Luxury rentals in Chatham

Cape Cod Gates

Welcome! Experience the charm of Cape Cod at our newly renovated retreat, 183 Sandwich Road, "Cape Cod Gates" This luxurious home offers 6 beds in 4 bedrooms, 2 baths, and ample space to relax. Located near the Bourne Bridge, it's perfect for exploring Boston or Cape. Enjoy our 38,000 sqft yard with a gazebo, heated pool, and parking for 3+ cars. Nearby, explore the Cape Cod Canal's trails, Scusset Beach, Old Silver Beach, Heritage Museum & Gardens. Book today and make unforgettable memories!

Steps to Beach + Game Room + Porch | Coastal Haven

Welcome to Coastal Haven! — a spacious seaside escape perfect for families or groups. Steps from the beach, Main St & Chatham Bars Inn, this elegant 10-bed retreat blends comfort, fun, and Cape Cod charm. 📍 0.4 mi to beach, 0.5 mi to charming Main St & Chatham Bars Inn 🌅 Tranquil front porch & lawn with kids’ playset 🎱 Game room: pool table, Apple TV, games ✨ Open-concept living with stunning 2-story glass walls 🧺 Full kitchen, laundry, fast WiFi 🛏️ 10 beds + soundproof divider setup

Brand New Osterville Luxury Estate

This brand‑new luxury estate in Osterville offers a private, resort‑style experience for large groups. The 7,000 sq ft home **sleeps up to 18 guests** with 5 spacious bedrooms and 6.5 bathrooms. Enjoy a private cinema room, gourmet kitchen, and expansive living areas. Outside, relax by the **heated saltwater pool** with automatic cover and entertain in the **fully equipped outdoor kitchen**. Minutes from beaches, boating, dining, and village shops.

Waterfront home w/ Beach access

At Après Sea you are surrounded by natural beauty - Scorton Creek on the back of the house & East Sandwich Beach across the street from the front of the house. You'll love quiet walks on the beach, Cape Cod bay, and the sunrises & sunsets. The house is perfect for entertaining with an open air deck, covered deck, natural gas BBQ, chef's kitchen, and 5 TVs. Parking for up to 6 cars. Welcoming World Cup 2026 supporters!

Cape Cod Family Vacation

Experience luxury and comfort in this stunning Cape Cod retreat. Perfect for families and groups, this beautifully designed home accommodates up to 12 guests with spacious living areas, elegant décor, and a relaxing coastal atmosphere. Enjoy unforgettable summer days and peaceful evenings while creating lasting memories with loved ones in one of the Cape’s most desirable destinations.

Spacious Cape Cod Retreat Near Beaches RPMS

Overlooking Snow's Creek with sunset on one side and sunrise on the other! Steps to beach with 2 beach passes. Close to area restaurants, shops and boats to the islands. Off season dates available and you can rent main home only.

Luxury home with 2 pools on the water RPMS081

Waterfront Luxury rental with 7 bedrooms, 2 pools, 2 hot tubs and dock. Cape Cods finest. Large yard.

Prime Chatham Retreat with Pool, Spa & Style

4 BED / 4.5 BATH / SLEEPS 10 / HEATED POOL AND SPA / 1.2 MILES TO BEACH

Luxurious Estate, Private Heated pool!

17718 - The Secret Garden: Luxurious Estate with Private Heated pool!

Elevate Your Chatham Stay: Luxury w/ Pool & Beach

6 BED / 6 BATH / SLEEPS 14 / WITH BEACH ACCESS / POOL / SPA

Sesuit Neck Stunner w/ Heated Pool and Spa

4 BED / 3.5 BATHS / SLEEPS 10 / HEATED POOL AND SPA

Exclusive Harwich Haven: Pool, Spa and More

4 BED / 4.5 BATH / HEATED POOL AND SPA / SLEEPS 10