Peaks Island Vacation Packages 2025/2026 from $465

Peaks Island flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

84 Main

$465

per person

Dec 19 - Dec 22

found 17 hours ago

Roundtrip flight included

Chicago (ORD) to Portland (PWM)

This condo doesn't skimp on freebies - guests receive free WiFi and free self parking. Luggage storage and laundry facilities are also provided.

Cliff House Maine

Save 100% on your flight

$915

per person

Dec 19 - Dec 22

found 17 hours ago

Roundtrip flight included

Chicago (ORD) to Portland (PWM)

A full-service spa, 2 restaurants, and an indoor pool are all featured at this smoke-free resort. Traveling on business? Take advantage of the business center, laundry service, and valet parking. Relax with a drink at one of the 2 poolside bars and enjoy perks like free self parking.

Hilton Garden Inn Freeport Downtown

$583

per person

Jan 28 - Feb 3

found 1 day ago

Roundtrip non-stop flight included

New Orleans (MSY) to Portland (PWM)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.

Best Western Freeport Inn

$509

per person

Jan 28 - Feb 3

found 1 day ago

Roundtrip non-stop flight included

New Orleans (MSY) to Portland (PWM)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. There's a seasonal outdoor pool on site, and a 24-hour front desk and express check-out are also provided.

Hampton Inn Bath (Brunswick Area)

$664

per person

Jan 28 - Feb 3

found 1 day ago

Roundtrip non-stop flight included

New Orleans (MSY) to Portland (PWM)

This hotel features an indoor pool and a 24-hour gym. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. A business center, a lobby fireplace, and express check-out are also on offer.

Top Peaks Island hotels deals

Inn On Peaks Island

33 Island Avenue, Peaks Island, ME

$161 nightly

$175 total

Nov 18 - Nov 19

Total with taxes and fees

A restaurant and a bar/lounge are featured at this inn. Guests will appreciate free perks like free self parking and WiFi in public areas. Wedding services are provided for your convenience.

Parking included

Free WiFi

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME

Free Cancellation

Reserve now, pay when you stay

$83 nightly

$92 total

Nov 20 - Nov 21

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Enjoy the hot tub and perks like free self parking and a free cruise terminal shuttle.

Pool

Hot Tub

The Westin Portland Harborview

157 High St, Portland, ME

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$98 total

Dec 2 - Dec 3

Total with taxes and fees

A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a bar/lounge on site, and laundry facilities and concierge services are also provided.

Spa

Pet friendly

Portland Harbor Hotel

468 Fore Street Portland ME

Free Cancellation

Reserve now, pay when you stay

$165 nightly

$183 total

Nov 23 - Nov 24

Total with taxes and fees

This hotel features 3 coffee shops/cafes and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll find a restaurant and a bar/lounge onsite for dining and drinks, along with a 24-hour front desk.

Pet friendly

Free WiFi

DoubleTree by Hilton Hotel Portland

363 Maine Mall Rd South Portland ME

Free Cancellation

Reserve now, pay when you stay

$81 nightly

$88 total

Nov 23 - Nov 24

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and perks like free self parking and a free airport shuttle. A business center, a coffee shop, and free WiFi in public areas are also on offer.

Pool

Free airport shuttle

Holiday Inn Portland-By the Bay by IHG

88 Spring St Portland ME

Free Cancellation

$78 nightly

$86 total

Nov 30 - Dec 1

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the 24-hour gym and perks like a free area shuttle.

Pool

Free airport shuttle

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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.

Popular places to visit

Fifth Maine Museum

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

Umbrella Cover Museum

You can spend time browsing the exhibits at Umbrella Cover Museum during your trip to Peaks Island. Experience the area's great live music and entertainment choices.

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.

Frequently asked questions

How much are vacation packages to Peaks Island?

Starting at just $465, flight and hotel packages are an excellent way to stretch your travel budget. Watch out Peaks Island — here you come!

Where can I get the best vacation package deals for Peaks Island?

Travelocity is the only place you need to go to score a sensational Peaks Island package deal. Select from as many as 400 airlines and 1,000,000 properties all over the globe and craft a vacation package that suits your style. With this amount of choice, it's easy to plan your next big adventure.

Why should I purchase my Peaks Island vacation bundle via Travelocity?

Whether you're on the hunt for the ultimate unplugged vacation or you crave the hustle and bustle of a towering metropolis, booking everything with Travelocity saves you time, hassle and money. No need to search through hundreds of different websites to find the best deal — our Price Match Guarantee ensures you'll always get the lowest possible price, and our professional customer service experts are available 24/7 should you need them.

Can I save money on my Peaks Island car rental if I combine it with a hotel or flight?

Bundling your bookings into a Peaks Island vacation package will leave you with some serious savings. Book a flight and car; a hotel, flight and car; or a car and hotel. There's no better way to discover the greater Peaks Island area than from the comfort of your own rental car. You can also add tours and experiences to your Travelocity package.