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Gray Vacation Packages

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Gray Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Save 100% on your flight
Price was $954, price is now $724 per person
$724
per person
Oct 13 - Oct 17
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

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Save 100% on your flight
Price was $2,861, price is now $2,158 per person
$2,158
per person
Oct 21 - Oct 25
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

Evalina Hotel

Evalina Hotel

2.5 out of 5
Price was $1,574, price is now $1,237 per person
$1,237
per person
Nov 4 - Nov 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this aparthotel in Portland. Enjoy free WiFi, parking (surcharge), and in-room washers/dryers. Popular attractions Thompson's Point and Portland Head Light are located nearby.

AWOL Kennebunkport

AWOL Kennebunkport

3 out of 5
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 1 day 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

Kennebunkport Captains Collection

4.5 out of 5
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 1 day 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.

Dormir

Dormir

3 out of 5
Price was $940, price is now $750 per person
$750
per person
Oct 15 - Oct 18
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this business-friendly hotel in Windham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Sebago Lake and Seacoast Adventure are located nearby.

White Barn Inn & Spa, Auberge Collection

White Barn Inn & Spa, Auberge Collection

5 out of 5
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 1 day 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

Inn By The Sea

Inn By The Sea

4 out of 5
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

Gray Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Save 100% on your flight
Price was $954, price is now $724 per person
$724
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $2,861, price is now $2,158 per person
$2,158
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Evalina Hotel

Evalina Hotel

2.5 out of 5
Downtown Portland
Price was $1,574, price is now $1,237 per person
$1,237
per person
Nov 4 - Nov 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
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 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.
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Moody
Price was $1,012, price is now $775 per person
$775
per person
Oct 18 - Oct 23
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Portland (PWM)
The Wolfeboro Inn

The Wolfeboro Inn

3.5 out of 5
Save 100% on your flight
Price was $1,375, price is now $942 per person
$942
per person
Oct 13 - Oct 19
found 1 day ago
Roundtrip flight included
Tampa (TPA) 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 $3,211, price is now $2,320 per person
$2,320
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Evalina Hotel

Evalina Hotel

2.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $4,355, price is now $3,248 per person
$3,248
per person
Oct 11 - Oct 17
found 6 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.

Breeze Airways
Wed, Oct 28 - Sat, Oct 31
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$196 Roundtrip, found 1 day ago
$196
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Oct 28 from Tampa Intl. to Portland Intl. Jetport, returning Sat, Oct 31, priced at $196 found 1 day ago
Bargain Flight
Sun, Sep 6 - Fri, Sep 11
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$226 Roundtrip, found 2 days ago
$226
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Sun, Sep 6 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Fri, Sep 11, priced at $226 found 2 days ago
Breeze Airways
Wed, Sep 23 - Wed, Sep 30
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$256 Roundtrip, found 4 days ago
$256
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Wed, Sep 23 from Orlando Intl. to Portland Intl. Jetport, returning Wed, Sep 30, priced at $256 found 4 days ago
Bargain Flight
Sun, Sep 6 - Wed, Sep 9
ATL
Hartsfield-Jackson Atlanta Intl.
PWM
Portland Intl. Jetport
$278 Roundtrip, found 15 hours ago
$278
Roundtrip
found 15 hours ago
Select Bargain Flight flight, departing Sun, Sep 6 from Hartsfield-Jackson Atlanta Intl. to Portland Intl. Jetport, returning Wed, Sep 9, priced at $278 found 15 hours ago