Bailey Island Bridge Tours

Some bridges could be the tallest, oldest or longest and may take trains, vehicles or pedestrians. Find out what sets Bailey Island Bridge apart and the long history behind it.

This longstanding structure in Bailey Island is popular with travelers, so make sure it features on your travel plans. Don't think that's all there is to do here, though. There are plenty more spots ready for you to explore after Bailey Island Bridge. Casco Bay, Land's End Gift Shop, and Paddleworks are not far away.

Plan a trip to see Bailey Island Bridge

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

84 Main

4 out of 5
Price was $845, price is now $650 per person
$650
per person
Mar 19 - Mar 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
10/10 Exceptional! (52 reviews)
Very spacious and relaxing. Nice view of Kennebunk quaint ice rink and Main Street. Coffee shop at Street level was a fantastic add! Beds and bedding were comfortable. Will visit again! Nothing lacking with respect to amenities.

Reviewed on Dec 29, 2025

The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,216, price is now $862 per person
$862
per person
Apr 18 - Apr 25
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
9.6/10 Exceptional! (249 reviews)
Room was very clean, neat vibe, tons of space! Made coming back from

Reviewed on Jan 23, 2026

The McKernan Inn

The McKernan Inn

3 out of 5
Price was $1,018, price is now $779 per person
$779
per person
Mar 19 - Mar 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
9/10 Wonderful! (83 reviews)
Gorgeous grounds and venue with a beautiful oceanfront view. Plenty of parking as part of SMCC campus. Short drive to downtown Portland and lots of stores around in South Portland. Very unique experience, would stay again without hesitation!

Reviewed on Dec 27, 2025

Popular places to visit

Two brown horses standing by a gate in a meadow on Wolfe Island, Ontario, Canada

Wolfe's Neck Farm

Explore the great outdoors at Wolfe's Neck Farm, a lovely green space in Freeport. Stroll along the area's seaside or simply enjoy its seafood restaurants.

Wolfe's Neck Farm
Osprey Nesting Grounds, Googins Island, Wolfe's Neck State Park, Freeport, Maine

Wolfe's Neck Woods State Park

You can take time to visit Wolfe's Neck Woods State Park during your travels to Freeport. Stroll along the area's seaside or simply enjoy its seafood restaurants.

Wolfe's Neck Woods State Park
Bradbury Mountain State Park featuring a small town or village, fall colors and landscape views

Bradbury Mountain State Park

Reach the summit of a mountain, have a picnic and count soaring hawks at this pretty park, one of Maine’s five original state parks.

Bradbury Mountain State Park
Harrington House

Harrington House

Delve into the history of southern Maine and life in the 19th century at this intriguing and well-preserved home in Freeport.

Harrington House

Cobwork Bridge

You can find out about the history of Bailey Island when you stop by Cobwork Bridge. Stroll along the seaside or seek out the hiking trails.

Cobwork Bridge

Paddleworks

Enjoy an outing to Paddleworks during your stay in Orrs Island. Wander the seaside and beaches in the area.

Paddleworks

Best Lodging Options Near Bailey Island Bridge

Orchid Harbor, Bailey Island 3BR

Orchid Harbor, Bailey Island 3BR

Harpswell ME
Orchid Harbor, Bailey Island 3BR
Sunset Hideaway on Bailey Island

Sunset Hideaway on Bailey Island

Harpswell ME
Sunset Hideaway on Bailey Island
Great location on Bailey Island

Great location on Bailey Island

Harpswell ME
Great location on Bailey Island
The Beach House Bailey Island Maine

The Beach House Bailey Island Maine

Harpswell ME
The Beach House Bailey Island Maine
Beautifully landscaped, Spacious home, conveniently located in Harpswell

Beautifully landscaped, Spacious home, conveniently located in Harpswell

Bailey Island ME
Beautifully landscaped, Spacious home, conveniently located in Harpswell
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

Bailey Island ME
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
Enjoy Stunning Ocean Views & Coastal Access at Sea Mist Overlook!

Enjoy Stunning Ocean Views & Coastal Access at Sea Mist Overlook!

Harpswell ME
Enjoy Stunning Ocean Views & Coastal Access at Sea Mist Overlook!
Classic 3 bedroom cape on the stunning coast of Maine, sleeps 8 people

Classic 3 bedroom cape on the stunning coast of Maine, sleeps 8 people

Harpswell ME
Classic 3 bedroom cape on the stunning coast of Maine, sleeps 8 people
Lowell's Getaway. Kayaking, beaches, dining and AC from this water view home.

Lowell's Getaway. Kayaking, beaches, dining and AC from this water view home.

Harpswell ME
Lowell's Getaway. Kayaking, beaches, dining and AC from this water view home.
See all 652 properties in Bailey Island Bridge
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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