Stay 30 - Vacation Rentals in Chatham Seaside Links

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From US $491

         

10.0 (116 Reviews)

House

Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

• Air Conditioner
• Parking
• TV

• Massachusetts
• Chatham

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From US $908

         

|

10.0 (6 Reviews)

House

1 Mile from Downtown Chatham Walk to Pier

• Air Conditioner
• Parking
• View

• Massachusetts
• Chatham

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From US $502

         

|

9.8 (212 Reviews)

Bed & Breakfast

Captain's House Inn

• Air Conditioner
• Parking
• TV

• Massachusetts
• Chatham

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From US $388

         

9.6 (24 Reviews)

House

Lovely Home Minutes from Beach in Chatham!

• Air Conditioner
• Parking
• TV

• Chatham
• West Chatham

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From US $713

         

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10.0 (3 Reviews)

House

Central AC Close to Beach Dog Friendly!

• Air Conditioner
• Parking
• Pet Friendly

• Chatham
• West Chatham

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From US $342

         

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9.6 (162 Reviews)

Bed & Breakfast

Old Harbor Inn

• Air Conditioner
• Parking
• TV

• Massachusetts
• Chatham

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From US $834

         

10.0 (129 Reviews)

House

Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach

• Air Conditioner
• Parking
• TV

• Massachusetts
• Chatham

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From US $499

         

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10.0 (3 Reviews)

House

Dreamcatcher

• Air Conditioner
• Balcony/Terrace
• Security/Safety

• Massachusetts
• Chatham

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From US $229

         

8.0 (159 Reviews)

Bed & Breakfast

Surfside Inn Chatham

• Air Conditioner
• Parking
• TV

• Massachusetts
• Chatham

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From US $675

         

10.0 (102 Reviews)

House

Walk to Chatham Main St., boutiques, restaurants, galleries, and nightlife!

• Air Conditioner
• Parking
• TV

• Massachusetts
• Chatham

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From US $523

         

10.0 (100 Reviews)

House

See the World Cup AND Enjoy a Chatham Vacation June 2026

• Air Conditioner
• Parking
• TV

• Chatham
• West Chatham

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From US $555

         

9.6 (55 Reviews)

House

Chatham-Walk to Ridgevale Beach, Pets Considered, Central Air, Bike Trail

• Air Conditioner
• Parking
• Pet Friendly

• Chatham
• West Chatham

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From US $390

         

10.0 (19 Reviews)

Cottage

Waterfront Chatham Retreat w/WiFi & Privacy

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Chatham

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From US $499

         

9.8 (46 Reviews)

House

Secluded Chatham Cape Cod House Stage Harbor Area

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Chatham

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From US $533

         

9.6 (8 Reviews)

House

The Cape Escape: Walk to Harding's Beach

• Air Conditioner
• Parking
• Pet Friendly

• Chatham
• West Chatham

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From US $289

         

9.4 (65 Reviews)

Apartment

Chatham Village: Large, Newly-Renovated 1 Bedroom Apartment in Antique Home

• Air Conditioner
• Parking
• TV

• Massachusetts
• Chatham

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From US $405

         

8.8 (27 Reviews)

House

Pet friendly home with central air (1998)

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Chatham

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From US $1,495

         

10.0 (6 Reviews)

House

Spend your quintessential Cape Cod vacation, in a beautifully renovated 1862 Farm House on Stage Harbor Road!

• Air Conditioner
• TV
• Balcony/Terrace

• Massachusetts
• Chatham

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From US $638

         

9.2 (5 Reviews)

House

Beautiful home overlooking Emery Pond

• Air Conditioner
• Pet Friendly
• TV

• Chatham
• West Chatham

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From US $1,075

         

10.0 (10 Reviews)

House

Charming Chatham Cottage!

• Air Conditioner
• Parking
• TV

• Massachusetts
• North Chatham

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From US $323

         

10.0 (170 Reviews)

Cottage

Chatham Seaside Cottage - Oceanfront Beach Cottage - Spectacular Views

• Air Conditioner
• Parking
• TV

• Chatham
• West Chatham

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From US $507

         

10.0 (119 Reviews)

House

Chatham walk to Cape Cod beach

• Air Conditioner
• Parking
• Pet Friendly

• Chatham
• West Chatham

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From US $769

         

10.0 (117 Reviews)

House

Water View-Walk town/beach, pets considered, Linen Option

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Chatham

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From US $218

         

10.0 (112 Reviews)

Apartment

Cape Cod Chatham Water View Retreat

• Air Conditioner
• Parking
• TV

• Massachusetts
• Chatham

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★ Pro Tip: Stay30 makes it easy to compare the best listings on Stay30 homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Stay30 homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Chatham Seaside Links.