Luxury rentals in Chatham

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Top-rated luxury holiday rentals in Chatham

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Luxe

Home in Chatham

4.88 out of 5 average rating, 56 reviews

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

Luxe

Home in Barnstable

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.

Luxe

The exterior of the house is viewed from an elevated angle, showcasing multiple levels with a light-colored facade. A spacious deck is visible, furnished with outdoor seating. Surrounding greenery and sandy areas lead to a view of the ocean in the background. Nearby homes are visible, highlighting the coastal setting.

Home in Sandwich

5.0 out of 5 average rating, 63 reviews

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!

Luxe

An aerial view showcases a spacious outdoor area highlighted by a heated pool, surrounded by a patio with lounge chairs and green umbrellas. An outdoor dining table, accommodating up to 14 people, is positioned nearby, surrounded by lush landscaping and comfortable seating areas.

Home in Barnstable

5.0 out of 5 average rating, 17 reviews

Luxury Historic Estate with Expansive Grounds

Beautifully restored, this home is only 10 minutes away from Sandy Neck beach and has everything you need for your summer vacation. The outside space is also perfect for family get-togethers, as there is a heated pool , plenty of seating around the gas fireplace and an outdoor dining table large enough to seat 14 people! The lush landscaping throughout the property is sure to make you feel like you're in paradise!

Luxe

Home in Barnstable

Cape Cod Luxury Escape: Pool, Fire Pit & Family

Escape to your dream Cape Cod retreat! This luxurious 7-bedroom, 5.5-bathroom home boasts a private heated pool, fire pit, and game room, perfect for unforgettable family vacations or group getaways. Enjoy resort-style amenities and a prime location near beaches, attractions, and shopping in Barnstable, MA. Experience the best of Cape Cod living in this spacious and well-equipped house.

Luxe

An aerial view of a spacious property surrounded by lush greenery, featuring a well-maintained lawn. The house displays a modern design with multiple gabled roofs. A swimming pool with lounge chairs is visible in the backyard, accentuated by a children's play structure and landscaped borders.

Home in Yarmouth Port

5.0 out of 5 average rating, 12 reviews

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.

Luxe

An outdoor deck area is featured, with a wooden dining table surrounded by four chairs. Two lounge chairs are positioned nearby, offering views of the calm water and surrounding natural landscape. The sky is adorned with soft clouds, reflecting the colors of the sunset.

Home in Hyannis Port

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.

Luxe