A rocky coastline with a clear blue sky and calm sea.

Hermit Island Vacations from $358

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Hermit Island Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Terrace/patio
    Dec 11 - Dec 13

    Admiral Peary Inn + Flight

    Fryeburg
    2 nights
    3.0 star property
    8.8/10 - Excellent (70 reviews)
    "Very unique and fun history."
    Reviewed October 27, 2026
    Roundtrip • Orlando (MCO) - Portland (PWM)
    MCO - BOS • 1 stop PSM - MCO • 1 stop
    $436
    $358
    per traveler
    found 1 day ago
    Admiral Peary Inn
  • A traditional living room with a fireplace, red sofa, patterned chairs, and a coffee table with books and magazines.
    Dec 11 - Dec 13

    Waldo Emerson Inn + Flight

    Kennebunk
    2 nights
    3.0 star property
    9.4/10 - Exceptional (357 reviews)
    "Our stay at the Waldo Emerson was nothing short of exceptional! From the moment we arrived, Amelia welcomed us with warm hospitality, and every detail of this charming property made us feel right at home. The accommodations were comfortable and full of character, and the property itself is absolutely beautiful. Each morning, we looked forward to a delicious, fresh, and thoughtfully prepared breakfast that was the perfect start to our day. What truly made our experience special were the..."
    Reviewed October 18, 2026
    Roundtrip • Orlando (MCO) - Portland (PWM)
    MCO - BOS • Nonstop PSM - MCO • 1 stop
    $654
    $551
    per traveler
    found 1 day ago
    Waldo Emerson Inn
  • A fire pit surrounded by wicker chairs in a garden setting.
    Dec 18 - Dec 21

    Portland Harbor Hotel + Flight

    Downtown Portland
    3 nights
    4.0 star property
    9.2/10 - Wonderful (1,865 reviews)
    "Location A+ with easy to walk to shops and restaurants. Bedroom was clean and had great wooden armoire, small refrigerator. Bathroom seemed clean but lighting very low. Water pressure could be improved. All in all a great place to stay."
    Reviewed November 6, 2026
    Roundtrip • Atlanta (ATL) - Portland (PWM)
    ATL - BOS • Nonstop BOS - ATL • 1 stop
    $566
    $486
    per traveler
    found 15 hours ago
    Portland Harbor Hotel
  • A backyard with a fire pit, wooden chairs, and a house with a porch.
    Dec 18 - Dec 21

    Inn By The Sea + Flight

    Cape Elizabeth
    3 nights
    4.0 star property
    9.6/10 - Exceptional (345 reviews)
    Roundtrip • Atlanta (ATL) - Portland (PWM)
    ATL - BOS • Nonstop BOS - ATL • 1 stop
    $715
    $617
    per traveler
    found 15 hours ago
    Inn By The Sea
  • A spacious living room with a large window, a round coffee table, and two wooden chairs.
    Dec 18 - Dec 21

    The Docent's Collection at 178 Middle Street + Flight

    Downtown Portland
    3 nights
    3.5 star property
    9.6/10 - Exceptional (86 reviews)
    "room was very modern, however some areas did not look well cleaned (edge if the bed had some dried white liquid). the surrounding area has nice shops but is very sketchy at night. did not feel comfortable with the parking situation. also at 6am sounded like maintenance or cleaning crew was constantly in and out of the elevator making tons of noise. was good for a night but wouldnt stay again."
    Reviewed October 27, 2026
    Roundtrip • Atlanta (ATL) - Portland (PWM)
    ATL - BOS • Nonstop BOS - ATL • 1 stop
    $787
    $685
    per traveler
    found 14 hours ago
    The Docent's Collection at 178 Middle Street

Hermit Island Hotel Deals

A spacious living area with a curved staircase, a round glass coffee table, and a seating arrangement.

The Federal

The Federal
3.5 star property
14.2 mi from Hermit Island
9.6 out of 10, Exceptional, (700 reviews)
$84 nightly
The price is $92
Nov 22 - Nov 23
Total with taxes and fees
The Federal
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.
See all properties in Hermit Island
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.