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Luxury rentals in Chatham

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Top-rated luxury holiday rentals in Chatham

Guests agree: these stays are highly rated for location, cleanliness and more.

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A spacious living area is highlighted by a large fireplace and a sleek television mounted above it. Comfortable seating arranged around a central coffee table invites relaxation. A leafy plant adds a touch of greenery, while natural light fills the space through nearby windows.

Home in Yarmouth Port

5 out of 5 average rating, 11 reviews

Cape Cod Family Vacation

This New Luxurious property for your vacation on Cape Cod , the house sleeping arrangements for 13-It's an Excellent choice for a family and a group of friends . Welcoming home has everything you'll need for a comfortable stay and relaxing vacation . Bring your family to enjoy the summer on Cape .

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.

A spacious luxury home is set against a clear blue sky, positioned just steps from the private beach. The exterior is characterized by light blue siding and large windows, with a wooden walkway leading to the sandy shore. Coastal grasses frame the scene.

Home in Barnstable

Life takes you down many paths,but my favorite one

Private beach Luxury rental home with hot tub and fire pit as well as 2-bedroom guest cottage. NEW for 2024. Lovely designer beach home.

An aerial view showcases a contemporary waterfront home surrounded by trees. The outdoor area includes a large pool, multiple lounge chairs, and an inviting stone patio. The house features numerous windows and sleek architectural lines, illuminated softly in the evening light.

Home in Barnstable

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.

An aerial view captures the spacious backyard featuring a private heated pool and spa, surrounded by manicured greenery. Lounge chairs are strategically placed around the pool area, providing ample space for relaxation. The exterior of the house showcases a blend of modern design and natural surroundings.

Home in Chatham

Sophisticated Chatham Oasis with Pool & Spa

5+ BED / 7 FULL 2 HALF BATH / PRIVATE HEATED POOL AND SPA / .3 MILES TO MAIN STREET CHATHAM

Home in Chatham

Prime Chatham Retreat with Pool, Spa & Style

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

Home in Harwich Port

4.74 out of 5 average rating, 27 reviews

Luxurious Estate, Private Heated pool!

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

Home in Chatham

Elevate Your Chatham Stay: Luxury w/ Pool & Beach

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

Home in East Dennis

Sesuit Neck Stunner w/ Heated Pool and Spa

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

The exterior of the home is showcased, highlighting a spacious heated saltwater pool surrounded by chaise loungers and umbrellas. Lush greenery and neatly arranged plants accentuate the space. A stone patio is visible, leading from the home to the pool, with ample outdoor dining options.

Home in Harwich

Exclusive Harwich Haven: Pool, Spa and More

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

The modern home is framed by a gravel driveway, with large windows reflecting the colorful sunset. Lush landscaping adds greenery to the exterior, complemented by a rooftop deck visible in the background. Elegant architectural lines create a striking silhouette against the evening sky.

Stunning Modern Masterpiece on the Beach in Truro

4 BED / 5.5 BATH / SLEEPS 12 / ON PRIVATE BEACH

The exterior of the home is shown, featuring a light-shingled façade with multiple gabled roofs. A welcoming front porch with blue accents leads to the entrance. The spacious driveway is lined with gravel, while well-kept grass and flower beds enhance the landscape.

Home in West Dennis

Tranquil Pond Oasis w/ Private Dock + B-Ball Court

4 BED, 3.5 BATH, SLEEPS 12, PONDFRONT w/ DOCK

Popular amenities for Chatham luxury holiday rentals

Free parking on premises

Air conditioning

Other great luxury holiday rentals in Chatham

A spacious luxury home is set against a clear blue sky, positioned just steps from the private beach. The exterior is characterized by light blue siding and large windows, with a wooden walkway leading to the sandy shore. Coastal grasses frame the scene.

Home in Barnstable

Life takes you down many paths,but my favorite one

An aerial view showcases a contemporary waterfront home surrounded by trees. The outdoor area includes a large pool, multiple lounge chairs, and an inviting stone patio. The house features numerous windows and sleek architectural lines, illuminated softly in the evening light.

Home in Barnstable

Luxury home with 2 pools on the water. RPMS081

Home in Harwich Port

4.74 out of 5 average rating, 27 reviews

Luxurious Estate, Private Heated pool!

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

A spacious living area is highlighted by a large fireplace and a sleek television mounted above it. Comfortable seating arranged around a central coffee table invites relaxation. A leafy plant adds a touch of greenery, while natural light fills the space through nearby windows.

Home in Yarmouth Port

5 out of 5 average rating, 11 reviews

Cape Cod Family Vacation

Home in Chatham

Prime Chatham Retreat with Pool, Spa & Style

The exterior of the home is showcased, highlighting a spacious heated saltwater pool surrounded by chaise loungers and umbrellas. Lush greenery and neatly arranged plants accentuate the space. A stone patio is visible, leading from the home to the pool, with ample outdoor dining options.

Home in Harwich

Exclusive Harwich Haven: Pool, Spa and More

Home in East Dennis

Sesuit Neck Stunner w/ Heated Pool and Spa

Destinations to explore