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

Harborline Hotel
Price was $854, price is now $699 per person
$699
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Rockland (RKD)
7.6/10 Good! (309 reviews)
They continue to renovate the hotel, making small improvements along the way. Went to Hotels.com for reservation. When we got to hotel, our confirmed room was not what we asked for, after some time with desk person who did her best but was not able to do much, manager came in and made a switch with us. Cont. breakfast was weak. Can't beat the location, a great spot.
Reviewed on Aug 22, 2026

The Craignair Inn & Restaurant
Price was $1,133, price is now $974 per person
$974
per person
Oct 27 - Nov 1
found 23 hours ago
Roundtrip non-stop flight included
Chicago (CHI) 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
Price was $953, price is now $825 per person
$825
per person
Oct 27 - Nov 1
found 23 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Rockland (RKD)
9.4/10 Exceptional! (1,006 reviews)
What a pretty place! The minute I turned off the road I felt like I was in a village. I will be back the next time that I am in Maine.
Reviewed on Aug 22, 2026
Stay near popular Main Street attractions
Best Lodging Options Near Main Street

36 Main
36 Main Street Castine ME

Comfy Downtown Getaway w/ Full Kitchen - Close to the Beach
Castine ME

Downtown Studio w/ Full Kitchen & Shared Porch - Walk Everywhere in Town
Castine ME

Downtown Getaway w/ Full Kitchen & Furnished Porch - Walk to the Beach/Harbor
Castine ME

Pentagoet Inn
26 Main St Castine ME

Charming Antique Cape, Water View, Historic Castine, Penobscot Bay.
Castine ME

Gorgeous oceanfront Home overlooking Penobscot Bay , Castine Maine
Castine ME

Charming Castine Coastal Getaway – Harbor Views, History & Outdoor Adventure
Castine ME

Family-Friendly Castine Escape | Games, Kayaks & Views
Castine ME
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.
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