Peaks Island Vacation Packages

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Your Peaks Island Vacation

With plenty of highlights as well as some hidden gems, this city is best experienced with a Peaks Island vacation package. Check out places to stay in Parkside, which is great for festivals, markets and walking. If taking in sights is on the agenda during your trip to Peaks Island, look around major attractions like Sand Beach, Fifth Maine Museum and Little Diamond Island. Check out Expedia's wide range of travel options and book your ideal vacation to Peaks Island today.

Top Peaks Island Vacation Deals

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
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
7.8/10 Good! (1,032 reviews)
Great option to explore Portland.

Reviewed on Aug. 3, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.2/10 Wonderful! (1,542 reviews)
We were pleased with the neighborhood and our actual room. The staff member who checked us in seemed intoxicated and smelled strongly of alcohol. We were told we had a credit to use in the hotel but were charged and never received the credit. The room was very clean and the bed was comfortable. We enjoyed the historic neighborhood.

Reviewed on Aug. 4, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
per person
Oct 16 - Oct 19
found 4 hours ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (1,008 reviews)
The Cliff House is a one of a kind! Always a fantastic visit!

Reviewed on Aug. 1, 2025

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (149 reviews)
Small bathroom. No safe. No storage space. Everything else was above average.

Reviewed on Jul. 16, 2025

The Docent's Collection

The Docent's Collection

3.5 out of 5
Downtown Portland
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (218 reviews)
Fantastic place to stay when visiting Portland. The location can't be beat -- within a couple of blocks to the ferry terminal and Old Town shops and restaurants. The building is next to a police station and my family and I felt very safe. The unit was immaculate, modern, and fully equipped. Onsite parking was a huge bonus, as was the friendly and helpful staff. I would, without hesitation, stay at The Docent's Collection again.

Reviewed on Jul. 31, 2025

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Peaks Island Hotel Deals

Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $210 per night from Aug 11 to Aug 12
CA $210
CA $232 total
Aug 11 - Aug 12
includes taxes & fees
7.8/10 Good! (1,001 reviews)
"Breakfast food served out of a closet was a little odd, but it did taste good."

Reviewed on Aug. 1, 2025

Clarion Hotel Portland
Days Inn by Wyndham Airport/Maine Mall

Days Inn by Wyndham Airport/Maine Mall

2 out of 5
461 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $151 per night from Aug 24 to Aug 25
CA $151
CA $165 total
Aug 24 - Aug 25
includes taxes & fees
7.8/10 Good! (1,110 reviews)
"I enjoyed my stay and thought was excellent value for the money. For old property it has been kept up well. I enjoyed they had pool and strong AC in the rooms."

Reviewed on Aug. 3, 2025

Days Inn by Wyndham Airport/Maine Mall
Comfort Inn Airport

Comfort Inn Airport

2.5 out of 5
90 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $185 per night from Sep 1 to Sep 2
CA $185
CA $202 total
Sep 1 - Sep 2
includes taxes & fees
8.4/10 Very Good! (1,444 reviews)
"Very friend staff"

Reviewed on Aug. 1, 2025

Comfort Inn Airport
See all 2,436 properties in Peaks Island
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.
All Inclusive Vacations
All Inclusive Vacations
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What to do in Peaks Island

Port City Light Cruise

Port City Lights Cruise

CA $53
per adult
100% of travellers recommend
Port City Lights Cruise
Portland: Maine Lighthouses Sightseeing Cruise with Drinks

Portland: Maine Lighthouses Sightseeing Cruise with Drinks

CA $95
per adult
Portland: Maine Lighthouses Sightseeing Cruise with Drinks
Portland: Sightseeing Cruise to Portland Head Light

Portland: Sightseeing Cruise to Portland Head Light

CA $49
per adult
98% of travellers recommend
Portland: Sightseeing Cruise to Portland Head Light
See all activities in Peaks Island

Frequently asked questions

How much does a Peaks Island vacation package cost?
You'll find cheap prices from CA $1,196 on Expedia for your Peaks Island break. However, factors like your choice of hotel, the season and length of stay will determine how much your vacation to Peaks Island costs.
What are the cheapest months to go to Peaks Island?
November, December and January are the best times to search for cheap Peaks Island vacation packages. Choosing to travel in less busy months means you can typically find lower prices on accommodations and flights.
How many days is enough for Peaks Island?
Peaks Island vacations come in many shapes and sizes, but to really get a feel for this destination, we'd suggest 2 days is a good ballpark. With this timeframe, you can fit in top sights like Portland Museum of Art and East End Beach along with lesser-known spots. Don't miss out on cool neighbourhoods such as Downtown Portland and Old Port either. If you're clever with your time, you can even allow for a day trip outside of Peaks Island too.
Is it worth booking a vacation package to Peaks Island?
Popular for its watersports, views and cycling, a Peaks Island vacation is a hit with all kinds of travellers. Be sure to check out top sights like Fifth Maine Museum and Richard Boyd Art Gallery, and consider renting a car for day trips to experience even more.
How to find the best Peaks Island package deals?
Landing a cheap Peaks Island package deal is easy with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, add a few filters and browse what's available. You can customize your search by "Amenities," "Property type," "Popular locations" and more. Sort the results by "Price: low to high" to discover the most affordable Peaks Island package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Peaks Island vacation as a package?
You can enjoy significant savings on your Peaks Island break by booking a customized vacation package. Check the "Package" heading, then enter your travel dates and destination to see some great airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Peaks Island?
If you have your Peaks Island travel dates confirmed, book as soon as you can to snap up some unbeatable deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for jetting off on a whim.
How to plan a trip to Peaks Island?

  1. Choose when to get away: Check your diary and get packing. Your favourite season and the type of activities on offer will also help you decide when to visit Peaks Island.
  2. Budget wisely: Besides the cost of your hotel, you'll need to consider other expenses too. These include transportation, food and flights. Also, set aside some extra funds for unexpected costs that may come up during your trip to Peaks Island.
  3. Decide your trip length: Consider how long you want to spend exploring Peaks Island. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a comfortable pace.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to find a Peaks Island vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.