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Gray Vacation Packages

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Gray Flight + Hotel Packages

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
Price was $737, price is now $588 per person
$588
per person
Dec 5 - Dec 10
found 18 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Thompson's Point and Cross Insurance Arena are located nearby.

Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 out of 5
Price was $1,328, price is now $959 per person
$959
per person
Dec 5 - Dec 10
found 18 hours ago
Roundtrip non-stop 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.
Beautiful place

Reviewed on Sep 20, 2026

The Docent's Collection at 178 Middle Street

The Docent's Collection at 178 Middle Street

3.5 out of 5
Price was $1,421, price is now $1,050 per person
$1,050
per person
Dec 5 - Dec 10
found 18 hours 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.
Staff was very very good and super quick to respond.. I really liked the location for my visit bc everything was easily walkable. Room was comfortable but a little interesting walking all the way across for bathroom. A few small glitches with electrical probably just bc it’s done recently renovated.

Reviewed on Sep 18, 2026

Evalina Hotel

Evalina Hotel

2.5 out of 5
Price was $1,266, price is now $942 per person
$942
per person
Dec 5 - Dec 10
found 18 hours ago
Roundtrip non-stop 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 Thompson's Point 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 $1,315, price is now $984 per person
$984
per person
Dec 5 - Dec 10
found 18 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and premium TV channels. Popular attractions Thompson's Point and Portland Head Light are located nearby.
Other than being a little hard to find, this spot was wonderful and so much nicer than a hotel room! Great location.

Reviewed on Sep 18, 2026

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Price was $1,437, price is now $1,106 per person
$1,106
per person
Dec 5 - Dec 10
found 18 hours ago
Roundtrip non-stop 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

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Price was $910, price is now $714 per person
$714
per person
Dec 5 - Dec 10
found 18 hours ago
Roundtrip non-stop 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 Cross Insurance Arena and Thompson's Point are located nearby.
The front desk ladies were the best!

Reviewed on Sep 21, 2026

Inn By The Sea

Inn By The Sea

4 out of 5
Price was $1,325, price is now $1,054 per person
$1,054
per person
Dec 14 - Dec 19
found 5 hours 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 Portland Head Light and Crescent Beach State Park are located nearby.

Gray Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 out of 5
West End
Price was $976, price is now $764 per person
$764
per person
Dec 3 - Dec 6
found 22 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Portland (PWM)
Evalina Hotel

Evalina Hotel

2.5 out of 5
Downtown Portland
Price was $1,181, price is now $832 per person
$832
per person
Dec 3 - Dec 6
found 22 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) 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 $1,160, price is now $856 per person
$856
per person
Dec 3 - Dec 6
found 22 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Portland (PWM)
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was $1,132, price is now $878 per person
$878
per person
Dec 3 - Dec 6
found 22 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Portland (PWM)

Gray Vacation Packages 5-7 Night Stays

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

Evalina Hotel

2.5 out of 5
Downtown Portland
Price was $1,266, price is now $942 per person
$942
per person
Dec 5 - Dec 10
found 18 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 out of 5
West End
Price was $1,328, price is now $959 per person
$959
per person
Dec 5 - Dec 10
found 18 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 $1,421, price is now $1,050 per person
$1,050
per person
Dec 5 - Dec 10
found 18 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
Save 100% on your flight
Price was $2,167, price is now $1,608 per person
$1,608
per person
Oct 29 - Nov 4
found 1 day ago
Roundtrip non-stop 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
Sat, Nov 7 - Sat, Nov 14
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$144 Roundtrip, found 14 hours ago
$144
Roundtrip
found 14 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 14 hours ago
Breeze Airways
Wed, Oct 28 - Sat, Oct 31
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$185 Roundtrip, found 4 hours ago
$185
Roundtrip
found 4 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 4 hours ago
Breeze Airways
Wed, Nov 11 - Wed, Dec 2
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$213 Roundtrip, found 8 hours ago
$213
Roundtrip
found 8 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 8 hours ago
JetBlue Airways
Thu, Oct 8 - Fri, Oct 23
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$297 Roundtrip, found 6 hours ago
$297
Roundtrip
found 6 hours ago
Select JetBlue Airways flight, departing Thu, Oct 8 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Fri, Oct 23, priced at $297 found 6 hours ago