Drakes Island Holidays from £888
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Top Drakes Island Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
84 Main
Price was £1,093, price is now £888 per person
£888
per person
13 Mar - 20 Mar
found 22 hours ago
Return direct flight included
London (LHR) to Portland (PWM)
10/10 Exceptional! (52 reviews)
Very spacious and relaxing. Nice view of Kennebunk quaint ice rink and Main Street. Coffee shop at Street level was a fantastic add! Beds and bedding were comfortable. Will visit again! Nothing lacking with respect to amenities.
Reviewed on 29 Dec 2025
The Weldon Hotel
Downtown Portland
Price was £1,302, price is now £1,155 per person
£1,155
per person
13 Mar - 20 Mar
found 22 hours ago
Return direct flight included
London (LHR) to Portland (PWM)
9.8/10 Exceptional! (86 reviews)
Location is excellent. Short walking distance to every good restaurant and shop. The property was very nice and clean. The kitchen is very well equipped. The gym is very good sized for the size of the apartment building with 13 units in it. The management’s communication was prompt and friendly and responded to all of our wishes. However, the place is advertised as a hotel, but don’t expect services as in a hotel. It resembles more a short term rental home - no cleaning service and no lobby. Otherwise everything was very nice in the apartment and we had a great time.
Reviewed on 3 Jan 2026
Kennebunkport Captains Collection
Price was £1,347, price is now £1,222 per person
£1,222
per person
13 Mar - 20 Mar
found 22 hours ago
Return direct flight included
London (LHR) to Portland (PWM)
9.4/10 Exceptional! (649 reviews)
The breakfast menu was fresh. The staff is friendly, helpful, and fantastic. Walkable to many things downtown for food but do note that many restaurants close during winter (off-season). Loved it! Would stay again.
Reviewed on 3 Jan 2026
Top hotels in Drakes Island
Anchorage Inn and Resort
265 Long Beach Avenue York Beach ME
The price is £79 per night from 9 Feb to 10 Feb
£79
9 Feb - 10 Feb
includes taxes & fees
8.8/10 Excellent! (1,063 reviews)
Outstanding staff response (assistance in operating the in room electronics and front desk attitude were commendable). Rooms were spotless.
Reviewed on 3 Feb 2026
Cliff House Maine
591 Shore Road Cape Neddick ME
The price is £441 per night from 26 Feb to 27 Feb
£441
26 Feb - 27 Feb
includes taxes & fees
9.4/10 Exceptional! (1,000 reviews)
Nearly everything was perfect at this hotel. Quality of the facilities, friendly staff, good restaurants, beautiful spa, all of it. The only minor negative was that there was live music in the lobby that was a little too loud one day. The musician was great, but it made it a little tough to enjoy ...
Reviewed on 31 Jan 2026
Old Orchard Beach Inn
6 Portland Ave Old Orchard Beach ME
Fully refundableReserve now, pay when you stay
8.2/10 Very Good! (957 reviews)
Beautiful quaint hotel. Clean rooms
Reviewed on 3 Jan 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
Old Marsh Country Club
Enjoy a round of golf in Wells at Old Marsh Country Club. Wander the beautiful beaches and seaside in the area.
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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.
