Bailey Island Vacation Packages

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Flight and hotel packages to Bailey Island

Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Airport/Maine Mall

Days Inn by Wyndham Airport/Maine Mall

2 out of 5
per person
Aug 14 - Aug 20
found 7 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
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 on-the-go breakfast and free self parking.
Ramada by Wyndham Saco/Old Orchard Beach Area

Ramada by Wyndham Saco/Old Orchard Beach Area

2.5 out of 5
Save 100% on your flight
per person
Aug 14 - Aug 20
found 7 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the business center and free internet in public areas. Enjoy the seasonal outdoor pool and conveniences like a 24-hour front desk and laundry facilities.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
per person
Aug 14 - Aug 20
found 7 hours 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.
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
Nasons Corner
Save 100% on your flight
per person
Aug 14 - Aug 20
found 7 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
This hotel features 2 restaurants, 2 spa tubs, and an indoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Howard Johnson Hotel by Wyndham South Portland

Howard Johnson Hotel by Wyndham South Portland

2 out of 5
per person
Aug 14 - Aug 20
found 7 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) 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. Enjoy the gym and free perks like on-the-go breakfast and free self parking.

Top Bailey Island hotel deals

The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St, Portland, ME
Free Cancellation
Reserve now, pay when you stay
The price is $161 per night
$161
per night
May 27 - May 28
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. Unwind with a drink at the bar/lounge and enjoy perks like a free area shuttle.
Pet friendly
Breakfast available
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street, Portland, ME
Free Cancellation
Reserve now, pay when you stay
The price is $206 per night
$206
per night
May 27 - May 28
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
Breakfast available
Casco Bay Hotel, Ascend Hotel Collection

Casco Bay Hotel, Ascend Hotel Collection

3.5 out of 5
80 John Roberts Rd., South Portland, ME
Free Cancellation
Reserve now, pay when you stay
The price is $89 per night
$89
per night
Jun 9 - Jun 10
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free self parking, and a free airport shuttle. Business travelers can take advantage of the free WiFi in public areas. There's a gym on site, and a 24-hour front desk and dry cleaning are also provided.
Pet friendly
Breakfast included
Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4 out of 5
9 Center Street, Portland, ME
Free Cancellation
Reserve now, pay when you stay
The price is $215 per night
$215
per night
May 27 - May 28
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
Breakfast available
La Quinta Inn & Suites by Wyndham Portland

La Quinta Inn & Suites by Wyndham Portland

2.5 out of 5
340 Park Ave, Portland, ME
Free Cancellation
Reserve now, pay when you stay
The price is $113 per night
$113
per night
May 27 - May 28
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free self parking, and a free airport shuttle. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the seasonal outdoor pool and conveniences like a 24-hour front desk and laundry facilities.
Pet friendly
Breakfast included
Comfort Inn Airport

Comfort Inn Airport

2.5 out of 5
90 Maine Mall Rd, South Portland, ME
Free Cancellation
Reserve now, pay when you stay
The price is $89 per night
$89
per night
May 27 - May 28
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.
Pet friendly
Breakfast included
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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 in Bailey Island

Image for Bailey Island Bridge

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.

Bailey Island Bridge
Image for Land's End Gift Shop

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.

Land's End Gift Shop
Image for Cobwork Bridge

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.

Cobwork Bridge

Photos of local treasures

Bailey Island showing general coastal views

Frequently asked questions

How much are vacation packages to Bailey Island?
Your vacation daydreams can become reality in Bailey Island from just $696. Packages include flights and hotels, and they’ll make booking your trip a breeze. All you’ll have to focus on is having an incredible time.
Where can I get the best vacation package deals for Bailey Island?
For the best Bailey Island package deal, no one compares to Travelocity. Select from 400 airlines and 1,000,000 worldwide properties to create your ultimate trip — it’s as easy as that.
Why should I book my Bailey Island vacation package with Travelocity?
With top-notch service, 24/7 support and some of the most perfect getaways around, you’ll never roam alone. And if you find a better price, we’ll match it. That’s our Price Match Guarantee.
Will I save money on my Bailey Island car rental if I combine it with hotels and flights?
Combining your bookings into a Bailey Island vacation package will save you a handsome sum. You can book a car and flight; a flight, hotel and car; or a car and hotel. There’s no better way to explore the greater Bailey Island region than from behind the wheel of your own rental car. You can also add activities and experiences to your Travelocity package.
What is the best time of year to go to Bailey Island?
Escape in and you can spend more money on experiences, not your hotel room. This is the least costly month to lock in a stay. Prices are at their highest in , so avoid traveling during this time if you’re trying to be thrifty. March, July and August are the peak season months for Bailey Island. You’ll need to book in advance and be ready to pay higher rates. November, December and January are the least popular months to travel.