Casco Bay Islands Vacation Packages 2025/2026 from $246

Casco Bay Islands flight + hotel vacation packages

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

Hampton Inn & Suites Wells-Ogunquit

$246

per person

Jan 17 - Jan 20

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Portland (PWM)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.

The Wolfeboro Inn

Save 100% on your flight

$424

per person

Jan 17 - Jan 20

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Portland (PWM)

This hotel features a coffee shop, wedding services, and free self parking. WiFi in public areas is free. A business center, a garden, and a library are also on offer.

Cliff House Maine

Save 100% on your flight

$915

per person

Dec 19 - Dec 22

found 5 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.

InnSeason Resorts The Falls at Ogunquit

$278

per person

Jan 17 - Jan 20

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Portland (PWM)

This motel features an indoor pool and a gym. Guests will appreciate free perks like free self parking and WiFi in public areas. Laundry facilities and barbecue grills are also provided.

84 Main

$465

per person

Dec 19 - Dec 22

found 5 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.

Top Casco Bay Islands hotels deals

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

Hampton Inn Portland Downtown - Waterfront

209 Fore St, Portland, ME

Free Cancellation

Reserve now, pay when you stay

$100 nightly

$111 total

Nov 23 - Nov 24

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Enjoy the free buffet breakfast each morning.

Pool

Breakfast included

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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

Sand Beach

If a restful vacation is part of your travel plans, Sand Beach might be the perfect place to seek out during your trip to Portland. Wander the area's waterfront or simply enjoy one of its seafood restaurants.

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.

Little John Island Preserve

Explore the great outdoors at Little John Island Preserve, a lovely green space in Yarmouth. Stroll along the area's waterfront or experience its entertainment choices.

Frequently asked questions

How much are vacation packages to Casco Bay Islands?

With vacation packages being sold from just $246, it's not necessary to empty your piggy bank for your visit to Casco Bay Islands. Travelocity is here to help. Bundle up experiences, hotels and flights into a package and land impressive discounts. The more you book, the bigger the savings.

Where can I get the best vacation package deals for Casco Bay Islands?

No matter your adventure, Travelocity can help you score an unbeatable Casco Bay Islands package deal. All you have to do is select a combination from our 400 airlines and 1,000,000 worldwide properties.

Why should I purchase my Casco Bay Islands vacation package with Travelocity?

Whether you're planning a month-long vacation or a last-minute weekend escape, we have many attractive destinations to choose from at a good price. In addition, we provide 24/7 assistance, top-notch service and a Price Match Guarantee. Save yourself money and time and reserve your dream vacation now.

Can I save on my Casco Bay Islands car rental if I book it with hotels and flights?

You can with our Casco Bay Islands vacation packages. With one of these, there are tons of ways to make your travel budget go further. Combine any two or more car, flight, hotel and tour bookings and watch your savings start to pile up. With your own ride, all the attractions around Casco Bay Islands are a memorable road trip away.

Which airport is best for Casco Bay Islands?

Portland Intl. Jetport Airport (PWM) is where many visitors choose to touch down. Depending on what you plan to do in Casco Bay Islands, Knox County Regional Airport (RKD) and Augusta State Airport (AUG) are also worth looking into.

What is there to do in Casco Bay Islands?

A vibrant and impressive destination, Casco Bay Islands is home to some terrific things to see and do. Sand Beach and Fifth Maine Museum are some of the favorites.