From The Clouds to The Cape

From The Clouds to The Cape

Travel in luxury, style and convenience as you're whisked away on a one-way or roundtrip private Tradewind charter flight to Chatham Airport from locations including Boston, Philadelphia, Bedford, Teterboro, Westchester and more paired with a luxurious overnight stay at Chatham Bars Inn. As soon as the wheels touch the ground, a complimentary Lexus shuttle will bring you to the Inn, which is just a 10-minute drive from Chatham Airport. During the drive, you'll relax while enjoying a bottle of chilled champagne, bypass check-in upon arrival and be escorted directly to your room or suite.

The starting price for a one-way route and one-night stay in a deluxe room is $5,500+ tax. Guests will also have the option to book a charter as an add-on to an existing overnight reservation at Chatham Bars Inn.

For details or to reserve, please call the Chatham Bars Inn Reservations Team directly at 800-527-4884.

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Named One of the World's Most Legendary Hotels by Forbes Travel Guide Hotel Icons List

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#1 Resort in Massachusetts in the 2025 Condé Nast Traveler's Readers' Choice Awards

The image shows a badge for "Best Waterfront Hotel/Resort" from USA Today 10Best Readers' Choice 2024, awarded to Chatham Bars Inn.

#1 Best Waterfront Hotel/Resort in the USA TODAY 2024 10Best Readers' Choice Travel Awards

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#1 Best Waterfront Restaurant in the USA TODAY 2025 & 2026 10Best Readers' Choice Travel Awards – Beach House Grill

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Forbes Travel Guide 2025 Hotel Icon. Recognized as one of 6 hotels in the US and 23 hotels worldwide.

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