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

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  3.  USA

  4.  Massachusetts

  5.  Essex

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86 Best Family Vacation Rentals in Essex (Starting from $226)

Great Marsh House
Great Marsh House
House
Essex, MA, USA
0.9k from Essex center

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

4 Bedrooms8 Guests
9.2

Superb

5 reviews

$586
Average price / night
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Winter deal!  Charming 3-bedroom house on one floor in Essex
Winter deal! Charming 3-bedroom house on one floor in Essex
House
Essex, MA, 01929, United States
0.3k from Essex center

AC, Dryer, Free Parking, Heater, Internet, Laundry, Living Area, Microwave, No Smoking

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$560
Average price / night
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Robbins Island Retreat
Robbins Island Retreat
House
Essex, MA, USA
3.1k from Essex center

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

2 Bedrooms4 Guests
New to Booking
$339
Average price / night
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Winter deal! Delightful 3-4 bed one floor, 3 baths, fireplace
Winter deal! Delightful 3-4 bed one floor, 3 baths, fireplace
House
Essex, MA, 01929, United States
0.4k from Essex center

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

4 Bedrooms10 Guests
9.8

Exceptional

6 reviews

$560
Average price / night
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Airstream and Ocean View Unique Gloucester Getaway
Airstream and Ocean View Unique Gloucester Getaway
House
Gloucester, MA, USA
4.6k from Essex center

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

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$287
Average price / night
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❤️ of Cape Ann, -  Historic Antique Colonial yet new & modern Close 2 Everything
❤️ of Cape Ann, - Historic Antique Colonial yet new & modern Close 2 Everything
House
Essex, MA, 01929, United States
0.7k from Essex center

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

4 Bedrooms8 Guests
9.6

Exceptional

27 reviews

$424
Average price / night
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Ipswich Cottage Beautiful Views, 5 Mins to Beach
Ipswich Cottage Beautiful Views, 5 Mins to Beach
House
Ipswich, MA, USA
5.0k from Essex center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Pet-friendly, Lodgings, Vacation rentals

4 Bedrooms5 Guests
6.0

Review score

1 reviews

$329
Average price / night
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Coastal Cottage on Private Island, overlooking the Essex Great Marsh
Coastal Cottage on Private Island, overlooking the Essex Great Marsh
Cottage
Essex, MA, 01929, United States
2.6k from Essex center

AC, Barbecue, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen, Microwave

2 Bedrooms5 Guests
10.0

Exceptional

10 reviews

$530
Average price / night
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2 Mi to Crane Beach Waterfront Ipswich Escape!
2 Mi to Crane Beach Waterfront Ipswich Escape!
House
Ipswich, MA, USA
5.2k from Essex center

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

2 Bedrooms4 Guests
9.5

Superb

2 reviews

$282
Average price / night
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WINTER 2025 PROMO -Lakefront 2 Bed / 3 bath + Extra Bed off of living room
WINTER 2025 PROMO -Lakefront 2 Bed / 3 bath + Extra Bed off of living room
Cottage
Essex, MA, 01929, United States
3.1k from Essex center

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

3 Bedrooms6 Guests
10.0

Exceptional

25 reviews

$549
Average price / night
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1 Mi to Beach Manchester-by-the-Sea Retreat!
1 Mi to Beach Manchester-by-the-Sea Retreat!
House
Manchester, MA, USA
6.0k from Essex center

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

3 Bedrooms6 Guests
New to Booking
$697
Average price / night
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First Period Colonial Lodging in Gloucester MA
First Period Colonial Lodging in Gloucester MA
House
Gloucester, MA, 01930, United States
3.3k from Essex center

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

3 Bedrooms8 Guests
10.0

Exceptional

17 reviews

$595
Average price / night
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Little River Retreat
Little River Retreat
House
Gloucester, MA, USA
6.4k from Essex center

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

2 Bedrooms4 Guests
6.0

Review score

1 reviews

$342
Average price / night
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The Barn at Asa Stone Farm
The Barn at Asa Stone Farm
House
Ipswich, MA, 01938, United States
4.2k from Essex center

