Sears Island Vacations from $719

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The Latest Sears Island vacation packages

Price found within the past 48 hours. Click for updated prices.
Harborline Hotel

Harborline Hotel

$719
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTT) to Rockland (RKD)
7.6/10 Good! (309 reviews)
Nice. Easy walking to shops and Park Street Grill across the street with great food and music

Reviewed on Aug 11, 2026

Homeport Inn and Tavern

Homeport Inn and Tavern

$827
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTT) to Rockland (RKD)
9.6/10 Exceptional! (300 reviews)
The owners were the most delightful couple who made my stay so delightful. This historical inn was absolutely stunning, each room more amazing than the last. I highly recommend the Homeport Inn!!

Reviewed on Aug 12, 2026

Trade Winds on the Bay

Trade Winds on the Bay

$722
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTT) to Rockland (RKD)
8.6/10 Excellent! (444 reviews)
The Craignair Inn & Restaurant

The Craignair Inn & Restaurant

$956
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTT) to Rockland (RKD)
9.2/10 Wonderful! (200 reviews)
We love the Craignair and this was our second visit. The staff are all wonderful and so accommodating. Our arrival was a bit rough because there was private event taking place, so we had to wait until the bartender found someone to check us in and then it felt a bit like we weren't supposed to be in the common areas until the event concluded. No big deal, but we might have planned differently had we known ahead of time that this was the case. Wait staff were a bit loud one night after dinner service, but quieted down when we asked. Still, I am impressed at how relaxed and homey the place feels even in high summer when tourists are everywhere. We had previously stayed in November and kind of had it to ourselves, so we were definitely spoiled by that experience, but were amazed at how peaceful it was even during the busy season. Loved hiking Craig Island and watching the birds and the waves every morning and evening from our balcony or the dining area. This place is truly a gem.

Reviewed on Aug 9, 2026

Glen Cove Inn & Suites

Glen Cove Inn & Suites

$755
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTT) to Rockland (RKD)
9.4/10 Exceptional! (1,006 reviews)
Room had many bugs, socks left behind by previous guest, floors very dirty. Wood smells in room and there is mold in bathroom due to no ventilation and fan not working. Rooms need upgrading.

Reviewed on Aug 11, 2026

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What to do in Sears Island

Private Family Treasure Hunter in Belfast

Belfast Family Treasure Hunt

$349
per traveler
Belfast Family Treasure Hunt
See all activities in Sears Island

Sears Island Hotel Deals

Colonial Gables Oceanfront Village

Colonial Gables Oceanfront Village

7 Eagle Avenue Belfast ME
Fully refundableReserve now, pay when you stay
$160 nightly
$174 total
Sep 7 - Sep 8
Total with taxes and fees
9.6/10 Exceptional! (1,004 reviews)
"Amazing place! Amenities and views are lovely. Staff kind and helpful!"

Reviewed on Aug 12, 2026

Colonial Gables Oceanfront Village
Belfast Harbor Inn

Belfast Harbor Inn

91 Searsport Ave Belfast ME
Fully refundableReserve now, pay when you stay
$169 nightly
$184 total
Aug 30 - Aug 31
Total with taxes and fees
9.6/10 Exceptional! (1,012 reviews)
"The staff was very helpful and courteous, the entire hotel (pools, hot tub, grounds, lobby, etc,,) was well-maintained and beautiful. Breakfast was excellent with good variety. What made it extra nice was having it while overlooking the water on the patio. The room was clean. The only negative I ..."

Reviewed on Aug 12, 2026

Belfast Harbor Inn
Fireside Inn & Suites - Belfast

Fireside Inn & Suites - Belfast

159 Searsport Avenue Belfast ME
Fully refundableReserve now, pay when you stay
$157 nightly
$171 total
Aug 31 - Sep 1
Total with taxes and fees
9/10 Wonderful! (1,028 reviews)
"Amazing hotel No need for the most expensive room. Anything on 3rd floor is amazing Stayed 3 times this summer and stay every year"

Reviewed on Aug 10, 2026

Fireside Inn & Suites - Belfast
See all 1,017 properties in Sears Island
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.

Find the Best Sears Island Vacation Packages

Sears Island Essential Information

Language
English
Currency
U.S dollars

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