Search Deals on
Bailey Island Vacation Packages

Build your package with 2 more options

Bailey Island Flight + Hotel Packages

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

Portland Harbor Hotel

4 out of 5
Price was $1,065, price is now $854 per person
$854
per person
Nov 4 - Nov 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Thompson's Point and Portland Head Light are located nearby.
For the price I would expect more amenities. The “free” food by the elevator was pretty sparse with a broken ice machine and coffee maker

Reviewed on Aug 29, 2026

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Save 100% on your flight
Price was $3,257, price is now $2,352 per person
$2,352
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and parking (surcharge). Popular attractions Thompson's Point and Portland Head Light are located nearby.
Enjoyable

Reviewed on Aug 28, 2026

The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Price was $1,337, price is now $1,025 per person
$1,025
per person
Nov 4 - Nov 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this luxury aparthotel in Portland. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions Thompson's Point and Portland Head Light are located nearby.
The room was very clean and nice. The only thing that was not so great was the loud motor going on and off for some of the night. Otherwise it was great!

Reviewed on Aug 26, 2026

Evalina Hotel

Evalina Hotel

2.5 out of 5
Price was $1,581, price is now $1,243 per person
$1,243
per person
Nov 4 - Nov 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this aparthotel in Portland. Enjoy free WiFi, parking (surcharge), and in-room washers/dryers. Popular attractions Thompson's Point and Portland Head Light are located nearby.

Inn By The Sea

Inn By The Sea

4 out of 5
Save 100% on your flight
Price was $2,273, price is now $1,803 per person
$1,803
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this luxury hotel in Cape Elizabeth. Enjoy free valet parking, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Crescent Beach State Park and Crescent Beach are located nearby.
Lovely property. Very well maintained and taken care of. The option of pool or beach is a plus. Although we didn’t utilize the activities available each day.. it seemed very family friendly. Definitely will be back but hopefully reserve a bigger room or suite. Charming outdoor seating on the huge lawn but mostly in the sun. An indoor lobby with some comfy seating would be great.

Reviewed on Aug 13, 2026

Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 out of 5
Price was $1,114, price is now $887 per person
$887
per person
Nov 4 - Nov 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and daily housekeeping. Popular attractions Thompson's Point and Maine Mall are located nearby.

The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was $1,465, price is now $1,181 per person
$1,181
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
Stay at this hotel in Ogunquit. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Ogunquit Beach and Marginal Way are located nearby.

The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Price was $1,694, price is now $1,376 per person
$1,376
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and premium TV channels. Popular attractions State Theatre and Thompson's Point are located nearby.
Splendid, great location!

Reviewed on Aug 30, 2026

Bailey Island Vacation Packages 3-4 Night Stays

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

The Wolfeboro Inn

3.5 out of 5
Price was $955, price is now $676 per person
$676
per person
Oct 15 - Oct 18
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Save 100% on your flight
Price was $2,961, price is now $2,229 per person
$2,229
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Price was $1,337, price is now $1,025 per person
$1,025
per person
Nov 4 - Nov 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Evalina Hotel

Evalina Hotel

2.5 out of 5
Downtown Portland
Price was $1,581, price is now $1,243 per person
$1,243
per person
Nov 4 - Nov 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)

Bailey Island Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Moody
Price was $1,257, price is now $980 per person
$980
per person
Oct 12 - Oct 17
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Save 100% on your flight
Price was $3,257, price is now $2,352 per person
$2,352
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
InnSeason Resorts The Falls at Ogunquit

InnSeason Resorts The Falls at Ogunquit

2.5 out of 5
Price was $1,332, price is now $1,004 per person
$1,004
per person
Oct 9 - Oct 16
found 6 hours ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)
The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was $1,374, price is now $1,085 per person
$1,085
per person
Oct 12 - Oct 17
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Breeze Airways
Wed, Oct 28 - Sat, Oct 31
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$196 Roundtrip, found 2 hours ago
$196
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Wed, Oct 28 from Tampa Intl. to Portland Intl. Jetport, returning Sat, Oct 31, priced at $196 found 2 hours ago
Bargain Flight
Sun, Sep 6 - Fri, Sep 11
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$220 Roundtrip, found 2 days ago
$220
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Sun, Sep 6 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Fri, Sep 11, priced at $220 found 2 days ago
United
Mon, Sep 21 - Wed, Sep 23
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$241 Roundtrip, found 6 hours ago
$241
Roundtrip
found 6 hours ago
Select United flight, departing Mon, Sep 21 from Newark Liberty Intl. Airport to Portland Intl. Jetport, returning Wed, Sep 23, priced at $241 found 6 hours ago
Breeze Airways
Wed, Oct 7 - Wed, Oct 14
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$244 Roundtrip, found 1 hour ago
$244
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Wed, Oct 7 from Orlando Intl. to Portland Intl. Jetport, returning Wed, Oct 14, priced at $244 found 1 hour ago