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.
DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland

4 out of 5
Price was CA $1,082, price is now CA $962 per person
CA $962
per person
Oct 27 - Oct 30
found 7 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PWM)
8/10 Very Good! (1,217 reviews)
It was very close to the airport and had a lot of options for food and gas nearby. Short drive to more touristy spots.

Reviewed on Aug. 25, 2025

Inn By The Sea

Inn By The Sea

4 out of 5
Price was CA $2,064, price is now CA $1,789 per person
CA $1,789
per person
Oct 27 - Oct 30
found 7 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PWM)
9.4/10 Exceptional! (279 reviews)
We chose Inn by the Sea because it was advertised as a “pet-friendly” property with beach access for pets, which was a key factor in our decision. Unfortunately, our experience didn’t quite align with those expectations. We arrived on a Sunday around noon and, as expected, our room wasn’t ready (check-in is at 4:00pm). However, unlike many hotels, we were not offered anything while we waited — no welcome drink, light refreshment, or even an early check-in estimate — despite having to wait the full four hours. Once we checked in, we were told our assigned room was not pet-friendly, and we would be charged for any accidents — despite booking under the premise that this was a pet-friendly stay. Additionally, the restaurant only allows pets in the outdoor seating area, and the pool area is not pet-friendly at all. So while the hotel does accommodate pets in some areas, it’s misleading to call it fully pet-friendly when the main guest amenities are off-limits. That said, the property is beautiful and most of the staff were friendly and professional, which we appreciated. But overall, if you’re traveling with a pet and hoping for a truly integrated experience, this may not be the best fit.

Reviewed on Aug. 18, 2025

Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 out of 5
West End
Price was CA $1,613, price is now CA $1,405 per person
CA $1,405
per person
Oct 27 - Oct 30
found 7 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PWM)
9.8/10 Exceptional! (115 reviews)
The Blind Tiger was a gem. It was convenient and private enough to enjoy with staff available 24/7 with and questions. The room, lobby and all areas were immaculate and brilliantly arranged. I would definitely go again!

Reviewed on Jul. 23, 2025

Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Price was CA $1,577, price is now CA $1,394 per person
CA $1,394
per person
Oct 27 - Oct 30
found 7 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PWM)
9.4/10 Exceptional! (608 reviews)
Walkable to downtown Kennebunkport shopping.

Reviewed on Aug. 24, 2025

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was CA $1,834, price is now CA $1,630 per person
CA $1,630
per person
Oct 27 - Oct 30
found 7 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PWM)
9.6/10 Exceptional! (150 reviews)
Small bathroom. No safe. No storage space. Everything else was above average.

Reviewed on Jul. 16, 2025

Ready to book your vacation to Peaks Island?

 

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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 Sep 2 to Sep 3
CA $210
CA $233 total
Sep 2 - Sep 3
includes taxes & fees
7.8/10 Good! (1,008 reviews)
"Consistent- we’ve chosen to stay many times both when we need Park and Fly and when going to local concerts at Thompson Point so we can walk over, and have the long drive home late at night. Clean, friendly and convenient. Price is reasonable."

Reviewed on Aug. 23, 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 $161 per night from Aug 28 to Aug 29
CA $161
CA $175 total
Aug 28 - Aug 29
includes taxes & fees
7.8/10 Good! (1,242 reviews)
"This Days Inn is a great place to stay."

Reviewed on Aug. 24, 2025

Days Inn by Wyndham Airport/Maine Mall
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
155 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $179 per night from Sep 1 to Sep 2
CA $179
CA $198 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (1,047 reviews)
"Property is good . Nice area and convenient"

Reviewed on Aug. 22, 2025

Ramada Plaza by Wyndham 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.
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What to do in Peaks Island

Afternoon Windjammer Cruise Along the Coast of Portland Maine

Afternoon Windjammer Cruise Along the Coast of Portland Maine

CA $92
per adult
Afternoon Windjammer Cruise Along the Coast of Portland Maine
Portland: Sightseeing Cruise to Portland Head Light

Portland: Sightseeing Cruise to Portland Head Light

CA $56
per adult
98% of travellers recommend
Portland: Sightseeing Cruise to Portland Head Light
Maine Whale Watching Tour in Portland

Maine Whale Watching Tour in Portland

CA $150
per adult
Maine Whale Watching Tour in Portland
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 $962 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.