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

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  4.  Massachusetts

  5.  Chatham
  6.  Chatham Windmill

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333 Best Family Vacation Rentals in Chatham Windmill (Starting from $318)

Full Renovation Amazing Spot with Views
Full Renovation Amazing Spot with Views
House
Chatham, MA, USA
0.4k from Chatham Windmill center

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

2 Bedrooms4 Guests
9.6

Exceptional

8 reviews

$593
Average price / night
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Beautiful Home In Chatham, MA. Private Pool. 2 Min Walk to Town, 8 to Beach! A/C
Beautiful Home In Chatham, MA. Private Pool. 2 Min Walk to Town, 8 to Beach! A/C
House
chatham, MA, 02633, United States
0.3k from Chatham Windmill center

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

3 Bedrooms10 Guests
9.6

Exceptional

82 reviews

$667
Average price / night
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Oyster Beach Bungalow
Oyster Beach Bungalow
Apartment
Chatham Windmill, Chatham, Massachusetts, USA
0.4k from Chatham Windmill center

Apartments, Cheap, Accommodations, Lodgings, Places to stay, Bungalows

1 Bedroom2 Guests
8.2

Very Good

14 reviews

$367
Average price / night
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Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach
Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach
House
Chatham, MA, 02633, United States
0.4k from Chatham Windmill center

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

5 Bedrooms10 Guests
10.0

Exceptional

130 reviews

$1115
Average price / night
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Walk to Main St and Oyster Pond in Chatham
Walk to Main St and Oyster Pond in Chatham
House
Chatham, MA, USA
0.5k from Chatham Windmill center

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

3 Bedrooms6 Guests
7.0

Good

1 reviews

$318
Average price / night
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Downtown Chatham Luxury 9 BR Home with Heated Pool.  Pets welcome!
Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!
House
Chatham, MA, 02633, United States
0.4k from Chatham Windmill center

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

9 Bedrooms21 Guests
10.0

Exceptional

40 reviews

$2956
Average price / night
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Walk to Oyster Pond and Main Street Chatham
Walk to Oyster Pond and Main Street Chatham
House
Chatham, MA, USA
0.5k from Chatham Windmill center

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

4 Bedrooms8 Guests
8.0

Good

1 reviews

$1074
Average price / night
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Charming 3 bedroom 2.5 bath sleeps 6 - Walk to Town & Oyster Pond
Charming 3 bedroom 2.5 bath sleeps 6 - Walk to Town & Oyster Pond
House
Chatham, MA, 02633, United States
0.5k from Chatham Windmill center

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

3 Bedrooms6 Guests
10.0

Exceptional

24 reviews

$1018
Average price / night
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388 Main Street Chatham Cape Cod - - The Priscilla House
388 Main Street Chatham Cape Cod - - The Priscilla House
House
Chatham, MA, USA
0.5k from Chatham Windmill center

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

1 Bedroom18 Guests
New to Booking
$1711
Average price / night
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Charming , very private 4 bedroom, 3.5 Bath Cape. Walk to Town & Oyster Pond
Charming , very private 4 bedroom, 3.5 Bath Cape. Walk to Town & Oyster Pond
Cottage
Chatham, MA, 02633, United States
0.6k from Chatham Windmill center

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

4 Bedrooms7 Guests
10.0

Exceptional

11 reviews

$916
Average price / night
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32 Bearses By Way Chatham Cape Cod - - Chatterbox
32 Bearses By Way Chatham Cape Cod - - Chatterbox
House
Chatham, MA, USA
0.6k from Chatham Windmill center

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

1 Bedroom8 Guests
10.0

Exceptional

1 reviews

$1050
Average price / night
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Water View-Walk town/beach, pets considered, Linen Option
Water View-Walk town/beach, pets considered, Linen Option
House
Chatham, MA, 02633, United States
0.7k from Chatham Windmill center

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

5 Bedrooms14 Guests
10.0

Exceptional

117 reviews

$928
Average price / night
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14 Hallet Lane Chatham Cape Cod - - Sand Simeon
14 Hallet Lane Chatham Cape Cod - - Sand Simeon
House
Chatham, MA, USA
0.8k from Chatham Windmill center

