Bailey Island, ME

Travel Guide

Bailey Island featuring rugged coastline and a house
Bailey Island showing general coastal views
Bailey Island which includes general coastal views
Bailey Island showing signage
Bailey Island which includes a bay or harbor as well as an individual femail
The Westin Portland Harborview
The Westin Portland Harborview
4 out of 5
157 High St, Portland, ME
The price is AED 749 per night from Jun 30 to Jul 1
AED 749
AED 841 total
includes taxes & fees
30 Jun - 1 Jul
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the bar and the helpful staff in ...
8.8/10 Excellent! (1,000 reviews)
"The weather was not great, so we spent more time than we thought in our room - comfortable, great layout for hanging out"

Reviewed on 25 May 2025

The Westin Portland Harborview
Portland Regency Hotel & Spa
Portland Regency Hotel & Spa
3.5 out of 5
20 Milk Street, Portland, ME
The price is AED 876 per night from Jun 3 to Jun 4
AED 876
AED 969 total
includes taxes & fees
3 Jun - 4 Jun
Stay at this 3.5-star spa hotel in Portland. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
9.2/10 Wonderful! (1,274 reviews)
"Beautiful property! Within walking distance of a lot of dining and shopping. Great location, easy to get to. Staff is super friendly and helpful. Enjoyed our stay here!"

Reviewed on 29 May 2025

Portland Regency Hotel & Spa
Portland Harbor Hotel
Portland Harbor Hotel
4 out of 5
468 Fore Street, Portland, ME
The price is AED 890 per night from Jun 16 to Jun 17
AED 890
AED 1,124 total
includes taxes & fees
16 Jun - 17 Jun
Stay at this 4-star business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the bar and the ...
9/10 Wonderful! (1,505 reviews)
"Everything was so unique! It was quick stay but we loved the style, friendly staff and delicious pastries in the morning:) plus the fire pit was just too perfect at the end of our day!"

Reviewed on 30 May 2025

Portland Harbor Hotel
See all 1,785 properties in Bailey Island
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.
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
Bailey Island
Stay at this cottage in Bailey Island. Enjoy a garden, laundry facilities, and patios. Popular attractions Land's End Gift Shop and Casco Bay are located ...
9.8/10 Exceptional! (75 reviews)
Great spot. Refreshing to stay in a real house!
"We sat and watched a major winter storm outside the window. Very exciting from within a cozy house. We enjoyed staying in a house where you could feel somebody's presence, rather than the "accessorized" vacation homes with welcoming signs from the Dollar store etc. Only thing lacking--place needs ..."

Reviewed on 1 March 2025

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
The Weldon Hotel
The Weldon Hotel
4.5 out of 5
54 York St, Portland, ME
Stay at this 4-star aparthotel in Portland. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions Thompson's Point and Maine ...
9.6/10 Exceptional! (60 reviews)
1st floor “apartment style” hotel room
"A great space,enjoyed having a full kitchen situated close to the popular restaurant and nightlife."

Reviewed on 25 May 2025

The Weldon Hotel
Oceanfront Cottage w/ Deck 2 Mi to Boothbay Harbor
Oceanfront Cottage w/ Deck 2 Mi to Boothbay Harbor
3 out of 5
West Boothbay Harbor
Stay at this 3-star beach cottage in West Boothbay Harbor. Enjoy free parking, a garden, and balconies. Popular attractions Juniper Point and Maine State Aquarium ...
Oceanfront Cottage w/ Deck 2 Mi to Boothbay Harbor
See all properties in Bailey Island
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.

Popular places to visit

Bailey Island Bridge

4.5/5(9 reviews)

Find out about the history of Bailey Island when you spend time at Bailey Island Bridge. Stroll along the seaside or seek out the hiking trails.

Bailey Island Bridge

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

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