Old Port Vacation Packages

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Top Holiday Package Deals in Old Port

Price found within the past 48 hours. Click for updated prices.
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
Nasons Corner
Price was CA $1,076, price is now CA $821 per person
CA $821
per person
Sep 25 - Sep 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
7.8/10 Good! (1,009 reviews)
I was supposed to have a King Bed with hot tub. That is what I paid for. Unfortunately, when I got to check in I was told that they didn't have any more of those rooms. I ended up downgraded to a room with a queen bed, no hot tub. I was not offered a refund on the difference in rooms. Breakfast was not offered at this location. Because I had a licensing examination the following morning, I took what was available. I don't think I will go back to this location in the future.

Reviewed on Jul 8, 2026

Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Moody
Price was CA $1,358, price is now CA $896 per person
CA $896
per person
Sep 25 - Sep 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
9/10 Wonderful! (1,008 reviews)
The rooms were spotless, the grounds looked great, everything was wonderful. I was a BIT disappointed in the breakfast though - they tell you breakfast is included in your stay but breakfast was bagels, cereal, toast, yogurt and muffins. Not my idea of breakfast. I was told because it wasn't peak season that's all wet get. I have stayed here in past years and had eggs, waffles, bacon, OJ, etc so that's what I was expecting. Besides this small hiccup, everything was great and I'd certainly stay there again.

Reviewed on Jul 9, 2026

The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was CA $3,183, price is now CA $2,162 per person
CA $2,162
per person
Aug 20 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
8.6/10 Excellent! (1,000 reviews)
Wonderful but be prepared to pay for breakfast. They have coffee and a sweet something but nothing healthy or hot unless you pay for it. Great location.

Reviewed on Jul 8, 2026

The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Downtown Portland
Price was CA $2,461, price is now CA $1,835 per person
CA $1,835
per person
Sep 25 - Sep 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
9.6/10 Exceptional! (345 reviews)
The room was very clean. The kitchen was well stocked with a few minor exceptions, namely no cutting boards (small thing). The location is perfect for exploring Old Town, highly recommend. The only improvement I would request would be some small fans in the rooms as the meager HVAC couldn't really circulate the air and it got a bit stale during the night. Very minor comfort issue. We will definitely consider staying with Docent again.

Reviewed on Jul 9, 2026

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was CA $2,041, price is now CA $1,563 per person
CA $1,563
per person
Aug 17 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (1,775 reviews)
Only 4 rooms that were having A/C problems. Of course we had one the rooms. If the A/C isn’t working, why continue to reserve the rooms and not just fix the A/C??? Front desk attendant Dennecia was wonderful and was able to get us moved for our last night in Portland. She made the experience enjoyable. She did as much as she could. Just not sure why the hotel couldn’t fix the A/C in the rooms with KNOWN issues.

Reviewed on Jul 8, 2026

Where to stay in Old Port

Find the best Old Port areas and neighborhoods for the activities you enjoy most. Learn more about Old Port
A tree-lined pathway leading to a brick building with a sign reading "Mercy Hospital Service Entrance".

Downtown Portland

5 out of top 10 points of interest in this area
4.5/5(11 area reviews)

Downtown Portland is known for its captivating waterfront views, and with sights like Cross Insurance Arena and Merrill Auditorium, you won't get bored spending a day wandering around this part of Portland.

Find hotels in Downtown Portland

Old Port Hotel Deals

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $510 per night from Jul 12 to Jul 13
CA $510
CA $618 total
Jul 12 - Jul 13
includes taxes & fees
9.4/10 Exceptional! (1,779 reviews)
"Only 4 rooms that were having A/C problems. Of course we had one the rooms. If the A/C isn’t working, why continue to reserve the rooms and not just fix the A/C??? Front desk attendant Dennecia was wonderful and was able to get us moved for our last night in Portland. She made the experience enjoyable. ..."

Reviewed on Jul 8, 2026

Portland Harbor Hotel
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $319 per night from Jul 12 to Jul 13
CA $319
CA $353 total
Jul 12 - Jul 13
includes taxes & fees
9.4/10 Exceptional! (1,698 reviews)
"Loved the place but the AC could not keep up with the heat. Room was 75 degrees."

