When you first began looking at Pretty Picky Properties for your vacation accommodations, you may have been surprised to discover that we are located just about everywhere you want to be during your Cape Cod travels. We believe our guests deserve choices, lots of choices, and because we are always on the lookout for ways to improve, we are also always on the lookout to add new properties to our inventory, expanding options for finding the Cape Cod escape that will master all the needs of today’s travelers. And although the list of new properties continues to grow daily, we thought today we would talk a little about all the ones we have added most recently, discussing why any of the 44 vacation rentals on Cape Cod, MA will be an excellent part of your vacation adventures!
Browse our 2025 Vacation Rentals on Cape Cod, MA Below
Welcome to Brewster
Brewster is known as the “Sea Captain’s Town” as it was once the hometown of dozens of sea captains, and today, many of their beautiful homes remain standing, serving as a reminder of those beautiful days. Also known as being home to Long Pond, the largest pond on Cape Cod, the town is always a popular one with travelers, and for that reason, we are excited that we obtained six new rentals in Brewster! These rentals range in size from 3 to 7 bedrooms, ensuring that guests will find the perfect home to shelter their entire traveling group, and that includes pets. Three of the new listings are pet friendly, and you probably already know that Cape Cod is a pet friendly vacation destination, so there will be plenty of things to do and places to eat with your sweet fur baby in tow. Also offering a beautiful selection of waterfront retreats, we are most excited about our newest listings in the Sea Captain’s Town!
The Charm of Chatham
There are many reasons you might choose Chatham in which to reside while exploring Cape Cod, including the Chatham Lighthouse and the realization that this beautiful place has had a role in a few different movies. It is the seven new rentals in Chatham, however, that will make it easy for you to find a place to call your own. Our new listings in this town are all family homes, offering large yards, barbecue grills, and 3 to 4 bedrooms that are large and luxurious. Also offering two properties with water views and two properties with their own pools, your stay in any of our new spaces will definitely be one that you will never forget!
New in Cotuit
Cotuit (pronounced kə-TOO-it) is one of the villages of Barnstable, and it was once a retreat for intellectuals, artists, and musicians. Today, this charming spot is quiet, offering a small-town feel that makes everyone who stays here feel like a local, but although it is small, we have acquired two new listings, both of which are spacious and welcoming. 4 bedrooms and an equal or a greater number of baths make these spaces great for traveling parties of 10 or less. Both offer pools, one is pet friendly, and one also offers a hot tub, ensuring that there will be plenty of fun had during a summer visit to Cotuit.
Delightful Dennis
The beaches of Dennis are family friendly ones, offering calm waters that are also warm, something we always appreciate here on Cape Cod. Also, home to one of the oldest summer theaters in the United States, The Cape Playhouse has been bringing Shakespeare to the people for nearly 100 years, and in that time, many super celebrities have performed on its stage, including the original superstar, Humphrey Bogart. Dennis is another extremely popular tourist town, and we are pleased to announce that in the last little while we have added seven new listings for your vacation pleasures. Four of our Dennis retreats offer water views, including one beautiful home that is located on the banks of Bass River. One new listing has a private pool, almost all offer firepits and barbecue grills, one is pet friendly, and one rental is especially unique, constructed in the shape of a circle and providing panoramic views of the beach and Nantucket Sound!
We Can’t Forget About Eastham
The history of Eastham is one that extends back to the pilgrim days, and its First Encounter Beach is where the pilgrims first met the Native Americans that were the original inhabitants of Cape Cod. There’s even a bronze plaque attached to a boulder that tells the story, should you be interested in learning more. We’ve added just one property to our inventory in Eastham, a charming 2-bedroom cottage that stands just across the street from Bay Beach and offers breathtaking views that you will be reluctant to step away from.
And How About Harwich?
The cranberry bogs of Harwich add an extra layer of excitement to your Cape Cod travels, as does the existence of the Harwich Mariners, a team that plays in the Cape Cod Baseball League. Some of the nation’s best players have played on these fields, and the all-American fun of baseball, peanuts, and crackerjack can be enjoyed here, being just a short drive from the seven new listings Pretty Picky Properties offers in Harwich, five of which are pet friendly. (We really do love animals on Cape Cod) Offering three properties on the water, including one with relaxing and serene views of Long Pond, two properties with private pools, and one especially wonderful property featuring a firepit, barbecue, and a hammock for napping as salt air breezes keep you cool, you’ll have plenty of great options if you choose to vacation in Harwich!
Proud to Be an American in Orleans
Military buffs love Orleans, as it is the only American site attacked by the Germans during WWII, but it is also rich in Native American history as the Nauset Heights area was the farming site of the Nauset Indians. We had a huge addition in inventory in Orleans with 10 new listings, all waiting to make your vacation experience a comfortable one for the whole family. And yes, five of our newest Cape Cod rentals in 2025 are pet friendly, six offer water views, and two of these escapes feature a crystal-clear private pool in the backyard, giving travelers all the wonderful amenities that make travel more fun.
Wellfleet, West Yarmouth, and Yarmouth
We’re nearing the end of our tour of new listings, and the towns of Wellfleet, West Yarmouth, and Yarmouth each offer one new retreat. The homes in these towns are classic New England retreats, located near the water and offering all the amenities you need for fun and relaxation. Most of our Wellfleet vacation rentals are pet friendly as well!
Cape Cod Rentals in 2025: The Numbers Keep Rising
As we continue to find new ways to make our guests feel welcome and at home, the number of new vacation rentals on Cape Cod, MA will continue to rise, but we can’t forget to mention all the ones that have been serving us well for years. Our already established properties will provide all the amenities listed, and of course, all the ones we spoke of today will have so many more. Reserve your favorite vacation rentals in Cape Cod, MA today, knowing you will be comfortable, happy, and making new memories in our homes!