When your dream Cape Cod vacation brings you to Chatham for a week, Pretty Picky Properties offers idyllic weekly rentals that will keep that dream alive. Offering modern conveniences blended with all the comforts of home and seasoned with a liberal does of luxury amenities, these charming abodes will definitely become an integral part of your vacation experience. This guide to your Cape Cod adventures spent cozily ensconced in our weekly vacation rentals in Chatham, MA will show you that good things do come to those who know what they are looking for, especially when they look in the direction of our Pretty Picky Properties vacation rentals!
Testimonials | FAQs
So Much to Do
The town of Chatham isn’t all that large, boasting a population of just 6,600 people and stretching out just 24.4 square miles in size, but even if you were only planning on keeping your Cape Cod explorations to this town, you would still need at least an entire week to see and experience all it has to offer! Home to the still working Chatham Light, a historic lighthouse that was constructed in 1808 and is still in operation today, the beach that lies in the shadow of the lighthouse is one of the most popular ones on Cape Cod.
Chatham has many charming shops, including the whimsical Ducks in the Window, a store popular with Jeep owners who visit our island town every year. Our favorite fine dining restaurant, the Impudent Oyster, also calls Chatham home, and Buffy’s Ice Cream Café offers the quintessential summer treat, guaranteed to be a memorable stop for you and your entire family.
And even though we have just touched on a few of the highlights of Chatham, we are sure that you can see there will be more than enough to keep you happy, satisfied, and entertained during your week on Cape Cod, especially when you come home to our weekly rentals every night of your stay.
Step into Comfort
The homes we offer in Chatham come in all shapes, styles, and sizes, and whether you need a cozy cottage with just 2 bedrooms and gardens of hydrangeas to make you happy, you have a special occasion planned and need to choose our spacious 8-bedroom rentals with swimming pools, hot tubs, and dream gourmet kitchen, or anything in between, you will find it here. Even better, no matter which property you choose, your favorite part of your at-home adventures will more than likely be the comfort that all of our properties provide.
Whether it’s our living rooms with plush sofas topped in soft fabrics, dining rooms with tables surrounded by cushioned chairs, and bedrooms with beds that may very well be considered the most comfortable on Cape Cod, comfort is key to a dream vacation, and Pretty Picky Properties will ensure you find yours.
Cozy and Cute
Our smaller weekly Chatham, Cape Cod vacation rentals, offering just 2 bedrooms, may provide a smaller footprint but will still provide the luxury amenities you will come to expect from our rentals. Gas fireplaces in the living room, televisions will be ultramodern and super-sized, available in both bedrooms and in the living room, and our gourmet kitchens will offer stone countertops, custom cabinetry, and name-brand appliances that will entice you to stay in some evenings and create your own meals. Also offering places to work, our high-speed internet will enable you to easily attend virtual meetings at work, and if you bring your laptop out to screened porches that may or may not offer glimpses of the sea, you are sure to earn the envy of everyone who attends those virtual meetings!
Testimonials
Andrew W.
Excellent for 8 people, amazing location and an overall beautiful home.
Brett Z.
Great house in great neighborhood. House exceeded expectations. Great views, great location. Clean and easy! Highly recommend
Don B.
Wonderful setting and accommodations. Had everything we needed
Spacious and Luxurious
Our largest weekly Chatham, Cape Cod vacation rentals offer as many as 8 bedrooms and room for up to 16 guests, perhaps making them perfect for destination weddings or family reunions, while also offering all the luxuries your family or guests deserve. Offering expansive backyards equipped with swimming pools, hot tubs, firepits, and beautiful gardens, there will always be places for every guest in your traveling party to sit and savor the beauty of a Cape Cod landscape, often with their favorite beverage in hand.
Your super-sized estate may feature its own guest house, complete with second kitchen, living area, and private bedrooms, ideal for the matriarch and/or patriarch of your family to reside in and offering privacy when the vacation becomes too people-y. Some may offer game rooms equipped with a variety of gaming needs, others may provide home theater with cushy chairs, super-sized screens, and a selection of movies that will be extensive enough that there will be something for everyone to enjoy.
Reserve Your Favorite Weekly Vacation Rentals in Chatham, MA Today
Whether the property you rent requires you to rent it on a weekly basis or you just happen to be spending a week with us, our Pretty Picky Properties retreats will be where your best vacation begins and ends.
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FAQs about our Weekly Vacation Rentals in Chatham, MA
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Are any of your weekly rentals pet-friendly?
Yes! We at Pretty Picky Properties love dogs, and we invite you to bring your pooch along while staying in our Chatham pets-considered retreats.
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We’re looking for something unique to do during our stay in Chatham, do you have any suggestions?
There are many wonderful activities that will entertain your entire family, but perhaps one of the most unusual activities would be participating in a shark tour with Chatham Shark Tours. Based at 98 Ryder’s Cove Road in North Chatham, the captain leads guests on a safe 2- or 4-hour tour where the sharks, including great whites, are known to frolic.
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Do you offer waterfront weekly rentals?
Yes! Although our waterfront rentals may not be on the ocean, we do offer a wonderful selection of rentals located on the rivers, ponds, and creeks of Chatham, providing a serenely beautiful vacation experience.
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Chatham looks like it is a dream vacation location, and we would like to learn more about it. Are there any history museums in the area that tell Chatham’s story?
The Atwood Museum, located at 347 Stage Harbor Road in Chatham, tells our town’s story from the base of one of the area’s oldest homes, the Joseph Atwood House, built 24 years before our country declared its independence.
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We are traveling with a large group and are planning on doing a lot of cooking at home, including baking. Do you offer any Chatham retreats with double ovens?
Yes! Our gourmet kitchens are the talk of the Cape, and some will have double ovens, others will have wine refrigerators, and all will feature coffee makers and/or Keurigs, in addition to the standard set of appliances.