Main Street Tours and Activities
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Price found within the past 48 hours. Click for updated prices.
Trade Winds on the Bay
Price was CA $1,158, price is now CA $1,071 per person
CA $1,071
per person
Aug 17 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rockland (RKD)
8.6/10 Excellent! (417 reviews)
Ok, nice view, horrible coffee, no windows, no screen on door, door didn't fully close, would not recommend
Reviewed on Jun 30, 2026
Glen Cove Inn & Suites
Price was CA $1,152, price is now CA $1,086 per person
CA $1,086
per person
Aug 17 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rockland (RKD)
9.4/10 Exceptional! (1,005 reviews)
Have stayed twice now at Glen Cove Inn with my family and once again we enjoyed every minute of it. The staff is super friendly. Our room was spotless and comfortable. The pool was clean and well taken care off. The breakfast on the deck was really great with a nice variety to choose from and the coffee was nice and hot. We will definitely stay again in the future.
Reviewed on Jun 29, 2026
Harborline Hotel
Price was CA $1,341, price is now CA $1,297 per person
CA $1,297
per person
Aug 17 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rockland (RKD)
7.6/10 Good! (274 reviews)
There was little to no hot water during our stay. The front desk staff assured us a manager would be in touch, but that never happened.
Reviewed on Jun 28, 2026
Stay near popular Main Street attractions
Best Lodging Options Near Main Street
Check availability on hotels close to Main Street
Comfy Downtown Getaway w/ Full Kitchen - Close to the Beach
Castine ME
Downtown Getaway w/ Full Kitchen & Furnished Porch - Walk to the Beach/Harbor
Castine ME
Downtown Studio w/ Full Kitchen & Shared Porch - Walk Everywhere in Town
Castine ME
Friendly home with our separate condos & free WiFi in the heart of downtown
Castine ME
Comfortable Getaway for Two w/ Kitchenette - Right in the Heart of Downtown
Castine ME
Pentagoet Inn
26 Main St Castine ME
Tiny home with Loft-Boho by the sea under the stars
Castine ME
Charming Antique Cape, Water View, Historic Castine, Penobscot Bay.
Castine ME
Gorgeous oceanfront Home overlooking Penobscot Bay , Castine Maine
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.