Vacations Close To Old Gaol
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Old Gaol Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Portland Regency Hotel & Spa
Downtown Portland
Save 100% on your flight
Price was $2,560, price is now $1,982 per person
$1,982
per person
Oct 18 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Portland (PWM)
The location was ideal for shopping and sight seeing. We love the breakfast and dinners at the hotel.
Reviewed on Sep 6, 2026
Inn By The Sea
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Price was $2,575, price is now $2,003 per person
$2,003
per person
Oct 18 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Portland (PWM)
Lovely property. Very well maintained and taken care of. The option of pool or beach is a plus. Although we didn’t utilize the activities available each day.. it seemed very family friendly. Definitely will be back but hopefully reserve a bigger room or suite. Charming outdoor seating on the huge lawn but mostly in the sun. An indoor lobby with some comfy seating would be great.
Reviewed on Aug 13, 2026
Kennebunkport Captains Collection
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Price was $2,234, price is now $1,792 per person
$1,792
per person
Oct 18 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Portland (PWM)
It was a charming and authentic historic stay in a great location close to everything. The staff were super friendly and helpful. And the bed was divinely comfortable!
Reviewed on Sep 6, 2026
Best Lodging Options Near Old Gaol
Ocean Sands at York Beach
277 Long Beach Avenue York Beach ME
2.76 km from Old Gaol
Book a stay at this beach motel in York Beach. Enjoy an outdoor pool, parking (surcharge), and a garden. Our guests praise the pool and the helpful staff in ...
Anchorage Inn and Resort
265 Long Beach Avenue York Beach ME
2.9 km from Old Gaol
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. ...
Ocean Surf at York Beach
780 York Street (Rte 1A) York Beach ME
2.26 km from Old Gaol
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 ...
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.