Family-Friendly Vacation Rentals in Gloucester, MA: Compare 10+ Sites & Save

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  2. Family Vacation Rentals
  3.  USA

  4.  Massachusetts

  5.  Gloucester

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145 Best Family Vacation Rentals in Gloucester (Starting from $173)

Gloucester Harbor Hideaway
Gloucester Harbor Hideaway
Apartment
Gloucester, MA, USA
0.1k from Gloucester center

Apartments, Cheap, Accommodations, Lodgings, Places to stay, Family

2 Bedrooms4 Guests
9.4

Superb

5 reviews

$402
Average price / night
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Fish & Ships on Waterway: Steps to Ocean, Beach, Boulevard, Park, Restaurants
Fish & Ships on Waterway: Steps to Ocean, Beach, Boulevard, Park, Restaurants
Apartment
Gloucester, MA, 01930, United States
0.7k from Gloucester center

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

2 Bedrooms4 Guests
New to Booking
$290
Average price / night
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Guest suite in historical district
Guest suite in historical district
Apartment
Gloucester, MA, USA
0.2k from Gloucester center

Parking, Air Conditioner, Security/Safety, Guest Services, Internet, Sports/Activities, Breakfast

2 Bedrooms4 Guests
9.1

Superb

43 reviews

$180
Average price / night
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Single Level Home - Steps to Downtown Gloucester & A/C throughout
Single Level Home - Steps to Downtown Gloucester & A/C throughout
House
Gloucester, MA, 01930, United States
0.7k from Gloucester center

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

2 Bedrooms4 Guests
10.0

Exceptional

47 reviews

$290
Average price / night
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Stay at Rocky Neck
Stay at Rocky Neck
House
Gloucester, MA, USA
0.6k from Gloucester center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

3 Bedrooms7 Guests
10.0

Exceptional

1 reviews

$1093
Average price / night
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Downtown Dahlias fully remodeled in the heart of Gloucester
Downtown Dahlias fully remodeled in the heart of Gloucester
House
Gloucester, MA, 01930, United States
0.7k from Gloucester center

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

3 Bedrooms6 Guests
10.0

Exceptional

22 reviews

$482
Average price / night
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A by the Bay - Stunning Seaside Apartment
A by the Bay - Stunning Seaside Apartment
Apartment
Gloucester, MA, USA
0.8k from Gloucester center

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

2 Bedrooms6 Guests
9.2

Superb

25 reviews

$559
Average price / night
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Stay at Smith Cove
Stay at Smith Cove
House
Gloucester, MA, 01930, United States
0.8k from Gloucester center

AC, Balcony, Barbecue, Crib, Dryer, Fireplace, Heater, Internet, Kitchen

2 Bedrooms7 Guests
10.0

Exceptional

7 reviews

$443
Average price / night
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Spacious 2nd floor Suite
Spacious 2nd floor Suite
Apartment
Gloucester, MA, USA
0.8k from Gloucester center

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

2 Bedrooms4 Guests
7.1

Good

7 reviews

$173
Average price / night
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Stay at The Neck
Stay at The Neck
House
Gloucester, MA, 01930, United States
0.8k from Gloucester center

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

3 Bedrooms7 Guests
10.0

Exceptional

1 reviews

$527
Average price / night
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Glorious Suite near Downtown with washer/dryer
Glorious Suite near Downtown with washer/dryer
Apartment
Gloucester, MA, USA
0.8k from Gloucester center

Parking, Internet, Security/Safety, Child Friendly

3 Bedrooms4 Guests
8.7

Fabulous

19 reviews

$291
Average price / night
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WATERFRONT- River & Harbors views, Walking Distance to Downtown, Beaches & Park
WATERFRONT- River & Harbors views, Walking Distance to Downtown, Beaches & Park
Condo
Gloucester, MA, 01930, United States
0.9k from Gloucester center

Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

1 Bedroom2 Guests
New to Booking
$396
Average price / night
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Bianca's House
Bianca's House
House
Gloucester, MA, USA
0.8k from Gloucester center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Places to stay

2 Bedrooms4 Guests
6.0

Review score

3 reviews

$326
Average price / night
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Ocean front and 3 beaches across,parks, short walk to historic downtown!
Ocean front and 3 beaches across,parks, short walk to historic downtown!
House
Gloucester, MA, 01930, United States
1.0k from Gloucester center

