Chatham & Orleans Properties rent Friday to Friday in 2023

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Property Walkthrough: Better Together


We at Pretty Picky Properties have learned a few things over the years we have been in the vacation rental business on Cape Cod. We have learned what colors make people feel comfortable, we have discovered the best spots to eat lobster, and we have learned that some things work best because they are better together! Better Together also just happens to be the name of one of our more...

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Property Walkthrough: Cummaquid Retreat: 334-Ba


You will have lots of opportunities for luxury and fun when you choose Pretty Picky Properties’ Cummaquid Retreat 334-Ba for your vacation sanctuary. Offering 3 beautiful bedrooms, 3 spacious baths, and a heated saltwater pool that will provide hours of entertainment options during your summer escape to the Cape, this Barnstable home is definitely a popular choice for travelers! Located close to the restaurants and shops that make Cape Cod...

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Property Walkthrough: Luxe On River


A vacation on Cape Cod is destined to be one you remember forever, especially when you choose a vacation rental that matches the wonders of our historic homebase! Offering long days of beachy adventures, fresh seafood meals to be enjoyed with sunset views, and a history that dates back to before the beginning of our independent nation, Cape Cod is exciting, adventurous, and when staying in Luxe On River, more...

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Property Walkthrough: Life Funny 303-C


Life can be funny. You spend your days feeling as if time is creeping by as you try to juggle work, school, family, AND play, but then one day, you wake up and realize that your babies are graduating from high school and you are no longer simply coloring your hair for a change, but to cover the gray! The speed of which life can pass us by makes it...

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Property Walkthrough: Stepping Stones Sanctuary 279-C


The history of Cape Cod is a long and storied one, but that doesn’t mean that the vacation home you stay in has to have the same. Some of us just love that “new home smell” and our Pretty Picky Properties Stepping Stones Sanctuary 279-C  offers just that! Built in 2022 while retaining the historic look of Cape Cod, this 4 bedroom, 3 bath escape located in Chatham is 100...

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Property Walkthrough: The Wellfleet Oyster 1440-W


The best vacations begin and end in the best vacation homes and we don’t think we are bragging when we say that Pretty Picky Properties offers some of the best escapes on Cape Cod! Every day will be an exercise in comfort, every night will be a joyous occasion of deep sleep and happy dreams, and when you choose the Wellfleet Oyster for your luxurious vacation haven, every minute will...

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Property Walkthrough: Grayduck 207C


A Cape Cod vacation is something that is on nearly everyone’s bucket list, and when your vacation destination dreams come true, it is only fair that the property you shelter in should be a vacation dream come true as well! We at Pretty Picky Properties understand what vacationers seek, and for the larger traveling groups Grayduck 207-C is a classic New England cottage rental with room for 10! Providing four spacious and...

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Property Walkthrough: Cahoon Lagoon 036-B


The stunning landscape found on America’s favorite summer playground, Cape Cod, is the ideal spot for one of our more popular Pretty Picky Properties vacation sanctuaries, Cahoon Lagoon 036-B. Offering six beautiful bedrooms, nine baths, and a location at the tip of Long Pond that ensures the views will be so fantastic you will never want to leave, this Cape Cod vacation property features room for up to 14 guests. Bring...

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Property Walkthrough: Shore Daze 096-C


Everyone deserves the type of vacation that spoils from start to finish. Visiting an exotic destination, spending long days at the beach, and wonderfully long evenings living in the lap of luxury in a vacation home that could be described as a vacation experience! When your upcoming journey brings you to the historic charms and sandy beaches of Chatham on Cape Cod and you decide that now is the time...

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Property Walkthrough: Grayduck 207C


A Cape Cod vacation is something that is on nearly everyone’s bucket list, and when your vacation destination dreams come true, it is only fair that the property you shelter in should be a vacation dream come true as well! We at Pretty Picky Properties understand what vacationers seek, and for the larger traveling groups Grayduck 207-C is a classic New England cottage with room for 10! Providing four spacious...

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