Chatham & Orleans Properties rent Friday to Friday during Summer Months

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As summer draws ever closer to its natural conclusion, we at Pretty Picky Properties are already starting to feel more than a bit melancholy. Cape Cod is a beautiful place to live and play, no matter which season we are in, but summers are when it really comes alive. Soon the crowds will thin, the beaches will empty, and some summer-oriented businesses will close for the season and quite frankly, we aren’t ready for that to happen! Fortunately, there is still one last summer holiday, a weekend that attracts visitors in droves, as people from all over the country arrive at our shores ready for a long weekend (or more) of doing nothing they HAVE to do and everything they have always wanted to do! If your summer journey brings you to Cape Cod for a stay in our holiday hideaways and all the exciting adventures our cape home offers in the season, this guide to spending Labor Day 2023 on Cape Cod will help you fill every minute with fun, relaxation, and more fun! (Because you deserve a double dose of FUN!) 

Farmers Markets on Cape Cod 

There is something quintessentially summer about spending a couple of hours exploring the aisles of a Farmers Market and Cape Cod offers plenty of opportunities to do just that, many of which will be close to your holiday hideaway! The Orleans Farmers Market, located at 19 Old Colony Way and open from 8 am until noon on Saturdays, is known for its fresh produce and small-batch vendors that also provide some very excellent sunscreen for buyers! Although Labor Day is on a Monday (September 4th this year) chances are you will be here on Tuesday as well and the Chatham Farmers Market, located at Our Lady of Grace Catholic Church in Chatham, is open on Tuesdays from 3-6 and its selection of fresh produce, homemade baked goods, and arts and crafts is unparalleled!   

This Way to the Beach 

A Cape Cod vacation will always revolve around the beach and that includes your Labor Day escape to the Cape. Offering the peace of the sea, sandy beaches to bury your toes in, and on many of our beaches, charming lighthouses that can be explored or can be used as a backdrop to your family pictures, life at the beach is laidback, relaxing, and important to the success of your getaway! Many of you will rent some of our oceanfront homes, reluctant for the sea to be out of sight for more than a few moments at a time and as you walk along the shore’s edge at sunrise, lounge on colorful beach towels with earbuds playing your favorite tunes and the sun warming your soul you will know that THIS is what a holiday weekend should be all about.  

Labor Day Festival of the Arts, September 1- 3, Drummer Boy Park in Brewster 

Looking for something specifically Cape Cod to bring back to your plant waterer, dog sitter, or mail gatherer? Look no further than this fun festival, the Labor Day Festival of the Arts held in Brewster from 10 AM to 3 PM. We especially love the jewelry you will find, including necklaces with lobster charms, but we can assure you that everything you find will be something you won’t be able to live without! And if you do stick with the smaller jewelry items, you don’t have to worry about finding room in your overstuffed suitcase upon your return to real life! South Yarmouth is holding its own Labor Day Weekend Craft Festival on September 2 and 3 at John Simpkins Field, so you might want to plan on a little road trip if you really love artsy gifts that exemplify the Cape Cod vibe! 

At Home with Pretty Picky Properties 

The best moments of your Labor Day adventures may just be the ones spent in the Pretty Picky Properties home-sweet vacation home of your choice. Family pool parties are expected in our homes with private pools, offering more opportunities for relaxation and many are heated for your comfort. Barbecue grills will help feed the group and as the smell of fresh grilled seafood wafts through the air you may be surprised at just how quickly you become ravenously hungry. State-of-the-art televisions offers clear pictures that will make guests feel as if they are sitting on the sidelines of the MLB game being watched on Labor Day. All our homes will make you feel relaxed and spoiled, providing comfy furnishings, modern conveniences, and all the comforts of home and if you aren’t careful, you may find yourself looking into the possibilities of returning year after year after year on this same glorious holiday weekend! Contact us and reserve your favorite Cape Cod escape today and start a new Labor Day tradition! 

Air Conditioning (Central)
Air Conditioning (split units)
Hot Tub
Luxury Collection
Near Bike Trails
Pets Considered
Pickleball Court
Pool - heated
Private Beach Access
Rents Saturday to Saturday during peak weeks
Rents Friday to Friday during peak weeks
Tennis Court
Updated Interior
Updated Kitchen
Vehicle Charging Station
Walk to Beach
Walk to Fresh Water Lake
Walk to Town/Village
Water View
Workspace Available
NEW Listing for 2024
Rates Just Reduced 2024!

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