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Experience Quintessential Cape Cod from Pleasant Chatham Cape Properties

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Feel Right at Home on Cape Cod

Experience the true essence of Cape Cod with Pleasant Chatham Cape Properties, where every stay is designed to create unforgettable coastal memories. Our carefully selected homes capture the relaxed, timeless charm of Chatham, offering you a perfect blend of comfort and classic Cape Cod style.

Whether it's mornings spent walking along the shore or evenings enjoying the ocean breeze, our properties are crafted to bring the best of Cape Cod to your doorstep. With personalized service and local knowledge, we're here to ensure your stay is seamless and special. Discover the authentic Cape experience at Pleasant Chatham Cape Properties—your home away from home.

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What Our Guests are Saying

Amazing Home!

Mary D., Boston, MA - June, 2024 - Stayed at Pleasant Chatham Cape

⭐️⭐️⭐️⭐️⭐️

"We had the most amazing week at Pleasant St! The home was wonderfully decorated and equipped. There were so many thoughtful touches throughout including extra pillows and blankets, bikes that we were able to take on the rail trail, and so much more. We also loved being able to bring our dog on vacation with us. There are so many dog friendly places to go and things to do on the Cape in the summer, so she had the best week. Having a fenced in yard was a huge plus too! The home is in walking distance to the beach (about 3/4 miles). We drove to drop our stuff off, then walked down! It was about 5 min to Harwichport and 10 min to downtown Chatham. Ubers are plentiful so we were able to enjoy the Port and the Squire at night! Jenn was amazing at communicating quickly with us and even stopped by as we checked in to see if we needed anything. Such an amazing home and location. We would absolutely book again!"


Private + Comfortable

-Mark, Newton, MA - August 2024 - stayed at Chatham Shenanigans

⭐️⭐️⭐️⭐️⭐️

"We were thrilled with the property. The house is off a main road but on a quiet street. Backyard is small but beautifully appointed and very private. Very comfortable outdoor lounging furniture as well as large outdoor dining table/umbrella, portable firepit and easy to use grill. House is clean, bright and perfectly sized for our family of four. Basement is comfortable with quality ping pong table, poker table and tv space. Living room is spacious with high ceilings, large TV over working fireplace. Adjoining kitchen has all the appliances you might need. Beds were comfortable. All clean and very quiet.
Location is great.
1 mile walk to Chatham town. Very close to great beaches (RIdgevale in particular). A few restaurants walking distance and plenty of places a short drive. Jennifer was very responsive. Always texted back within 10 mins..."


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