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

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  6.  Chatham Windmill

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389 Best Pet-Friendly Rentals in Chatham Windmill (Starting from $519)

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 house that is a walk to downtown!
Beautiful house that is a walk to downtown!
House
Chatham, MA, 02633, United States
0.2k from Chatham Windmill center

AC, Barbecue, Laundry, Microwave, No Smoking, Patio, TV, Washer

3 Bedrooms6 Guests
New to Booking
$862
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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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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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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Town Center-Walk To All Stores-Free Shuttle To Beach- 2026 Total Reno-2Bedroom
Town Center-Walk To All Stores-Free Shuttle To Beach- 2026 Total Reno-2Bedroom
Cottage
Chatham, MA, 02633, United States
0.4k from Chatham Windmill center

AC, Free Parking, Heater, Internet, Kitchen, Laundry, No Smoking, TV

2 Bedrooms4 Guests
New to Booking
$677
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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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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Located in the heart of downtown Chatham, this gem offers an easy walk to everything.
Located in the heart of downtown Chatham, this gem offers an easy walk to everything.
House
Chatham, MA, 02633, United States
0.4k from Chatham Windmill center

AC, Barbecue, Crib, Laundry, Microwave, No Smoking, Outdoor Space, Patio, TV

4 Bedrooms8 Guests
8.6

Fabulous

4 reviews

$938
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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FOUR BEDROOM IN TOWN LOCATION -- CLOSE TO OYSTER POND BEACH AREA.
FOUR BEDROOM IN TOWN LOCATION -- CLOSE TO OYSTER POND BEACH AREA.
House
Chatham, MA, 02633, United States
0.4k from Chatham Windmill center

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

3 Bedrooms8 Guests
10.0

Exceptional

5 reviews

$800
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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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 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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Historic Sea Captain's Home in Downtown Chatham
Historic Sea Captain's Home in Downtown Chatham
House
Chatham, MA, 02633, United States
0.5k from Chatham Windmill center

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

8 Bedrooms18 Guests
9.8

Exceptional

35 reviews

$1843
Average price / night
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37 Clam Shell Drive Chatham - Slow M'Ocean
37 Clam Shell Drive Chatham - Slow M'Ocean
House
Chatham, MA, USA
1.1k from Chatham Windmill center

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

1 Bedroom8 Guests
New to Booking
$1112
Average price / night
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Location Location! Perfect 2-Bedroom Condo On Main Street In Chatham
Location Location! Perfect 2-Bedroom Condo On Main Street In Chatham
Condo
Chatham, MA, 02633, United States
0.5k from Chatham Windmill center

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

2 Bedrooms6 Guests
10.0

Exceptional

95 reviews

$519
Average price / night
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27 Clam Shell Drive Chatham - Need A Name
27 Clam Shell Drive Chatham - Need A Name
House
Chatham, MA, USA
1.1k from Chatham Windmill center

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

1 Bedroom6 Guests
New to Booking
$1125
Average price / night
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Pet friendly, water views and lush lawns!
Pet friendly, water views and lush lawns!
House
Chatham, MA, 02633, United States
0.6k from Chatham Windmill center

AC, Barbecue, Microwave, No Smoking, Patio, Tennis Court, TV, Washer

3 Bedrooms8 Guests
New to Booking
$1105
Average price / night
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Private Beach Water Views Incredible Location
Private Beach Water Views Incredible Location
House
Chatham, MA, USA
1.3k from Chatham Windmill center

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

3 Bedrooms8 Guests
New to Booking
$874
Average price / night
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Spacious 4-bedroom house in Chatham - Walkable to Oyster Bay Pond & Downtown.
Spacious 4-bedroom house in Chatham - Walkable to Oyster Bay Pond & Downtown.
House
Chatham, MA, 02633, United States
0.7k from Chatham Windmill center

AC, Dryer, Heater, Internet, Kitchen, Laundry, No Smoking, Patio, Washer

5 Bedrooms10 Guests
New to Booking
$993
Average price / night
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Quintessential Cape directly on the Cape Cod Rail Dog Friendly
Quintessential Cape directly on the Cape Cod Rail Dog Friendly
House
Chatham, MA, USA
1.9k from Chatham Windmill center

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

4 Bedrooms8 Guests
9.5

Superb

2 reviews

$549
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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Panoramic Water Views w Private Beach
Panoramic Water Views w Private Beach
House
Chatham, MA, USA
2.0k from Chatham Windmill center

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

5 Bedrooms10 Guests
New to Booking
$2160
Average price / night
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Sand Simeon - Relax, Unwind, Repeat!!
Sand Simeon - Relax, Unwind, Repeat!!
House
Chatham, MA, 02633, United States
0.8k from Chatham Windmill center

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

6 Bedrooms14 Guests
9.6

Exceptional

13 reviews

$2200
Average price / night
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Lovely Home Near Bike Path Dog Welcome!
Lovely Home Near Bike Path Dog Welcome!
House
Chatham, MA, USA
2.2k from Chatham Windmill center

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

4 Bedrooms8 Guests
8.0

Good

1 reviews

$523
Average price / night
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Walk to Beach and Town, Hot tub, Sleeps 8, Pet Friendly
Walk to Beach and Town, Hot tub, Sleeps 8, Pet Friendly
House
Chatham, MA, 02633, United States
0.8k from Chatham Windmill center

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

3 Bedrooms8 Guests
10.0

Exceptional

17 reviews

$1329
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 Pet-Friendly Rentals in Chatham Windmill.

Chatham Windmill Pet-Friendly Rentals on the Map

Frequently Asked Questions

You can explore 389 verified pet-friendly rentals in Chatham Windmill. These include a range of homes, cabins, and condos that welcome pets, making it easier to plan a trip with your companion.

Pet fees in Chatham Windmill vary by property and may include a nightly charge or a one-time fee. Rates for pet-friendly rentals typically start from around $519 per night, with additional fees depending on the host’s policy.

Some pet-friendly rentals in Chatham Windmill may have weight or breed restrictions, while others are more flexible. It’s recommended to review the property’s house rules or contact the host to confirm whether your pet is allowed.

Some pet-friendly rentals in Chatham Windmill include fenced or partially enclosed outdoor spaces, which can be helpful for pets. Checking the listing details can help you find properties that offer secure outdoor areas.

Pet-friendly properties can be in high demand, especially during peak travel seasons, so booking 90 to 120 days in advance is recommended for the best selection. Availability may be more flexible during off-peak periods.

Pet-friendly rentals in Chatham Windmill may include amenities such as Pet Friendly, Fireplace/Heating, and Internet. These features help make stays more comfortable for both pets and their owners.

You can use map-based search features to find rentals located near dog parks, walking trails, or pet-friendly outdoor areas. This can help you choose a location that is convenient for daily walks and outdoor activities with your pet.