Bailey Island Vacation Packages 2025 from $462

Bailey Island flight + hotel vacation packages

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

Best Western Freeport Inn

per person

Aug 15 - Aug 19

found 3 hours ago

Roundtrip flight included

Dallas (DFW) to Portland (PWM)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. There's a seasonal outdoor pool on site, and a 24-hour front desk and express check-out are also provided.

Cliff House Maine

Save 100% on your flight

per person

Jul 20 - Jul 27

found 19 hours ago

Roundtrip flight included

Dallas (DFW) to Portland (PWM)

A full-service spa, 2 restaurants, and an indoor pool are all featured at this smoke-free resort. Traveling on business? Take advantage of the business center, laundry service, and valet parking. Relax with a drink at one of the 2 poolside bars and enjoy perks like free self parking.

Nautical Mile

per person

Aug 30 - Sep 2

found 9 hours ago

Roundtrip non-stop flight included

Minneapolis (MSP) to Portland (PWM)

A seasonal outdoor pool is featured at this aparthotel, along with free self parking. A picnic area and a computer station are also provided.

Blind Tiger Portland - Danforth Street.

West End

Save 100% on your flight

per person

Jul 20 - Jul 24

found 1 day ago

Roundtrip flight included

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

This bed & breakfast doesn't skimp on freebies - guests receive free breakfast and free WiFi. Luggage storage and concierge services are also provided.

Blind Tiger Portland – Carleton Street

West End

Save 100% on your flight

per person

Aug 8 - Aug 11

found 5 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Portland (PWM)

This bed & breakfast features free WiFi in public areas, concierge services, and free self parking. Enjoy the free local cuisine breakfast each morning. A terrace and a garden are also provided.

Top Bailey Island hotels deals

BAILEY ISLAND MOTEL

2041 Harpswell Islands Rd, Bailey Island, ME

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This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A seasonal outdoor pool is also provided.

Pool

Parking included

La Quinta Inn & Suites by Wyndham Portland

340 Park Ave, Portland, ME

Free Cancellation

Reserve now, pay when you stay

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This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and a free airport shuttle. Business travelers can take advantage of the business center. Enjoy the seasonal outdoor pool and conveniences like a 24-hour front desk and laundry facilities.

Pool

Breakfast included

The Westin Portland Harborview

157 High St, Portland, ME

Free Cancellation

Reserve now, pay when you stay

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A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a bar/lounge on site, and laundry facilities and concierge services are also provided.

Spa

Pet friendly

Inn at St John Portland In-Town

939 Congress St, Portland, ME

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This bed & breakfast features free WiFi in public areas, concierge services, and free self parking. Enjoy the free continental breakfast each morning. A lobby fireplace, a computer station, and luggage storage are also on offer.

Breakfast included

Pet friendly

Canopy by Hilton Portland Waterfront

9 Center Street, Portland, ME

Free Cancellation

Reserve now, pay when you stay

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This hotel features 2 restaurants and a 24-hour gym. WiFi in public areas is free. Valet parking, a lobby fireplace, and a communal living room are also offered.

Pet friendly

Free WiFi

Portland Harbor Hotel

468 Fore Street, Portland, ME

Free Cancellation

Reserve now, pay when you stay

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This hotel features 3 coffee shops/cafes and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll find a restaurant and a bar/lounge onsite for dining and drinks, along with a 24-hour front desk.

Pet friendly

Free WiFi

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See all available properties in Bailey Island

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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.

Popular places to visit

Bailey Island Bridge

4.5/5(9 reviews)

Find out about the history of Bailey Island when you spend time at Bailey Island Bridge. Stroll along the seaside or seek out the hiking trails.

Land's End Gift Shop

Enjoy an outing to Land's End Gift Shop during your stay in Bailey Island. While you're in the area, find time to visit its shops.

Cobwork Bridge

You can find out about the history of Bailey Island when you stop by Cobwork Bridge. Stroll along the seaside or seek out the hiking trails.

Frequently asked questions

How much are vacation packages to Bailey Island?

Vacation packages, which provide both flights and hotels in Bailey Island, start at just $462. Make your travel fantasies come to life and secure your vacation with Travelocity today.

Where can I get the best vacation package deals for Bailey Island?

With around 400 partner airlines and 1,000,000 properties across the globe, you can’t beat Travelocity. Browse our comprehensive range and score an incredible Bailey Island package deal. Don’t you love it when travel is that easy?

Why should I book my Bailey Island vacation bundle with Travelocity?

With exceptional service, customer support available 24/7 and some of the most perfect escapes on offer, you’ll never wander alone. And if you find a better price, we’ll match it. That’s our Price Match Guarantee.

Can I save money on my Bailey Island car rental if I bundle it with my hotel or flight?

Bundling your bookings into a Bailey Island vacation package will leave you with a nice chunk of spare change. You can bundle a car and flight; a hotel, flight and car; or a hotel and car. You won’t find a better way to explore the greater Bailey Island region than with your own ride. You can also add experiences and tours to your Travelocity package.