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 $654, price is now $499 per person
$499
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
10/10 Exceptional! (51 reviews)
Wonderful stay overall! My husband and I came up for a family reunion and greatly enjoyed the property and loved revisiting old stomping grounds. There was a tiny bit of confusion with the access codes as it was noted we were on the fourth floor in the email but we figured out quickly it was really the third floor. Smooth sailing from there and the condo was beautiful, clean and loved the amenities! Highly recommend and we looking forward to coming back soon!

Reviewed on Apr 14, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
Price was $2,370, price is now $1,686 per person
$1,686
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (1,002 reviews)
We had an amazing stay at Cliffhouse and were pleasantly surprised by how beautiful it is. The only minor issues we encountered were that the pullout couch was quite uncomfortable for our kids, and it was frustrating that children aren’t allowed in the main pool—everyone with kids ends up crowded around a small pool off to the side. Aside from that, everything else was fantastic!

Reviewed on Aug 9, 2025

Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Save 100% on your flight
Price was $1,503, price is now $1,085 per person
$1,085
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (608 reviews)
We stayed in one of the older / darker rooms. It had charm but in hindsight, I would have preferred the brighter rooms which were pictured on the website. A hot breakfast is included with one hot dish each morning as well as fruits and yogurt. One of our egg dishes was undercooked and the yogurt offered was underwhelming- most likely from store bought containers. It is a great location, walking distance to all of the restaurants, bars and shopping. We had our car so we were able to drive to other popular sites including the beach.

Reviewed on Aug 18, 2025

Popular places to visit

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

Ash Cove Pottery

Enjoy an outing to Ash Cove Pottery during your stay in Harpswell. Amble around the area's seaside, or seek out its hiking trails.

Ash Cove Pottery

Land's End Gift Shop

Enjoy an outing to Land's End Gift Shop during your stay in Bailey Island. While you're in the area, find time to visit its shops.

Land's End Gift Shop

Best Lodging Options Near Bailey Island Bridge

Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

Bailey Island
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage

Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage

Bailey Island
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage
Orchid Harbor, Bailey Island 3BR

Orchid Harbor, Bailey Island 3BR

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

Sunset Hideaway on Bailey Island

Harpswell
Sunset Hideaway on Bailey Island
Enjoy breathtaking sunsets from this newly renovated studio on Bailey Island

Enjoy breathtaking sunsets from this newly renovated studio on Bailey Island

Bailey Island
Enjoy breathtaking sunsets from this newly renovated studio on Bailey Island
The Beach House Bailey Island Maine

The Beach House Bailey Island Maine

Harpswell
The Beach House Bailey Island Maine
Ocean Watch - Relax and let the ocean sweep you away at this charming retreat

Ocean Watch - Relax and let the ocean sweep you away at this charming retreat

Orr's Island
Ocean Watch - Relax and let the ocean sweep you away at this charming retreat
Beautifully landscaped, Spacious home, conveniently located in Harpswell

Beautifully landscaped, Spacious home, conveniently located in Harpswell

Bailey Island
Beautifully landscaped, Spacious home, conveniently located in Harpswell
The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home

The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home

Bailey Island
The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home
See all 647 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.