The Windmill Cottage NEW! Windmill Cottage! Walk to Beach & Town!!

  • Unique and rich in character and charm, this recently restored vintage and historic windmill has two bedrooms, a kitchen, combined living and dining room and a full bath.
    Unique and rich in character and charm, this recently restored vintage and historic windmill has two bedrooms, a kitchen, combined living and dining room and a full bath.
  • Private entrance and a high privacy hedge separates the Windmill from the 2 other rental units in the compound.
    Private entrance and a high privacy hedge separates the Windmill from the 2 other rental units in the compound.
  • Warm and inviting private entrance with a mahogany screen door designed with the windmill motif. No mistaking this famous building!
    Warm and inviting private entrance with a mahogany screen door designed with the windmill motif. No mistaking this famous building!
  • Front and side yards are fully fenced and a gate with an arbor separate the compound from the rear parking lot. Professionally landscaped with in ground irrigation and flowering shrubs and trees throughout the property.
    Front and side yards are fully fenced and a gate with an arbor separate the compound from the rear parking lot. Professionally landscaped with in ground irrigation and flowering shrubs and trees throughout the property.
  • Outdoor table for four with an umbrella located on a round paver patio in the front yard. Bluestone walkway connects the Windmill to the main yard walkway and also connects the Windmill Cottage to it's own private outdoor shower.
    Outdoor table for four with an umbrella located on a round paver patio in the front yard. Bluestone walkway connects the Windmill to the main yard walkway and also connects the Windmill Cottage to it's own private outdoor shower.
  • The roof is capped with an original boating oar as the buildings primary weathervane and reflects a rich maritime history of this area. The compound was designed and built by a well known naval architect that called the compound home for many years.
    The roof is capped with an original boating oar as the buildings primary weathervane and reflects a rich maritime history of this area. The compound was designed and built by a well known naval architect that called the compound home for many years.
  • Side view of Windmill Cottage with 1st floor master bedroom and first floor bathroom off the rear of the main windmill building.
    Side view of Windmill Cottage with 1st floor master bedroom and first floor bathroom off the rear of the main windmill building.
  • Classic Cape Cod style quarterboard although there is no mistaking which building is the Windmill Cottage!
    Classic Cape Cod style quarterboard although there is no mistaking which building is the Windmill Cottage!
  • The octogonal shape of the original windmill allow for an incline of the sidewalls from the first floor to the second supporting a classic and steep red cedar round roof.
    The octogonal shape of the original windmill allow for an incline of the sidewalls from the first floor to the second supporting a classic and steep red cedar round roof.
  • Fairy Tale Setting! Live in your very own Windmill !!!
    Fairy Tale Setting! Live in your very own Windmill !!!
  • The large windsails are fully operable but remain tied down and secured to eliminate noise and ensure guest comfort and safety.
    The large windsails are fully operable but remain tied down and secured to eliminate noise and ensure guest comfort and safety.
  • The Windmill Cottage is part of the Mill Pond Cottage compound with easy access to Stage Harbor and Nantucket Sound. The Windmill Cottage is one of three signature units and is a historically significant property in Chatham's Old Village District.
    The Windmill Cottage is part of the Mill Pond Cottage compound with easy access to Stage Harbor and Nantucket Sound. The Windmill Cottage is one of three signature units and is a historically significant property in Chatham's Old Village District.
  • Rear view of the Windmill Cottage building reflecting the addition in the rear that include the kitchenette, master bedroom and bathroom.
    Rear view of the Windmill Cottage building reflecting the addition in the rear that include the kitchenette, master bedroom and bathroom.
  • Front entry steps into a warm and inviting combined living and dining room which sit in the octogonal main building. Large windows open up into the front of the building facing the patio.
    Front entry steps into a warm and inviting combined living and dining room which sit in the octogonal main building. Large windows open up into the front of the building facing the patio.
  • Kitchenette, 1st floor bedroom and bathroom extend to the rear of the original main Windmill building.
    Kitchenette, 1st floor bedroom and bathroom extend to the rear of the original main Windmill building.
  • Comfortable seating in the combined living and dining room which sit within the original octagonal windmill building.
    Comfortable seating in the combined living and dining room which sit within the original octagonal windmill building.
  • First floor entry into the combined living and dining area through your private front yard entrance.
    First floor entry into the combined living and dining area through your private front yard entrance.
  • Smart flat panel HDTV located in the living room with WiFi throughout the cottage and extending to the front patio area. Family board games, puzzles and playing cards available in the living room cabinet.
    Smart flat panel HDTV located in the living room with WiFi throughout the cottage and extending to the front patio area. Family board games, puzzles and playing cards available in the living room cabinet.
  • Large exposed beams reflect the rich character and design of the Windmill with cross buck walls that surround the living and dining room areas.
    Large exposed beams reflect the rich character and design of the Windmill with cross buck walls that surround the living and dining room areas.
