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.
Portland Harbor Hotel
Downtown Portland
CA $831
per person
Nov 20 - Nov 24
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.2/10 Wonderful! (1,864 reviews)
This was our favorite hotel on our trip. The property is very clean and well maintained. The restaurant food was delicious. Valet service was great. Location in town was perfect very close to shopping and activities.
Reviewed on Oct 15, 2026
The Docent's Collection at 121 Middle Street
Downtown Portland
CA $1,101
per person
Nov 20 - Nov 24
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.6/10 Exceptional! (400 reviews)
Amazing location and lots of space in Portland Maine. We loved it!!
Reviewed on Oct 14, 2026
Ready to book your vacation to Peaks Island?
Peaks Island Hotel Deals
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
CA $118
CA $131 total
Nov 1 - Nov 2
includes taxes & fees
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
CA $163
CA $181 total
Nov 16 - Nov 17
includes taxes & fees
Fireside Inn & Suites Portland
81 Riverside St Portland ME
Fully refundableReserve now, pay when you stay
CA $126
CA $140 total
Oct 29 - Oct 30
includes taxes & fees
8.2/10 Very good! (1,021 reviews)
"Basic room...comfy bed....sauna and whirlpool area was nice....small very basic gym area but ok...nice grab and bag breakfast small but basic and tasty...staff was very nice tried to help with wi fi sign in but my outlook was not operating there....parking ample...close to amenities ie eateries....shopping...and ..."
Reviewed on Oct 15, 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.
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.
Umbrella Cover Museum
You can spend time browsing the exhibits at Umbrella Cover Museum during your trip to Peaks Island. Experience the area's entertainment choices and great live music.
Battery Steele
After visiting Battery Steele, make a plan to see the other sights and activities in Peaks Island. Experience the area's festivals and art scene.
Richard Boyd Art Gallery
You can spend time studying the exhibits at Richard Boyd Art Gallery during your trip to Peaks Island. Stroll along the area's waterfront or experience its entertainment choices.
What to do in Peaks Island
Sunset Windjammer Cruise Along the Coast of Portland Maine
CA $108
per adult
90% of travellers recommend
Portland: Casco Bay Morning Lighthouse Cruise
CA $83
per adult
80% of travellers recommend
Portland Smartphone Audio Tour: Self-Guided Drive
CA $24
per traveller
100% of travellers recommend
Frequently asked questions
How much does a Peaks Island vacation package cost?
You'll find cheap prices from CA $673 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?
- 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.
- 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.
- 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.
- 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.
