Bailey Island Vacation Packages 2025/2026 from $762

Bailey Island flight + hotel vacation packages

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

The Docent's Collection

Downtown Portland

Save 100% on your flight

per person

Oct 27 - Oct 31

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) 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.

The Weldon Hotel

Downtown Portland

Save 100% on your flight

per person

Oct 27 - Oct 31

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) to Portland (PWM)

A 24-hour gym, self parking, and a virtual front desk are featured at this aparthotel. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. Free WiFi in public areas is also provided.

Portland Harbor Hotel

Downtown Portland

Save 100% on your flight

per person

Oct 8 - Oct 13

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) 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.

Cliff House Maine

Save 100% on your flight

per person

Sep 18 - Sep 21

found 1 day ago

Roundtrip flight included

Cleveland (CLE) 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.

Kennebunkport Captains Collection

Save 100% on your flight

per person

Oct 27 - Oct 31

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) to Portland (PWM)

This hotel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free continental breakfast each morning. A garden, luggage storage, and concierge services are also on offer.

Top Bailey Island hotels deals

Days Inn by Wyndham Airport/Maine Mall

461 Maine Mall Rd, South Portland, ME

$116 nightly

$127 total

Aug 20 - Aug 21

Total includes taxes and fees

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

Clarion Hotel Portland

1230 Congress St, Portland, ME

Free Cancellation

Reserve now, pay when you stay

$152 nightly

$168 total

Aug 25 - Aug 26

Total includes taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Enjoy the hot tub and perks like free self parking and a free cruise terminal shuttle.

Pool

Hot Tub

Germaine Inn South Portland

675 Main Street I-95, Rt 1-I95 ex 45-I295 Ex 3, South Portland, ME

Free Cancellation

$97 nightly

$106 total

Aug 25 - Aug 26

Total includes taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and WiFi in public areas. Enjoy the indoor pool and free perks like continental breakfast and free self parking.

Pool

Breakfast included

Ramada Plaza by Wyndham Portland

155 Riverside St, Portland, ME

$131 nightly

$145 total

Sep 2 - Sep 3

Total includes taxes and fees

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

Comfort Inn Airport

90 Maine Mall Rd, South Portland, ME

Free Cancellation

Reserve now, pay when you stay

$130 nightly

$142 total

Sep 14 - Sep 15

Total includes taxes and fees

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and a free airport shuttle. Traveling on business? Take advantage of the express check-out, laundry service, and free train station pick-up. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Breakfast included

Free airport shuttle

La Quinta Inn & Suites by Wyndham Portland

340 Park Ave, Portland, ME

$143 nightly

$158 total

Sep 2 - Sep 3

Total includes taxes and fees

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

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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

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 $762. 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.