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Gray Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
InnSeason Resorts The Falls at Ogunquit

InnSeason Resorts The Falls at Ogunquit

2.5 out of 5
Price was $380, price is now $302 per person
$302
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
New York (JFK) 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.
Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
Price was $1,136, price is now $702 per person
$702
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
New York (JFK) 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.
River View Resort

River View Resort

2.5 out of 5
Price was $597, price is now $457 per person
$457
per person
Jan 30 - Feb 2
found 6 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
Stay at this motel in Bethel. Enjoy free WiFi, free parking, and 4 outdoor pickleball courts. Our guests praise the helpful staff in our reviews. Popular attractions Sunday River and Bethel Pathway are located nearby.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Price was $712, price is now $547 per person
$547
per person
Feb 5 - Feb 8
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.
The Docent's Collection - New Opening

The Docent's Collection - New Opening

2 out of 5
Price was $857, price is now $667 per person
$667
per person
Feb 5 - Feb 8
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 daily housekeeping. Popular attractions Thompson's Point and Maine Mall are located nearby.
Snowvillage Inn

Snowvillage Inn

4 out of 5
Price was $540, price is now $430 per person
$430
per person
Jan 30 - Feb 2
found 6 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
Stay at this 4-star beach B&B in Eaton Center. Enjoy free WiFi, free parking, and a garden. Popular attractions King Pine Ski Area and Conway Lake are located nearby.
AWOL Kennebunkport

AWOL Kennebunkport

3 out of 5
Price was $496, price is now $405 per person
$405
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
New York (JFK) 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.
Greenwood Manor Inn

Greenwood Manor Inn

3.5 out of 5
Price was $535, price is now $442 per person
$442
per person
Jan 30 - Feb 2
found 6 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
Stay at this 3.5-star B&B in Harrison. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Deertrees Theatre and Cultural Center and Highland Lake are located nearby.

Gray Vacation Packages 3-4 Night Stays

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

River View Resort

2.5 out of 5
Price was $597, price is now $457 per person
$457
per person
Jan 30 - Feb 2
found 6 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
Price was $1,136, price is now $702 per person
$702
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $712, price is now $547 per person
$547
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
The Docent's Collection - New Opening

The Docent's Collection - New Opening

2 out of 5
Downtown Portland
Price was $857, price is now $667 per person
$667
per person
Feb 5 - Feb 8
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.
Casco Bay Inn

Casco Bay Inn

2 out of 5
Price was $848, price is now $772 per person
$772
per person
Dec 18 - Dec 23
found 6 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Hilton Garden Inn Freeport Downtown

Hilton Garden Inn Freeport Downtown

3 out of 5
Price was $963, price is now $857 per person
$857
per person
Dec 18 - Dec 23
found 6 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Hampton Inn Bath (Brunswick Area)

Hampton Inn Bath (Brunswick Area)

3 out of 5
Price was $996, price is now $901 per person
$901
per person
Dec 18 - Dec 23
found 6 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
The Docent's Collection - New Opening

The Docent's Collection - New Opening

2 out of 5
Downtown Portland
Price was $1,428, price is now $1,303 per person
$1,303
per person
Dec 22 - Dec 27
found 15 hours 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, Dec 20 - Wed, Dec 24
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$186 Roundtrip, found 1 hour ago
$186
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Sat, Dec 20 from Orlando Intl. to Portland Intl. Jetport, returning Wed, Dec 24, priced at $186 found 1 hour ago
American Airlines
Thu, Jan 15 - Mon, Jan 19
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$189 Roundtrip, found 1 hour ago
$189
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Thu, Jan 15 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Mon, Jan 19, priced at $189 found 1 hour ago
Bargain Flight
Wed, Dec 31 - Thu, Jan 8
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$226 Roundtrip, found 4 days ago
$226
Roundtrip
found 4 days ago
Select Bargain Flight flight, departing Wed, Dec 31 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Thu, Jan 8, priced at $226 found 4 days ago
American Airlines
Thu, Nov 27 - Wed, Dec 3
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$229 Roundtrip, found 5 days ago
$229
Roundtrip
found 5 days ago
Select American Airlines flight, departing Thu, Nov 27 from Tampa Intl. to Portland Intl. Jetport, returning Wed, Dec 3, priced at $229 found 5 days ago