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Gray Flight + Hotel Packages

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

The McKernan Inn

3 out of 5
Save 100% on your flight
Price was $507, price is now $347 per person
$347
per person
Jan 11 - Jan 14
found 17 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Stay at this 3-star beach inn in South Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Thompson's Point and Maine Mall are located nearby.
The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Price was $1,305, price is now $917 per person
$917
per person
Dec 20 - Dec 26
found 12 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Portland (PWM)
Stay at this 4.5-star luxury aparthotel in Portland. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions Thompson's Point and Maine Mall are located nearby.
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Save 100% on your flight
Price was $637, price is now $484 per person
$484
per person
Jan 11 - Jan 14
found 17 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.
84 Main

84 Main

4 out of 5
Price was $456, price is now $347 per person
$347
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Stay at this 4-star condo in Kennebunk. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Dock Square and Wells Beach are located nearby.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Price was $920, price is now $714 per person
$714
per person
Dec 20 - Dec 26
found 12 hours ago
Roundtrip non-stop flight included
Detroit (DTW) 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.
The Docent's Collection - New Opening

The Docent's Collection - New Opening

2 out of 5
Price was $1,077, price is now $853 per person
$853
per person
Dec 20 - Dec 26
found 12 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and daily housekeeping. Popular attractions Thompson's Point and Maine Mall are located nearby.
The Wolfeboro Inn

The Wolfeboro Inn

3.5 out of 5
Price was $439, price is now $350 per person
$350
per person
Dec 5 - Dec 7
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Portland (PWM)
Stay at this 3.5-star beach hotel in Wolfeboro. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff in our reviews. Popular attractions Lake Winnipesaukee and Hampshire Pewter Co. are located nearby.
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Price was $992, price is now $812 per person
$812
per person
Dec 20 - Dec 26
found 12 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Portland (PWM)
Stay at this 3.5-star spa hotel in Portland. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.

Gray Vacation Packages 3-4 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 $411, price is now $276 per person
$276
per person
Jan 11 - Jan 14
found 17 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
The McKernan Inn

The McKernan Inn

3 out of 5
Save 100% on your flight
Price was $507, price is now $347 per person
$347
per person
Jan 11 - Jan 14
found 17 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $504, price is now $347 per person
$347
per person
Jan 11 - Jan 14
found 17 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
The Docent's Collection - New Opening

The Docent's Collection - New Opening

2 out of 5
Downtown Portland
Price was $425, price is now $305 per person
$305
per person
Jan 11 - Jan 14
found 17 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)

Gray Vacation Packages 5-7 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 $947, price is now $663 per person
$663
per person
Jan 12 - Jan 17
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Price was $1,305, price is now $917 per person
$917
per person
Dec 20 - Dec 26
found 12 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Portland (PWM)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $920, price is now $714 per person
$714
per person
Dec 20 - Dec 26
found 12 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Portland (PWM)
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was $1,096, price is now $852 per person
$852
per person
Jan 12 - Jan 17
found 1 day 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.

United
Tue, Nov 11 - Wed, Nov 12
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$137 Roundtrip, found 6 days ago
$137
Roundtrip
found 6 days ago
Select United flight, departing Tue, Nov 11 from Newark Liberty Intl. Airport to Portland Intl. Jetport, returning Wed, Nov 12, priced at $137 found 6 days ago
Delta
Mon, Nov 10 - Sat, Nov 15
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$147 Roundtrip, found 16 hours ago
$147
Roundtrip
found 16 hours ago
Select Delta flight, departing Mon, Nov 10 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Sat, Nov 15, priced at $147 found 16 hours ago
Delta
Sat, Nov 8 - Thu, Nov 13
LGA
LaGuardia
PWM
Portland Intl. Jetport
$150 Roundtrip, found 6 days ago
$150
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Nov 8 from LaGuardia to Portland Intl. Jetport, returning Thu, Nov 13, priced at $150 found 6 days ago
Delta
Mon, Nov 24 - Thu, Nov 27
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$209 Roundtrip, found 5 days ago
$209
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, Nov 24 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Thu, Nov 27, priced at $209 found 5 days ago