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Bailey Island Vacation Packages

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Bailey Island Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Docent's Collection at 178 Middle Street

The Docent's Collection at 178 Middle Street

3.5 out of 5
Price was $864, price is now $685 per person
$685
per person
Dec 3 - Dec 5
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Cross Insurance Arena and Thompson's Point are located nearby.
Great place and location to everything. Very cool building and modern. Staff was great.

Reviewed on Sep 25, 2026

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Price was $1,381, price is now $1,003 per person
$1,003
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) 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 Cross Insurance Arena and Thompson's Point are located nearby.

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Price was $1,738, price is now $1,405 per person
$1,405
per person
Nov 4 - Nov 8
found 9 hours 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.
Place was charming and quirky. Very comfortable and well located.

Reviewed on Sep 18, 2026

Evalina Hotel

Evalina Hotel

2.5 out of 5
Price was $1,250, price is now $1,013 per person
$1,013
per person
Nov 21 - Nov 24
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 Cross Insurance Arena and Maine Mall are located nearby.
This is a very nice hotel in a great location. It’s new and wonderfully appointed. Everything about it is first class.

Reviewed on Sep 24, 2026

Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 out of 5
Price was $1,601, price is now $1,321 per person
$1,321
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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.
Beautiful place

Reviewed on Sep 20, 2026

The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
Price was $1,219, price is now $1,023 per person
$1,023
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Portland (PWM)
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Cross Insurance Arena and Maine Mall are located nearby.
The room was clean, the hotel is spacious, and well located in the city. The interior has multiple flights of stairs to drag suitcases which made it somewhat difficult. It was difficult to navigate the wifi in the room and the off site parking requires that they accurately enter your license plate number. We got temporarily stuck in the garage.

Reviewed on Sep 24, 2026

The Francis

The Francis

3.5 out of 5
Price was $1,307, price is now $1,105 per person
$1,105
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.
Very pleasant and attentive staff, nice location and easy free-parking options. But the room was too small to contain a couple of large suitcases, and the mini fridge was so packed with minibar items that you couldn’t fit in one bottle of water. Being on the ground floor, we could hear the steps of the people in the room above us. Good, nice, but that’s it.

Reviewed on Sep 24, 2026

Inn By The Sea

Inn By The Sea

4 out of 5
Price was $1,468, price is now $1,263 per person
$1,263
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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.

Bailey Island Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
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 $1,248, price is now $1,013 per person
$1,013
per person
Dec 19 - Dec 23
found 17 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
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 $1,332, price is now $1,070 per person
$1,070
per person
Dec 19 - Dec 23
found 17 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was $1,738, price is now $1,405 per person
$1,405
per person
Nov 4 - Nov 8
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Evalina Hotel

Evalina Hotel

2.5 out of 5
Downtown Portland
Price was $1,250, price is now $1,013 per person
$1,013
per person
Nov 21 - Nov 24
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.
Inn at St John Portland In-Town

Inn at St John Portland In-Town

2.5 out of 5
Valley Street
Price was $550, price is now $407 per person
$407
per person
Dec 11 - Dec 16
found 13 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Portland (PWM)
Evalina Hotel

Evalina Hotel

2.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,176, price is now $732 per person
$732
per person
Dec 11 - Dec 16
found 13 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Portland (PWM)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $759, price is now $547 per person
$547
per person
Dec 11 - Dec 16
found 13 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Portland (PWM)
The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,793, price is now $1,318 per person
$1,318
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Portland (PWM)

Top Flight Deals

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

Breeze Airways
Sat, Nov 7 - Sat, Nov 14
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$144 Roundtrip, found 7 hours ago
$144
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Sat, Nov 7 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Sat, Nov 14, priced at $144 found 7 hours ago
Breeze Airways
Wed, Oct 28 - Sat, Oct 31
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$185 Roundtrip, found 6 hours ago
$185
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Wed, Oct 28 from Tampa Intl. to Portland Intl. Jetport, returning Sat, Oct 31, priced at $185 found 6 hours ago
Breeze Airways
Wed, Nov 11 - Wed, Dec 2
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$213 Roundtrip, found 4 hours ago
$213
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Wed, Nov 11 from Orlando Intl. to Portland Intl. Jetport, returning Wed, Dec 2, priced at $213 found 4 hours ago
Delta
Tue, Oct 20 - Sat, Oct 31
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$301 Roundtrip, found 2 days ago
$301
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Oct 20 from Newark Liberty Intl. Airport to Portland Intl. Jetport, returning Sat, Oct 31, priced at $301 found 2 days ago