Deals on vacations and trips to Bailey Island

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Price found within the past 48 hours. Click for updated prices.
Inn at St John Portland In-Town

Inn at St John Portland In-Town

2.5 out of 5
Valley Street
Price was $433, price is now $338 per person
$338
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Columbus (CMH) to Portland (PWM)
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.
Evalina Hotel

Evalina Hotel

2.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,359, price is now $1,012 per person
$1,012
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Columbus (CMH) to Portland (PWM)
Free WiFi in public areas is available at this aparthotel. Take advantage of the self parking.
The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was $1,124, price is now $847 per person
$847
per person
Oct 18 - Oct 23
found 13 hours ago
Roundtrip non-stop flight included
Columbus (CMH) to Portland (PWM)
2 hot tubs, an indoor pool, and a gym are all featured at this smoke-free hotel. Enjoy the seasonal outdoor pool and free perks like continental breakfast and free self parking. There's a restaurant and a bar/lounge for dining and drinks, and also a sauna on site.
The Docent's Collection at 178 Middle Street

The Docent's Collection at 178 Middle Street

3.5 out of 5
Downtown Portland
Price was $1,406, price is now $1,073 per person
$1,073
per person
Oct 9 - Oct 11
found 1 day ago
Roundtrip flight included
Columbus (CMH) to Portland (PWM)
This hotel features free WiFi in public areas, concierge services, and self parking. Express check-in and luggage storage are also provided.
Inn By The Sea

Inn By The Sea

4 out of 5
Save 100% on your flight
Price was $2,062, price is now $1,607 per person
$1,607
per person
Oct 18 - Oct 23
found 13 hours ago
Roundtrip non-stop flight included
Columbus (CMH) to Portland (PWM)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Families will appreciate the playground, onsite laundry facilities, and free supervised childcare. Enjoy the outdoor pool and perks like free valet parking.

Top Bailey Island hotels deals

Quality Inn & Suites South Portland

Quality Inn & Suites South Portland

2.5 out of 5
738 Main Street South Portland ME
Free Cancellation
$76 nightly
The price is $82 total per night
$82 total
Sep 9 - Sep 10
Total with taxes and fees
This hotel features free WiFi in public areas, free newspapers, and free self parking. Enjoy the free continental breakfast each morning. A garden and a picnic area are also provided.
Breakfast included
Pet friendly
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

3.5 out of 5
80 John Roberts Rd. South Portland ME
Free Cancellation
$116 nightly
The price is $127 total per night
$127 total
Sep 9 - Sep 10
Total with taxes and fees
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.
Breakfast included
Free airport shuttle
Clarion Pointe South Portland

Clarion Pointe South Portland

2 out of 5
675 Main Street I-95 South Portland ME
Free Cancellation
$68 nightly
The price is $74 total per night
$74 total
Sep 17 - Sep 18
Total with 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
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Free Cancellation
Reserve now, pay when you stay
$86 nightly
The price is $95 total per night
$95 total
Sep 10 - Sep 11
Total with 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
Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

3 out of 5
81 Riverside St Portland ME
Free Cancellation
Reserve now, pay when you stay
$110 nightly
The price is $122 total per night
$122 total
Sep 15 - Sep 16
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the seasonal outdoor pool and perks like free self parking.
Pool
Hot Tub
Comfort Inn South Portland Airport

Comfort Inn South Portland Airport

2.5 out of 5
90 Maine Mall Rd South Portland ME
Free Cancellation
$120 nightly
The price is $131 total per night
$131 total
Sep 7 - Sep 8
Total with 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
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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.

Stay near popular Bailey Island attractions

Bailey Island Bridge

9.2/10 (10 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.
See properties

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 $338. 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.

Photos of local treasures

Browse Bailey Island vacation photos for more inspiration

A rocky shoreline with a boat, a house, and a forest in the background.
A wooden pier extending into calm waters with a red and white boat docked at the end.
A green netted buoy attached to a wooden post by a curved metal hook, with a wooden fence and a body of water in the background.
A sign for Morse Lobster, open Monday to Sunday, with a lobster and lobster traps displayed.
A wooden bridge over water with a yellow kayak, boats, and a motel in the background.