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Gray Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Best Western Freeport Inn

Best Western Freeport Inn

3 out of 5
Price was $589, price is now $467 per person
$467
per person
Feb 8 - Feb 15
found 18 hours ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
Stay at this hotel in Freeport. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions LL Bean Flagship Store and Eartha 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 $1,602, price is now $1,109 per person
$1,109
per person
Dec 30 - Jan 4
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and concierge services. Popular attractions Victoria Mansion and Portland Club are located nearby.
The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Price was $995, price is now $729 per person
$729
per person
Dec 24 - Dec 27
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 Victoria Mansion and Charles Q. Clapp House are located nearby.
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
Price was $688, price is now $521 per person
$521
per person
Feb 7 - Feb 14
found 18 hours ago
Roundtrip non-stop flight included
New York (JFK) to Portland (PWM)
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Happy Wheels Skate Center and Fore River Sanctuary are located nearby.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Price was $683, price is now $531 per person
$531
per person
Feb 13 - Feb 16
found 23 hours ago
Roundtrip non-stop flight included
Nashville (BNA) 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 Fore Street Gallery are located nearby.
Cliff House Maine

Cliff House Maine

4.5 out of 5
Price was $1,243, price is now $985 per person
$985
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
Book a stay at this 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 Perkins Cove and Marginal Way are located nearby.
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Price was $672, price is now $535 per person
$535
per person
Feb 13 - Feb 16
found 23 hours ago
Roundtrip non-stop flight included
Nashville (BNA) to Portland (PWM)
Book a stay at this 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 N.W. Barrett Gallery and Fore Street Gallery are located nearby.
Inn By The Sea

Inn By The Sea

4 out of 5
Price was $853, price is now $680 per person
$680
per person
Feb 13 - Feb 16
found 23 hours ago
Roundtrip non-stop flight included
Nashville (BNA) to Portland (PWM)
Book a stay at this 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.

Gray Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
AWOL Kennebunkport

AWOL Kennebunkport

3 out of 5
Price was $601, price is now $467 per person
$467
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
New York (JFK) 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 $701, price is now $477 per person
$477
per person
Jan 8 - Jan 12
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $683, price is now $531 per person
$531
per person
Feb 13 - Feb 16
found 23 hours ago
Roundtrip non-stop flight included
Nashville (BNA) to Portland (PWM)
Cliff House Maine

Cliff House Maine

4.5 out of 5
Price was $1,243, price is now $985 per person
$985
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
New York (JFK) 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
Save 100% on your flight
Price was $901, price is now $631 per person
$631
per person
Feb 7 - Feb 14
found 18 hours ago
Roundtrip non-stop flight included
New York (JFK) to Portland (PWM)
The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,346, price is now $872 per person
$872
per person
Feb 7 - Feb 14
found 18 hours ago
Roundtrip non-stop flight included
New York (JFK) to Portland (PWM)
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,081, price is now $717 per person
$717
per person
Feb 7 - Feb 14
found 18 hours ago
Roundtrip non-stop flight included
New York (JFK) to Portland (PWM)
The Docent's Collection - Boyd Block

The Docent's Collection - Boyd Block

2 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,311, price is now $870 per person
$870
per person
Feb 7 - Feb 14
found 18 hours ago
Roundtrip non-stop flight included
New York (JFK) to Portland (PWM)

Top Flight Deals

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

United
Mon, Dec 15 - Mon, Dec 15
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$171 Roundtrip, found 1 day ago
$171
Roundtrip
found 1 day ago
Select United flight, departing Mon, Dec 15 from Newark Liberty Intl. Airport to Portland Intl. Jetport, returning Mon, Dec 15, priced at $171 found 1 day ago
Breeze Airways
Mon, Dec 22 - Wed, Dec 31
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$178 Roundtrip, found 1 day ago
$178
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Mon, Dec 22 from Orlando Intl. to Portland Intl. Jetport, returning Wed, Dec 31, priced at $178 found 1 day ago
Bargain Flight
Mon, Jan 12 - Wed, Jan 21
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$184 Roundtrip, found 1 day ago
$184
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Mon, Jan 12 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Wed, Jan 21, priced at $184 found 1 day ago
Breeze Airways
Fri, Jan 2 - Tue, Jan 6
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$192 Roundtrip, found 3 days ago
$192
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Fri, Jan 2 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Tue, Jan 6, priced at $192 found 3 days ago