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Gray Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Meadowmere Resort

Meadowmere Resort

2.5 out of 5
Price was $572, price is now $468 per person
$468
per person
Nov 5 - Nov 9
found 16 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Book a stay at this spa hotel in Ogunquit. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Ogunquit Beach and Marginal Way are located nearby.
Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
Price was $1,543, price is now $1,096 per person
$1,096
per person
Nov 15 - Nov 19
found 6 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this 4.5-star luxury resort in Cape Neddick. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Ogunquit Beach and Perkins Cove are located nearby.
Inn By The Sea

Inn By The Sea

4 out of 5
Save 100% on your flight
Price was $831, price is now $616 per person
$616
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Stay at this 4-star luxury hotel in Cape Elizabeth. Enjoy free valet parking, a full-service spa, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Crescent Beach State Park and Crescent Beach are located nearby.
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Price was $1,256, price is now $1,013 per person
$1,013
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this 3.5-star B&B in Portland. Enjoy free breakfast, free WiFi, and concierge services. Popular attractions Thompson's Point and Maine Mall are located nearby.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Price was $847, price is now $688 per person
$688
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this 4-star business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.
InnSeason Resorts The Falls at Ogunquit

InnSeason Resorts The Falls at Ogunquit

2.5 out of 5
Price was $679, price is now $557 per person
$557
per person
Dec 19 - Dec 21
found 8 hours ago
Roundtrip non-stop flight included
Nashville (BNA) to Portland (PWM)
Stay at this motel in Ogunquit. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Ogunquit Beach and Moody Beach are located nearby.
AWOL Kennebunkport

AWOL Kennebunkport

3 out of 5
Save 100% on your flight
Price was $802, price is now $659 per person
$659
per person
Nov 8 - Nov 11
found 1 day ago
Roundtrip flight included
Nashville (BNA) to Portland (PWM)
Stay at this 3-star hotel in Kennebunkport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Dock Square and Wells Beach are located nearby.
Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Price was $1,075, price is now $885 per person
$885
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this 4.5-star luxury hotel in Kennebunkport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Dock Square and Wells Beach are located nearby.

Gray Vacation Packages 3-4 Night Stays

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

The McKernan Inn

3 out of 5
Price was $698, price is now $543 per person
$543
per person
Dec 11 - Dec 14
found 10 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
Price was $1,543, price is now $1,096 per person
$1,096
per person
Nov 15 - Nov 19
found 6 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Inn By The Sea

Inn By The Sea

4 out of 5
Save 100% on your flight
Price was $831, price is now $616 per person
$616
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was $1,256, price is now $1,013 per person
$1,013
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)

Gray Vacation Packages 5-7 Night Stays

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

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $906, price is now $676 per person
$676
per person
Nov 13 - Nov 19
found 2 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,175, price is now $823 per person
$823
per person
Nov 13 - Nov 19
found 2 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) 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 $1,789, price is now $1,356 per person
$1,356
per person
Nov 13 - Nov 19
found 2 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
Inn By The Sea

Inn By The Sea

4 out of 5
Save 100% on your flight
Price was $1,525, price is now $1,167 per person
$1,167
per person
Nov 13 - Nov 19
found 2 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)

Top Flight Deals

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

JetBlue Airways
Tue, Oct 21 - Fri, Oct 24
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$119 Roundtrip, found 5 days ago
$119
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Tue, Oct 21 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Fri, Oct 24, priced at $119 found 5 days ago
Breeze Airways
Sat, Nov 8 - Sat, Nov 15
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$143 Roundtrip, found 2 days ago
$143
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, Nov 8 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Sat, Nov 15, priced at $143 found 2 days ago
United
Fri, Oct 24 - Sun, Oct 26
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$185 Roundtrip, found 5 days ago
$185
Roundtrip
found 5 days ago
Select United flight, departing Fri, Oct 24 from Newark Liberty Intl. Airport to Portland Intl. Jetport, returning Sun, Oct 26, priced at $185 found 5 days ago
American Airlines
Sun, Nov 16 - Sun, Nov 23
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$220 Roundtrip, found 5 days ago
$220
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sun, Nov 16 from Orlando Intl. to Portland Intl. Jetport, returning Sun, Nov 23, priced at $220 found 5 days ago