  • Dropleaf dining table with seating for four. Kitchen is fully stocked with indoor and outdoor dish and glassware to accommodate your dining plans.
    Dropleaf dining table with seating for four. Kitchen is fully stocked with indoor and outdoor dish and glassware to accommodate your dining plans.
  • Kitchenette is fully stocked with cookware, dishware, glassware, utensils, countertop appliances, spices, etc... Retro refrigerator/freezer with ice maker and a 4 burner gas stove. Both a Keurig and a traditional drip coffee maker are available.
    Kitchenette is fully stocked with cookware, dishware, glassware, utensils, countertop appliances, spices, etc... Retro refrigerator/freezer with ice maker and a 4 burner gas stove. Both a Keurig and a traditional drip coffee maker are available.
  • Queen size bed in 1st floor bedroom. Nightstand equipped with convenient power strip with USB ports and standard outlets for charging your devices.
    Queen size bed in 1st floor bedroom. Nightstand equipped with convenient power strip with USB ports and standard outlets for charging your devices.
  • Built-in shelving, dresser drawers and clothes closet in 1st floor bedroom.
    Built-in shelving, dresser drawers and clothes closet in 1st floor bedroom.
  • 1st floor bathroom adjacent to 1st floor bedroom with a walk-in stall shower and a nautically inspired bath vanity.
    1st floor bathroom adjacent to 1st floor bedroom with a walk-in stall shower and a nautically inspired bath vanity.
  • Stairwell to the second floor bedroom loft is rather steep and follows the contour of the angled exterior wall as it tapers in towards the roof. Trap door at the top can close the stairwell to allow for privacy in the 2nd floor bedroom.
    Stairwell to the second floor bedroom loft is rather steep and follows the contour of the angled exterior wall as it tapers in towards the roof. Trap door at the top can close the stairwell to allow for privacy in the 2nd floor bedroom.
  • Full size bed in second floor loft bedroom.
    Full size bed in second floor loft bedroom.
  • 2nd floor bedroom loft includes a writing desk overlooking the front yard and Windmill patio as well as peeks of Mill Pond to the right.
    2nd floor bedroom loft includes a writing desk overlooking the front yard and Windmill patio as well as peeks of Mill Pond to the right.
  • Loft bedroom ceiling with exposed Windmill gearshaft that turns exterior wind sails. Don't worry, it's locked during your stay so there is no noise to disturb your sleep!
    Loft bedroom ceiling with exposed Windmill gearshaft that turns exterior wind sails. Don't worry, it's locked during your stay so there is no noise to disturb your sleep!
  • The second floor loft bedroom is open to the ceiling which encompasses the sophisticated engineering of the gears and crankshaft that turn the exterior wind sails.
    The second floor loft bedroom is open to the ceiling which encompasses the sophisticated engineering of the gears and crankshaft that turn the exterior wind sails.
  • Lovely professionally landscaped yard and gardens make this a wonderful retreat for your morning coffee or an afternoon of reading a beach novel. Weber gas grill is located near the patio along the side stockade fence.
    Lovely professionally landscaped yard and gardens make this a wonderful retreat for your morning coffee or an afternoon of reading a beach novel. Weber gas grill is located near the patio along the side stockade fence.
  • Private outdoor shower is located to the rear of the patio and side of the Windmill.
    Private outdoor shower is located to the rear of the patio and side of the Windmill.
  • Roomy and private outdoor cedar shower is located around the side of the windmill off of the front patio.
    Roomy and private outdoor cedar shower is located around the side of the windmill off of the front patio.
  • Privacy shutters in the outdoor shower permit you to shutter the kitchen window from the outside.
    Privacy shutters in the outdoor shower permit you to shutter the kitchen window from the outside.
  • Skip to content  Start your search Switch to hosting    Old Village-Windmill Cottage/Walk to Beach & Town! 󰀄 5.0(7) · 󰀃 Superhost · Chatham, Massachusetts, United States  Share  Saved      Show all photos Entire cottage hosted by Edward 4 guests · 2 bedr
    Skip to content Start your search Switch to hosting Old Village-Windmill Cottage/Walk to Beach & Town! 󰀄 5.0(7) · 󰀃 Superhost · Chatham, Massachusetts, United States Share Saved Show all photos Entire cottage hosted by Edward 4 guests · 2 bedr
  • Rear yard entry to the professionally landscaped and maintained compound
    Rear yard entry to the professionally landscaped and maintained compound
  • Gorgeous blossoming trees in the spring with colorful perennials and annuals throughout the yard
    Gorgeous blossoming trees in the spring with colorful perennials and annuals throughout the yard
  • Launch your kayaks or paddle boards from our private launch or arrange for a mooring or dockspace with our neighboring boatworks
    Launch your kayaks or paddle boards from our private launch or arrange for a mooring or dockspace with our neighboring boatworks
  • Private boat launch and dock space on Mill Pond available through First Light Boatworks
    Private boat launch and dock space on Mill Pond available through First Light Boatworks
  • Incredible sunsets over Mill Pond visible from property and our private resident boat launch.
    Incredible sunsets over Mill Pond visible from property and our private resident boat launch.
  • Breathtaking sunsets on Mill Pond & Evening Stars are endlessly visible at night.
    Breathtaking sunsets on Mill Pond & Evening Stars are endlessly visible at night.
  • Private launch on Mill Pond. Great clamming right from our backyard!
    Private launch on Mill Pond. Great clamming right from our backyard!
  • Mill Pond looking to shore at the Mill Pond Cottage Compound and First Light Boatworks
    Mill Pond looking to shore at the Mill Pond Cottage Compound and First Light Boatworks
$149-390/night
2 Bedrooms • 1 Bathroom • Sleeps 2-4
Allows pets Internet Near Ocean Downtown (more...)

