New Gloucester Vacation Packages
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Your New Gloucester Vacation
Our New Gloucester vacation packages let you customize your own adventure. Tailor your getaway to your style and interests and make every moment count in this exciting city. Sabbathday Lake and Spring Meadows Golf Course are among the major attractions to explore during your trip to New Gloucester. A few quick clicks is all it takes to put together the ideal New Gloucester vacation on Expedia.
Top New Gloucester Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Portland Harbor Hotel
Downtown Portland
Price was CA $2,990, price is now CA $2,236 per person
CA $2,236
per person
Jun 11 - Jun 17
found 12 hours ago
Roundtrip flight included
Winnipeg (YWG) to Portland (PWM)
9.2/10 Wonderful! (1,776 reviews)
We could have moved right in and been happy for life. Flawless.
Reviewed on Mar 30, 2026
Blind Tiger Portland - Danforth Street.
West End
Price was CA $3,743, price is now CA $2,988 per person
CA $2,988
per person
Jun 11 - Jun 17
found 12 hours ago
Roundtrip flight included
Winnipeg (YWG) to Portland (PWM)
9.6/10 Exceptional! (175 reviews)
The Blind Tiger was one of the best accommodations I've ever stayed in! The location was perfect – far enough away from the "bustle" of downtown but close enough to walk to many spots (Smalls was a favorite!). The daily breakfast was so great and the room, my goodness! Adorable, perfect, comfortable... best sleep of my life! Maggie was so helpful and accommodating and made our stay really special. All in all, highly recommend!
Reviewed on Mar 10, 2026
HomeAwhile
Price was CA $1,438, price is now CA $1,168 per person
CA $1,168
per person
Jun 10 - Jun 16
found 12 hours ago
Roundtrip flight included
Winnipeg (YWG) to Portland (PWM)
No reviews
Brand new, clean, and affordable. Check in process is done via kiosk and the front desk is usually not occupied but it was easy.
Reviewed on Apr 2, 2026
Quality Inn & Suites South Portland
Sunset Park
Price was CA $1,393, price is now CA $1,155 per person
CA $1,155
per person
Jun 10 - Jun 16
found 12 hours ago
Roundtrip flight included
Winnipeg (YWG) to Portland (PWM)
6.6/10 (1,006 reviews)
Needs some repairs, regular maintenance. Fridge gasket falling off, not closing properly. Bathroom door wouldn’t close. Tub drain wouldn’t close. Had better, had worse. Mid.
Reviewed on Mar 8, 2026
New Gloucester Hotel Deals
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $194 per night from Apr 20 to Apr 21
CA $194
CA $214 total
Apr 20 - Apr 21
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
Breakfast was really good, free shuttle to town helped, the only problem was the bad was too small, but the rest was really good.
Reviewed on Mar 29, 2026
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
The price is CA $120 per night from Apr 13 to Apr 14
CA $120
CA $133 total
Apr 13 - Apr 14
includes taxes & fees
8/10 Very Good! (1,405 reviews)
Everything was good except be nice if they didn’t charge for breakfast
Reviewed on Mar 31, 2026
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
Fully refundable
The price is CA $158 per night from Apr 7 to Apr 8
CA $158
CA $212 total
Apr 7 - Apr 8
includes taxes & fees
9.4/10 Exceptional! (1,183 reviews)
Breakfast was excellent as was the room. We especially liked the room which was bright and airy and provided a view of the rooftop lounge. The decor and the layout of the room was very contemporary and a welcome change from the typical hotel room. Location was great, too!
Reviewed on Apr 2, 2026
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
