Search Deals on
Gray Vacation Packages

Build your package with 2 more options

Gray Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
Price was $411, price is now $367 per person
$367
per person
Dec 9 - Dec 12
just found
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Thompson's Point and State Theatre are located nearby.
Na

Reviewed on Nov 5, 2026

The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was $906, price is now $745 per person
$745
per person
Dec 15 - Dec 18
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this hotel in Ogunquit. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Marginal Way and Ogunquit Beach are located nearby.

Inn By The Sea

Inn By The Sea

4 out of 5
Price was $1,021, price is now $854 per person
$854
per person
Dec 9 - Dec 12
just found
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 Crescent Beach State Park and Crescent Beach 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 $733, price is now $615 per person
$615
per person
Dec 9 - Dec 12
just found
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and premium TV channels. Popular attractions State Theatre and Thompson's Point are located nearby.

Nautical Mile

Nautical Mile

2.5 out of 5
Price was $867, 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)
Stay at this aparthotel in Wells. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Moody Beach and Footbridge Beach are located nearby.

84 Main

84 Main

4 out of 5
Price was $1,030, price is now $871 per person
$871
per person
Dec 20 - Dec 23
found 3 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Stay at this condo in Kennebunk. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Dock Square and Kennebunk Free Library are located nearby.
The property was very spacious, well equipped, and well taken care of. There was lots of natural light and a very large outdoor deck accessible from all bedrooms and the living room.

Reviewed on Jul 17, 2026

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Price was $577, price is now $492 per person
$492
per person
Dec 9 - Dec 12
just found
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 State Theatre and Thompson's Point are located nearby.
Great location and spacious rooms. We brought our dog too! Loved grabbing a pre dinner drink and sitting by the cozy fireplace.

Reviewed on Nov 4, 2026

Cliff House Maine

Cliff House Maine

4.5 out of 5
Price was $1,336, price is now $1,190 per person
$1,190
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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.

Gray Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Downtown Portland
Price was $733, price is now $615 per person
$615
per person
Dec 9 - Dec 12
just found
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was $906, price is now $745 per person
$745
per person
Dec 15 - Dec 18
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Inn By The Sea

Inn By The Sea

4 out of 5
Price was $1,021, price is now $854 per person
$854
per person
Dec 9 - Dec 12
just found
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Nautical Mile

Nautical Mile

2.5 out of 5
Price was $867, 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)

Gray Vacation Packages 5-7 Night Stays

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
Valley Street
Price was $796, price is now $711 per person
$711
per person
Dec 26 - Jan 1
found 1 day 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 $2,013, price is now $1,744 per person
$1,744
per person
Dec 26 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Peaceful Home With Forest Views & Great Yard - Minutes to Town

Peaceful Home With Forest Views & Great Yard - Minutes to Town

2.5 out of 5
Price was $3,109, price is now $2,804 per person
$2,804
per person
Dec 26 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
White Barn Inn & Spa, Auberge Collection

White Barn Inn & Spa, Auberge Collection

5 out of 5
Price was $2,341, price is now $2,120 per person
$2,120
per person
Dec 25 - Dec 30
found 21 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)

Top Flight Deals

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

American Airlines
Thu, Nov 26 - Wed, Dec 2
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$215 Roundtrip, found 12 hours ago
$215
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Thu, Nov 26 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Wed, Dec 2, priced at $215 found 12 hours ago
Breeze Airways
Wed, Nov 11 - Wed, Dec 2
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$228 Roundtrip, found 1 hour ago
$228
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Wed, Nov 11 from Orlando Intl. to Portland Intl. Jetport, returning Wed, Dec 2, priced at $228 found 1 hour ago
Breeze Airways
Tue, Nov 10 - Wed, Nov 18
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$258 Roundtrip, found 1 day ago
$258
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Tue, Nov 10 from Tampa Intl. to Portland Intl. Jetport, returning Wed, Nov 18, priced at $258 found 1 day ago
United
Sat, Dec 5 - Tue, Dec 15
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$267 Roundtrip, found 6 hours ago
$267
Roundtrip
found 6 hours ago
Select United flight, departing Sat, Dec 5 from Newark Liberty Intl. Airport to Portland Intl. Jetport, returning Tue, Dec 15, priced at $267 found 6 hours ago