Chatham Rentals

Chatham Rentals Specializing in matching our customers to the perfect vacation rental property!

From quaint cottages to luxury estates in Chatham, Orleans and Harwich Port, we hold the key to your seaside vacation.

Steps to the beach, seconds to town, and a front-row seat to Mill Pond. This home makes it easy to slow down and stay aw...
05/29/2026

Steps to the beach, seconds to town, and a front-row seat to Mill Pond. This home makes it easy to slow down and stay awhile.

June is just a few days away! Don’t miss your chance to experience a glorious summer getaway on the Cape. Book soon!

📍77 Mill Pond Road in Chatham

From blooming backyard gardens to sandy walks at Jacknife Beach, every day feels calm and connected at this rental in Ch...
05/27/2026

From blooming backyard gardens to sandy walks at Jacknife Beach, every day feels calm and connected at this rental in Chatham! Come home to space, sunshine, and the simple joy of being together.

📍58 Echo Lane in Chatham

Park once, then explore everything on foot. With a cozy home base and Chatham right outside your door, summer days feel ...
05/24/2026

Park once, then explore everything on foot. With a cozy home base and Chatham right outside your door, summer days feel effortless here. 🌊

Don’t forget to book your summer rental soon - spots are filling up quickly!

📍35 Ocean View Terrace in Chatham

Steps to the sand, days at a lifeguarded beach, and evenings grilling while the kids play outside. It’s an easy Cape Cod...
05/22/2026

Steps to the sand, days at a lifeguarded beach, and evenings grilling while the kids play outside. It’s an easy Cape Cod rhythm, especially with your pup along for the fun.🐾

📍93 Deep Hole Road in Harwich

A little tucked away, a little closer to nature, and just right for a Cape escape. With water views, fresh air, and spac...
05/21/2026

A little tucked away, a little closer to nature, and just right for a Cape escape. With water views, fresh air, and space for everyone (including the dog!), this is summer done right. 🌊🐾

📍97 Captains Walk in North Chatham

Park the car and let the days unfold on foot. Breakfast, beach, and Main Street all just steps away! Evenings end with d...
05/19/2026

Park the car and let the days unfold on foot. Breakfast, beach, and Main Street all just steps away! Evenings end with dinner on the patio and a movie in town. It’s Chatham made easy!

📍35 Shattuck Place in Chatham

Whitewashed calm, pops of color, and salty air just outside your door. Walk to Oyster Pond, Lighthouse Beach, or into to...
05/16/2026

Whitewashed calm, pops of color, and salty air just outside your door. Walk to Oyster Pond, Lighthouse Beach, or into town...it’s all within reach! Simple, peaceful, and just right for a Cape getaway.

If you’ve been waiting for a sign, this is it! Don’t wait to book your summer rental any longer. 🌊

📍411 Stage Harbor Road Sea Crest in Chatham

From sunrise reflections on Emery Pond to breezy rides along the bike path, every day feels a little lighter here. And y...
05/14/2026

From sunrise reflections on Emery Pond to breezy rides along the bike path, every day feels a little lighter here. And yes, your pup is welcome to join in on the fun! 🐾

📍44 Ethelma Drive in Chatham

A little slice of Chatham heaven! Nautical charm, ocean breezes, and everything within walking distance. Summer is close...
05/10/2026

A little slice of Chatham heaven! Nautical charm, ocean breezes, and everything within walking distance. Summer is closer than you think. 🌊

📍73 Main Street #10 in Chatham

Start with the beach, come back to the pool, and end the night under the stars. Between the sunroom, patio, and cozy liv...
05/08/2026

Start with the beach, come back to the pool, and end the night under the stars. Between the sunroom, patio, and cozy living spaces, there’s always somewhere to unwind!

Book now and secure your 2026 Cape Cod vacation.☀️

📍99 Bishops Terrace in Chatham

Address

1181 Main Street
Chatham, MA
02633

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