartment - Near Airport/Downtown - Free Parking!
House
Chelsea, MA, 02150, United States
1.9k from Courageous Sailing Center center

AC, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

5 Bedrooms10 Guests
9.2

Superb

13 reviews

$533
Average price / night
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Location+Comfort+Convenience
Location+Comfort+Convenience
Apartment
Boston, MA, USA
1.0k from Courageous Sailing Center center

Apartments, Cheap, Accommodations, Lodgings, Vacation rentals, Places to stay, Family, Self-catering

3 Bedrooms6 Guests
8.8

Fabulous

57 reviews

$571
Average price / night
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Cozy/warm Near-Commuter rail, Boston, Airport, Casino and More !
Cozy/warm Near-Commuter rail, Boston, Airport, Casino and More !
Apartment
Chelsea, MA, 02150, United States
2.1k from Courageous Sailing Center center

AC, Balcony, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

2 Bedrooms4 Guests
9.8

Exceptional

41 reviews

$290
Average price / night
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Spacious Sunlit 3BR • Downtown Boston • Family Favorite
Spacious Sunlit 3BR • Downtown Boston • Family Favorite
Apartment
Boston, MA, 02111, United States
2.1k from Courageous Sailing Center center

AC, Dryer, Elevator, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms8 Guests
10.0

Exceptional

61 reviews

$1771
Average price / night
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Ultimate Cambridge Mansion Sleeps 14 with Spa Bath, HUGE Game Room & 2 Parking
Ultimate Cambridge Mansion Sleeps 14 with Spa Bath, HUGE Game Room & 2 Parking
House
Cambridge, MA, 02141, United States
2.3k from Courageous Sailing Center center

AC, Arcade, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

5 Bedrooms14 Guests
10.0

Exceptional

1 reviews

$2327
Average price / night
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Newly renovated historic home in Beacon Hill
Newly renovated historic home in Beacon Hill
House
Boston, MA, 02108, United States
2.4k from Courageous Sailing Center center

AC, Dryer, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space

5 Bedrooms6 Guests
New to Booking
$3140
Average price / night
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Modern 2 bed,2 bath Gem MIT | Central Cambridge
Modern 2 bed,2 bath Gem MIT | Central Cambridge
Apartment
Cambridge, MA, 02141, United States
2.4k from Courageous Sailing Center center

AC, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

2 Bedrooms6 Guests
9.6

Exceptional

9 reviews

$399
Average price / night
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Charming 2-bedroom condo in delightful Chelsea with WiFi, AC
Charming 2-bedroom condo in delightful Chelsea with WiFi, AC
Condo
Chelsea, MA, 02150, United States
2.5k from Courageous Sailing Center center

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

2 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$443
Average price / night
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Boston-Harvard Mansion Sleeps 14 w/ Spacious Game Room and Spa Bath
Boston-Harvard Mansion Sleeps 14 w/ Spacious Game Room and Spa Bath
House
Cambridge, MA, 02141, United States
2.5k from Courageous Sailing Center center

AC, Arcade, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

5 Bedrooms14 Guests
10.0

Exceptional

1 reviews

$2756
Average price / night
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3BR2Bth MIT/Harvard/TD Garden/BOS/3 Parking Spaces
3BR2Bth MIT/Harvard/TD Garden/BOS/3 Parking Spaces
Apartment
Somerville, MA, 02145, United States
2.7k from Courageous Sailing Center center

AC, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms8 Guests
10.0

Exceptional

11 reviews

$448
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 Family Vacation Rentals in Courageous Sailing Center.

Where to stay in Courageous Sailing Center? Best neighborhoods & areas

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Frequently Asked Questions

You can explore 749 verified family-friendly vacation rentals in Courageous Sailing Center. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Courageous Sailing Center vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $224 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Courageous Sailing Center offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in Courageous Sailing Center are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Courageous Sailing Center often include amenities such as Child Friendly, Fireplace/Heating, and Guest Services. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.