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.
Stage Neck Inn

Stage Neck Inn

4 out of 5
Price was CA $1,938, price is now CA $1,783 per person
CA $1,783
per person
Dec 2 - Dec 7
found 3 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PWM)
9.4/10 Exceptional! (551 reviews)
Great place to stay and relax!

Reviewed on Oct 17, 2026

Sauna Hot Tub Game Room Theater Firepit

Sauna Hot Tub Game Room Theater Firepit

2 out of 5
Price was CA $7,517, price is now CA $6,569 per person
CA $6,569
per person
Dec 20 - Dec 26
found 3 hours ago
Roundtrip flight included
Montreal (YUL) to Portland (PWM)
No reviews

River View Resort

River View Resort

2.5 out of 5
Price was CA $3,172, price is now CA $2,780 per person
CA $2,780
per person
Dec 20 - Dec 26
found 3 hours ago
Roundtrip flight included
Montreal (YUL) to Portland (PWM)
9/10 Wonderful! (337 reviews)

Close to Sunday River Hot Tub Sauna Cold Plunge

Close to Sunday River Hot Tub Sauna Cold Plunge

2 out of 5
Price was CA $7,306, price is now CA $6,403 per person
CA $6,403
per person
Dec 20 - Dec 26
found 3 hours ago
Roundtrip flight included
Montreal (YUL) to Portland (PWM)
No reviews

Admiral Peary Inn

Admiral Peary Inn

3 out of 5
Price was CA $2,430, price is now CA $2,242 per person
CA $2,242
per person
Dec 20 - Dec 26
found 3 hours ago
Roundtrip flight included
Montreal (YUL) to Portland (PWM)
8.8/10 Excellent! (65 reviews)
The host was quick in responding to texts - long day and I was confused iver simple things…. Breakfast is not to be missed - fruit cobbler bake was scrumptious!

Reviewed on Oct 25, 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 $151 per night from Nov 19 to Nov 20
CA $151
CA $167 total
Nov 19 - Nov 20
includes taxes & fees
The Westin Portland Harborview
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Fully refundable
The price is CA $117 per night from Nov 2 to Nov 3
CA $117
CA $129 total
Nov 2 - Nov 3
includes taxes & fees
Clarion Hotel Portland Airport ME
Quality Inn & Suites South Portland

Quality Inn & Suites South Portland

2.5 out of 5
738 Main Street South Portland ME
Fully refundable
The price is CA $101 per night from Nov 19 to Nov 20
CA $101
CA $110 total
Nov 19 - Nov 20
includes taxes & fees
Quality Inn & Suites South Portland
See all 2,374 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
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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

Harbor Lights and Sights Cruise

Harbor Lights and Sights Cruise

CA $86
per adult
90% of travellers recommend
Harbor Lights and Sights Cruise
Sunset Windjammer Cruise Along the Coast of Portland Maine

Sunset Windjammer Cruise Along the Coast of Portland Maine

CA $109
per adult
92% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
Portland: Casco Bay Morning Lighthouse Cruise

Portland: Casco Bay Morning Lighthouse Cruise

CA $83
per adult
80% of travellers recommend
Portland: Casco Bay Morning Lighthouse Cruise
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 $1,783 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.