Bailey Island Vacation Packages 2025 from $668

Bailey Island flight + hotel vacation packages

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

River View Resort

Save 100% on your flight

per person

Sep 5 - Sep 10

found 9 hours ago

Roundtrip non-stop flight included

Omaha (OMA) to Portland (PWM)

This motel features an indoor pool and a gym. Enjoy the hot tub and perks like free self parking and free WiFi. Enjoy the sauna and conveniences like a terrace and barbecue grills.

The Docent's Collection

Downtown Portland

Save 100% on your flight

per person

Aug 28 - Aug 31

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Portland (PWM)

This hotel features free WiFi in public areas, a virtual front desk, and self parking. Express check-out and dry cleaning are also provided.

Chebeague Island Inn

per person

Aug 28 - Aug 31

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Portland (PWM)

A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate perks like free WiFi and a free ferry terminal shuttle. A garden, a lobby fireplace, and a picnic area are also on offer.

Portland Harbor Hotel

Downtown Portland

per person

Aug 28 - Aug 31

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Portland (PWM)

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.

Dormir

per person

Aug 28 - Aug 31

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Portland (PWM)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

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

Hyatt Place Portland Downtown - Old Port Square

433 Fore St, Portland, ME

Free Cancellation

Reserve now, pay when you stay

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This hotel features 2 bars/lounges and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. A restaurant, a 24-hour front desk, and a coffee shop are also provided.

Free airport shuttle

Pet friendly

Days Inn by Wyndham Airport/Maine Mall

461 Maine Mall Rd, South Portland, ME

Free Cancellation

Reserve now, pay when you stay

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This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Guests will appreciate freebies like continental breakfast and free self parking.

Pool

Breakfast included

Ramada Plaza by Wyndham Portland

155 Riverside St, Portland, ME

Free Cancellation

Reserve now, pay when you stay

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2 hot tubs, an indoor pool, and a gym are all featured at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy a meal from the a restaurant and perks like free self parking.

Pool

Hot Tub

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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 $668. 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.