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Oswego Island

Bermuda, Atlantic Ocean

$1,609 USD Per Night

Welcome to Oswego Island – a serene haven nestled between St. Davids Island and Smith's Island in the tranquil waters of Smith's Sound in the Atlantic Ocean. This 3.2-acre private retreat invites you to immerse yourself in the simple pleasures of island living.

Unveiling the Oswego House, a 3000 sq. ft masterpiece designed by the acclaimed architect Jacob Hocking of CTX. This three-bedroom dwelling seamlessly marries traditional Bermudian architecture with contemporary design, creating a harmonious space that invites the island breeze to dance through its open-plan layout. A minimum week's stay is recommended to fully savor the tranquility of Oswego Island.

Island Overview:

Your exclusive island experience begins with the newly constructed Oswego House, a boat shed, a southern-facing dock with a spacious floating dock, and a northern-facing dock – both offering deepwater access. The lush 3.2-acre island is adorned with mature vegetation, ensuring complete privacy and a serene ambiance. Meandering garden paths and grass terraces provide shaded retreats to embrace the natural habitat.

Oswego House:

Discover Oswego House, a thoughtfully designed retreat featuring open-plan living spaces, cozy bedrooms with ensuite bathrooms, and a games room. The kitchen, adorned with modern lines, boasts an oversized island, perfect for casual family-style dining. The tower's unique architectural detail allows natural light to cascade through the home. The highlight? Folding glass walls that seamlessly merge the interior with the outdoor porch, ideal for entertaining or enjoying the island's fresh air.

Culinary Delights:

Choose between self-provisioning and self-catering or indulge in pre-stocked, prepared, or catered meals by a personal chef, available upon pre-arrangement. Tailor your stay to your preferences – contact us for more details on these additional services.


Water taxi pick-up from the airport is available exclusively for Oswego Island through our exclusive partnership with Honey Badger Express. Nighttime boating is not recommended, and life jackets are mandatory. Land transportation options include buses and taxis, with tours available upon arrangement.

Along with your rental, we've got you covered with a small boat for your use. Alternatively, bring your own boat and dock at the island's deepwater dock, accommodating vessels 100 ft and larger for an additional fee covering power and amenities.

Other Essentials:

Housekeeping at the end of your stay is included, with additional services available upon pre-arrangement. Complimentary boat tours, recreational equipment instruction, and a tour and orientation of Oswego Island are provided at the beginning of your stay.


Indulge in this island paradise with rates starting at $1609 per night plus 4.5% gov tax and $350 service/cleaning fee. or $9,999 per week (7 nights) plus 4.5% gov tax and $350 service/cleaning fee. A minimum stay of 3 nights is required, accommodating 3 couples and 2 children. Additional cots are available upon request. Rates include electricity, local calls, gardening, boat service, orientation, and weekly maid service.


Whether you seek adventure or relaxation, Oswego Island has it all. Engage in snorkeling, sailing, kayaking, or simply bask in the sun on the dock. The active types can enjoy reef fishing, deep-sea/sport fishing, and water sports with pre-arrangement. For the little ones, explore the island, engage in water-based activities, and discover a variety of amenities in the boat shed.

Escape to Oswego Island – where the beauty of Bermuda meets contemporary comfort, creating an unforgettable island retreat.

  • Acres: 3.2
  • Bedrooms: 3
  • Bathrooms: 3


  • self-service
  • family
  • weddings


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