Bailey Island Hotels

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check Bailey Island hotel prices

Tomorrow night
This weekend
Next weekend

Filter by

Guest rating
Guest rating
Property class

Top 10 trending Bailey Island hotels

Portland Harbor Hotel
4.0 star property
9.2 out of 10, Wonderful, (1400)
"The hotel is wonderful. They seemed very short on staff. Coffee and tea stations were sparsely stocked. Always out of coffee. The menu for dinner at the restaurant could be greatly improved and have a few more offerings. The breakfast staff was inexperienced and very understaffed. Other than that everything was great, as usual"
The price is €168
includes taxes & fees
3 Dec - 4 Dec
Portland Harbor Hotel
Howard Johnson Hotel by Wyndham South Portland
2.0 star property
7.2 out of 10, Good, (1001)
"Pillows were comfortable "
The price is €78
includes taxes & fees
1 Dec - 2 Dec
Howard Johnson Hotel by Wyndham South Portland
Holiday Inn Portland-By the Bay, an IHG Hotel
3.0 star property
8.8 out of 10, Excellent, (1076)
"Excellent experience"
The price is €95
includes taxes & fees
1 Dec - 2 Dec
Holiday Inn Portland-By the Bay, an IHG Hotel
Canopy by Hilton Portland Waterfront
4.0 star property
9.4 out of 10, Exceptional, (837)
"Staff was awesome, property was in excellent condition, check in and out couldn't have been easier. Had a little trouble with the light switches in the room, but may have been operator error."
The price is €120
includes taxes & fees
3 Dec - 4 Dec
Canopy by Hilton Portland Waterfront
Clarion Hotel Portland
2.5 star property
7.8 out of 10, Good, (1003)
"Room is large and very clean. The bathroom layout isn't great for two people bit it works."
The price is €83
includes taxes & fees
4 Dec - 5 Dec
Clarion Hotel Portland
Inn at St John Portland In-Town
2.5 star property
8.8 out of 10, Excellent, (1064)
"The whole building is very unique. It’s almost like a maze. It’s very bright there’s a lot of art in the hallways. The bathrooms are extremely clean."
The price is €94
includes taxes & fees
24 Nov - 25 Nov
Inn at St John Portland In-Town
Hilton Garden Inn Portland Downtown Waterfront
3.0 star property
9.2 out of 10, Wonderful, (1001)
"Everything great. Wonderful staff!"
The price is €108
includes taxes & fees
8 Dec - 9 Dec
Hilton Garden Inn Portland Downtown Waterfront
Portland Regency Hotel & Spa
3.5 star property
9.4 out of 10, Exceptional, (1235)
"The hotel was beautiful and the room very cozy. "
The price is €176
includes taxes & fees
4 Dec - 5 Dec
Portland Regency Hotel & Spa
Hyatt Place Portland-Old Port
3.0 star property
8.8 out of 10, Excellent, (1038)
"Place was fantastic "
The price is €135
includes taxes & fees
16 Dec - 17 Dec
Hyatt Place Portland-Old Port
Cambria Hotel Portland Downtown-Old Port
3.0 star property
9.2 out of 10, Wonderful, (701)
"Had a wonderful stay here. Room and property are very clean,the staff was very friendly and helpful. Great location in town, easily walkable to many restaurants and shops."
The price is €138
includes taxes & fees
4 Dec - 5 Dec
Cambria Hotel Portland Downtown-Old Port
The Westin Portland Harborview
4.0 star property
8.8 out of 10, Excellent, (1001)
"Excellent every time. "
The price is €94
includes taxes & fees
22 Dec - 23 Dec
The Westin Portland Harborview
La Quinta Inn & Suites by Wyndham Portland
2.5 star property
9.0 out of 10, Wonderful, (2017)
"I enjoyed my stay, room was quiet, slept well 4 nights!!! Only downside was skimpy breakfast compared to la quinta in Harrisburg earlier on our trip."
The price is €86
includes taxes & fees
22 Dec - 23 Dec
La Quinta Inn & Suites by Wyndham Portland
Quality Inn & Suites
2.5 star property
7.0 out of 10, Good, (1002)
"Convenient location good bang for buck continental breakfast and coffee great staff I stay here Everytime I'm in portland"
The price is €71
includes taxes & fees
24 Nov - 25 Nov
Quality Inn & Suites
Aloft Portland Downtown Waterfront ME
3.0 star property
8.8 out of 10, Excellent, (781)
"Staff so friendly! Hotel was alittle noisy but otherwise great location and very comfortable bed! "
The price is €93
includes taxes & fees
3 Dec - 4 Dec
Aloft Portland Downtown Waterfront ME
Hampton Inn Portland Downtown - Waterfront
2.5 star property
8.8 out of 10, Excellent, (1000)
"Clean room. Easy check-in. "
The price is €107
includes taxes & fees
22 Dec - 23 Dec
Hampton Inn Portland Downtown - Waterfront
AC Hotel by Marriott Portland Downtown/Waterfront, ME
3.5 star property
9.2 out of 10, Wonderful, (1002)
"Staff was great and room was beautiful "
The price is €116
includes taxes & fees
15 Dec - 16 Dec
AC Hotel by Marriott Portland Downtown/Waterfront, ME
Casco Bay Inn
2.0 star property
8.6 out of 10, Excellent, (1002)
"Liked everything except the walls are thin."
The price is €83
includes taxes & fees
24 Nov - 25 Nov
Casco Bay Inn
Longfellow Hotel
3.5 star property
9.0 out of 10, Wonderful, (44)
"Excellent. Brand new hotel with attentive staff and nice rooms. Pleasant bar and good size and amenities. If anything was wrong, it’s a little off the main drag with some odd and rundown neighbors. "
The price is €229
includes taxes & fees
28 Nov - 29 Nov
Longfellow Hotel
Best Western Merry Manor Inn
2.5 star property
8.8 out of 10, Excellent, (1002)
"Perfect spot for all my needs "
The price is €106
includes taxes & fees
8 Dec - 9 Dec
Best Western Merry Manor Inn
The Press Hotel, Marriott Autograph Collection
4.0 star property
9.4 out of 10, Exceptional, (910)
"We loved the spaciousness of the room and the ambiance of the lobby. I just wanted to kick back with a coffee and book. We also loved the restaurant attached. Favorite meal we had in Portland."
The price is €138
includes taxes & fees
8 Dec - 9 Dec
The Press Hotel, Marriott Autograph Collection
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.
Don't see what you're looking for?
See all available properties in Bailey Island
Save an average of 15% on thousands of hotels when you're signed in

