A pathway through tall grass with the sun setting in the background.
Photo by Jocey Hurt
Open Photo by Jocey Hurt

Bermuda Vacations from US$ 373

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The Latest Bermuda Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A swimming pool with a water slide, lounge chairs, and a basketball hoop.
    10 Dec - 14 Dec

    The Colonies at Williamsburg + Flight

    Williamsburg
    4 nights
    3.0 star property
    9.0/10 - Wonderful (1,228 reviews)
    Roundtrip • Orlando (MCO) - Richmond (RIC)
    MCO - RIC • Nonstop RIC - MCO • Nonstop
    US$ 509
    US$ 373
    per traveler
    found 1 day ago
    The Colonies at Williamsburg
  • A hotel with a swimming pool, outdoor seating, and a large building with multiple windows and a tower.
    10 Dec - 14 Dec

    Westgate Historic Williamsburg Resort + Flight

    Midtown
    4 nights
    3.5 star property
    8.6/10 - Excellent (1,000 reviews)
    Roundtrip • Orlando (MCO) - Richmond (RIC)
    MCO - RIC • Nonstop RIC - MCO • Nonstop
    US$ 883
    US$ 455
    per traveler
    found 1 day ago
    Westgate Historic Williamsburg Resort
  • A hotel with a covered entrance, a fountain, and a reflection pool.
    10 Dec - 14 Dec

    Holiday Inn Club Vacations Williamsburg Resort by IHG + Flight

    Williamsburg
    4 nights
    3.5 star property
    9.0/10 - Wonderful (606 reviews)
    Roundtrip • Orlando (MCO) - Richmond (RIC)
    MCO - RIC • Nonstop RIC - MCO • Nonstop
    US$ 781
    US$ 538
    per traveler
    found 1 day ago
    Holiday Inn Club Vacations Williamsburg Resort by IHG
  • A modern lobby with a glass-top table, comfortable seating, a brick fireplace, and a large window.
    10 Dec - 14 Dec

    Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel + Flight

    Colonial Williamsburg
    4 nights
    3.0 star property
    8.8/10 - Excellent (2,067 reviews)
    "Love the free breakfast. Lots of choices."
    Reviewed November 7, 2026
    Roundtrip • Orlando (MCO) - Richmond (RIC)
    MCO - RIC • Nonstop RIC - MCO • Nonstop
    US$ 630
    US$ 494
    per traveler
    found 1 day ago
    Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
  • A swimming pool with lounge chairs and a covered area, surrounded by buildings with a brick facade and a clear blue sky.
    10 Dec - 14 Dec

    Club Wyndham Governor’s Green + Flight

    Williamsburg
    4 nights
    3.0 star property
    9.2/10 - Wonderful (269 reviews)
    Roundtrip • Orlando (MCO) - Richmond (RIC)
    MCO - RIC • Nonstop RIC - MCO • Nonstop
    US$ 777
    US$ 620
    per traveler
    found 1 day ago
    Club Wyndham Governor’s Green

Discover the most popular places to visit in Bermuda

A traditional thatched-roof house surrounded by trees.

Henricus Historical Park

8.0/10 (63 reviews)
Explore the great outdoors at Henricus Historical Park, a lovely green space in Chester. You can attend a sporting event while in the area.
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Bermuda Hotel Deals

A modern dining area with hexagonal pendant lights, large windows, and a flat-screen TV on the wall.

SpringHill Suites Chester

SpringHill Suites Chester
2.5 star property
1.1 km from Bermuda
8.8 out of 10, Excellent, (930 reviews)
SpringHill Suites Chester
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.