Enjoy your vacation in this classic, historic property in Chatham's Old Village neighborhood. Short walk to town and beach as well as the Chatham Lighthouse from this incredibly charming cottage. Fully restored and updated. This classic property was designed and built by a famous naval architect and exhibits the rich, maritime style he was known for. The Windmill Cottage was relocated and rebuilt on this site back in the 1940's and remains one of Chatham's crown jewels in the Old Village!

The Windmill Cottage is rich in history and exudes character and charm with many of it's custom made built-ins and unique, nautically inspired features. You will be in awe as you enter the main windmill building and see the incredible craftsmanship with it's large exposed beams and cross buck exterior walls. The warmth and nostalgia of being in this cottage harkens back to a fairy tale setting you read when you were a child. This cottage has a first floor bedroom with a queen bed and second floor loft with a double bed and can accommodate to four people. The stairs to the loft are rather steep and follow the contour of the slanted walls. Once in the loft you will be amazed at the intricate mechanical's of the widshaft and gears that turn with the exterior wind sails. A truly remarkable property that will provide you an equally remarkable vacation experience that you will remember for a lifetime.

The Windmill has it's own patio, gas grill and outdoor shower. This area is separated by a privacy hedge that opens up into a common yard area where you will find a boathouse with beach chairs, beach umbrella's, coolers and children's beach toys for your personal use. The Windmill Cottage has a dedicated parking space along the fence in the rear yard. Park your vehicle and enjoy a short walk to town or the beach and avoid the hassle of parking in the downtown area as you are already there!

We are a small, family owned boutique hospitality business and own 5 rental properties with the downtown area of Chatham. We are focused on the comfort and enjoyment of our guests where you can be assured of a unique, yet traditional Old Cape Cod vacation experience. Our properties are historic and have been restored to retain their rich character, while ensuring they are upgraded to ensure your safety and comfort with special emphasis on the amenities and furnishings you would expect in your own home. These are not second homes for our family but are intended to serve our guests as their own vacation home without the clutter or personal items of the owner. Come RELAX, REFLECT & RESTORE in one of our signature Chatham vacation properties.

