Drakes Island Holidays from £584
Book a Hotel + Flight or Car together to unlock savings
Top Drakes Island Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Portland Harbor Hotel
Downtown Portland
Price was £677, price is now £584 per person
£584
per person
7 Oct - 9 Oct
found 1 day ago
Return flight included
Orlando (MCO) to Portland (PWM)
9.4/10 Exceptional! (1,775 reviews)
Only 4 rooms that were having A/C problems. Of course we had one the rooms. If the A/C isn’t working, why continue to reserve the rooms and not just fix the A/C??? Front desk attendant Dennecia was wonderful and was able to get us moved for our last night in Portland. She made the experience enjoyable. She did as much as she could. Just not sure why the hotel couldn’t fix the A/C in the rooms with KNOWN issues.
Reviewed on 8 Jul 2026
Ogunquit River Inn & Suites
Moody
Price was £1,481, price is now £1,002 per person
£1,002
per person
28 Aug - 3 Sept
found 1 day ago
Return flight included
London (LON) to Portland (PWM)
9/10 Wonderful! (1,008 reviews)
The property was beautiful and the staff members were all really kind and helpful!
Reviewed on 11 Jul 2026
The Weldon Hotel
Downtown Portland
Price was £788, price is now £631 per person
£631
per person
7 Oct - 9 Oct
found 1 day ago
Return flight included
Orlando (MCO) to Portland (PWM)
9.8/10 Exceptional! (101 reviews)
Spacious with plenty of room for my family of four. Excellent kitchen, washer and dryer and stellar location close to Waterfront district.
Reviewed on 5 Jul 2026
The Docent's Collection at 121 Middle Street
Downtown Portland
Price was £766, price is now £649 per person
£649
per person
7 Oct - 9 Oct
found 1 day ago
Return flight included
Orlando (MCO) to Portland (PWM)
9.6/10 Exceptional! (345 reviews)
Great little boutique hotel. Walking distance to all the downtown Portland sites and restaurants. Large, modern rooms and very friendly and helpful staff. Would definitely stay here again.
Reviewed on 10 Jul 2026
Top hotels in Drakes Island
Ogunquit - The Milestone
687 Main Street Ogunquit ME
The price is £173 per night from 11 Aug to 12 Aug
£173
11 Aug - 12 Aug
includes taxes & fees
8.8/10 Excellent! (1,393 reviews)
"Absolutely cannot complain about anything at this property for the price. Very clean, staff was super friendly. Water pressure was amazing in the shower, super hot. It included a continental breakfast which I couldn’t even believe. The pool was sparkling clean. The only thing was the jacuzzi tub ..."
Reviewed on 11 Jul 2026
Anchorage Inn and Resort
265 Long Beach Avenue York Beach ME
The price is £308 per night from 22 Jul to 23 Jul
£308
22 Jul - 23 Jul
includes taxes & fees
9/10 Wonderful! (1,223 reviews)
"Excellent location right across from the beach. Hotel restaurant had great breakfast choices. Room was older but clean."
Reviewed on 10 Jul 2026
Ocean Surf at York Beach
780 York Street (Rte 1A) York Beach ME
The price is £380 per night from 10 Aug to 11 Aug
£380
10 Aug - 11 Aug
includes taxes & fees
9/10 Wonderful! (37 reviews)
"Our room had water damaged walls, dirty floors and an ant infestation. Pool and staff were good."
Reviewed on 10 Jul 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.
What to do in Drakes Island
Explore a world of travel with Expedia
* 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.
