Once Labor Day weekend is over, life in Chatham begins to quiet down, but as much as we love the gentler vibe, we sure do appreciate the last of summer shenanigans that may occur over the holiday. Shops offer fantastic sales, restaurants bring their best to the table, and our Pretty Picky Properties holiday hideaways offer a happy and restful experience that will bring joy. This guide to our Chatham rentals in Massachusetts for Labor Day, along with a peek into the fun you can have over the holiday, will help you start planning your weekend trip of a lifetime.
Book our Chatham Rentals in Massachusetts Below
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Why Chatham Is a Top Choice for Labor Day Weekend on Cape Cod
There are many reasons you may want to choose our Cape Cod town for your Chatham rental property. Our beautiful beaches, the renowned Chatham lighthouse, and even the traditions that accompany this end-of-season holiday are just a few examples.
There are 9 public beaches in our small Cape Cod town, but the most popular is Chatham Lighthouse Beach, allowing visitors to enjoy a fantastic beach day and the beauty of the lighthouse. The weather will still be warm in the daytime, the sun will still be shining, and all the restaurants, even the seasonal ones, will still be open. The Beach House Grill on Shore Road is one of our favorite end-of-summer traditions, offering a sumptuous, elevated seafood menu and a patio with unobstructed views of the sea. September is the start of oyster season, so be sure to order some while you’re here.
Beach Homes and Cottages Available for Labor Day Weekend
Our Chatham rental properties will be an integral part of your vacation experience. Nearly every traveler has dreamed about staying in a beach-view cottage with weather-beaten shingles, sitting on the edge of the sand. They imagine sitting on porches, protected from the elements, watching the storms blow in, the sun setting over the horizon, and all the fun holiday revelers can enjoy while splashing in the surf. And because not all traveling parties are small ones, others dream about luxury beach homes, chock full of elevated amenities and all the ways to relax and be spoiled.
Amenities That Make Labor Day Stays More Comfortable
Our Chatham rentals in Massachusetts offer many amenities to make your stay perfect. Many holiday travelers visit with their families and seek family-friendly rentals, and while one person may feel a hot tub and an outdoor firepit are the most comfortable extras, another may need an indoor gas fireplace and a couch so plush they sink into it whenever they sit to relax. Many of our Labor Day retreats offer these amenities and more. Spacious showers and deep tubs for soaking your troubles away in the bathroom, and outdoor showers for washing off the sand from the beach. King-sized beds with high thread count linens, game rooms with arcade and pool tables, and even cozy libraries with more plush seating options. Every comfy amenity you can imagine, you will find in our Chatham holiday rentals.
Things to Do Around Chatham During Labor Day Weekend
From beach days to free concerts and craft fairs to fresh oysters, Labor Day weekend offers plenty of activities. Kate Gould Park is where much of the action happens, including:
- Art in the Park – Mid-June through mid-September – Your walk in the park will have a creative twist to it as you walk amongst exhibits of sharks and whales, all painted by local artists. Love one of the pieces? They are auctioned off at the end of summer with proceeds going to local charities.
- Chatham Band Friday Night Concerts – Labor Day weekend is the last free concert of the year, with music being performed by a group of musicians in uniforms. Marching music, folk dances, and even community sing-alongs celebrate the season with joy. Music starts at 8, bring lawn chairs or blankets for comfort.
- The Annual Labor Day Weekend Craft Festival is held in Brewster, just 10 miles outside of Chatham. Drummer Boy Park is the site of this festival that lasts the entire 3 days. Known as the “biggest little show on Cape Cod,” it features the best works of local artisans and craft vendors.
Book One of Our Chatham Labor Day Rentals Today
Every one of our Chatham rental properties is sure to offer that something special that makes you feel comfortable and at home. Contact us to reserve your favorite holiday hideaway today!