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.
Explore our Properties
What Our Guests are Saying
The Perfect Cape Cod Vacation
Maggie, Boston, MA - July 2025 - Stayed at The Nook
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"I cannot say enough how wonderful our stay was at Jenn's home! First off, right off the bat, Jen was extremely accommodating and let us check in early as well as provided a list of recommendations for the area. Not only was the house beautiful and comfortable, but it was full of everything you could need for the perfect Cape vacation (bikes, beach chairs, beach games, etc.).
The location of the home was unmatched as well, being less than a minute from the bike path and basketball courts, and less than a 5 minute drive to downtown Chatham, we never ran out of activities! The home had the perfect outside set up with a wonderful outdoor shower and the perfect deck with a grill to have the perfect 4th of July BBQ! On top of it, the solo stove at night was amazing to watch fireworks from!
We felt at home from the minute we stepped into Jenn's home and were so sad when we had to leave! We would love to stay at Jenn's home again and cannot thank her enough for her hospitality!!"
Wonderful Stay in Chatham!
Rebecca A., Minnesota - June, 2025 - Stayed at Pleasant Chatham Cape
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"We had a great experience at the Pleasant Chatham Cape House. The home was clean, cozy, and had everything we needed. The location was very convenient to all that Chatham has to offer. Jenn was very responsive and helpful, making our first rental experience smooth and positive. Highly recommend!"
Amazing Home!
Mary D., Boston, MA - June, 2024 - Stayed at Pleasant Chatham Cape
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"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
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"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..."
Frequently Asked Questions
What time is check-in and check-out?
Check-in is anytime after 3:00 PM, and check-out is by 10:00 AM sharp. Late check-outs are subject to a $50/hour fee to ensure our cleaners can prep for the next guests.
Are your properties pet-friendly?
Yes — some are!
🐾 Pleasant Chatham Cape welcome well-behaved dogs.
🚫 The Nook and Chatham Shenanigans are pet-free.
Always double-check the listing or contact us if you’re unsure.
Is parking available at the properties?
Yes, all homes have private driveway parking for 2–4 cars, depending on the property. Street parking is not allowed, and we ask guests to avoid neighbors’ driveways out of courtesy.
What’s included in the rental?
Each home includes:
• High-speed Wi-Fi
• Washer/dryer with laundry supplies
• Fully equipped kitchen + grill
• Beach chairs + umbrella
• Smart TVs and streaming access
• Starter supplies (soaps, paper goods, etc.)
What’s nearby?
You’re never far from fun:
• Hardings Beach – 5–10 minutes away
• Cape Cod Rail Trail – easy access for biking
• Downtown Chatham – shops + dining galore
We also provide bikes, beach gear, and a guide with our favorite local picks.