Drakes Island Vacation Packages for 2026

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Top Hotel Deals

Anchorage Inn and Resort

Anchorage Inn and Resort

3 out of 5
265 Long Beach Avenue York Beach ME
19.42 km from Drakes Island
Book a stay at this beach hotel in York Beach. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
Ogunquit - The Milestone

Ogunquit - The Milestone

2 out of 5
687 Main Street Ogunquit ME
7.57 km from Drakes Island
Book a stay at this business-friendly motel in Ogunquit. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the pool in ...
Cliff House Maine

Cliff House Maine

4.5 out of 5
591 Shore Road Cape Neddick ME
11.97 km from Drakes Island
Book a stay at this luxury resort in Cape Neddick. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the helpful staff and the property ...
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
17 Post Road Ogunquit ME
6.99 km from Drakes Island
Book a stay at this business-friendly hotel in Ogunquit. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Terrace by the Sea

Terrace by the Sea

2.5 out of 5
23 Wharf Ln Ogunquit ME
9.38 km from Drakes Island
Stay at this hotel in Ogunquit. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Grand Beach Inn

Grand Beach Inn

3 out of 5
198 East Grand Avenue Old Orchard Beach ME
27.77 km from Drakes Island
Stay at this hotel in Old Orchard Beach. Enjoy free WiFi, free parking, and room service. Our guests praise the restaurant and the helpful staff in our reviews. ...
Anchor Inn and Cottages Wells-Ogunquit

Anchor Inn and Cottages Wells-Ogunquit

2.5 out of 5
424 Post Rd Wells ME
5.66 km from Drakes Island
Stay at this motel in Wells. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
Anchorage by the Sea

Anchorage by the Sea

3 out of 5
125 Shore Road Ogunquit ME
9.65 km from Drakes Island
Book a stay at this business-friendly hotel in Ogunquit. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the property ...
Ogunquit Tides Resort

Ogunquit Tides Resort

2 out of 5
548 Main Street (U.S. Route 1) Ogunquit ME
8.23 km from Drakes Island
Book a stay at this beach motel in Ogunquit. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the pool in our reviews. ...
Waves Oceanfront Resort

Waves Oceanfront Resort

3 out of 5
87 W Grand Ave Old Orchard Beach ME
24.82 km from Drakes Island
Book a stay at this beach hotel in Old Orchard Beach. Enjoy free parking, an outdoor pool, and a beach locale. Our guests praise the helpful staff and the clean ...
Ocean Surf at York Beach

Ocean Surf at York Beach

3 out of 5
780 York Street (Rte 1A) York Beach ME
20.39 km from Drakes Island
Book a stay at this beach motel in York Beach. Enjoy free WiFi, breakfast (surcharge), and parking (surcharge). Our guests praise the pool and the helpful staff ...
Old Orchard Beach Inn

Old Orchard Beach Inn

2.5 out of 5
6 Portland Ave Old Orchard Beach ME
25.62 km from Drakes Island
Stay at this B&B in Old Orchard Beach. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. ...
Port Inn & Suites Kennebunk, an Ascend Collection Hotel

Port Inn & Suites Kennebunk, an Ascend Collection Hotel

2.5 out of 5
55 York St Kennebunk ME
5.95 km from Drakes Island
Stay at this motel in Kennebunk. Enjoy free breakfast, an outdoor pool, and WiFi (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
The Colony Hotel

The Colony Hotel

3 out of 5
140 Ocean Ave Kennebunkport ME
7.02 km from Drakes Island
Book a stay at this business-friendly hotel in Kennebunkport. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our ...
Wells-Ogunquit Resort Motel & Cottages

Wells-Ogunquit Resort Motel & Cottages

2.5 out of 5
203 Post Road Wells ME
6.38 km from Drakes Island
Book a stay at this business-friendly hotel in Wells. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
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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.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Breeze Airways
Wed, Sep 2 - Wed, Sep 16
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$157 Roundtrip, found 3 days ago
$157
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Wed, Sep 2 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Wed, Sep 16, priced at $157 found 3 days ago
JetBlue Airways
Thu, Jul 9 - Tue, Jul 14
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$157 Roundtrip, found 21 hours ago
$157
Roundtrip
found 21 hours ago
Select JetBlue Airways flight, departing Thu, Jul 9 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Tue, Jul 14, priced at $157 found 21 hours ago
American Airlines
Tue, Sep 8 - Fri, Sep 11
LGA
LaGuardia
PWM
Portland Intl. Jetport
$181 Roundtrip, found 4 days ago
$181
Roundtrip
found 4 days ago
Select American Airlines flight, departing Tue, Sep 8 from LaGuardia to Portland Intl. Jetport, returning Fri, Sep 11, priced at $181 found 4 days ago
Delta
Tue, Sep 8 - Fri, Sep 11
LGA
LaGuardia
PWM
Portland Intl. Jetport
$181 Roundtrip, found 4 days ago
$181
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Sep 8 from LaGuardia to Portland Intl. Jetport, returning Fri, Sep 11, priced at $181 found 4 days ago
United
Tue, Sep 8 - Fri, Sep 11
LGA
LaGuardia
PWM
Portland Intl. Jetport
$185 Roundtrip, found 4 days ago
$185
Roundtrip
found 4 days ago
Select United flight, departing Tue, Sep 8 from LaGuardia to Portland Intl. Jetport, returning Fri, Sep 11, priced at $185 found 4 days ago