Chatham Rentals

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Chatham, MA
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.

10/23/2026

Beautiful water views! 🌊

This brand-new 3,000 sq ft custom home has clean, modern lines, all-new furnishings, and views across to the Provincetown Monument. It has a first-floor king suite, three bedrooms with private decks, and an open layout made for entertaining. Grill on the patio, rinse off in the outdoor shower after a day at Head of the Meadow Beach (less than a mile away), and enjoy being close to Provincetown, Wellfleet, and Truro.

Call Chatham Rentals today to plan your 2027 visit! ☀️

📍22 Cliff Rd, Truro

10/21/2026

Breathtaking views of Nantucket Sound! 🌅

This unique 3-bedroom home sleeps 6 and borders a tidal salt marsh conservation area, perfect for birdwatching. Sip morning coffee on the deck overlooking the ocean, then walk just 500 feet to the beach. After a day in the sun, rinse off in the outdoor shower, fire up the grill, and watch the sunset over the water. Mini-golf, go-karts, ice cream, and more are just a quick drive away, and dogs are welcome too!

Contact Chatham Rentals to plan your 2027 visit! ☀️

📍76 Sea Shells Dr, South Chatham

10/19/2026

A piece of Chatham history! 🏫

Built in 1869 as the Old Village Elementary School, this charming home now has 4 bedrooms and 3.5 baths, with historic character and modern comfort. The second-floor primary suite has its own kitchenette, bath, and laundry. You're a short walk from Lighthouse Beach, shops, and restaurants. Sip morning coffee on the upper deck overlooking Mill Pond, grill dinner after the beach, then head into town for band concerts and ice cream. Don't miss the sunsets from the deck!

Contact Chatham Rentals to plan your 2027 stay! ☀️

📍82 School St, Chatham

10/17/2026

Three cozy ways to fall for downtown Chatham! 🍂

These charming rentals on Cross Street put you steps from Main Street, so park the car and stroll to morning coffee, cozy dinners, shopping, and a movie in the village. Catch a crisp sunrise at Oyster Pond Beach, then come home to your own little retreat:

🏡 The Main House: 3 bedrooms with original Captain's Stairs, an updated kitchen, and a private back deck for grilling under the stars.
🌿 The Cottage: 3 bedrooms, central A/C, and a private patio made for reading with your morning coffee.
☕ The Apartment: A cozy one-bedroom with its own entrance, a full kitchen, and a private deck and patio with a gas grill.

Contact Chatham Rentals to plan your fall escape! 🍁
📍54 Cross St (Main House), Chatham
📍52 Cross St (Cottage), Chatham
📍54 Cross St (Apartment), Chatham

10/15/2026

Wake up to fall views over Emery Pond! 🍂

This modern Chatham home has vaulted ceilings and floor-to-ceiling windows that frame the changing season. It has 2 bedrooms plus an open loft with a king bed, a kitchen with new appliances and granite counters, and sliders that open to the deck for crisp morning coffee. Take the path down to the water and bring your fishing pole, or head out on the nearby bike path for a fall ride. Downtown, Oyster Pond, and the Nantucket Sound beaches are a short drive away, and dogs are welcome too!

Contact Chatham Rentals to plan your fall escape! 🍁

📍44 Ethelma Dr, Chatham

10/13/2026

Escape to North Chatham this fall! 🍂

This private, dog-friendly retreat has three bedrooms, each with its own en suite bath, plus a den with a queen sleeper sofa. The bright, open living and dining area leads straight out to the back deck, with water views just beyond the trees. Start crisp fall mornings with coffee and a sunrise while you watch the birds, spend the afternoon at the beach, then come back to dinner off the grill.

Contact Chatham Rentals to plan your fall escape! 🍁

📍97 Captains Walk, North Chatham

10/10/2026

Fall in love with Chatham this season! 🍂

This charming 4-bedroom home on sought-after School Street is the perfect fall getaway, with classic Cape Cod décor and a private cottage with its own en suite bedroom. Gather around the breakfast bar, spread out in the spacious living room and den, or curl up with a book in the upstairs loft. Enjoy crisp mornings on the deck, take quiet walks on Lighthouse Beach without the summer crowds, and stroll into downtown Chatham for dinner and a movie.

Contact Chatham Rentals to plan your fall escape! 🍁

📍61 School St, Chatham

10/07/2026

Wake up to breathtaking fall sunrises over the Atlantic! 🍂

This spacious 4-bedroom Chatham beach retreat sleeps 10 and has 180-degree water views of the Outer Beach, plus direct access to a private beach. Sip crisp morning coffee on the upper deck, unwind on the beachside swing, or gather on the patio for a BBQ. The landscaped lawns leave plenty of room for games, and the finished basement family room is perfect for cozy movie nights. Downtown Chatham's restaurants and shops are just a short drive away.

Contact Chatham Rentals to plan your fall escape! 🍁

📍480 Old Harbor Rd, North Chatham

09/02/2026

Trust us locals: there’s nothing quite like September in Chatham!

08/31/2026

If an end-of-summer escape is calling your name, now's the perfect time to book your Cape Cod getaway!

This Chatham rental perfectly blends cozy with coastal charm. With Lighthouse Beach within walking distance, just imagine spending the afternoon at with your toes in the sand and the sound of the waves in the distance. That’s Cape Cod perfection!

📍24 Wilderwood Lane in Chatham

Address

1181 Main Street
Chatham, MA
02633

Website

https://shor.by/ChathamRentals

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