SPECIAL COVD19 MESSAGE TO OUR GUESTS

As a business within the hospitality industry, we have always been highly focused on hosting our guests in impeccably clean and safe surroundings and it is one of the frequent comments you will see in many of our past reviews. However, in the era of COVID19, we remain concerned about the safety of our guests, our staff and ourselves and the potential "unseen" implications of the virus. We have therefore adopted additional steps and are using new disinfectants so that we go beyond the current CDC recommended cleaning protocols.

We use a dedicated housekeeping team that manages the cleaning, sanitizing and disinfecting of all our properties. This season we are also using a special solution that is listed by the CDC as a germicide known to kill certain live bacteria and viruses including COVID19.

In addition to our normal cleaning regimen we are now using this disinfectant on all countertops, faucet and plumbing fixtures, kitchen appliance knobs and handles, countertop appliance switches, cabinet knobs and drawer handles, wall thermostats, interior and exterior door handles, handrails, all light switches, TV remote controls, dresser knobs, window latches and handles, pull down window shades, table and floor lamp switches outdoor grill knobs and handles, patio umbrella cranks, etc...

While this adds considerable time to each of our cleaning periods, we have added an additional custodian who is simply focused on these specific cleaning activities. Our cleaning crew is required to complete a checklist and as each task is completed, they check the items off and then formally sign off on the housekeeping checklist before leaving the property.

Essentially, we are cleaning our property with the same intensity as if we ourselves were about to move in. Prior to new guests checking into our property, all bedspreads, blankets, pillow covers, shams, mattress pads and dish towels are replaced with freshly laundered ones. Our guests remain responsible for providing their own personal bed sheets as well as their own bath and beach towels. You may bring your own or use one of the many linen service companies available in the area. We would be happy to refer to you one if you so choose.

Lastly, we ask that our guests remove their shoes when entering the property to help reduce the likelihood of introducing contaminants into the home. We are also requesting that guests not permit visitors inside the property if they are not staying with you as part of your reservation. Our guests are certainly always welcome to entertain visitors in the yard and other common areas on the outside of the home while practicing social distance guidelines as recommended by the CDC and the State of MA Department of Health.

We remain vigilant in ensuring the safety and comfort for all our guests and want our patrons to have confidence in their surroundings and in choosing us. We pride ourselves on the longstanding following we have with many families that stay with us year after year and we are intent on ensuring that they and future guests have continued confidence in us and the value they receive when staying at any of our properties.

We thank you in advance for the opportunity to possibly host you in the future and are happy to answer any other questions you might have.

Be well and stay safe.

