Bailey Island Vacation Packages 2025 from $626

Bailey Island flight + hotel vacation packages

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

Admiral Peary Inn

Save 100% on your flight

per person

Jul 17 - Jul 23

found 9 hours ago

Roundtrip non-stop flight included

Austin (AUS) to Portland (PWM)

This bed & breakfast 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. A coffee shop, a garden, and a snack bar/deli are also on offer.

River View Resort

Save 100% on your flight

per person

Jul 17 - Jul 23

found 9 hours ago

Roundtrip non-stop flight included

Austin (AUS) 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.

White Barn Inn & Spa, Auberge Resorts Collection

Save 100% on your flight

per person

Aug 14 - Aug 17

found 14 hours ago

Roundtrip non-stop flight included

Minneapolis (MSP) to Portland (PWM)

A full-service spa, 2 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and airport shuttle. Enjoy the seasonal outdoor pool and perks like free valet parking.

Nautical Mile

Save 100% on your flight

per person

Jul 28 - Aug 1

found 1 day ago

Roundtrip 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.

Hilton Garden Inn Portland Airport

Save 100% on your flight

per person

Jul 16 - Jul 22

found 1 day ago

Roundtrip non-stop flight included

Austin (AUS) to Portland (PWM)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. There's a gym on site, and a 24-hour front desk and a terrace are also provided.

Top Bailey Island hotels deals

The Westin Portland Harborview

157 High St, Portland, ME

Free Cancellation

Reserve now, pay when you stay

$191 nightly

$211 total

Jun 4 - Jun 5

Total includes taxes and fees

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.

Portland Regency Hotel & Spa

20 Milk Street, Portland, ME

Free Cancellation

Reserve now, pay when you stay

$245 nightly

$271 total

Jun 8 - Jun 9

Total includes taxes and fees

A full-service spa, a hot tub, and a restaurant are all featured at this smoke-free hotel. Unwind with a drink at one of the 2 bars/lounges and enjoy freebies like WiFi in public areas and a roundtrip airport shuttle. There's a gym on site, and laundry facilities and concierge services are also offered.

Portland Harbor Hotel

468 Fore Street, Portland, ME

Free Cancellation

Reserve now, pay when you stay

$281 nightly

$311 total

Jun 15 - Jun 16

Total includes taxes and fees

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.

Inn at St John Portland In-Town

939 Congress St, Portland, ME

$99 nightly

$108 total

Jun 3 - Jun 4

Total includes taxes and fees

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

La Quinta Inn & Suites by Wyndham Portland

340 Park Ave, Portland, ME

Free Cancellation

Reserve now, pay when you stay

$126 nightly

$140 total

Jun 9 - Jun 10

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

Clarion Hotel Portland

1230 Congress St, Portland, ME

Free Cancellation

Reserve now, pay when you stay

$101 nightly

$112 total

Jun 4 - Jun 5

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.

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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 $626. 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.