New Gloucester Vacations
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New Gloucester Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Portland Harbor Hotel
Downtown Portland
$996
per person
Nov 3 - Nov 10
found 7 hours ago
Roundtrip non-stop flight included
Appleton (ATW) 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 Cross Insurance Arena and Thompson's Point are located nearby.
Evalina Hotel
Downtown Portland
$1,500
per person
Nov 3 - Nov 10
found 7 hours ago
Roundtrip non-stop flight included
Appleton (ATW) to Portland (PWM)
Stay at this aparthotel in Portland. Enjoy free WiFi, parking (surcharge), and in-room washers/dryers. Popular attractions Cross Insurance Arena and Thompson's Point are located nearby.
Blind Tiger Portland – Carleton Street
West End
$1,369
per person
Nov 3 - Nov 10
found 7 hours ago
Roundtrip non-stop flight included
Appleton (ATW) 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.
Beautiful place
Reviewed on Sep 20, 2026
The Docent's Collection at 121 Middle Street
Downtown Portland
$1,338
per person
Nov 3 - Nov 10
found 7 hours ago
Roundtrip non-stop flight included
Appleton (ATW) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and premium TV channels. Popular attractions Thompson's Point and Portland Head Light are located nearby.
Other than being a little hard to find, this spot was wonderful and so much nicer than a hotel room! Great location.
Reviewed on Sep 18, 2026
The Docent's Collection at 178 Middle Street
Downtown Portland
$1,327
per person
Nov 3 - Nov 10
found 7 hours ago
Roundtrip non-stop flight included
Appleton (ATW) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Cross Insurance Arena and Thompson's Point are located nearby.
Staff was very very good and super quick to respond.. I really liked the location for my visit bc everything was easily walkable. Room was comfortable but a little interesting walking all the way across for bathroom. A few small glitches with electrical probably just bc it’s done recently renovated.
Reviewed on Sep 18, 2026
Blind Tiger Portland - Danforth Street.
West End
$1,623
per person
Nov 3 - Nov 10
found 7 hours ago
Roundtrip non-stop flight included
Appleton (ATW) 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.
Place was charming and quirky. Very comfortable and well located.
Reviewed on Sep 18, 2026
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Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
80 John Roberts Rd. South Portland ME
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
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 ...
Comfort Inn South Portland Airport
90 Maine Mall Rd South Portland ME
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and ...
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
340 Park Ave Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the breakfast and the helpful ...
Portland Harbor Hotel
468 Fore Street Portland ME
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 ...
Fireside Inn & Suites Portland
81 Riverside St Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean ...
The Westin Portland Harborview
157 High St Portland ME
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Spark by Hilton Portland Airport Maine Mall
461 Maine Mall Rd South Portland ME
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant ...
Inn at St John Portland In-Town
939 Congress St Portland ME
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Holiday Inn Portland-By the Bay by IHG
88 Spring St Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
Portland Regency Hotel & Spa
20 Milk Street Portland ME
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
Embassy Suites by Hilton Portland Maine
1050 Westbrook Street Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the ...
Hampton Inn Portland Downtown - Waterfront
209 Fore St Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
Tru by Hilton Portland Airport Area
369 Maine Mall Road South Portland ME
Stay at this hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Sat, Jan 9 - Wed, Jan 20
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$179
Roundtrip
found 6 days ago
Tue, Nov 10 - Tue, Nov 17
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$219
Roundtrip
found 5 days ago
Tue, Nov 10 - Tue, Nov 17
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$227
Roundtrip
found 5 days ago
Tue, Nov 10 - Tue, Nov 17
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$227
Roundtrip
found 5 days ago
Tue, Nov 10 - Tue, Nov 17
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$277
Roundtrip
found 5 days ago
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