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.

Some vacations are even better when the whole family comes along—dogs included!Wake up to a slow Cape Cod morning, strol...
08/26/2026

Some vacations are even better when the whole family comes along—dogs included!

Wake up to a slow Cape Cod morning, stroll down to Little Pleasant Bay Beach, spend the day exploring nearby Chatham and Orleans, then come home to relax on the patio beneath the summer sky. This charming cottage is the perfect place to make the most of the season together.

📍7 Ellerslie Rd in Orleans

Some places are more than a getaway. They become a tradition. 🐚🦞⚓
08/25/2026

Some places are more than a getaway. They become a tradition. 🐚🦞⚓

Tucked beside conservation land and Goose Pond, yet close to beaches, the Rail Trail, and downtown Chatham, this beautif...
08/22/2026

Tucked beside conservation land and Goose Pond, yet close to beaches, the Rail Trail, and downtown Chatham, this beautifully updated home is a place where every day can unfold a little differently.

Swim, bike, browse the local shops, catch a Cape League game, or simply enjoy the peaceful surroundings with your favorite people (and your dog!).

If you're looking for a home that feels as relaxing as the vacation itself, this is the perfect place to settle in for an end-of-summer escape.

📍 297 Sam Ryder Road in Chatham

Originally built in 1869 as Chatham's Old Village Elementary School, this one-of-a-kind retreat has been thoughtfully re...
08/19/2026

Originally built in 1869 as Chatham's Old Village Elementary School, this one-of-a-kind retreat has been thoughtfully reimagined into a place where history, character, and Cape Cod charm come together.

If you're looking for a getaway that's every bit as memorable as the destination itself, this historic Chatham home is waiting to welcome you. Book soon!

📍82 School Street in Chatham

Tucked away in Chatham's peaceful Riverbay neighborhood, this is the kind of home where everyone can settle into vacatio...
08/17/2026

Tucked away in Chatham's peaceful Riverbay neighborhood, this is the kind of home where everyone can settle into vacation mode.

Ready for one last Cape Cod escape? Book your end-of-summer stay before the season slips away.

📍595 Riverview Drive in Chatham

Some of the best Cape Cod memories are the simplest ones: morning bike rides through a quiet neighborhood, afternoons ex...
08/14/2026

Some of the best Cape Cod memories are the simplest ones: morning bike rides through a quiet neighborhood, afternoons exploring the tidal pools at Ridgevale Beach, and evenings gathered on the porch as the sun begins to set.

Whether you're planning one last family vacation before summer slips away or looking for a place where everyone can truly unwind, this is the kind of home you'll want to return to year after year.

📍35 John Street in Chatham

Don’t let August slip away into a moment in time! Plan the beach trip, buy the lobster roll, and never say no to an afte...
08/13/2026

Don’t let August slip away into a moment in time! Plan the beach trip, buy the lobster roll, and never say no to an after-dinner ice cream.

Tucked between Chatham and Orleans, this cozy cottage makes it easy to explore both sides of the Cape. And don’t forget ...
07/01/2026

Tucked between Chatham and Orleans, this cozy cottage makes it easy to explore both sides of the Cape. And don’t forget the pup! This one is dog-friendly. 🐾

📍7 Ellerslie Rd in Orleans

Summer weeks on School Street are in high demand...now is the perfect time to start planning your Cape escape!Start the ...
06/28/2026

Summer weeks on School Street are in high demand...now is the perfect time to start planning your Cape escape!

Start the day with coffee on the deck, spend the afternoon at the Lighthouse Beach, and come home to a backyard made for gathering. There’s room for everyone to settle in and stay awhile.☀️

📍61 School Street in Chatham

Lighthouse Beach around the corner. Main Street a short walk away. A beautiful home waiting at the end of the day. Now t...
06/26/2026

Lighthouse Beach around the corner. Main Street a short walk away. A beautiful home waiting at the end of the day. Now that's a winning combination for a perfect Cape Cod summer!

📍24 Wilderwood Lane in Chatham

Address

1181 Main Street
Chatham, MA
02633

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