Sincerely,

Chatham Village Vacation Properties, LLC

Roomy and private outdoor cedar shower.
Property Type Cottage
House Rules
  • Maximum occupancy: 4
  • Children welcome
  • Infants welcome
  • Pets considered
  • Smoking not allowed
  • Wheelchair inaccessible
  • Minimum age of primary renter: 26
  • Long term rental allowed
Setting & View
  • Beach
  • Downtown
  • Near Ocean
  • Town
  • Village
General
  • Internet
  • Air Conditioning
  • Central Heating
  • Hot Water
  • Private Living Room
  • Hair Dryer
  • Iron & Board
  • Wifi
  • Laptop Friendly Workspace
  • Basic Soaps
  • Paper Towels
  • Shampoo
  • Toilet Paper
  • Hangers
  • Private Entrance
  • Extra Pillows & Blankets
Kitchen
  • Kitchen
  • Refrigerator
  • Stove
  • Oven
  • Microwave
  • Dishes & Utensils
  • Spices/Pantry Items
  • Coffee Maker
  • Toaster
  • Ice Maker
  • Freezer
  • Blender
  • Kettle
  • Lobster Pot
  • Kitchenette
  • Pots & Pans
Bathrooms 1 Bathroom
  • 1st Floor Bathroom – Outdoor Shower, Shower, Toilet
1st floor bathroom with walk-in shower
Bedrooms 2 Bedrooms, sleeps 2-4
  • Bedroom 1 – 1 Queen bed
  • Bedroom 2 – 1 Double bed
Double bed in unique 2nd floor loft with exposed beams and windmill sail gear shaft and mechanical's.
Entertainment
  • Television
  • Satellite/Cable
  • Stereo
  • Games
  • Books
Family
  • Baby Gate
  • Pack N Play/Travel Crib
Outdoor
  • Outdoor Grill
  • Deck/Patio (uncovered)
  • Lawn/Garden
  • Water Sports Gear
  • Beach Essentials
Vehicles
  • Free Parking
  • Street Parking
  • Free Parking On Premises
Theme
  • Adventure
  • Family
  • Historic
  • Romantic
  • Tourist Attractions
Attractions
  • Bay/Sound
  • Coin Laundry
  • Health/Beauty Spa
  • Marina
  • Museums
  • Winery Tours
Leisure
  • Antiquing
  • Bird Watching
  • Eco Tourism
  • Horseback Riding
  • Outlet Shopping
  • Paddle Boating
  • Whale Watching
  • Boating
  • Shopping
  • Wildlife Viewing
  • Water Sports
Sports & Adventure
  • Basketball Court
  • Cycling
  • Deepsea Fishing
  • Fishing
  • Bay/Sound Fishing
  • Fly Fishing
  • Freshwater Fishing
  • Surf Fishing
  • Golf
  • Hiking
  • Kayaking
  • Parasailing
  • Pier Fishing
  • Sailing
  • Scuba Diving/Snorkeling
  • Snorkeling
  • Snorkeling/Diving
  • Spelunking
  • Surfing
  • Swimming
  • Wind Surfing
Safety
  • Carbon Monoxide Detector
  • Deadbolt Lock
  • Fire Extinguisher
  • First Aid Kit
  • Exterior Lighting
  • Smoke Detector
Expectations
  • Requires Stairs
Season Rate
SUMMER PEAK SEASON
Jun 19, 2021 - Sep 11, 2021
Weekly
$2,450
AUTUMN PEAK SEASON
Sep 12, 2021 - Oct 16, 2021
Night
$249
Weekend Night
$299
Weekly
$1,893
LATE AUTUMN SEASON
Oct 17, 2021 - Nov 23, 2021
Night
$199
Weekend Night
$249
Weekly
$1,389
Monthly
$5,003
THANKSGIVING HOLIDAY
Nov 24, 2021 - Nov 27, 2021
Night
$299
Weekend Night
$299
EARLY WINTER
Nov 28, 2021 - Dec 20, 2021
Night
$199
Weekend Night
$249
Weekly
$1,389
HOLIDAY SEASON
Dec 21, 2021 - Jan 1, 2022
Night
$249
Weekend Night
$299
Weekly
$1,893
WINTER SEASON 2022
Jan 2, 2022 - Mar 31, 2022
Night
$149
Weekend Night
$199
Weekly
$1,074
Monthly
$3,878
SPRING SEASON 2022
Apr 1, 2022 - May 14, 2022
Night
$199
Weekend Night
$249
Weekly
$1,389
Monthly
$5,003
SPRING PEAK SEASON 2022
May 15, 2022 - Jun 10, 2022
Night
$300
Weekend Night
$350
Weekly
$2,250
SUMMER PEAK SEASON 2022
Jun 11, 2022 - Sep 17, 2022
Weekly
$2,730
AUTUMN PEAK SEASON 2022
Sep 18, 2022 - Oct 15, 2022
Night
$300
Weekend Night
$350
Weekly
$2,250
LATE AUTUMN SEASON 2022
Oct 16, 2022 - Nov 22, 2022
Night
$149
Weekend Night
$199
Weekly
$1,074
Monthly
$3,878
THANKSGIVING HOLIDAY 2022
Nov 23, 2022 - Nov 26, 2022
Night
$300
Weekend Night
$300
EARLY WINTER 2022
Nov 27, 2022 - Dec 22, 2022
Night
$199
Weekend Night
$249
Weekly
$1,389
HOLIDAY SEASON 2022
Dec 23, 2022 - Jan 1, 2023
Night
$300
Weekend Night
$350
Weekly
$2,250

Cancellation Policy: Guest receives 100 % if cancellation occurs at least 30 days before arrival; Guest receives 50 % if cancellation occurs at least 14 days before arrival; No refunds within 14 days of arrival.