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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.

Hampton Inn Portland Downtown - Waterfront

2.5 out of 5

Price was $382, price is now $304 per person

$304

per person

Feb 6 - Feb 9

found 18 hours ago

Roundtrip flight included

Dallas (DAL) to Portland (PWM)

Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.

Portland Harbor Hotel

4 out of 5

Save 100% on your flight

Price was $493, price is now $317 per person

$317

per person

Feb 6 - Feb 9

found 18 hours ago

Roundtrip flight included

Dallas (DAL) to Portland (PWM)

Stay at this 4-star business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.

The Docent's Collection - New Opening

2 out of 5

Save 100% on your flight

Price was $774, price is now $520 per person

$520

per person

Jan 22 - Jan 26

found 20 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Portland (PWM)

Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and daily housekeeping. Popular attractions Thompson's Point and Maine Mall are located nearby.

Cliff House Maine

4.5 out of 5

Save 100% on your flight

Price was $1,330, price is now $928 per person

$928

per person

Feb 6 - Feb 9

found 18 hours ago

Roundtrip non-stop flight included

Dallas (DAL) to Portland (PWM)

Stay at this 4.5-star 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 Ogunquit Beach and Perkins Cove are located nearby.

River View Resort

2.5 out of 5

Price was $597, price is now $457 per person

$457

per person

Jan 30 - Feb 2

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Portland (PWM)

Stay at this motel in Bethel. Enjoy free WiFi, free parking, and 4 outdoor pickleball courts. Our guests praise the helpful staff in our reviews. Popular attractions Sunday River and Bethel Pathway are located nearby.

The Docent's Collection

3.5 out of 5

Save 100% on your flight

Price was $665, price is now $512 per person

$512

per person

Jan 22 - Jan 26

found 20 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Portland (PWM)

Stay at this 3.5-star hotel in Portland. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Thompson's Point and Maine Mall are located nearby.

Blind Tiger Portland - Danforth Street.

3.5 out of 5

Save 100% on your flight

Price was $787, price is now $610 per person

$610

per person

Jan 22 - Jan 26

found 20 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Portland (PWM)

Stay at this 3.5-star B&B in Portland. Enjoy free breakfast, free WiFi, and concierge services. Popular attractions Thompson's Point and Maine Mall are located nearby.

Snowvillage Inn

4 out of 5

Price was $540, price is now $430 per person

$430

per person

Jan 30 - Feb 2

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Portland (PWM)

Stay at this 4-star beach B&B in Eaton Center. Enjoy free WiFi, free parking, and a garden. Popular attractions King Pine Ski Area and Conway Lake are located nearby.