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Bailey Island Vacation Packages

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Bailey Island featuring rugged coastline and a house

Bailey Island
Maine
United States of America
North America
Hotwire.com

Bailey Island Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.

Portland Harbor Hotel

4 out of 5

Price was $566, price is now $436 per person

$436

per person

Feb 13 - Feb 15

found 6 hours ago

Roundtrip flight included

Chicago (ORD) to Portland (PWM)

Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Cross Insurance Arena and Fore Street Gallery are located nearby.

The Kennebunk Inn

2.5 out of 5

Save 100% on your flight

Price was $587, price is now $447 per person

$447

per person

Mar 26 - Apr 1

found 4 hours ago

Roundtrip flight included

Chicago (ORD) to Portland (PWM)

Stay at this hotel in Kennebunk. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions Dock Square and Kennebunk Free Library are located nearby.

Blind Tiger Portland - Danforth Street.

3.5 out of 5

Price was $847, price is now $681 per person

$681

per person

Feb 13 - Feb 15

found 6 hours ago

Roundtrip flight included

Chicago (ORD) to Portland (PWM)

Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and concierge services. Popular attractions Victoria Mansion and Portland Club are located nearby.

Meadowmere Resort

2.5 out of 5

Save 100% on your flight

Price was $747, price is now $610 per person

$610

per person

Mar 26 - Apr 1

found 4 hours ago

Roundtrip flight included

Chicago (ORD) to Portland (PWM)

Book a stay at this spa hotel in Ogunquit. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Marginal Way and Ogunquit Beach are located nearby.

Portland Regency Hotel & Spa

3.5 out of 5

Price was $565, price is now $462 per person

$462

per person

Feb 13 - Feb 15

found 6 hours ago

Roundtrip flight included

Chicago (ORD) to Portland (PWM)

Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions N.W. Barrett Gallery and Fore Street Gallery are located nearby.

Inn By The Sea

4 out of 5

Price was $639, price is now $527 per person

$527

per person

Feb 13 - Feb 15

found 6 hours ago

Roundtrip flight included

Chicago (ORD) to Portland (PWM)

Book a stay at this luxury hotel in Cape Elizabeth. Enjoy free valet parking, a full-service spa, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Crescent Beach State Park and Crescent Beach are located nearby.

Cliff House Maine

4.5 out of 5

Price was $1,648, price is now $1,421 per person

$1,421

per person

Feb 12 - Feb 15

found 9 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) to Portland (PWM)

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 condition in our reviews. Popular attractions Perkins Cove and Marginal Way are located nearby.

The Docent’s Collection – Thompson Block

3.5 out of 5

Price was $581, price is now $506 per person

$506

per person

Mar 24 - Mar 26

found 9 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) to Portland (PWM)

Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Maine Sports Hall of Fame and Cathedral of the Immaculate Conception are located nearby.