Frequently asked questions

What's the best place to stay in Bailey Island?

Located 18.3 mi (29.5 km) from the heart of Bailey Island, Casco Bay Hotel, Ascend Hotel Collection is a top choice for your stay, based on our traveller data. Other good choices for your visit to the area are Portland Harbor Hotel and The Westin Portland Harborview. See all available top hotels, or vacation rentals in Bailey Island.

What are some of the best holiday rentals that Bailey Island has to offer?

Elegant condo - walk to Portland's best restaurants & Old Port: This holiday home rental outside of Bailey Island is in the city centre, and equipped with air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. See all vacation rentals in Bailey Island.

If I need to cancel my hotel reservation in Bailey Island, will I receive a refund?

Yes! Most hotel bookings are refundable if you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of your arrival date. If you have a reservation that's non-refundable, you might be able to still cancel and receive a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Bailey Island.

What are some accommodation options with pools in Bailey Island?

La Quinta Inn & Suites by Wyndham Portland: Hotel located near Thompson's Point. Features daily, a seasonal outdoor pool and free self parking. Days Inn by Wyndham Airport/Maine Mall and Holiday Inn Portland-By the Bay, an IHG Hotel are a couple of other choices that feature an on-site pool. View all hotels with pools in Bailey Island.

What is staying in Bailey Island like?

Visitors can enjoy all that Bailey Island has to offer, including the shopping, seafood restaurants and local tours. Tourists can also enjoy so much more including its monuments. In Bailey Island, there are 71 hotels and other accommodation options to choose from. Find out more about Bailey Island.

What should I do while I'm visiting Bailey Island?

Landmarks like Bailey Island Bridge and Cobwork Bridge might be worth a visit. A couple of additional sights to add to your itinerary are Land's End Gift Shop and Ragged Island. Take a look at what more there is to see and do in Expedia's Bailey Island guide.

What's the weather like in Bailey Island?

The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Bailey Island are January, April, March and February, with each month seeing an average of 24 cm of snowfall.