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New Gloucester Vacation Packages

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New Gloucester Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Chebeague Island Inn

Chebeague Island Inn

4 out of 5
Price was $1,016, price is now $757 per person
$757
per person
Aug 24 - Aug 27
found 3 hours ago
Roundtrip flight included
Columbus (CMH) to Portland (PWM)
Book a stay at this beach hotel in Chebeague Island. Enjoy free WiFi, breakfast (surcharge), and a free ferry terminal shuttle. Popular attractions Little John Island Preserve and Winslow Memorial Park are located nearby.
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Save 100% on your flight
Price was $1,861, price is now $1,164 per person
$1,164
per person
Aug 14 - Aug 19
found 13 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this business-friendly hotel in Ogunquit. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ogunquit Beach and Perkins Cove are located nearby.
The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Save 100% on your flight
Price was $2,204, price is now $1,411 per person
$1,411
per person
Aug 14 - Aug 19
found 13 hours 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 Ogunquit Beach and Perkins Cove are located nearby.
Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
Price was $2,491, price is now $1,847 per person
$1,847
per person
Aug 23 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) 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 Marginal Way and Ogunquit Beach are located nearby.
Inn By The Sea

Inn By The Sea

4 out of 5
Save 100% on your flight
Price was $2,379, price is now $1,765 per person
$1,765
per person
Sep 13 - Sep 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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 Higgins Beach and Portland Head Light are located nearby.
Bourne's Ocean Acres Ogunquit

Bourne's Ocean Acres Ogunquit

2.5 out of 5
Price was $1,013, price is now $782 per person
$782
per person
Aug 14 - Aug 19
found 13 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this motel in Ogunquit. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ogunquit Beach and Marginal Way are located nearby.
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Price was $2,060, price is now $1,641 per person
$1,641
per person
Sep 5 - Sep 9
found 12 hours 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 State Theatre and Thompson's Point are located nearby.
And.N Lodging

And.N Lodging

2 out of 5
Price was $1,290, price is now $1,039 per person
$1,039
per person
Aug 25 - Sep 1
found 13 hours ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
Stay at this guesthouse in Casco. Enjoy free WiFi, free parking, and a sauna. Popular attractions Sebago Lake and Thomas Pond are located nearby.

New Gloucester Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Chebeague Island Inn

Chebeague Island Inn

4 out of 5
Price was $1,016, price is now $757 per person
$757
per person
Aug 24 - Aug 27
found 3 hours ago
Roundtrip flight included
Columbus (CMH) to Portland (PWM)
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Moody
Save 100% on your flight
Price was $1,141, price is now $771 per person
$771
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Portland (PWM)
The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Save 100% on your flight
Price was $1,368, price is now $929 per person
$929
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Portland (PWM)
Cliff House Maine

Cliff House Maine

4.5 out of 5
Bald Head
Save 100% on your flight
Price was $1,959, price is now $1,432 per person
$1,432
per person
Aug 24 - Aug 27
found 3 hours ago
Roundtrip flight included
Columbus (CMH) to Portland (PWM)

New Gloucester 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
Save 100% on your flight
Price was $1,861, price is now $1,164 per person
$1,164
per person
Aug 14 - Aug 19
found 13 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Save 100% on your flight
Price was $2,204, price is now $1,411 per person
$1,411
per person
Aug 14 - Aug 19
found 13 hours ago
Roundtrip non-stop 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 $3,627, price is now $2,440 per person
$2,440
per person
Aug 25 - Sep 1
found 13 hours ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,964, price is now $1,354 per person
$1,354
per person
Aug 14 - Aug 19
found 13 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.

Bargain Flight
Tue, Aug 18 - Sat, Aug 22
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$210 Roundtrip, found 6 days ago
$210
Roundtrip
found 6 days ago
Select Bargain Flight flight, departing Tue, Aug 18 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Sat, Aug 22, priced at $210 found 6 days ago
Bargain Flight
Tue, Jul 7 - Fri, Jul 10
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$212 Roundtrip, found 4 hours ago
$212
Roundtrip
found 4 hours ago
Select Bargain Flight flight, departing Tue, Jul 7 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Fri, Jul 10, priced at $212 found 4 hours ago
Breeze Airways
Mon, Aug 17 - Tue, Aug 25
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$221 Roundtrip, found 1 day ago
$221
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Mon, Aug 17 from Orlando Intl. to Portland Intl. Jetport, returning Tue, Aug 25, priced at $221 found 1 day ago
JetBlue Airways
Tue, Jul 28 - Thu, Aug 6
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$256 Roundtrip, found 6 days ago
$256
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Tue, Jul 28 from Tampa Intl. to Portland Intl. Jetport, returning Thu, Aug 6, priced at $256 found 6 days ago