We are constantly arguing over which shows we want to watch, are there televisions in the bedrooms to help us avoid squabbles?

Most, if not all our bedrooms will offer their own televisions, they just may not be as large as the ones in the public areas.

Besides the beach, is there any fun activities we can engage in as a large group staying in your Orleans retreats?

We figured we didn’t have to tell you about the roominess of the beach, but we can tell you how much fun you will have at the Alley, Bowling & Barbecue. Located at 191 MA 6A and offering 12 candlepin lanes (much easier than traditional bowling, and you get three balls per turn instead of just two!), the barbecue is delicious, and the beverages are always flowing.

We really love movies, do any of your 10-bedroom spaces offer private theaters?

As a matter of fact, more than a few of our 10+ bedroom homes offering home theaters, furnished with plush sectionals or rows of leather recliners.

Did we hear that there is still a drive-in movie theater on Cape Cod?

Yes, you heard correctly, the Wellfleet Drive In, located at 51 US6 in nearby Wellfleet, offers first run double features nightly as well as providing a sweet glimpse into the history of most Gen Xers!

Sleeps Ten or More

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A Beautiful Part of Your Vacation Experience

The adventures waiting to be had during your mega-sized Cape Cod vacation are going to make your dreams come true, and the best part of choosing our Pretty Picky Properties retreats for 10 or more guests is the realization that as much fun as you have during your explorations, you will still be excited to come home every evening. Our vacation rentals on Cape Cod, Massachusetts will be a beautiful part of your vacation experience, providing a welcoming vibe, a warm embrace, and comfortable adventures you will find yourself excitedly talking about when you regale those at home with tales of your dream vacation come true. And we envy you. Climbing the steps that lead up to the front door for the first time, standing outside that door, waiting for the click that tells you the code was input correctly, and watching the door swing open, revealing a vacation experience that will be unlike any others. This moment is where all the plans and to do list suddenly fall into place and your life takes on a new glow as you step inside and begin the vacation you will never forget.

Loud and Exciting

A large group of people is not a quiet one, and if we were to give that group a name (such as a murder of crows or a clowder of cats) we would have to say a raucous of people, and that’s ok. In addition to being large and in charge, our 10+ bedroom homes are set off by themselves, often featuring a long driveway that leads back to your mini manse of the week (also providing plenty of spaces to park all the rental cars you might need!) and the noisy nature of your traveling party will only be heard by timid deer or slippery sea creatures swimming in the nearby waters. We’re not saying that you should throw a large party, of course, but YOUR large party doesn’t have to worry about tiptoeing around so as not to disturb the neighbors. And even better, many of our 10-bedroom retreats accept pets of a certain size, adding to the excitement!

Rentals on Cape Cod Designed for Living

Every traveler has an idea of what constitutes the perfect vacation rental, and our job is to combine all those ideas into an idyllic home, and we like to think we get it right. The world changed forever a few years back, and one of the advantages of that time is that it also showed us that in most instances, jobs can get done when working remote, and if your vacation can’t exclusively be fun and relaxing, we’ve provided quiet niches equipped with desks, high-speed internet, and the ability to work from our home while still feeling pampered and spoiled. Take your meeting out on decks that overlook pools, hot tubs, or the waters that surround our Cape Cod beachfront rentals and see the envy on the faces of those working from their kitchens, bedrooms, or worse, from their desks back at the office!

Testimonials

What Our Guests Are Saying

Justin S.

The house, amenities, and location were unbelievable! Big thank you to Kris and his staff. My family and I look forward to staying there for years to come! The pool, close walk to the private beach, and close drive to Harwich Port made the trip!

Penny J.

We always use Pretty Picky when we visit the cape and they have never let us down. The properties are gorgeous and there always seems to be something "extra" about them. Most recently, the EXTRA was this view that I couldn't get enough of.

Carolyn M.

Our family vacation, 2024, on the Cape was fantastic! The house we rented from Pretty Picky Properties exceeded our expectations. It was clean, loaded with amenities, great location and the staff from PPP was always promptly attentive to any of our concerns, of which there were very few. When asking one of my grandchildren how he would rate the property, he replied, "It was great; I'd give it a five, but then everyone will want to rent it and it might not be available for us!" We loved it!

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The Hungry Horde

You are definitely going to want to sample the deliciousness that awaits you at Cape Cod restaurants, but going out to dinner for every meal and feeding up to 24 hungry travelers can be prohibitively expensive, which is where our fully equipped kitchens come into play. Built to handle the workload of feeding a hungry horde, these high-end rooms will be a delight to play in, offering, in some cases, multiple dishwashers, refrigerators, and outdoor kitchens that will allow you to split kitchen duties amongst your group. If your group is particularly large, it may take more than one or two tables to hold you all, but we assure you that there will be a seat for everyone in your traveling party, and we predict that long, leisurely dinners filled with laughter and conversation will be in your vacation future! There will even be outdoor dining spaces, tucked away under covered patios, umbrellas, and even the canopy of trees, ensuring your meal will remain shaded and cool in the summer months.

Privacy Included

A more the merrier vacation can have its moments where life gets a little too people-y, but in addition to being open and spacious, our vacation rentals on Cape Cod, Massachusetts will also offer private areas to which you can retreat and revel in quiet and tranquility. Private balconies off primary suites will provide the perfect place to sip and savor, taking in the views that will become a new obsession, and offering a hiding place that will feed your soul. Some bedrooms will also offer separate sitting areas where guests can sip coffee in the mornings, wine in the evenings, and make plans for more adventures. Offering nearly as many baths as bedrooms ensures that many guests will have their own ensuites and morning traffic jams will be fewer. Reserve your favorite Mid Cape rentals today!