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

4 Bedrooms8 Guests
10.0

Exceptional

13 reviews

$1115
Average price / night
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Elegant Gloucester Beach Getaway with Ocean Views!
Elegant Gloucester Beach Getaway with Ocean Views!
House
Gloucester, MA, USA
7.3k from Essex center

Cheap, Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Vacation rentals

5 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$589
Average price / night
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Elegant farmhouse in Ipswich near Crane Beach and Estate
Elegant farmhouse in Ipswich near Crane Beach and Estate
House
Ipswich, MA, 01938, United States
4.6k from Essex center

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

5 Bedrooms10 Guests
10.0

Exceptional

2 reviews

$2325
Average price / night
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Black Cove Cottage
Black Cove Cottage
House
Manchester, MA, USA
7.4k from Essex center

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

2 Bedrooms5 Guests
5.0

Review score

1 reviews

$495
Average price / night
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1 Mile from Cranes Beach
1 Mile from Cranes Beach
Apartment
Ipswich, MA, 01938, United States
4.8k from Essex center

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

2 Bedrooms6 Guests
10.0

Exceptional

41 reviews

$334
Average price / night
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Garden Cottage By The Sea
Garden Cottage By The Sea
House
Manchester, MA, USA
7.4k from Essex center

Cheap, Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach, Places to stay

2 Bedrooms5 Guests
7.0

Good

2 reviews

$517
Average price / night
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Beautiful Views, 1 Mi to Beach! Ipswich Cottage
Beautiful Views, 1 Mi to Beach! Ipswich Cottage
Cottage
Ipswich, MA, 01938, United States
5.0k from Essex center

Dryer, Free Parking, Kitchen, Laundry, No Smoking, Outdoor Space, Patio, TV, Washer

4 Bedrooms5 Guests
8.2

Very Good

25 reviews

$226
Average price / night
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Gloucester Home with Large Yard 1 Mi to Beach!
Gloucester Home with Large Yard 1 Mi to Beach!
House
Gloucester, MA, USA
7.6k from Essex center

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

2 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$474
Average price / night
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 Spacious 1790  Captain's estate,  large pool,  near beautiful beach
Spacious 1790 Captain's estate, large pool, near beautiful beach
House
Manchester-by-the-Sea, MA, 01944, United States
5.1k from Essex center

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

5 Bedrooms12 Guests
10.0

Exceptional

49 reviews

$886
Average price / night
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 Beach dreaming??
Beach dreaming??
Apartment
Manchester-by-the-Sea, MA, 01944, United States
5.7k from Essex center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

2 Bedrooms4 Guests
10.0

Exceptional

20 reviews

$461
Average price / night
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Secluded 20 acre 10BR ultra contemporary retreat
Secluded 20 acre 10BR ultra contemporary retreat
Villa
Manchester-by-the-Sea, MA, 01944, United States
5.7k from Essex center

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

10 Bedrooms14 Guests
10.0

Exceptional

2 reviews

$1718
Average price / night
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Walk to the T: North Shore Retreat Near Salem Fun!
Walk to the T: North Shore Retreat Near Salem Fun!
House
Manchester-by-the-Sea, MA, 01944, United States
6.0k from Essex center

AC, Barbecue, Crib, Free Parking, Heater, Kitchen, Living Area, Microwave, No Smoking

3 Bedrooms6 Guests
10.0

Exceptional

6 reviews

$578
Average price / night
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Stay at Little River
Stay at Little River
House
Gloucester, MA, 01930, United States
6.4k from Essex center

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

4 Bedrooms7 Guests
10.0

Exceptional

5 reviews

$674
Average price / night
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Elegant Italian Villa On The Scenic Coast of New England
Elegant Italian Villa On The Scenic Coast of New England
House
Manchester, MA, 01944, United States
6.4k from Essex center

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

10 Bedrooms18 Guests
9.4

Superb

125 reviews

$1500
Average price / night
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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 Essex.

Essex Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 86 verified family-friendly vacation rentals in Essex. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Essex vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $226 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Essex 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 Essex 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 Essex often include amenities such as Child Friendly, Fireplace/Heating, and Balcony/Terrace. 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.