Chatham may be a long way from Germany, but that has never stopped us from celebrating Oktoberfest in ways that would make the German people stand up and take notice! Chatham’s annual Oktoberfest celebration is something that shouldn’t be missed, and if you are planning your vacation on Cape Cod for some time in mid-October, you will also want to take a look at our Pretty Picky Properties Chatham festival rentals! Located close to the festival so that your rideshare costs won’t be too high after consuming all the beer, this guide to the festival, our Oktoberfest vacation rentals in Chatham, and the wonders of October on Cape Cod will help your anticipation levels reach new heights.
Testimonials | FAQs
Don’t Forget Your Lederhosen!
Ok, you don’t HAVE to wear lederhosen to have a good time at Oktoberfest, but rest assured, many attendees will be wearing them, adding to the authentic nature of the celebration. Held at Kate Gould Park and the Town Hall parking lot, the family-friendly celebration begins at 11AM, closing down its beer garden by 4:30 PM. Offering kid-friendly activities, including games, bubble machines, and photo stand-ins that may not up their selfie game but will give your older kids a cool pic to post, and all the brats and beer you can eat or drink, the festival may not last long, but it packs a lot into 5.5 hours. Also offering vendors selling merch you can’t live without, live music, and a day of sunshine and crisp fall air, you won’t regret planning your Cape Cod vacation in the fall instead of the summer! Oh, and did we mention the beer? Yes, we know we did, but it is worth repeating, especially as the beer garden could be considered the main reason we love to celebrate Oktoberfest on Cape Cod.
Our Festival Vacation Rentals in Chatham
The town of Chatham is known for Monomoy National Wildlife Refuge, for the Chatham Lighthouse, and for being the site of many, many, many of our Pretty Picky Properties vacation retreats. Ranging in size from cozy 2-bedroom cottages to spacious 8-bedroom escapes, most will be located on or near the many beaches that populate the area, your stay with us will definitely give you an authentic Cape Cod experience. Is there anything better than a romantic vacation spent with your favorite human in a cottage on the beach? Its weathered shingles standing the test of time, outdoor showers that bring you closer to nature, and cool nights spent cuddled in front of a roaring fire after a long day of celebrating Oktoberfest? Well, some would say a Cape Cod extended family vacation spent in a historic sea captain’s house, one that has stood in the same location near the bay for over 200 years, might be a little better than a romantic getaway, but we say both are right. There is no better vacation experience than the one that suits your traveling party best and the plethora of Chatham rental houses will ensure that you find the home that fits!
Testimonials
Kathryn C.
This is an incredibly beautiful property. My friends and I enjoyed the heated pool, hot tub and fire pit. It was very convenient to shopping & Chatham Bars Inn. Highly recommend!
Karen P.
This is a great house. Has all of the amenities - pool, hot tub, fire pit, porch, outdoor dining, indoor dining. Can walk to town. Property manager was incredible! Highly recommend and will be renting it again!
Beth W.
Great property - beautifully maintained. Easy access to town of Chatham and beaches. Pretty Picky Properties was a pleasure to deal with. No need to use VRBO for this property - all they did was collect a fee.
Quiet and Serene Getaway for Two
After the raucous fun of the festival, you and your favorite traveling companion will be more than ready for some peace, quiet, and serenity, and as you relax and fall deeper in love in our waterfront cottages, you will forget that anyone else exists in the world. Enjoy your morning coffee while watching the sun rise, your evening glass of wine while watching the sun set, and savor every moment in between, knowing there is no place else on earth you would rather be. An October visit may be too cold to enjoy a breakfast out on patios or decks that overlook the water, but our fully equipped kitchens will likely provide a breakfast bar built for two—as well as a dining table nearby!
Historic, Not Outdated
Our older Chatham rental houses will feature all the charm of the past while providing all the modern details travelers need, and so our kitchens will offer new appliances (including dishwashers), and the televisions that are in the living and bedrooms will often be smart ones on which you can stream your favorite shows. Outside, you may find private pools, hot tubs, and fire pits, while inside, period details (wide planked wood floors and built in cabinets that have kept treasures safe for centuries) will remind you of gentler days. Choose our Chatham, MA cottages for privacy, but also for the many conveniences they provide.
Reserve Your Favorite Oktoberfest Vacation Rental Today
The joy a Cape Cod vacation brings will be enhanced when you choose Pretty Picky Properties for your festival rental. Our goal is to make your vacation one you will never forget, and we achieve that by providing comfort, luxury, and style for all who reside within! If you’re planning a getaway full of luxury, check out our Chatham luxury rentals instead!
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FAQs about our Vacation Rentals in Chatham
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Is there a purpose behind the shingles that cover the front of so many of your Chatham escapes or is it just for style?
The weather on Cape Cod can be harsh, especially during the winter months, and although the shingles do offer a charm that is authentically New England in style, they also serve to protect them from the elements, standing strong against wind, snow, and salt air.
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My kid is obsessed with sharks, is there any place I can take him to learn about them?
The AWSC (Atlantic White Shark Conservancy) Shark Center, located at 235 Orleans Road, is THE place every shark fan should visit and it just happens to be located right here in Chatham. Offering interactive exhibits, videos, and displays, if you weren’t a shark fan before stepping inside you soon will be.
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Are the pools heated, and if so, when do you close them down for the season?
Many of our private pools are heated, enabling guests to swim a little later than normal, but most are still shut down by the time Columbus Day rolls around. It’s just too cold for the heaters to work after that.
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We’re not ready for the evening to end, where’s a good place to hang out and enjoy more beer?
The Red Nun Bar & Grill, 746 Main Street in Chatham, stays open until 1 AM, offering karaoke nights, trivia nights, and live music, making it a popular hangout spot for residents and locals.
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Can I take a real shower in the outdoor shower (washing my hair, moisturizing, etc.) or is it just meant for rinsing the sand off after a beach day?
The outdoor showers of our Pretty Picky Properties rentals can be used for both!