Search Deals onGray Vacation Packages
Gray Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Inn at Diamond Cove
Price was $1,005, price is now $824 per person
$824
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, 2 restaurants, and a marina. Our guests praise the helpful staff in our reviews. Popular attractions State Theatre and Portland Head Light are located nearby.
Trip was amazing. Place is so well maintained and staff is friendly, responsive and hard working
Reviewed on Sep 1, 2026
Blind Tiger Portland - Danforth Street.
Save 100% on your flight
Price was $3,193, price is now $2,359 per person
$2,359
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and parking (surcharge). Popular attractions Thompson's Point and Maine Mall are located nearby.
Enjoyable
Reviewed on Aug 28, 2026
AWOL Kennebunkport
Save 100% on your flight
Price was $1,802, price is now $1,417 per person
$1,417
per person
Oct 18 - Oct 23
found 19 hours ago
Roundtrip flight included
Tampa (TPA) to Portland (PWM)
Stay at this 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.
large rooms, helpful staff
Reviewed on Aug 31, 2026
Kennebunkport Captains Collection
Save 100% on your flight
Price was $1,734, price is now $1,380 per person
$1,380
per person
Oct 13 - Oct 17
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this 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.
White Barn Inn & Spa, Auberge Collection
Save 100% on your flight
Price was $6,409, price is now $5,170 per person
$5,170
per person
Oct 5 - Oct 9
found 24 hours ago
Roundtrip non-stop flight included
Memphis (MEM) to Portland (PWM)
Book a stay at this luxury hotel in Kennebunk. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Dock Square and Wells Beach are located nearby.
An amazing experience.
Wonderful place, wonderful accommodation (we had the loft suite). Staff was great and smiling.
Reviewed on Aug 10, 2026
The Docent's Collection at 121 Middle Street
Price was $1,694, price is now $1,376 per person
$1,376
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and premium TV channels. Popular attractions Thompson's Point and Maine Mall are located nearby.
We had two amazing stays at Docent 178 and Docent 121. Beautiful apartments situated in the heart of Old Port, Portland. You are in walking distance to some of the best food found in Maine. The staff were also incredibly helpful and one text message away. Maine in the summer is expensive, but if you are going to spend on hotels anyway, might as well do it with Docent!
Reviewed on Aug 31, 2026
Inn By The Sea
Price was $1,965, price is now $1,598 per person
$1,598
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Lovely property. Very well maintained and taken care of. The option of pool or beach is a plus. Although we didn’t utilize the activities available each day.. it seemed very family friendly. Definitely will be back but hopefully reserve a bigger room or suite. Charming outdoor seating on the huge lawn but mostly in the sun. An indoor lobby with some comfy seating would be great.
Reviewed on Aug 13, 2026
The Meadowmere Resort
Price was $1,456, price is now $1,185 per person
$1,185
per person
Oct 11 - Oct 16
found 1 day ago
Roundtrip 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 Ogunquit Beach and Marginal Way are located nearby.
Clean room
Reviewed on Sep 1, 2026
Gray Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Gray Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Wed, Oct 28 - Sat, Oct 31
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$196 Roundtrip, found 14 hours ago
$196
Roundtrip
found 14 hours ago
Sun, Sep 6 - Fri, Sep 11
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$226 Roundtrip, found 1 day ago
$226
Roundtrip
found 1 day ago
Wed, Oct 7 - Wed, Oct 14
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$233 Roundtrip, found 13 hours ago
$233
Roundtrip
found 13 hours ago
Sun, Sep 6 - Wed, Sep 9
ATL
Hartsfield-Jackson Atlanta Intl.
PWM
Portland Intl. Jetport
$278 Roundtrip, found 5 hours ago
$278
Roundtrip
found 5 hours ago
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