Sears Island Vacation Packages 2026 from $439

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The Latest Sears Island vacation packages

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

Trade Winds on the Bay

$439

per person

Nov 13 - Nov 17

found 13 hours ago

Roundtrip non-stop flight included

Greensboro (GSO) to Rockland (RKD)

8.6/10 Excellent! (468 reviews)

Harborline Hotel

$464

per person

Nov 13 - Nov 17

found 13 hours ago

Roundtrip non-stop flight included

Greensboro (GSO) to Rockland (RKD)

7.4/10 Good! (367 reviews)

Staff wouldn’t come out of the office to answer a question. Also didn’t have a blow dryer.

Reviewed on Sep 17, 2026

The Craignair Inn & Restaurant

$732

per person

Nov 13 - Nov 17

found 13 hours ago

Roundtrip non-stop flight included

Greensboro (GSO) to Rockland (RKD)

9.2/10 Wonderful! (201 reviews)

Glen Cove Inn & Suites

$567

per person

Nov 13 - Nov 17

found 13 hours ago

Roundtrip non-stop flight included

Greensboro (GSO) to Rockland (RKD)

9.4/10 Exceptional! (1,007 reviews)

Elegant Ocean View Home With Breathtaking Views, Private hot tub & Large Deck

Save 100% on your flight

$3,820

per person

Nov 13 - Nov 17

found 13 hours ago

Roundtrip non-stop flight included

Greensboro (GSO) to Rockland (RKD)

No reviews

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What to do in Sears Island

Private Family Treasure Hunter in Belfast

Belfast Family Treasure Hunt

$349

per traveler

See all activities in Sears Island

Sears Island Hotel Deals

Belfast Harbor Inn

91 Searsport Ave Belfast ME

Fully refundableReserve now, pay when you stay

$169 nightly

$184 total

Sep 28 - Sep 29

Total with taxes and fees

9.6/10 Exceptional! (1,001 reviews)

"Beautiful place! Rooms were clean and spacious! Breakfast was fabulous!! All the staff were kind and helpful! Highly recommend!"

Reviewed on Sep 19, 2026

Colonial Gables Oceanfront Village

7 Eagle Avenue Belfast ME

Fully refundableReserve now, pay when you stay

$149 nightly

$162 total

Oct 19 - Oct 20

Total with taxes and fees

9.6/10 Exceptional! (1,009 reviews)

"The room was clean and the beds and pillows were comfy. The HVAC was almost silent so we slept well. The back porch overlooking the water was relaxing. We appreciated the hot cider and freshly baked cookies upon our arrival. The front desk and staff were gracious and helpful. It is small and no frills ..."

Reviewed on Sep 18, 2026

Fireside Inn & Suites - Belfast

159 Searsport Avenue Belfast ME

Fully refundableReserve now, pay when you stay

$163 nightly

$177 total

Oct 19 - Oct 20

Total with taxes and fees

9/10 Wonderful! (1,006 reviews)

"Lovely balcony, big rooms, easy parking, very friendly staff, great food and state park nearby, and best of all — dog friendly hotel!!"

Reviewed on Sep 18, 2026

See all 992 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.