Stay in a Chatham Windmill! Beautiful Water View, Steps to Beach & Main Street

Chatham, Massachusetts
$504 avg/night Minimum Stay 1 Nights
Bed 1

Bed

Bath 1

Bath

Home Private Vacation Home

Property Type

Sleep 2

Max Sleeps

Night 1 nights

Min Stay

NEWLY RENOVATED CHATHAM WINDMILL for your special Cape Cod vacation experience!

Located overlooking Chatham's beautiful Oyster Pond, enjoy the opportunity to stay in this classic Chatham Windmill for a cozy and memorable vacation! This windmill retreat is the perfect location for your Chatham vacation. Take advantage of the beach just outside your door or wander down the street into Chatham center! Enjoy so much of Chatham - without even getting in your car!

This unique Windmill vacation rental has one bedroom with king sized bed on the second floor, with small full kitchen and dining area, two sitting/TV areas and a full bathroom on the first floor. The Windmill also has a private patio with BBQ grill, dining table and chairs. Enjoy the beautiful water view from Adirondack chairs, just outside your door.

Linens (bed and bath) are included. This property has two adjacent units (the Sea Captain's House and the Carriage House) that share the driveway and parking. If you are interested in booking these units as well, for a larger group, please inquire.

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • BEACH

    Beach Sun Loungers Beach Towels Near The Beach
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Not Reported (host Has Not Indicated Whether There Is A Carbon Monoxide Detector On The Property; Consider Bringing A Portable Detector) Smoke Detector Not Reported (host Has Not Indicated Whether There Is A Smoke Detector On The Property)
  • BEDROOM

    1 Bedroom Bed Sheets Provided
  • KITCHEN

    Coffee/tea Maker Dishwasher Electric Kettle Lobster/crab Pot Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Near Laundromat Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Barbecue Grill Garden Patio
  • BATHROOMS

    1 Bathroom Bathtub Or Shower Towels Provided
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Cycling Nearby Fishing Nearby Golf Nearby Marina Nearby Power Boating Nearby Swimming Nearby Water Skiing Nearby Whale Watching Nearby Windsurfing Nearby
  • ENTERTAINMENT

    Foosball Table Table Tennis Smart TV With Cable/satellite Service
  • CLIMATE CONTROL

    Air Conditioning Heating
  • LOCATION HIGHLIGHTS

    In A Village In The City Center Near A Health Or Beauty Spa Near The Bay On The Waterfront
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 2

Map Map

School District Rates & Availability

Review Review

  • Meghan K.

    Submitted Sep 13, 2025

    Stayed Aug 24, 2025

    The windmill was beautiful, surprisingly spacious, and conveniently located! Clearly renovated and decorated with care, with a great view of oyster pond. We loved being just a short walk into town. Check in and out check was easy and the hosts were easy to communicate with.

  • Anthony A.

    Submitted Sep 12, 2025

    Stayed Sep 5, 2025

    It truly is a very short walk to downtown.the only challenge we had where the steep stairs to the bedroom. The windmill was well furnished and very clean and we enjoyed staying there and hope to return in the future.

  • Lindsey H.

    Submitted Nov 25, 2024

    Stayed Nov 22, 2024

    My husband and I stayed here for a little birthday getaway and it was just perfect. The place is extremely clean and tidy and it was really convenient to have clean towels provided and the bed already made. There were lots of little thoughtful amenities provided as well such as mini shampoos and conditioners. The view is beautiful and we really enjoyed how close of a walk it was to all the restaurants and stores on Main Street. We are looking forward to booking again soon!!

  • AMY G.

    Submitted Oct 31, 2024

    Stayed Oct 16, 2024

    This Chatham windmill is fun. Small, perfect for 2! The stairs to the bedroom are very steep!

  • Anna P.

    Submitted Aug 27, 2024

    Stayed Jul 8, 2024

    My husband and I stayed here on our honeymoon for a week and it was perfect! The house is small, but if there’s only 2 people then it’s not an issue. The stairs are very steep so our luggage stayed in the living room, but even then it was still enough room. The location is the best part! Gorgeous views of the water, and walkable to downtown (we walked to shops, dinner, and ice cream every day). Hosts were friendly and accommodating to work with.

  • Dorothy I.

    Submitted Jul 3, 2024

    Stayed Jun 27, 2024

    What a wonderful spot for 2 people! Walking distance to town! Lovely furnishings and well appointed kitchen! The views from the lawn are lovely! Steps to the bedroom are a bit steep but manageable. We would definitely stay again!

  • Kristen D.

    Submitted Nov 13, 2023

    Stayed Nov 9, 2023

    A once in a lifetime opportunity for a real Cape Cod experience. The windmill cottage provides a clean, hospitable and simple environment with incredible views! Hosts were welcoming and interested in providing a perfect stay. Comfortable bed, easy TV to navigate, clean, with everything you might need. Great location to town and activities. Thank you for an incredible stay.

  • Submitted Oct 23, 2023

    Stayed Oct 19, 2023

    What a wonderful place and location! This property has everything you need to enjoy a lovely stay in the Chatham, MA area. We love the sleepy, quiet neighborhood. Very classy. Absolutely beautiful surroundings, withing easy walking distance to the shore and downtown restaurants and shops, we couldn't think of a better location! You have thought of everything. It was meticulous. We also appreciate the friendly communication. We will absolutely book here again. Thank you!

  • Jürgen W.

    Submitted Sep 22, 2023

    Stayed Sep 17, 2023

    We had a wonderful 5-night-stay at this beautiful property. The Windmill is perfect furnished, extremly clean. The kitchen is very well equipped, the bed is very comfortable and the outside area with a view of the water is also very nice. Chatham is a good starting point to explore Cape Cod.

  • Gareth M.

    Submitted Aug 17, 2023

    Stayed Jul 29, 2023

    Unique and very nice, clean, well maintained property in a tremendous location for Chatham and with a beautiful view over Oyster Pond. The property is ideal for a couple, is comfortable and quiet and has everything you would need for a comfortable vacation stay. The stairs to the second floor are a little steep but otherwise this was an ideal location,

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Total

Includes taxes and fees
$504+
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