Bailey Island Holidays from £1,263
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Your Bailey Island Holiday
With one of our holiday packages to Bailey Island, you'll have endless opportunities for relaxation and adventure. There's lots to experience, including its coastal scenery and spectacular views. If sightseeing is on the cards during your trip to Bailey Island, check out popular attractions like Bailey Island Bridge, Lands End Gift Shop and Ragged Island. A few quick clicks is all it takes to build a customised Bailey Island holiday on Expedia.
Top Bailey Island Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
The Docent's Collection at 121 Middle Street
Downtown Portland
Price was £2,431, price is now £1,966 per person
£1,966
per person
1 Jul - 7 Jul
found 17 hours ago
Return direct flight included
London (LON) to Portland (PWM)
9.6/10 Exceptional! (299 reviews)
Super easy to find, the apartment was very clean, the complimentary water and coffee were excellent! We loved our stay!!
Reviewed on 26 Apr 2026
The Weldon Hotel
Downtown Portland
Price was £2,474, price is now £2,071 per person
£2,071
per person
1 Jul - 7 Jul
found 17 hours ago
Return direct flight included
London (LON) to Portland (PWM)
9.8/10 Exceptional! (100 reviews)
Lovely suite! Comfy king bed, everything spotless,
Great location. Would stay here again
Reviewed on 23 Apr 2026
The Docent's Collection at 178 Middle Street
Downtown Portland
Price was £2,583, price is now £2,174 per person
£2,174
per person
1 Jul - 7 Jul
found 17 hours ago
Return direct flight included
London (LON) to Portland (PWM)
9.6/10 Exceptional! (10 reviews)
So lovely to be in a space big enough for four that felt more like “home” than hotel. Great location in Old Port. Friendly, responsive staff. Comfy beds. Amazing high ceilings and aesthetically minimalist. Looking forward to another stay.
Reviewed on 24 Apr 2026
Portland Regency Hotel & Spa
Downtown Portland
Price was £1,938, price is now £1,662 per person
£1,662
per person
1 Jul - 7 Jul
found 17 hours ago
Return direct flight included
London (LON) to Portland (PWM)
9.4/10 Exceptional! (1,630 reviews)
Enjoyed the hotel for a long weekend. Room was clean and very convenient. Fitness room and spa were nice additions. Staff very friendly, courteous, and prompt. Terrific location for navigating Portland. Would definitely stay again and recommend.
Reviewed on 29 Apr 2026
Bailey Island Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Portland Intl. Jetport Airport (PWM) |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 21ºC |
Top Sights | Thomas Point Beach, Maine State Music Theatre and Sand Beach |
Top hotels in Bailey Island
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is £160 per night from 3 May to 4 May
£160
3 May - 4 May
includes taxes & fees
9.2/10 Wonderful! (1,755 reviews)
We (and our kids!) loved the “pantry” on each floor — fruit, snacks, cookies, tea, coffee. It was a much-appreciated surprise. Room was clean and quiet, and all staff were friendly and helpful.
Reviewed on 29 Apr 2026
HomeAwhile
205 Southborough Drive Scarborough ME
Fully refundableReserve now, pay when you stay
The price is £101 per night from 27 May to 28 May
£101
27 May - 28 May
includes taxes & fees
9.2/10 Wonderful! (30 reviews)
Check in was a nightmare. Key machine did not work and it took over an hour to get in to a room where the key only worked once. After finally getting in I was assigned a different room as we couldn’t get the key to work.
Reviewed on 30 Apr 2026
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
Fully refundable
The price is £134 per night from 3 May to 4 May
£134
3 May - 4 May
includes taxes & fees
9.4/10 Exceptional! (1,201 reviews)
I could not have asked for a better hotel and room for my stay in Portland. This is now my second stay in a Cambria property and this stay was even better than my previous 5 star stay. Great location, walk to everything, the best restaurants, Old Town, the waterfront. The room was immaculate, spacious, ...
Reviewed on 29 Apr 2026
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
Find out about the history of Bailey Island with a stop at Bailey Island Bridge. Stroll along the seaside or seek out the hiking trails.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
