Chatham & Orleans Properties rent Friday to Friday during Summer Months

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Summer is when Cape Cod comes to life and if you are like thousands of other travelers you are in the process of making your way to our sandy shores for an all-American vacation adventure you never want to forget. The first step to a perfect vacation, is of course, choosing the perfect vacation home. Since you are on this page it already looks as if you have found the homes you will fall in love with, which are our Pretty Picky Properties havens! After you book the one that calls your name the loudest, it will be time to explore all the fun you can have on Cape Cod, starting with this list of upcoming events that will help fill all the seconds, minutes, and hours of your stay!  

Sandwich Farmers Market, Tuesdays from 10 AM until 1 PM, All Summer Long, 20 Main Street 

Every summer vacation deserves a visit to the local Farmers Market and the one in Sandwich is well known and loved across the Cape and the nation! You don’t even need to wake up early to enjoy the shopping experience, and as you walk through the aisles stopping by each vendor to explore fresh produce, handmade baked goods, even arts and crafty types of items that you just KNOW you have to have, you will feel the relaxation and satisfaction creep in, even as you get your step count elevated! 

11th Annual Brewster Summer Arts & Crafts Festival, July 29th & 30, Drummer Boy Park  

The joy of a summer day is enhanced with shopping opportunities, especially those that can be experienced outside under the summer sun and the 11th Annual Brewster Summer Arts & Crafts Festival will give you all the options to shop! Offering 100 booths of juried American crafts made from all art materials, there will also be specialty foods that can help stock the kitchen in your vacation escape, including dips, desserts, olive oils and more. Open from 10 AM to 5 PM on Saturday and 10 AM to 4 PM on Sunday. 

Taste of Chatham, July 31, Chase Park 

Every vacation revolves around relaxation, exploration, fun, and food and when you take part in the Taste of Chatham, it gives you a chance to do all three! Offering up a taste of summer in Chatham, this evening of tastings is presented by more than 20 of the best restaurants and bars in town and is held under a large tent in the center of Chase Park for the enjoyment of all who purchase tickets! Proceeds go towards Chatham’s Family Resource Center, Monomoy Community Services and the event begins at 6, lasting until 8:30. 

The Bayberry Quilt Show, August 2 through 4, 351 Pleasant Lake Avenue in Harwich 

Quilting is rapidly on its way to becoming an endangered art and when you catch your first glimpse of the colorful blankets on display in the Bayberry Quilt Show you are going to wish that you had the talent to take up the art! Americans have been keeping warm with blankets made of colorful bits of fabric for centuries and some of the best of our local quilter’s works will bring you joy. Open from noon to 7 on Wednesday, 9:30 to 4 on Thursday, and 9:30 to 3 on Friday, admission costs $12. 

Cape Cod Classic Car Show, August 31, Lobster & Chowder House in South Wellfleet 

The show is free, the cars are unbelievably stunning, and because you can also purchase food and beverage as you explore these fine examples of automotive history, the hours you spend at the Cape Cod Classic Car Show are destined to be the ones you remember best! Shiny, colorful, and painstakingly restored, the cars bring back memories of simpler times, days when the Sunday car ride was a family tradition, and seatbelts were not yet invented! The show starts at 4 and conveniently ends in time for dinner at 6, so be sure to bring your appetite! 

Labor Day Weekend, September 1-4, Anywhere on Cape Cod 

The sadness of saying so long to summer is tempered slightly with one last weekend of fun and carefree excitement. There is guaranteed to be something wonderful to enjoy this last official weekend of summer, no matter where you stay on the Cape, including the West Dennis Beach Party & Fireworks on September 3 at West Dennis Beach. This fireworks show can be seen from nearby beaches, including Smugglers Beach in South Yarmouth. Take a Wellfleet SPAT Shellfish Tour and discover how our delicious shellfish are grown and harvested, with the tours taking place on September 2nd, 5th, and 16th. Or maybe you will just stay home and enjoy the amenities of our Pretty Picky Properties holiday havens, enjoying a family barbecue, swimming in private pools and simply enjoying the last moments of summer in homes filled with luxury and style. Reserve your favorite today! 

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
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Rates Just Reduced 2024!

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