Deals on vacations and trips to Bailey Island

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

84 Main

4 out of 5
Price was $728, price is now $580 per person
$580
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
This condo doesn't skimp on freebies - guests receive free WiFi and free self parking. Luggage storage and laundry facilities are also provided.
The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was $882, price is now $697 per person
$697
per person
Nov 19 - Nov 23
found 15 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.
Nautical Mile

Nautical Mile

2.5 out of 5
Price was $874, price is now $738 per person
$738
per person
Dec 24 - Dec 27
found 24 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) 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.
Cape Arundel Inn and Resort

Cape Arundel Inn and Resort

3 out of 5
Price was $1,356, price is now $1,147 per person
$1,147
per person
Dec 24 - Dec 27
found 24 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
A restaurant and a seasonal outdoor pool are featured at this guesthouse. Guests will appreciate free perks like free self parking and WiFi in public areas. Concierge services are provided for your convenience.
The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Downtown Portland
Price was $1,033, price is now $900 per person
$900
per person
Dec 24 - Dec 27
found 24 hours 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 is also provided.

Top Bailey Island hotels deals

Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Free Cancellation
$83 nightly
The price is $92 total per night
$92 total
Oct 26 - Oct 27
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
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
$108 nightly
The price is $119 total per night
$119 total
Nov 18 - Nov 19
Total with 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.
Spa
Pet friendly
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
$87 nightly
The price is $96 total per night
$96 total
Oct 25 - Oct 26
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
Quality Inn & Suites South Portland

Quality Inn & Suites South Portland

2.5 out of 5
738 Main Street South Portland ME
Free Cancellation
$72 nightly
The price is $79 total per night
$79 total
Nov 9 - Nov 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
Inn at St John Portland In-Town

Inn at St John Portland In-Town

2.5 out of 5
939 Congress St Portland ME
Free Cancellation
Reserve now, pay when you stay
$89 nightly
The price is $97 total per night
$97 total
Nov 1 - Nov 2
Total with 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
Clarion Pointe South Portland

Clarion Pointe South Portland

2 out of 5
675 Main Street I-95 South Portland ME
Free Cancellation
$51 nightly
The price is $56 total per night
$56 total
Nov 18 - Nov 19
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
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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 $580. 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.