Reviewed on Jul 8, 2026

Portland Regency Hotel & Spa
Hilton Garden Inn Portland Downtown Waterfront

Hilton Garden Inn Portland Downtown Waterfront

3 out of 5
65 Commercial St Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $416 per night from Jul 12 to Jul 13
CA $416
CA $460 total
Jul 12 - Jul 13
includes taxes & fees
9.4/10 Exceptional! (1,005 reviews)
"Thanks"

Reviewed on Jul 8, 2026

Hilton Garden Inn Portland Downtown Waterfront
See all 2,435 properties in Old Port
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Frequently asked questions

How much does an Old Port vacation package cost?
From as low as CA $821. Yes, you read that right. Our Old Port vacation packages are a simple way to stretch your budget. Bundle your hotels, flights and rental car and get to know this exciting destination.
How do I get a cheap travel package to Old Port?
You'll save big if you bundle your car rentals, hotels and flights into an Old Port vacation package. Sometimes cheap means fewer choices. But not with Expedia. We offer more than 550 partner airlines and 1,000,000 hotels globally, so you'll always have plenty of variety to choose from. Eager to save even more? Add some popular activities to your package deal to unlock even bigger bargains! After all, travel is about more than simply getting to your destination.
Where should I stay in Old Port?
A trip to Old Port isn't complete until you've seen University of Southern Maine and Portland Museum of Art. Look for somewhere to stay as close as possible so you can easily access these awesome sights.
What are the top hotels in Old Port?
If this will be your first visit to Old Port, book a room at The Docents Collection or Canopy by Hilton Portland Waterfront. Both will make you feel at home and are top options with many travelers.
How far in advance should I book my Old Port vacation?
Get rewarded with the biggest variety and the cheapest prices by booking your Old Port adventure early. Airlines generally advertise flight tickets around a year before departure, so start your planning as soon as you can. Having said that, Expedia is committed to giving you the best deals around, so it's never a bad time to book your dream vacation!
What does an Expedia Old Port travel package include?
Much of that is up to you. You can select from a range of Old Port bundles, such as a hotel, rental car and flight. You can also book a flight and a hotel, or a rental car and a flight. Once you've made your booking, you can add the fun stuff like experiences and activities. Whatever your ideal Old Port trip looks like, get set to save!
What should I know before booking an Old Port travel package?
Whether it's adventure or relaxation you're craving, an Old Port vacation package lets you plan your escape your way. Plus, you'll get access to great discounts just for combining your accommodations with your flights and rental car. The more you bundle, the bigger the savings!
Can I choose my airline with an Old Port Expedia vacation package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines around the world. Our vacation packages give you the freedom to take your pick of available flights, hotels and activities that suit you.
If I'm not able to travel, can I cancel my Old Port vacation package?
Yes you can, and we're here to help. You may be able to amend or cancel your Old Port vacation package for free within 24 hours of booking. However, you may be charged a fee by your airline, hotel or car rental company if you booked more than 24 hours ago. If life throws you a curveball, visit our Customer Service Portal for more information.

Stay near popular Old Port attractions

Cross Insurance Arena

8.6/10 (275 reviews)
Catch an event at Cross Insurance Arena during your trip to Portland. Stroll along the area's waterfront or experience its entertainment choices.
See properties

Things to do

Portland Explorer: Cultural/Historical & 3 Lighthouses Tour

Portland Explorer | Maine History, Culture, & 3 Lighthouses Tour

CA $112
per adult
100% of travellers recommend
Portland Explorer | Maine History, Culture, & 3 Lighthouses Tour
Afternoon Windjammer Cruise Along the Coast of Portland Maine

Afternoon Windjammer Cruise Along the Coast of Portland Maine

CA $98
per adult
94% of travellers recommend
Afternoon Windjammer Cruise Along the Coast of Portland Maine
Sunset Windjammer Cruise Along the Coast of Portland Maine

Sunset Windjammer Cruise Along the Coast of Portland Maine

CA $109
per adult
88% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
See all activities in Portland
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.