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.
Inn at Diamond Cove

Inn at Diamond Cove

3.5 out of 5
Price was CA $1,198, price is now CA $850 per person
CA $850
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
8.8/10 Excellent! (200 reviews)

Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Moody
Price was CA $1,746, price is now CA $1,117 per person
CA $1,117
per person
Aug 29 - Sep 3
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
9/10 Wonderful! (1,008 reviews)

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was CA $2,139, price is now CA $1,525 per person
CA $1,525
per person
Aug 29 - Sep 3
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (1,781 reviews)
The property is in a great location minutes walk away from stores, great food and sights and trips. But as a property itself it lacks amenities and maintenance levels to fully justify the high seasonal pricing

Reviewed on Jul 28, 2026

The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was CA $1,406, price is now CA $1,032 per person
CA $1,032
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
8.6/10 Excellent! (1,000 reviews)

Driftaway Hotel and Pool

Driftaway Hotel and Pool

2 out of 5
Price was CA $1,496, price is now CA $1,164 per person
CA $1,164
per person
Aug 29 - Sep 3
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
8.6/10 Excellent! (1,005 reviews)

Ready to book your vacation to Peaks Island?

 

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Peaks Island Hotel Deals

The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $422 per night from Aug 23 to Aug 24
CA $422
CA $467 total
Aug 23 - Aug 24
includes taxes & fees
9/10 Wonderful! (1,017 reviews)
"nice clean well maintained large hotel -- not close to tourist destinations"

Reviewed on Jul 28, 2026

The Westin Portland Harborview
Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

3 out of 5
81 Riverside St Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $217 per night from Aug 12 to Aug 13
CA $217
CA $240 total
Aug 12 - Aug 13
includes taxes & fees
8.2/10 Very good! (1,030 reviews)
"Very nice hotel. Two pools, hot tub and sauna and gym. Very quiet. Nice gift shop and staff was helpful and friendly."

Reviewed on Jul 28, 2026

Fireside Inn & Suites Portland
Waves Oceanfront Resort

Waves Oceanfront Resort

3 out of 5
87 W Grand Ave Old Orchard Beach ME
The price is CA $409 per night from Aug 28 to Aug 29
CA $409
CA $446 total
Aug 28 - Aug 29
includes taxes & fees
8.4/10 Very good! (622 reviews)
"The AC was on one side of the room and with a divided room the other queen size bed did not get any AC so that was quite uncomfortable. The coffee was very poor quality and there was no microwave in the room"

Reviewed on Jul 27, 2026

Waves Oceanfront Resort
See all 2,389 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.
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Stay near popular Peaks Island attractions

Fifth Maine Museum

You can spend time studying the exhibits at Fifth Maine Museum during your travels in Peaks Island. Experience the area's entertainment choices and great live music.
See properties

What to do in Peaks Island

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
Morning Lighthouse Cruise Along the Coast of Portland Maine

Morning Lighthouse Cruise Along the Coast of Portland Maine

CA $84
per adult
Morning Lighthouse Cruise Along the Coast of Portland Maine
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 $850 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.