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

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Family Vacation Rentals
  3.  USA

  4.  Massachusetts

  5.  Nantucket
  6.  Old Gaol

Refine your search

Price per night

Amenity Filter

Rating

246 Best Family Vacation Rentals in Old Gaol (Starting from $229)

Sea Lyon
Sea Lyon
House
Nantucket, MA, USA
0.6k from Old Gaol center

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

7 Bedrooms14 Guests
New to Booking
$3386
Average price / night
Check Availability
Brand New Luxury ACK Home in Town w/ Heated Pool & Outdoor Shower!
Brand New Luxury ACK Home in Town w/ Heated Pool & Outdoor Shower!
House
Nantucket, MA, 02554, United States
0.0k from Old Gaol center

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

5 Bedrooms10 Guests
9.8

Exceptional

10 reviews

$1691
Average price / night
Check Availability
Ireland Time
Ireland Time
House
Nantucket, MA, USA
0.7k from Old Gaol center

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

4 Bedrooms8 Guests
8.7

Fabulous

3 reviews

$1062
Average price / night
Check Availability
Gorgeous home in town 3Bed 3 bath. screened porch- 3 levels of living & parking
Gorgeous home in town 3Bed 3 bath. screened porch- 3 levels of living & parking
House
Nantucket, MA, 02554, United States
0.2k from Old Gaol center

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

3 Bedrooms6 Guests
10.0

Exceptional

40 reviews

$1467
Average price / night
Check Availability
Meadow's End
Meadow's End
House
Nantucket, MA, USA
0.7k from Old Gaol center

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

3 Bedrooms8 Guests
5.0

Review score

1 reviews

$1205
Average price / night
Check Availability
Prime Nantucket Town Location, Ferry Tickets
Prime Nantucket Town Location, Ferry Tickets
House
Nantucket, MA, 02554, United States
0.2k from Old Gaol center

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

5 Bedrooms10 Guests
10.0

Exceptional

9 reviews

$1407
Average price / night
Check Availability
45A Pleasant St
45A Pleasant St
House
Nantucket, MA, USA
0.7k from Old Gaol center

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

4 Bedrooms12 Guests
10.0

Exceptional

1 reviews

$1800
Average price / night
Check Availability
LUXURIOUS New Cottage!  5-min. walk to Main St. And Harbor Beaches
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches
House
Nantucket, MA, 02554, United States
0.2k from Old Gaol center

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

1 Bedroom4 Guests
10.0

Exceptional

178 reviews

$1403
Average price / night
Check Availability
45B Pleasant St
45B Pleasant St
House
Nantucket, MA, USA
0.7k from Old Gaol center

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

7 Bedrooms16 Guests
10.0

Exceptional

2 reviews

$2080
Average price / night
Check Availability
6 BDR, Pet-friendly, newly remodeled whaling captain’s house downtown Nantucket!
6 BDR, Pet-friendly, newly remodeled whaling captain’s house downtown Nantucket!
House
Nantucket, MA, 02554, United States
0.2k from Old Gaol center

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

6 Bedrooms12 Guests
10.0

Exceptional

48 reviews

$1172
Average price / night
Check Availability
Carlisle House Inn
Carlisle House Inn
Cabin
Old Gaol, Nantucket, Massachusetts, USA
0.8k from Old Gaol center

Accommodations, Lodges, Cabins, Lodgings, Places to stay, Family

13 Bedrooms28 Guests
9.6

Exceptional

25 reviews

$229
Average price / night
Check Availability
Newly built 5BR house w/ Cabana, pool and big yard--walk to town, bike to beach!
Newly built 5BR house w/ Cabana, pool and big yard--walk to town, bike to beach!
House
Nantucket, MA, 02554, United States
0.3k from Old Gaol center

AC, Balcony, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub

5 Bedrooms12 Guests
10.0

Exceptional

4 reviews

$3448
Average price / night
Check Availability
52 Union
52 Union
Villa
Old Gaol, Nantucket, Massachusetts, USA
1.0k from Old Gaol center

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

3 Bedrooms6 Guests
New to Booking
$2150
Average price / night
Check Availability
Walk to town! Bright & Spacious/ AC
Walk to town! Bright & Spacious/ AC
House
Nantucket, MA, 02554, United States
0.3k from Old Gaol center

