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

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  4.  Massachusetts

  5.  South Chatham

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587 Best Family Vacation Rentals in South Chatham (Starting from $256)

Close to Bike Path 1 Mile to Beaches
Close to Bike Path 1 Mile to Beaches
House
Chatham, MA, USA
0.3k from South Chatham center

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

3 Bedrooms6 Guests
8.0

Good

1 reviews

$507
Average price / night
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Enjoy your own private pool in Chatham! (2252)
Enjoy your own private pool in Chatham! (2252)
House
Chatham, MA, 02659, United States
0.3k from South Chatham center

AC, Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet

4 Bedrooms10 Guests
9.4

Superb

3 reviews

$867
Average price / night
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Beautiful Home w Artistic Flair
Beautiful Home w Artistic Flair
House
Chatham, MA, USA
0.3k from South Chatham center

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

3 Bedrooms7 Guests
10.0

Exceptional

1 reviews

$540
Average price / night
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The Boarding House, King bed comfort. Close to Nantucket Sound beaches.
The Boarding House, King bed comfort. Close to Nantucket Sound beaches.
House
Chatham, MA, 02659, United States
0.5k from South Chatham center

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

4 Bedrooms8 Guests
10.0

Exceptional

16 reviews

$457
Average price / night
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Sun Room Beaches and Dog Welcome
Sun Room Beaches and Dog Welcome
House
Chatham, MA, USA
0.3k from South Chatham center

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

3 Bedrooms6 Guests
8.7

Fabulous

3 reviews

$513
Average price / night
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South Chatham cottage walk to beaches, dining, tennis, shops, bike path.
South Chatham cottage walk to beaches, dining, tennis, shops, bike path.
House
Chatham, MA, 02659, United States
0.6k from South Chatham center

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

2 Bedrooms4 Guests
9.4

Superb

19 reviews

$260
Average price / night
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Newly Renovated Modern Pond Access
Newly Renovated Modern Pond Access
House
Chatham, MA, USA
0.3k from South Chatham center

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

4 Bedrooms10 Guests
6.0

Review score

1 reviews

$838
Average price / night
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Jean's Dream - Newly Renovated Cape House .9Miles from the Beach
Jean's Dream - Newly Renovated Cape House .9Miles from the Beach
House
Chatham, MA, 02659, United States
0.6k from South Chatham center

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

2 Bedrooms7 Guests
10.0

Exceptional

12 reviews

$735
Average price / night
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Bring your pups to Chatham Direct access to the Cape Cod Rail Trail
Bring your pups to Chatham Direct access to the Cape Cod Rail Trail
House
Chatham, MA, USA
0.3k from South Chatham center

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

3 Bedrooms7 Guests
New to Booking
$413
Average price / night
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Beach Chic Chatham 5 Star 5 Min Walk to Beach-Newly Renovated Private Retreat AC
Beach Chic Chatham 5 Star 5 Min Walk to Beach-Newly Renovated Private Retreat AC
House
Chatham, MA, 02659, United States
0.7k from South Chatham center

AC, Arcade, Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Fitness Equipment, Free Parking

4 Bedrooms10 Guests
10.0

Exceptional

80 reviews

$479
Average price / night
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Seashell Wishes-Salty Kisses
Seashell Wishes-Salty Kisses
House
Chatham, MA, USA
0.3k from South Chatham center

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

2 Bedrooms4 Guests
8.0

Good

1 reviews

$256
Average price / night
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Beautiful Chatham,  Sun Sand & Surf.  8/10 mile to  beaches ,pet friendly home
Beautiful Chatham, Sun Sand & Surf. 8/10 mile to beaches ,pet friendly home
House
Chatham, MA, 02659, United States
0.8k from South Chatham center

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

4 Bedrooms8 Guests
10.0

Exceptional

44 reviews

$677
Average price / night
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Wrap-Around Porch Mins to Beach
Wrap-Around Porch Mins to Beach
House
Chatham, MA, USA
0.4k from South Chatham center

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

2 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$597
Average price / night
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Charming Walk to Beach Chatham-Bayview Cottage 3 BR--Central A/C; Wi-Fi
Charming Walk to Beach Chatham-Bayview Cottage 3 BR--Central A/C; Wi-Fi
House
Chatham, MA, 02633, United States
0.8k from South Chatham center

