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

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  2. Family Vacation Rentals
  3.  USA

  4.  Massachusetts

  5.  Gloucester
  6.  Dogtown

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141 Best Family Vacation Rentals in Dogtown (Starting from $173)

Waterfront Escape Dock & More
Waterfront Escape Dock & More
House
Gloucester, MA, USA
1.9k from Dogtown center

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

4 Bedrooms12 Guests
New to Booking
$1025
Average price / night
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Amazing Waterfront/Access 4BDRM in Riggs Point
Amazing Waterfront/Access 4BDRM in Riggs Point
Cottage
Gloucester, MA, 01930, United States
1.6k from Dogtown center

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

4 Bedrooms8 Guests
9.2

Superb

15 reviews

$504
Average price / night
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OFFICIAL SITE - Buoy 23 Vacation Home Gloucester, MA Deepwater dock
OFFICIAL SITE - Buoy 23 Vacation Home Gloucester, MA Deepwater dock
House
Gloucester, MA, USA
1.9k from Dogtown center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

4 Bedrooms7 Guests
New to Booking
$615
Average price / night
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Oceanfront Dock Escape ~ Kayaks & Paddleboards
Oceanfront Dock Escape ~ Kayaks & Paddleboards
House
Gloucester, MA, 01930, United States
1.9k from Dogtown center

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

4 Bedrooms10 Guests
10.0

Exceptional

5 reviews

$910
Average price / night
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Bianca's House
Bianca's House
House
Gloucester, MA, USA
2.3k from Dogtown 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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Waterfront Home with Spectacular Viewsof the Annisquam River
Waterfront Home with Spectacular Viewsof the Annisquam River
House
Gloucester, MA, 01930, United States
2.0k from Dogtown center

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

6 Bedrooms10 Guests
9.8

Exceptional

69 reviews

$654
Average price / night
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Spacious 2nd floor Suite
Spacious 2nd floor Suite
Apartment
Gloucester, MA, USA
2.4k from Dogtown 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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Downtown Dahlias fully remodeled in the heart of Gloucester
Downtown Dahlias fully remodeled in the heart of Gloucester
House
Gloucester, MA, 01930, United States
2.1k from Dogtown 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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Glorious Suite near Downtown with washer/dryer
Glorious Suite near Downtown with washer/dryer
Apartment
Gloucester, MA, USA
2.4k from Dogtown center

Parking, Internet, Security/Safety, Child Friendly

3 Bedrooms4 Guests
8.7

Fabulous

19 reviews

$291
Average price / night
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Waterfront Living w Stunning Views, Beautiful Decor, Kayaks, Private drive
Waterfront Living w Stunning Views, Beautiful Decor, Kayaks, Private drive
House
Gloucester, MA, 01930, United States
2.3k from Dogtown center

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

3 Bedrooms6 Guests
10.0

Exceptional

66 reviews

$619
Average price / night
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Massachusetts Abode with Deck and Grill Near Beaches!
Massachusetts Abode with Deck and Grill Near Beaches!
House
Gloucester, MA, USA
2.4k from Dogtown center

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

2 Bedrooms4 Guests
9.3

Superb

4 reviews

$425
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
2.3k from Dogtown 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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Guest suite in historical district
Guest suite in historical district
Apartment
Gloucester, MA, USA
2.7k from Dogtown 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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The Haabah Beach Retreat—4 Minute Walk to Beach
The Haabah Beach Retreat—4 Minute Walk to Beach
House
Gloucester, MA, 01930, United States
2.4k from Dogtown center

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

2 Bedrooms6 Guests
9.8

Exceptional

6 reviews

$608
Average price / night
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Gloucester Harbor Hideaway
Gloucester Harbor Hideaway
Apartment
Gloucester, MA, USA
2.7k from Dogtown 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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Seaside Escape just steps to Good Harbor beach in Gloucester
Seaside Escape just steps to Good Harbor beach in Gloucester
House
Gloucester, MA, 01930, United States
2.4k from Dogtown center

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

2 Bedrooms5 Guests
10.0

Exceptional

11 reviews

$470
Average price / night
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Longview House
Longview House
House
Gloucester, MA, USA
2.8k from Dogtown 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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Good Harbor Beach House - walk to beach, close to restaurants and shopping!
Good Harbor Beach House - walk to beach, close to restaurants and shopping!
Cottage
Gloucester, MA, 01930, United States
2.7k from Dogtown center

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

4 Bedrooms8 Guests
10.0

Exceptional

220 reviews

$614
Average price / night
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Ocean Breeze-8min Walk to Beach
Ocean Breeze-8min Walk to Beach
Apartment
Gloucester, MA, USA
2.8k from Dogtown center

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

1 Bedroom4 Guests
9.6

Exceptional

32 reviews

$249
Average price / night
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Experience seaside charm near Good Harbor Beach!
Experience seaside charm near Good Harbor Beach!
House
Gloucester, MA, 01930, United States
2.7k from Dogtown center

AC, Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Hot Tub

5 Bedrooms8 Guests
9.8

Exceptional

8 reviews

$654
Average price / night
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The Chill-a-Vista
The Chill-a-Vista
Apartment
Dogtown, Gloucester, Massachusetts, USA
3.0k from Dogtown center

Parking, Air Conditioner, Child Friendly

4 Bedrooms8 Guests
New to Booking
$535
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
2.7k from Dogtown center

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

2 Bedrooms6 Guests
10.0

Exceptional

72 reviews

$319
Average price / night
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Stay at East Gloucester
Stay at East Gloucester
House
Gloucester, MA, 01930, United States
2.8k from Dogtown 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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Perfect Good Harbor Beach vacation home for large and/or extended family getaway
Perfect Good Harbor Beach vacation home for large and/or extended family getaway
House
Gloucester, MA, 01930, United States
2.8k from Dogtown center

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

5 Bedrooms16 Guests
9.8

Exceptional

80 reviews

$965
Average price / night
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Pool open for the season! Single family home, 5-Min walk to Good Harbor Beach!
Pool open for the season! Single family home, 5-Min walk to Good Harbor Beach!
House
Gloucester, MA, 01930, United States
3.0k from Dogtown center

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

3 Bedrooms8 Guests
9.6

Exceptional

10 reviews

$617
Average price / night
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Elegant Bayview Victorian Home; walk to beach
Elegant Bayview Victorian Home; walk to beach
House
Gloucester, MA, 01930, United States
3.1k from Dogtown center

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

6 Bedrooms12 Guests
9.0

Fabulous

2 reviews

$600
Average price / night
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Oceanside Estate: Main House & Apt w/beach access
Oceanside Estate: Main House & Apt w/beach access
House
Gloucester, MA, 01930, United States
3.1k from Dogtown center

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

4 Bedrooms10 Guests
New to Booking
$826
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 Dogtown.

Dogtown Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 141 verified family-friendly vacation rentals in Dogtown. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Dogtown 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 Dogtown 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 Dogtown 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 Dogtown often include amenities such as Child Friendly, Fireplace/Heating, and View. 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.