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

4 Bedrooms11 Guests
10.0

Exceptional

14 reviews

$1412
Average price / night
Check Availability
Sail Away Cottage
Sail Away Cottage
House
Nantucket, MA, USA
1.3k from Old Gaol center

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

3 Bedrooms8 Guests
8.5

Very Good

4 reviews

$1326
Average price / night
Check Availability
Renovated Cottage off Main Street- Great Location
Renovated Cottage off Main Street- Great Location
Cottage
Nantucket, MA, 02554, United States
0.3k from Old Gaol center

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

2 Bedrooms5 Guests
10.0

Exceptional

165 reviews

$558
Average price / night
Check Availability
Charming 3BR Home in Nantucket's Natural Beauty home
Charming 3BR Home in Nantucket's Natural Beauty home
House
Nantucket, MA, USA
1.3k from Old Gaol center

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

3 Bedrooms8 Guests
New to Booking
$1361
Average price / night
Check Availability
Newly renovated 5BR cottage w/ deck and small yard--walk to town, bike to beach!
Newly renovated 5BR cottage w/ deck and small yard--walk to town, bike to beach!
House
Nantucket, MA, 02554, United States
0.3k from Old Gaol center

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

5 Bedrooms16 Guests
10.0

Exceptional

20 reviews

$1895
Average price / night
Check Availability
Peace & Quiet on ACK
Peace & Quiet on ACK
House
Nantucket, MA, USA
4.2k from Old Gaol center

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

2 Bedrooms8 Guests
New to Booking
$600
Average price / night
Check Availability
Off-season on Nantucket? Create magical memories!
Off-season on Nantucket? Create magical memories!
House
Nantucket, MA, 02554, United States
0.3k from Old Gaol center

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

4 Bedrooms8 Guests
10.0

Exceptional

23 reviews

$949
Average price / night
Check Availability
Historical Main Street Captain's House.  Fantastic Location!!!!
Historical Main Street Captain's House. Fantastic Location!!!!
House
Nantucket, MA, 02554, United States
0.3k from Old Gaol center

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

5 Bedrooms10 Guests
9.6

Exceptional

14 reviews

$2602
Average price / night
Check Availability
Cottage in Prime ~In-Town~ Location
Cottage in Prime ~In-Town~ Location
House
Nantucket, MA, 02554, United States
0.3k from Old Gaol center

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

2 Bedrooms4 Guests
10.0

Exceptional

16 reviews

$781
Average price / night
Check Availability
Charming Historic Downtown Cottage
Charming Historic Downtown Cottage
Cottage
Nantucket, MA, 02554, United States
0.3k from Old Gaol center

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

2 Bedrooms6 Guests
9.8

Exceptional

17 reviews

$976
Average price / night
Check Availability
Charming Pet Friendly Cottage
Charming Pet Friendly Cottage
Cottage
Nantucket, MA, 02554, United States
0.3k from Old Gaol center

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

4 Bedrooms8 Guests
9.8

Exceptional

25 reviews

$1089
Average price / night
Check Availability
Chic 2-bedroom townhouse, 10-minute walk to town
Chic 2-bedroom townhouse, 10-minute walk to town
House
Nantucket, MA, 02554, United States
0.4k from Old Gaol center

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

2 Bedrooms5 Guests
10.0

Exceptional

11 reviews

$962
Average price / night
Check Availability
Large charming historic home on quiet street near Nantucket town center
Large charming historic home on quiet street near Nantucket town center
House
Nantucket, MA, 02554, United States
0.4k from Old Gaol center

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

7 Bedrooms14 Guests
9.8

Exceptional

36 reviews

$1414
Average price / night
Check Availability
Newly Renovated Nantucket Downtown Luxury House
Newly Renovated Nantucket Downtown Luxury House
House
Nantucket, MA, 02554, United States
0.4k from Old Gaol center

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

5 Bedrooms14 Guests
New to Booking
$3951
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 Old Gaol.

Where to stay in Old Gaol? Best neighborhoods & areas

Old Gaol Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 246 verified family-friendly vacation rentals in Old Gaol. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Old Gaol vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $229 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Old Gaol 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 Old Gaol 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 Old Gaol often include amenities such as Child Friendly, Laundry, 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.