Sears Island Vacations from $516
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Sears Island Vacation Packages
Price found within the past 48 hours. Click for updated prices.
- Glen Cove Inn & Suites
Sep 14 - Sep 17Glen Cove Inn & Suites + Flight
Rockport3 nights2.5 star property9.4/10 - Exceptional (1,004 reviews)"Wonderful and welcoming "old school" motel on the Rockport/Rockland border. Beautiful trees and greenery insulate the property from the road noise of Route 1. Our room had a back porch looking out on trees and flowers. Friendly staff welcomed us, and greeted us again for our free and delicious breakfast on the breezy cool porch of the main house. My wife and I will stay here again on our next trip to Maine. Five Stars!"Reviewed July 18, 2026Roundtrip • Boston (BOS) - Rockland (RKD)BOS - RKD • Nonstop RKD - BOS • Nonstop$583$516found 1 day agoper traveler - Trade Winds on the Bay
Sep 14 - Sep 17Trade Winds on the Bay + Flight
Rockland3 nights3.5 star property8.6/10 - Excellent (431 reviews)"This was the second time we stayed here. The check in was easy and the man at the check in desk was very friendly and very polite. It’s a great location. The bed was comfortable and the room was very clean."Reviewed July 20, 2026Roundtrip • Boston (BOS) - Rockland (RKD)BOS - RKD • Nonstop RKD - BOS • Nonstop$647$534found 1 day agoper traveler - Harborline Hotel
Sep 14 - Sep 17Harborline Hotel + Flight
Rockland3 nights3.0 star property7.6/10 - Good (294 reviews)"Staff pleasant and we liked the use of codes rather than keys for doors. Location was ideal The one major detractor was noise if people walking in room above us. Just the walking across floor by whomever was upstairs was vexing at times."Reviewed July 19, 2026Roundtrip • Boston (BOS) - Rockland (RKD)BOS - RKD • Nonstop RKD - BOS • Nonstop$662$576found 1 day agoper traveler - The Craignair Inn & Restaurant
Sep 14 - Sep 17The Craignair Inn & Restaurant + Flight
Spruce Head3 nights3.5 star property9.2/10 - Wonderful (200 reviews)"Synday brunch was very good"Reviewed December 22, 2025Roundtrip • Boston (BOS) - Rockland (RKD)BOS - RKD • Nonstop RKD - BOS • Nonstop$718$637found 1 day agoper traveler - Bee Hive Cottage, Romantic Maine Waterfront Cottag
Sep 27 - Oct 2Bee Hive Cottage, Romantic Maine Waterfront Cottag + Flight
Cushing5 nights2.0 star propertyRoundtrip • Houston (HOU) - Rockland (RKD)IAH - RKD • 1 stop RKD - IAH • 2 stops$2,263$2,064found 1 day agoper traveler
Sears Island Hotel Deals
Colonial Gables Oceanfront Village
Colonial Gables Oceanfront Village2.5 star property
4.5 mi from Sears Island
9.6 out of 10, Exceptional, (1,009 reviews)
9.6/10
Exceptional
(1,009 reviews)
"Beautiful view!"
$165 nightly
The price is $180
$180 total
Jul 21 - Jul 22
Total with taxes and fees
9.2 out of 10, Wonderful, (120 reviews)
9.2/10
Wonderful
(120 reviews)
"A charming 75 year old inn. The room was comfortable, beautiful flowers on the property added to its charm. A very nice room and patio available for continental breakfast."
$153 nightly
The price is $167
$167 total
Jul 21 - Jul 22
Total with taxes and fees
9.6 out of 10, Exceptional, (1,002 reviews)
9.6/10
Exceptional
(1,002 reviews)
$214 nightly
The price is $233
$233 total
Jul 28 - Jul 29
Total with taxes and fees
9.6 out of 10, Exceptional, (297 reviews)
9.6/10
Exceptional
(297 reviews)
"This place was a delight! The room was great, we loved the pool room and breakfast was simple but perfect. Staff was really friendly and helpful too when I asked for a recommendation."
$225 nightly
The price is $245
$245 total
Jul 21 - Jul 22
Total with taxes and fees
10.0 out of 10, Exceptional, (65 reviews)
10/10
Exceptional
(65 reviews)
"Such a fun unique property. Like going to some camp. Every detail was well thought out. Campfire with s'mores in the evening... No problem. The cotton little breakfast was great.. Even homemade bagels."
$172 nightly
The price is $188
$188 total
Aug 16 - Aug 17
Total with taxes and fees
Fireside Inn & Suites - Belfast
Fireside Inn & Suites - Belfast3.0 star property
4.9 mi from Sears Island
9.0 out of 10, Wonderful, (1,003 reviews)
9.0/10
Wonderful
(1,003 reviews)
"It was a very nice property. I especially liked the big grassy area and the deck in the back lawn"
$185 nightly
The price is $202
$202 total
Jul 21 - Jul 22
Total with taxes and fees
10.0 out of 10, Exceptional, (136 reviews)
10/10
Exceptional
(136 reviews)
"The owners Ginny & Lori were very hospitable and accommodating. They made sure I was able to get whatever I needed. They served a delicious home-cooked breakfast each morning in their tastefully decorated dining room. The entire property is very warm and inviting and filled with rich history. I will be going back again!!"
$183 nightly
The price is $200
$200 total
Jul 27 - Jul 28
Total with taxes and fees
9.6 out of 10, Exceptional, (155 reviews)
9.6/10
Exceptional
(155 reviews)
$184 nightly
The price is $200
$200 total
Jul 28 - Jul 29
Total with taxes and fees
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.
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.