Casco Bay Islands Vacation Packages 2025/2026 from $373

Casco Bay Islands flight + hotel vacation packages

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

Casco Bay Inn

$373

per person

Nov 20 - Nov 23

found 2 hours ago

Roundtrip non-stop flight included

Pittsburgh (PIT) to Portland (PWM)

This hotel features free self parking and free WiFi in public areas. Enjoy the free continental breakfast each morning. A terrace is also provided.

Spinneys Guesthouse & Beach Cottages

$487

per person

Nov 20 - Nov 23

found 2 hours ago

Roundtrip non-stop flight included

Pittsburgh (PIT) to Portland (PWM)

A restaurant and a bar/lounge are featured at this guesthouse. Free self parking and a picnic area are also offered on site.

The Freeport Hotel, an Ascend Collection Hotel

$378

per person

Nov 20 - Nov 23

found 2 hours ago

Roundtrip non-stop flight included

Pittsburgh (PIT) to Portland (PWM)

This motel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. Dry cleaning, laundry facilities, and free newspapers are also on offer.

Holiday Inn Express Hotel & Suites Freeport by IHG

$399

per person

Nov 20 - Nov 23

found 2 hours ago

Roundtrip non-stop flight included

Pittsburgh (PIT) 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. Guests will appreciate freebies like buffet breakfast and free self parking.

Hilton Garden Inn Freeport Downtown

$458

per person

Nov 20 - Nov 23

found 2 hours ago

Roundtrip non-stop flight included

Pittsburgh (PIT) 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.

Top Casco Bay Islands hotels deals

Portland Harbor Hotel

468 Fore Street, Portland, ME

Free Cancellation

Reserve now, pay when you stay

$164 nightly

$181 total

Nov 2 - Nov 3

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

Germaine Inn South Portland

675 Main Street I-95, Rt 1-I95 ex 45-I295 Ex 3, South Portland, ME

Free Cancellation

$90 nightly

$98 total

Oct 22 - Oct 23

Total with taxes and fees

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

Pool

Breakfast included

Fireside Inn & Suites Portland

81 Riverside St, Portland, ME

Free Cancellation

Reserve now, pay when you stay

$105 nightly

$116 total

Nov 3 - Nov 4

Total with taxes and fees

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

Pool

Pet friendly

Clarion Hotel Portland

1230 Congress St, Portland, ME

Free Cancellation

Reserve now, pay when you stay

$84 nightly

$93 total

Nov 2 - Nov 3

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

LivAway Suites Portland-Scarborough

83 Mussey Rd, Scarborough, ME

Free Cancellation

Reserve now, pay when you stay

$100 nightly

$109 total

Nov 2 - Nov 3

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, express check-in, and laundry facilities are also on offer.

Pet friendly

Parking included

Comfort Inn Airport

90 Maine Mall Rd, South Portland, ME

Free Cancellation

Reserve now, pay when you stay

$80 nightly

$87 total

Nov 3 - Nov 4

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and a free airport shuttle. Traveling on business? Take advantage of the express check-out, laundry service, and free train station pick-up. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Breakfast included

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

Sand Beach

4.5/5(22 reviews)

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 entertainment choices and great live music.

Little Diamond Island

Commune with nature and explore the great outdoors at Little Diamond Island during your travels in Portland. Stroll along the area's waterfront or experience its acclaimed theater scene.

Frequently asked questions

How much are vacation packages to Casco Bay Islands?

With vacation packages being sold from just $373, 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.