The town of Eastham on Cape Cod is known for its long and rich history including the fun fact that it is home to First Encounter Beach, the spot where pilgrims met Native Americans, and it is also home to the oldest working windmill, an attraction that is celebrated with an entire weekend of fun in September. And because Pretty Picky Properties offers vacation escapes all we offer in our Eastham retreats. This guide to the Eastham Windmill Weekend and our wonderful Eastham, MA rentals will offer up an exciting example of what you can expect during your Massachusetts journey in September.
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Eastham Windmill Weekend
Held the first weekend after Labor Day, the Eastham Windmill Weekend has been a local tradition for nearly 50 years, offering fun activities, delicious food, and of course, a chance to see the windmill in person. This weekend celebrates the famous traveling Eastham Windmill, which was constructed in 1680 in Plymouth, moved to Truro in 1770, and then moved again to its present location in 1793. It is believed that this windmill is the oldest and last working gristmill on Cape Cod, attracting visitors from all over the world and as you shop the arts and crafts stalls that line the Windmill Green, participate in or simply cheer on the performers in the talent show, and watch the parade that runs along Route 6 starting at Old Orchard Road and ending at Windmill Green, you may think there isn’t much more they could offer in just three days, and you would be so very wrong! Also offering a road race, a classic car show, sand art contest, delicious food trucks, live entertainment and a raffle you can enter, perhaps winning one of the 70 prices donated by local businesses, by day’s end you will be more than ready to come home to our Pretty Picky Properties Eastham escapes!
Close to the Celebration
You could choose to stay pretty much anywhere on Cape Cod (our properties are spread out all over the area!) but as we mentioned above, with all the activities being offered during Windmill Weekend, you are going to want to be staying somewhere close. Our Eastham, MA rentals range from cozy 2-bedroom cottages that rest just steps away from the beach to spacious and welcoming 4-bedroom retreats that also rest just steps away from the beach and although not all of our Eastham Windmill Weekend homes are this close to the water, most are within a short distance, ensuring you will never be far from the serenity of the sea.
Play Hard, Relax Harder
Real life is way too busy and hard and your vacation is supposed to counteract all that chaos and hectic activities and of course, our Pretty Picky Properties are designed to do just that. If you choose a beachfront escape, other than when you are sleeping you won’t spend a lot of time inside, but that doesn’t mean we skimp on the amenities.
Every Eastham retreat is chock full of luxuries enabling guests to play hard and then relax even harder, perhaps feeling reluctant to leave the boundaries of your rental. Lobster pots, blenders, and wine refrigerators may be found in our fully equipped kitchens, beach gear, kayaks, or paddleboards may be discovered tucked away in a closet or garage, and video games, gaming tables, and state of the art televisions may be spread throughout each space. More is more in these elevated escapes, offering guests the opportunity to play, relax, and enjoy a life of leisure, adding that extra sparkle to a getaway that already shines bright.
Hidden Depths
There is a lot of sparkle in our Eastham, MA rentals, but beneath the sparkle you will find hidden depths that truly show how well we know our guests. Most of our weekly rentals in Cape Cod can only be rented for a minimum of a week at a time during peak season and not all travelers are able to take that much time off. Our high-speed internet and cozy desk areas, however, ensure that everyone has the opportunity to relax with us, even if they are forced to work from our home as they do.
Laundry rooms or closets in which stackable washer and dryers are tucked away enable travelers to pack light and save room for the souvenirs they will surely be purchasing. And outdoor showers offer an otherworldly showering experience, while also helping keep the sand outside where it belongs. If you think we are as close to perfect as can be, we urge you to look a little deeper and discover all the reasons we are even better than you first thought!
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When you’re pretty picky about the Eastham vacation rentals you choose to rent, only Pretty Picky Properties will do!