Deals on vacations and trips to Bailey Island
Save when you book Bailey Island package deals
Bailey Island flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Ogunquit River Inn & Suites
Save 100% on your flight
Price was $939, price is now $645 per person
$645
per person
Jun 18 - Jun 21
found 23 hours ago
Roundtrip flight included
Nashville (BNA) to Portland (PWM)
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the business center and free internet in public areas. There's a seasonal outdoor pool on site, and a terrace and a garden are also provided.
The Meadowmere Resort
Save 100% on your flight
Price was $1,734, price is now $1,222 per person
$1,222
per person
Jul 30 - Aug 3
found 10 hours ago
Roundtrip flight included
Minneapolis (MSP) 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.
84 Main
Price was $1,366, price is now $1,002 per person
$1,002
per person
Jul 2 - Jul 5
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) 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.
Saco Bay Hotel
Price was $1,246, price is now $917 per person
$917
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free self parking, and a free airport shuttle. Traveling on business? Take advantage of the business center and WiFi in public areas. Enjoy the outdoor pool and conveniences like a 24-hour front desk and laundry facilities.
The Docent's Collection at 121 Middle Street
Downtown Portland
Price was $1,757, price is now $1,303 per person
$1,303
per person
Jun 25 - Jun 28
found 1 day ago
Roundtrip 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
Portland Harbor Hotel
468 Fore Street Portland ME
Free Cancellation
Reserve now, pay when you stay
$241 nightly
The price is $266 total per night
$266 total
May 25 - May 26
Total with 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.
Pet friendly
Free WiFi
Portland Regency Hotel & Spa
20 Milk Street Portland ME
Free Cancellation
Reserve now, pay when you stay
$157 nightly
The price is $174 total per night
$174 total
May 26 - May 27
Total with 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.
Hot Tub
Spa
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
Free Cancellation
$177 nightly
The price is $196 total per night
$196 total
May 26 - May 27
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A safe deposit box is provided and the front desk is staffed around-the-clock.
Pet friendly
Free WiFi
HomeAwhile
205 Southborough Drive Scarborough ME
Free Cancellation
Reserve now, pay when you stay
$139 nightly
The price is $152 total per night
$152 total
May 19 - May 20
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. The front desk is staffed around-the-clock and laundry facilities are on offer.
Pet friendly
Parking included
Inn at St John Portland In-Town
939 Congress St Portland ME
Free Cancellation
Reserve now, pay when you stay
$129 nightly
The price is $141 total per night
$141 total
May 19 - May 20
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
Holiday Inn Portland-By the Bay by IHG
88 Spring St Portland ME
Free Cancellation
$140 nightly
The price is $155 total per night
$155 total
May 25 - May 26
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the 24-hour gym and perks like a free area shuttle.
Pool
Free airport shuttle
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
Photos of local treasures
Browse Bailey Island vacation photos for more inspiration