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

5 Bedrooms10 Guests
10.0

Exceptional

37 reviews

$1127
Average price / night
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Longview House
Longview House
House
Gloucester, MA, USA
0.8k from Gloucester center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay, Family, Accessible hotels

4 Bedrooms9 Guests
6.0

Review score

2 reviews

$383
Average price / night
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 Victorian home, family and pet friendly close to beaches, harbor, restaurants
Victorian home, family and pet friendly close to beaches, harbor, restaurants
House
Gloucester, MA, 01930, United States
1.1k from Gloucester center

Barbecue, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking, Outdoor Space

3 Bedrooms6 Guests
10.0

Exceptional

11 reviews

$728
Average price / night
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3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views
3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views
House
Gloucester, MA, 01930, United States
1.1k from Gloucester center

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

3 Bedrooms8 Guests
9.8

Exceptional

46 reviews

$518
Average price / night
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The Chill-a-Vista
The Chill-a-Vista
Apartment
Gloucester, Massachusetts, USA
0.8k from Gloucester center

Parking, Air Conditioner, Child Friendly

4 Bedrooms8 Guests
New to Booking
$535
Average price / night
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3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8
House
Gloucester, MA, 01930, United States
1.2k from Gloucester center

Balcony, Barbecue, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

3 Bedrooms8 Guests
10.0

Exceptional

7 reviews

$536
Average price / night
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CbytheSea - Ocean View Penthouse
CbytheSea - Ocean View Penthouse
Apartment
Gloucester, MA, USA
0.8k from Gloucester center

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

1 Bedroom4 Guests
9.5

Superb

39 reviews

$507
Average price / night
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Stay at East Gloucester
Stay at East Gloucester
House
Gloucester, MA, 01930, United States
1.4k from Gloucester center

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

4 Bedrooms7 Guests
9.4

Superb

3 reviews

$389
Average price / night
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Coastal retreat steps to the beach with smart TVs, desk, grill, children's items
Coastal retreat steps to the beach with smart TVs, desk, grill, children's items
House
Gloucester, MA, 01930, United States
1.4k from Gloucester center

AC, Barbecue, Dryer, Free Parking, Kitchen, Laundry, Living Area, Microwave, No Smoking

3 Bedrooms6 Guests
9.4

Superb

39 reviews

$435
Average price / night
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Charming Retreat
Charming Retreat
Apartment
Gloucester, MA, 01930, United States
1.6k from Gloucester center

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

2 Bedrooms4 Guests
9.8

Exceptional

15 reviews

$300
Average price / night
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Stay at Niles Beach
Stay at Niles Beach
House
Gloucester, MA, 01930, United States
1.6k from Gloucester center

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

3 Bedrooms7 Guests
10.0

Exceptional

39 reviews

$514
Average price / night
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Quaint Neighborhood / Close to Beaches
Quaint Neighborhood / Close to Beaches
Apartment
Gloucester, MA, 01930, United States
1.6k from Gloucester center

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

3 Bedrooms5 Guests
10.0

Exceptional

13 reviews

$272
Average price / night
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5 minute walk to Beach, Stage Fort Park, and Gloucester Promenade!
5 minute walk to Beach, Stage Fort Park, and Gloucester Promenade!
House
Gloucester, MA, 01930, United States
1.7k from Gloucester center

AC, Barbecue, Crib, Dryer, Fireplace, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms10 Guests
10.0

Exceptional

13 reviews

$477
Average price / night
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WALK TO BEACH! Great Location! Booking 2026! Close to Salem!!
WALK TO BEACH! Great Location! Booking 2026! Close to Salem!!
House
Gloucester, MA, 01930, United States
1.9k from Gloucester center

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

2 Bedrooms6 Guests
10.0

Exceptional

72 reviews

$319
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 Gloucester.

Stay Near Gloucester's Top Attractions

VacationByOwnerRentals can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.

Gloucester Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 145 verified family-friendly vacation rentals in Gloucester. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Gloucester vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $173 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Gloucester 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 Gloucester 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 Gloucester often include amenities such as Child Friendly, Fireplace/Heating, and Wellness Facilities. 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.