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.
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Moody
Price was CA $1,010, price is now CA $762 per person
CA $762
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
9/10 Wonderful! (1,008 reviews)
This is a clean quiet beautifully kept excellent service . We've stayed at beach places that didn't even make the bed or give clean towels. We will spend time again there soon

Reviewed on Jul 28, 2026

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)

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)

Evalina Hotel

Evalina Hotel

2.5 out of 5
Downtown Portland
Price was CA $3,024, price is now CA $2,354 per person
CA $2,354
per person
Sep 28 - Oct 2
found 21 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PWM)
10/10 Exceptional! (5 reviews)
Truly a wonderful place with an unbeatable location. Highly recommend for a visit to Portland.

Reviewed on Jul 26, 2026

The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Price was CA $2,449, price is now CA $2,017 per person
CA $2,017
per person
Sep 28 - Oct 2
found 21 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PWM)
9.8/10 Exceptional! (102 reviews)
Really nice room and location

Reviewed on Jul 27, 2026

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 17 to Aug 18
CA $217
CA $240 total
Aug 17 - Aug 18
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 $325 per night from Aug 27 to Aug 28
CA $325
CA $354 total
Aug 27 - Aug 28
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 $762 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.