Pleasant Chatham Cape

03/07/2026

I’m manifesting Spring on this chilly March day! If you are too, now is your time to book your ! Both Pleasant Chatham Cape and The Nook have availability through June. We are happy to say July and August are fully booked for this season!

Check out our direct booking website
www.pleasantchathamcape.com

Reach out with any questions!

★★★★★ Chatham vacation rentals: pet-friendly homes with fenced yards, free bikes & beach access. 3-4BR properties. Book direct & save!

12/23/2025

Wrap up your holiday festivities by spending New Years on Cape Cod! Chatham has First Night celebrations you and your family will love. We have availability at both The Nook and Pleasant Chatham Cape. Check our website and message with any questions.

★★★★★ Chatham vacation rentals: pet-friendly homes with fenced yards, free bikes & beach access. 3-4BR properties. Book direct & save!

12/17/2025

Now is the ideal time to reserve your Cape Cod vacation at The Nook, with prime dates available for Summer 2026. Book directly and save up to 15 percent.

The Nook on Nob Hill Chatham United States, Massachusetts

11/04/2025

Still no plans for thanksgiving? Come spend it in Chatham and get in the holiday spirit!

10/26/2025

Summer 2026 Availability at The Nook is wide open! Why not cross one thing off your to-do list and get your next scheduled and booked? The Nook is ready to welcome you!

And if you typically book through Airbnb or Homeaway - booking direct with us saves you $$$.

Reach out with any questions - happy to help you plan your stay!

The Nook on Nob Hill Chatham United States, Massachusetts

10/05/2025

Calendars are open for Summer 2026 at our family-managed vacation rentals - The Nook on Nob Hill and Pleasant Chatham Cape - both located in Chatham.
The Nook has prime weeks available June - August
Pleasant Chatham Cape has June and August availability.
DM with questions or check out our website @ www.pleasantchathamcape.com
We would love to host you!
Jenn

★★★★★ Chatham vacation rentals: pet-friendly homes with fenced yards, free bikes & beach access. 3-4BR properties. Book direct & save!

09/19/2025

Thrilled that Capeology included our property, The Nook, in their Top 10 Places to Stay on Cape in the Fall! We are proud to provide incredible 5-star guest experiences in Chatham and are so happy our guests have loved this home this summer as much as we do.

When are you coming to stay?

Planning a Cape Cod fall getaway? From cozy cottages to seaside escapes, explore our Top 10 places to stay this autumn and experience the Cape's charm, beaches, and coastal beauty.

08/21/2025

Hi Friends! It's hard to believe that is almost over! I'm already dreaming of next year and spending time at the Cape, are you?

I thought so! So to help you get through the end of summer blues, I've opened up the calendars for planning your 2026 summer !

Calendars for all 3 properties are open:
-Pleasant Chatham Cape, our flagship property, has June and August availability.
-The Nook, our newest 5-star vacation property, has open availability
-Our home away from home, Chatham Shenanigans, has the last 2-weeks in August available.

We are booking Saturday to Saturday, with a 7-night minimum.

Book direct on our website for best rates.

Comment or DM with questions!

All properties

08/07/2025

Hi Friends!

We will be opening the calendar for summer 2026 but before I do, I wanted to let this amazing group know so you can have first dibs before anyone else. If you are considering a Cape Cod getaway next year or were unable to book with us this year - now is the time to get ahead of the game! Commnt below or shoot me a DM if you are interested in any of our properties next summer!

Pleasant Chatham Cape is a dog-friendly 4BR, 2BA home which comfortably sleeps 6 located in Chatham on Cape Cod. Book your next Cape Cod getaway direct to get the best price.

07/27/2025

Another 5-star review for Tirrell’s Way!

🎃🍂 Fall on Cape Cod = Local Summer vibes. If you’ve never experienced September and October here, you’re in for something special. Think empty beaches, cool mornings, golden sunsets, and two can’t-miss events:

🦪 Wellfleet Oyster Fest (Oct 18-19)
🍺 Chatham Oktoberfest (Oct 18)

✨ Tirrell’s Way is open for fall bookings!

Enjoy:
• 4 bedrooms, 3 levels of living space
• Huge back deck & gas grill
• Fully stocked kitchen for cozy dinners in
• Access to the Cape Cod Rail Trail right from the road
• Central A/C, mini splits, beach gear & more
• Dog-friendly for one well-behaved pup 🐾

📣 PS: If you’re a Cape Cod homeowner thinking about short-term rentals this fall (or beyond), we’re now accepting new co-hosting partners. From guest messaging to maintenance, Pleasant Chatham Capes handles it all — professionally and personally. DM us to chat!

07/24/2025

Enter to win a free stay at our latest vacation rental! Good luck!🍀👍