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

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35 Best Family Vacation Rentals in Whitehead (Starting from $104)

Ocean View Cozy Stay
Ocean View Cozy Stay
Apartment
Hull, MA, USA
0.7k from Whitehead center

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

2 Bedrooms5 Guests
8.5

Very Good

2 reviews

$400
Average price / night
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Beachfront on Nantasket - Renovated Cottage
Beachfront on Nantasket - Renovated Cottage
House
Hull, MA, 02045, United States
0.5k from Whitehead center

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

4 Bedrooms10 Guests
9.8

Exceptional

8 reviews

$409
Average price / night
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Nantasket Beach - JULY 4th holiday - Summer 2026
Nantasket Beach - JULY 4th holiday - Summer 2026
House
Hull, MA, USA
1.2k from Whitehead center

Accommodations, Parking, Homestays, Lodgings, Vacation rentals, Beach, Places to stay, Beach rentals

4 Bedrooms8 Guests
New to Booking
$274
Average price / night
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Perfect for Large Families, Yard, Ocean Views. 4 Floors, 2 Living Rooms, Office
Perfect for Large Families, Yard, Ocean Views. 4 Floors, 2 Living Rooms, Office
House
Hull, MA, 02045, United States
0.5k from Whitehead center

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

5 Bedrooms10 Guests
10.0

Exceptional

6 reviews

$925
Average price / night
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Cozy Weymouth cottage, walk to beach
Cozy Weymouth cottage, walk to beach
Apartment
Weymouth, MA, USA
7.3k from Whitehead center

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

2 Bedrooms6 Guests
9.5

Superb

4 reviews

$221
Average price / night
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Private unique home short 5 minutes walk to the beach and the bay.
Private unique home short 5 minutes walk to the beach and the bay.
House
Hull, MA, 02045, United States
0.6k from Whitehead center

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

1 Bedroom4 Guests
9.8

Exceptional

20 reviews

$339
Average price / night
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Calm and Stylish Weymouth Apartment
Calm and Stylish Weymouth Apartment
Apartment
MA, USA
7.3k from Whitehead center

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

1 Bedroom2 Guests
6.5

Good

4 reviews

$207
Average price / night
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Bay view beach cottage with loft in tranquil Hull
Bay view beach cottage with loft in tranquil Hull
Cottage
Hull, MA, 02045, United States
0.9k from Whitehead center

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

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$542
Average price / night
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Weymouth Waterfront Getaway with Swim Spa and Hot Tub
Weymouth Waterfront Getaway with Swim Spa and Hot Tub
House
Weymouth, MA, USA
7.9k from Whitehead center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Spa, Cottages, Pet-friendly

3 Bedrooms8 Guests
9.6

Exceptional

6 reviews

$546
Average price / night
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Walk to the beach, take a dip in the salt water inground pool.
Walk to the beach, take a dip in the salt water inground pool.
House
Hull, MA, 02045, United States
1.2k from Whitehead center

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

4 Bedrooms8 Guests
8.8

Fabulous

13 reviews

$746
Average price / night
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Modern bedroom in Weymouth with private bath
Modern bedroom in Weymouth with private bath
House
Weymouth, MA, USA
8.0k from Whitehead center

Cheap, Accommodations, Parking, Homestays, Lodgings, Places to stay

1 Bedroom2 Guests
9.0

Fabulous

2 reviews

$125
Average price / night
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All Season Charming Hull Beach House. ONLY 3 minute walk to Beach!
All Season Charming Hull Beach House. ONLY 3 minute walk to Beach!
House
Hull, MA, 02045, United States
1.6k from Whitehead center

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

2 Bedrooms4 Guests
9.8

Exceptional

37 reviews

$104
Average price / night
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Weymouth Apartment Close to Beaches and Boston!
Weymouth Apartment Close to Beaches and Boston!
Apartment
Weymouth, MA, USA
8.4k from Whitehead center

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

2 Bedrooms4 Guests
10.0

Exceptional

3 reviews

$322
Average price / night
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Beachfront House - Can't get any closer to the beach than this home!
Beachfront House - Can't get any closer to the beach than this home!
House
Hull, MA, 02045, United States
2.0k from Whitehead center

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

4 Bedrooms12 Guests
9.2

Superb

5 reviews

$462
Average price / night
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284 - 5BR Boston - Peaceful House near England Aqua
284 - 5BR Boston - Peaceful House near England Aqua
House
Whitehead, Hull, Massachusetts, USA
8.7k from Whitehead center