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

1 Bedroom14 Guests
New to Booking
$1999
Average price / night
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Chatham-Walk to Town/Beach-Multi Family Friendly
Chatham-Walk to Town/Beach-Multi Family Friendly
House
Chatham, MA, 02633, United States
0.7k from Chatham Windmill center

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

5 Bedrooms12 Guests
10.0

Exceptional

57 reviews

$847
Average price / night
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201 Main Street Chatham Cape Cod - - Sandpiper
201 Main Street Chatham Cape Cod - - Sandpiper
House
Chatham, MA, USA
0.8k from Chatham Windmill center

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

1 Bedroom8 Guests
New to Booking
$2500
Average price / night
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Location and Luxury
Location and Luxury
House
Chatham, MA, 02633, United States
0.7k from Chatham Windmill center

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

3 Bedrooms6 Guests
10.0

Exceptional

23 reviews

$1183
Average price / night
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Centrally Located Home w Patio Fire Pit
Centrally Located Home w Patio Fire Pit
House
Chatham, MA, USA
0.9k from Chatham Windmill center

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

4 Bedrooms9 Guests
9.0

Fabulous

2 reviews

$1183
Average price / night
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Chatham's Best Location / Oceanside / Walk to Town and Beaches
Chatham's Best Location / Oceanside / Walk to Town and Beaches
House
Chatham, MA, 02633, United States
0.8k from Chatham Windmill center

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

4 Bedrooms6 Guests
9.8

Exceptional

12 reviews

$2042
Average price / night
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Steps to Oyster Pond Private Dock!
Steps to Oyster Pond Private Dock!
House
Chatham, MA, USA
0.9k from Chatham Windmill center

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

5 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$1961
Average price / night
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Walk to town and beach from this updated 3BR house in historic Chatham
Walk to town and beach from this updated 3BR house in historic Chatham
House
Chatham, MA, 02633, United States
0.9k from Chatham Windmill center

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

3 Bedrooms7 Guests
10.0

Exceptional

2 reviews

$906
Average price / night
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Walk to Downtown Chatham Steps to Beach
Walk to Downtown Chatham Steps to Beach
House
Chatham, MA, USA
0.9k from Chatham Windmill center

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

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$999
Average price / night
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GREAT LOCATION - Water View, Walk to beach & Town!
GREAT LOCATION - Water View, Walk to beach & Town!
House
Chatham, MA, 02633, United States
0.9k from Chatham Windmill center

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

3 Bedrooms6 Guests
10.0

Exceptional

73 reviews

$837
Average price / night
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Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room
Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room
House
Chatham, MA, 02633, United States
0.9k from Chatham Windmill center

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

5 Bedrooms12 Guests
10.0

Exceptional

21 reviews

$3013
Average price / night
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22 Veterans’ Field Rd., Chatham, MA: Home Plate
22 Veterans’ Field Rd., Chatham, MA: Home Plate
House
Chatham, MA, 02633, United States
0.9k from Chatham Windmill center

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

4 Bedrooms12 Guests
9.8

Exceptional

14 reviews

$768
Average price / night
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Downtown Chatham Home - Near Oyster Pond - Spacious Patio - Family Friendly
Downtown Chatham Home - Near Oyster Pond - Spacious Patio - Family Friendly
House
Chatham, MA, 02633, United States
1.0k from Chatham Windmill center

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

3 Bedrooms6 Guests
10.0

Exceptional

22 reviews

$1017
Average price / night
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Newly renovated! Perfect family home, short walk to Chatham!
Newly renovated! Perfect family home, short walk to Chatham!
House
Chatham, MA, 02633, United States
1.1k from Chatham Windmill center

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

4 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$653
Average price / night
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Sunny Updated Chatham Village 2 Bedroom Condo W/ Large Private Deck
Sunny Updated Chatham Village 2 Bedroom Condo W/ Large Private Deck
Condo
Chatham, MA, 02633, United States
1.1k from Chatham Windmill center

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

2 Bedrooms5 Guests
10.0

Exceptional

33 reviews

$498
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 Chatham Windmill.

Chatham Windmill Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 333 verified family-friendly vacation rentals in Chatham Windmill. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Chatham Windmill vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $318 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Chatham Windmill 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 Chatham Windmill 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 Chatham Windmill 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.