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

3 Bedrooms6 Guests
10.0

Exceptional

55 reviews

$557
Average price / night
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Corner Cottage
Corner Cottage
House
Chatham, MA, USA
0.4k from South Chatham center

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

3 Bedrooms6 Guests
9.3

Superb

4 reviews

$531
Average price / night
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Cockle Cottage - Renovated Chatham Cape House .9 Miles from Beach
Cockle Cottage - Renovated Chatham Cape House .9 Miles from Beach
House
Chatham, MA, 02659, United States
0.8k from South Chatham center

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

2 Bedrooms4 Guests
8.8

Fabulous

10 reviews

$621
Average price / night
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9-Min Walk to Water Fire Pit
9-Min Walk to Water Fire Pit
House
Chatham, MA, USA
0.5k from South Chatham center

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

4 Bedrooms8 Guests
New to Booking
$513
Average price / night
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 Walk to the warm waters of Nantucket sound 3B/2B home CA, W & D, all amenities
Walk to the warm waters of Nantucket sound 3B/2B home CA, W & D, all amenities
House
Chatham, MA, 02633, United States
1.0k from South Chatham center

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

3 Bedrooms6 Guests
9.8

Exceptional

22 reviews

$396
Average price / night
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18 Bearberry Lane South Chatham - Rhododendron Cottage
18 Bearberry Lane South Chatham - Rhododendron Cottage
House
South Chatham, MA, USA
0.5k from South Chatham center

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

1 Bedroom8 Guests
New to Booking
$500
Average price / night
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Renovated, modern Chatham beach house with lots of cozy charm
Renovated, modern Chatham beach house with lots of cozy charm
House
Chatham, MA, 02659, United States
1.0k from South Chatham center

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

4 Bedrooms8 Guests
9.8

Exceptional

45 reviews

$469
Average price / night
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Coastal Charm in South Chatham – Walk to Beach & Bike Trail!
Coastal Charm in South Chatham – Walk to Beach & Bike Trail!
House
Chatham, MA, 02633, United States
1.1k from South Chatham center

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

3 Bedrooms6 Guests
9.8

Exceptional

62 reviews

$258
Average price / night
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Charming two year old 3Bd Rm 4 bath home .6mi to Ridgevale Beach
Charming two year old 3Bd Rm 4 bath home .6mi to Ridgevale Beach
House
Chatham, MA, 02633, United States
1.1k from South Chatham center

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

3 Bedrooms8 Guests
10.0

Exceptional

8 reviews

$788
Average price / night
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3br, huge private yard, halfway between Harwichport and Downtown Chatham!
3br, huge private yard, halfway between Harwichport and Downtown Chatham!
House
Chatham, MA, 02659, United States
1.2k from South Chatham center

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

3 Bedrooms7 Guests
10.0

Exceptional

3 reviews

$440
Average price / night
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5BR 3.5 BA, 2 Wing Home, AC, Foosball, Fenced Yard, Beach ~1 mi
5BR 3.5 BA, 2 Wing Home, AC, Foosball, Fenced Yard, Beach ~1 mi
House
Harwich, MA, 02645, United States
1.2k from South Chatham center

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

5 Bedrooms10 Guests
9.8

Exceptional

40 reviews

$622
Average price / night
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Spacious, private cottage just a few minutes walk to Ridgevale Beach!
Spacious, private cottage just a few minutes walk to Ridgevale Beach!
House
Chatham, MA, 02633, United States
1.2k from South Chatham center

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

3 Bedrooms6 Guests
10.0

Exceptional

41 reviews

$466
Average price / night
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Walk to the beach! The Salty Breeze sleeps 10; updated house, bikes, beach toys!
Walk to the beach! The Salty Breeze sleeps 10; updated house, bikes, beach toys!
House
Chatham, MA, 02659, United States
1.2k from South Chatham center

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

3 Bedrooms8 Guests
9.8

Exceptional

16 reviews

$686
Average price / night
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Classic Cape House Walking Distance to the Beach - Many recent upgrades
Classic Cape House Walking Distance to the Beach - Many recent upgrades
House
Chatham, MA, 02659, United States
1.2k from South Chatham center

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

3 Bedrooms6 Guests
9.8

Exceptional

20 reviews

$758
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 South Chatham.

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South Chatham Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 587 verified family-friendly vacation rentals in South Chatham. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in South Chatham vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $256 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in South Chatham 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 South Chatham 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 South Chatham often include amenities such as Fireplace/Heating, Child Friendly, 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.