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

5 Bedrooms17 Guests
10.0

Exceptional

2 reviews

$539
Average price / night
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Hingham Harbor Retreat ~ Sunsets ~ Family Gatherings ~ Trails at World’s End
Hingham Harbor Retreat ~ Sunsets ~ Family Gatherings ~ Trails at World’s End
House
Hingham,, MA, 02043, United States
2.2k from Whitehead center

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

5 Bedrooms11 Guests
9.8

Exceptional

46 reviews

$1150
Average price / night
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555-2 6BR Quincy - Spacious Apt near Perry Beach
555-2 6BR Quincy - Spacious Apt near Perry Beach
Apartment
Quincy, MA, USA
8.9k from Whitehead center

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

6 Bedrooms21 Guests
10.0

Exceptional

2 reviews

$714
Average price / night
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Enjoy Gorgeous Sunsets From Your Waterfront Beach House.
Enjoy Gorgeous Sunsets From Your Waterfront Beach House.
House
Hull, MA, 02045, United States
2.3k from Whitehead center

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

3 Bedrooms6 Guests
9.6

Exceptional

29 reviews

$445
Average price / night
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Sunset Sanctuary: Minot Beach Scituate
Sunset Sanctuary: Minot Beach Scituate
House
Scituate, MA, USA
9.3k from Whitehead center

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

1 Bedroom7 Guests
New to Booking
$494
Average price / night
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Anchors Away Inn 2 Br Apt 1 min walk to the Beach King & Queen
Anchors Away Inn 2 Br Apt 1 min walk to the Beach King & Queen
House
Hull, MA, 02045, United States
2.6k from Whitehead center

AC, Barbecue, Crib, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave

2 Bedrooms5 Guests
9.8

Exceptional

15 reviews

$432
Average price / night
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NEW Charming Walk to beach 2-bedroom Coastal Home
NEW Charming Walk to beach 2-bedroom Coastal Home
Apartment
Hull, MA, 02045, United States
3.1k from Whitehead center

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

2 Bedrooms7 Guests
10.0

Exceptional

4 reviews

$471
Average price / night
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Great Location on pond 1 minute from beautiful beach
Great Location on pond 1 minute from beautiful beach
House
Hull, MA, 02045, United States
3.1k from Whitehead center

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

3 Bedrooms5 Guests
9.6

Exceptional

5 reviews

$362
Average price / night
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Beautiful Hingham Family Estate, Heated Pool and Game Room.
Beautiful Hingham Family Estate, Heated Pool and Game Room.
House
Hingham, MA, 02043, United States
4.3k from Whitehead center

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

5 Bedrooms12 Guests
10.0

Exceptional

16 reviews

$1673
Average price / night
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Beautiful Victorian Waterfront home minutes to Boston Ferry
Beautiful Victorian Waterfront home minutes to Boston Ferry
House
Hull, MA, 02045, United States
4.3k from Whitehead center

Barbecue, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

4 Bedrooms9 Guests
9.0

Fabulous

4 reviews

$779
Average price / night
Check Availability
Shore House Steps to the ocean, 18 min Ferry to Boston
Shore House Steps to the ocean, 18 min Ferry to Boston
Cottage
Hull, MA, 02045, United States
5.3k from Whitehead center

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

4 Bedrooms8 Guests
8.8

Fabulous

3 reviews

$668
Average price / night
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Cohasset gem steps to Sandy Beach! 2 and 3 bed cottages, 2 baths
Cohasset gem steps to Sandy Beach! 2 and 3 bed cottages, 2 baths
Cottage
Cohasset, MA, 02025, United States
6.1k from Whitehead center

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

2 Bedrooms6 Guests
10.0

Exceptional

28 reviews

$586
Average price / night
Check Availability
Cozy 1-bedroom house in delightful Weymouth with AC, WiFi
Cozy 1-bedroom house in delightful Weymouth with AC, WiFi
Apartment
Weymouth, MA, 02189, United States
7.2k from Whitehead center

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

1 Bedroom2 Guests
9.4

Superb

11 reviews

$362
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 Whitehead.

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Frequently Asked Questions

You can explore 35 verified family-friendly vacation rentals in Whitehead. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Whitehead vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $104 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Whitehead 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 Whitehead 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 Whitehead often include amenities such as Child Friendly, View, and Fireplace/Heating. 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.