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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.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Save 100% on your flight
Price was $830, price is now $597 per person
$597
per person
Nov 5 - Nov 9
found 1 hour ago
Roundtrip non-stop flight included
Columbus (CMH) 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 Thompson's Point and Portland Head Light are located nearby.
The main issue with this hotel were the prices. $45 per day to park. $18 for an ordinary glass of wine. $6 for a piece of toast at breakfast. The wait staff was excellent though.

Reviewed on Aug 26, 2026

The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Save 100% on your flight
Price was $1,086, price is now $726 per person
$726
per person
Nov 5 - Nov 9
found 1 hour ago
Roundtrip non-stop flight included
Columbus (CMH) to Portland (PWM)
Book a stay at this luxury aparthotel in Portland. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions Thompson's Point and Portland Head Light are located nearby.
The room was very clean and nice. The only thing that was not so great was the loud motor going on and off for some of the night. Otherwise it was great!

Reviewed on Aug 26, 2026

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Save 100% on your flight
Price was $1,478, price is now $994 per person
$994
per person
Nov 5 - Nov 9
found 1 hour ago
Roundtrip non-stop flight included
Columbus (CMH) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and parking (surcharge). Popular attractions Thompson's Point and Portland Head Light are located nearby.
Perfect location & beautiful stay! Very unique property. Great recommendations & lovely hospitality. We will definitely come back the next time we’re in Portland! :)

Reviewed on Aug 23, 2026

Evalina Hotel

Evalina Hotel

2.5 out of 5
Save 100% on your flight
Price was $1,371, price is now $940 per person
$940
per person
Nov 5 - Nov 9
found 1 hour ago
Roundtrip non-stop flight included
Columbus (CMH) 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.

Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 out of 5
Save 100% on your flight
Price was $880, price is now $617 per person
$617
per person
Nov 5 - Nov 9
found 1 hour ago
Roundtrip non-stop flight included
Columbus (CMH) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and daily housekeeping. Popular attractions Thompson's Point and Maine Mall are located nearby.

Newagen Seaside Inn

Newagen Seaside Inn

3.5 out of 5
Price was $1,405, price is now $1,019 per person
$1,019
per person
Sep 27 - Oct 2
found 16 hours ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)
Book a stay at this family-friendly hotel in Southport. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Coastal Maine Botanical Gardens and Southport Memorial Library are located nearby.

Inn By The Sea

Inn By The Sea

4 out of 5
Save 100% on your flight
Price was $1,119, price is now $841 per person
$841
per person
Nov 5 - Nov 9
found 1 hour ago
Roundtrip non-stop flight included
Columbus (CMH) 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 Portland Head Light and Crescent Beach State Park 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

Nautical Mile

Nautical Mile

2.5 out of 5
Price was $1,053, price is now $793 per person
$793
per person
Oct 14 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Stay at this aparthotel in Wells. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Ogunquit Beach and Wells Beach are located nearby.
Bel endroit où séjourner! Tout près de Well’s Beach.

Reviewed on Jul 27, 2026

New Gloucester Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 out of 5
West End
Save 100% on your flight
Price was $880, price is now $617 per person
$617
per person
Nov 5 - Nov 9
found 1 hour ago
Roundtrip non-stop flight included
Columbus (CMH) to Portland (PWM)
The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,086, price is now $726 per person
$726
per person
Nov 5 - Nov 9
found 1 hour ago
Roundtrip non-stop flight included
Columbus (CMH) 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 $1,478, price is now $994 per person
$994
per person
Nov 5 - Nov 9
found 1 hour ago
Roundtrip non-stop flight included
Columbus (CMH) to Portland (PWM)
Evalina Hotel

Evalina Hotel

2.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,371, price is now $940 per person
$940
per person
Nov 5 - Nov 9
found 1 hour ago
Roundtrip non-stop 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.
Nautical Mile

Nautical Mile

2.5 out of 5
Price was $1,053, price is now $793 per person
$793
per person
Oct 14 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Moody
Price was $1,923, price is now $1,385 per person
$1,385
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Newagen Seaside Inn

Newagen Seaside Inn

3.5 out of 5
Price was $1,405, price is now $1,019 per person
$1,019
per person
Sep 27 - Oct 2
found 16 hours ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)
The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was $1,581, price is now $1,182 per person
$1,182
per person
Oct 14 - Oct 20
found 1 day 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.

Bargain Flight
Tue, Sep 1 - Wed, Sep 2
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$214 Roundtrip, found 6 days ago
$214
Roundtrip
found 6 days ago
Select Bargain Flight flight, departing Tue, Sep 1 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Wed, Sep 2, priced at $214 found 6 days ago
Bargain Flight
Sun, Sep 6 - Fri, Sep 11
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$216 Roundtrip, found 2 days ago
$216
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 $216 found 2 days ago
Breeze Airways
Wed, Oct 28 - Sat, Oct 31
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$219 Roundtrip, found 1 day ago
$219
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 $219 found 1 day ago
Breeze Airways
Wed, Sep 23 - Wed, Sep 30
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$266 Roundtrip, found 4 hours ago
$266
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Wed, Sep 23 from Orlando Intl. to Portland Intl. Jetport, returning Wed, Sep 30, priced at $266 found 4 hours ago