Short-Term Rentals in Chatham Windmill, MA: Compare 10+ Sites & Save

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879 Best Short-Term Rentals in Chatham Windmill (Starting from $201)

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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Classic Waterfront Chatham Estate
Classic Waterfront Chatham Estate
House
Chatham, MA, 02633-2250, United States
0.2k from Chatham Windmill center

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

5 Bedrooms10 Guests
New to Booking
$978
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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Gorgeous panoramic views of Mill Pond and just a short walk to downtown Chatham!
Gorgeous panoramic views of Mill Pond and just a short walk to downtown Chatham!
House
Chatham, MA, 02633, United States
0.2k from Chatham Windmill center

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

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$861
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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Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
House
Chatham, MA, 02633, United States
0.2k from Chatham Windmill center

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

2 Bedrooms5 Guests
10.0

Exceptional

117 reviews

$488
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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Vacation in downtown Chatham close to Lighthouse Beach
Vacation in downtown Chatham close to Lighthouse Beach
House
Chatham, MA, 02633, United States
0.2k from Chatham Windmill center

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

6 Bedrooms11 Guests
10.0

Exceptional

1 reviews

$1440
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 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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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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Four Bedroom - Short Distance to Downtown Chatham --  2/10's mile to Oyster Pond Beach Area
Four Bedroom - Short Distance to Downtown Chatham -- 2/10's mile to Oyster Pond Beach Area
House
Chatham, MA, 02633-2218, United States
0.2k from Chatham Windmill center

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

4 Bedrooms7 Guests
10.0

Exceptional

2 reviews

$1083
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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4-bedroom house in charming Chatham steps from Main Street and the Mill Pond
4-bedroom house in charming Chatham steps from Main Street and the Mill Pond
House
Chatham, MA, 02633, United States
0.3k from Chatham Windmill center

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

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$801
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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Enjoy beautiful water views right in downtown Chatham!
Enjoy beautiful water views right in downtown Chatham!
House
Chatham, MA, 02633, United States
0.3k from Chatham Windmill center

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

3 Bedrooms6 Guests
New to Booking
$1825
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 Village - Adorable Studio Apartment in Antique Home
Chatham Village - Adorable Studio Apartment in Antique Home
Apartment
Chatham, MA, 02633, United States
0.3k from Chatham Windmill center

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

1 Bedroom2 Guests
9.4

Superb

87 reviews

$201
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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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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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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Chatham Village:  Lovely 1-Bedroom Apartment in Antique Home
Chatham Village: Lovely 1-Bedroom Apartment in Antique Home
Apartment
Chatham, MA, 02633, United States
0.3k from Chatham Windmill center

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

1 Bedroom2 Guests
9.8

Exceptional

109 reviews

$243
Average price / night
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Chatham Village - Lovely 2 bedroom apartment in the antique home
Chatham Village - Lovely 2 bedroom apartment in the antique home
Apartment
Chatham, MA, 02633, United States
0.3k from Chatham Windmill center

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

2 Bedrooms4 Guests
9.8

Exceptional

72 reviews

$415
Average price / night
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Chatham Village:  Large, Newly-Renovated 1 Bedroom Apartment in Antique Home
Chatham Village: Large, Newly-Renovated 1 Bedroom Apartment in Antique Home
Apartment
Chatham, MA, 02633, United States
0.3k from Chatham Windmill center

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

1 Bedroom2 Guests
9.4

Superb

66 reviews

$283
Average price / night
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Steps to Chatham's Historic Downtown
Steps to Chatham's Historic Downtown
Condo
Chatham, MA, 02633, United States
0.4k from Chatham Windmill center

AC, Balcony, Dryer, Free Parking, Internet, Kitchen, Laundry, No Smoking, TV

2 Bedrooms4 Guests
New to Booking
$594
Average price / night
Check Availability
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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Charming Downtown Chatham
Charming Downtown Chatham
Condo
Chatham, MA, 02633, United States
0.4k from Chatham Windmill center

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

2 Bedrooms4 Guests
10.0

Exceptional

42 reviews

$365
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 Short-Term Rentals in Chatham Windmill.

Chatham Windmill Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 879 verified short-term rentals in Chatham Windmill, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Chatham Windmill vary depending on location, property size, and travel dates. Rates typically start from around $201 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Chatham Windmill include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Chatham Windmill, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Chatham Windmill often include amenities such as Fireplace/Heating, Internet, and Laundry, providing a comfortable and convenient stay.

Short-term rentals in Chatham Windmill are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.