A lakeside town with autumn-colored trees, a church, and a large white building with a green roof.

Bear Island Vacations from $706

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The Latest Bear Island Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A covered porch with two rocking chairs facing a sunset view.
    Dec 14 - Dec 17

    The Ballard House Inn + Flight

    Meredith
    3 nights
    3.5 star property
    9.8/10 - Exceptional (335 reviews)
    "The home was quaint the old setting were very nice I like antique and the host was very friendly and made eggs Benedict for breakfast the experience was nice will most likely go back next year."
    Reviewed November 8, 2026
    Roundtrip • Oklahoma City (OKC) - Concord (CON)
    OKC - BOS • 1 stop BOS - OKC • 1 stop
    $738
    $706
    per traveler
    found 17 hours ago
    The Ballard House Inn
  • A covered patio with wicker furniture and large windows offering views of a red building and greenery.
    Dec 19 - Dec 23

    Chestnut Inn + Flight

    Sandwich
    4 nights
    2.0 star property
    Roundtrip • Chicago (ORD) - Laconia (LCI)
    ORD - MHT • 1 stop MHT - ORD • 1 stop
    $1,251
    $1,105
    per traveler
    found 1 hour ago
    Chestnut Inn
  • A living room with a fireplace, a blue armchair, a red sofa, and a coffee table.
    Dec 19 - Dec 23

    Meredith Inn + Flight

    Meredith
    4 nights
    2.0 star property
    10/10 - Exceptional (176 reviews)
    Roundtrip • Chicago (ORD) - Concord (CON)
    ORD - MHT • 1 stop MHT - ORD • 1 stop
    $841
    $781
    per traveler
    found 3 hours ago
    Meredith Inn

Bear Island Hotel Deals

A Holiday Inn Express building with a covered entrance and multiple floors.

Holiday Inn Express Hotel & Suites Tilton - Lakes Region by IHG

Holiday Inn Express Hotel & Suites Tilton - Lakes Region by IHG
2.5 star property
15.3 mi from Bear Island
9.4 out of 10, Exceptional, (1,003 reviews)
"Had a great stay!"
$105 nightly
The price is $114
Nov 29 - Nov 30
Total with taxes and fees
Holiday Inn Express Hotel & Suites Tilton - Lakes Region by IHG
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 Bear Island
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.