Cumberland County Vacation Packages 2026 from $717

Search vacation packages deals in Cumberland County's top destinations

Portland

Vacations

Cumberland County flight + hotel vacation packages

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

Ogunquit River Inn & Suites

$717

per person

May 30 - Jun 4

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Portland (PWM)

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the business center and free internet in public areas. There's a seasonal outdoor pool on site, and a terrace and a garden are also provided.

Boston Lodge and Suites

Dorchester

Save 100% on your flight

$906

per person

Apr 13 - Apr 17

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Boston (BOS)

Free WiFi in public areas, a terrace, and a garden are available at this hotel. Families will appreciate the playground, onsite laundry facilities, and in-room childcare. A hair salon, a picnic area, and express check-out are also on offer.

Portland Harbor Hotel

Downtown Portland

$728

per person

May 15 - May 20

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Portland (PWM)

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.

The Langham, Boston

Downtown Boston

Save 100% on your flight

$1,388

per person

May 15 - May 18

found 1 day ago

Roundtrip non-stop flight included

Denver (DEN) to Boston (BOS)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the 24-hour gym and perks like free WiFi.

Top Cumberland County hotels deals

The Westin Portland Harborview

157 High St Portland ME

Free Cancellation

Reserve now, pay when you stay

$98 nightly

$108 total

Mar 29 - Mar 30

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.

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME

Free Cancellation

Reserve now, pay when you stay

$77 nightly

$85 total

Mar 24 - Mar 25

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.

Portland Regency Hotel & Spa

20 Milk Street Portland ME

Free Cancellation

Reserve now, pay when you stay

$132 nightly

$147 total

Mar 17 - Mar 18

Total with taxes and fees

A full-service spa, a hot tub, and a restaurant are all featured at this smoke-free hotel. Unwind with a drink at one of the 2 bars/lounges and enjoy freebies like WiFi in public areas and a roundtrip airport shuttle. There's a gym on site, and laundry facilities and concierge services are also offered.

Holiday Inn Portland-By the Bay by IHG

88 Spring St Portland ME

$78 nightly

$86 total

Mar 16 - Mar 17

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.

Cambria Hotel Portland Downtown-Old Port

25 HANCOCK STREET Portland ME

Free Cancellation

$116 nightly

$128 total

Mar 23 - Mar 24

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking and a safe deposit box are also offered on site.

Pet friendly

Free WiFi

Portland Harbor Hotel

468 Fore Street Portland ME

Free Cancellation

Reserve now, pay when you stay

$161 nightly

$178 total

Mar 15 - Mar 16

Total with taxes and fees

Pet friendly

Free WiFi

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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.

Photos of local treasures

Browse Cumberland County vacation photos for more inspiration

Cape Elizabeth Lighthouse near Portland, Maine. Located in a park just outside of Portland with some nice walking trails and great scenery.

Breathtaking sunrises and views of the Atlantic, a wonderful lighthouse, and a huge beautiful park, what else can you ask for? We went there very early on a cold September morning and it was worth the effort. The place is in the middle of a big park with plenty of parking spaces.
#MyBackyard

A little drive outside of Portland, Maine and you arrive at the oldest lighthouse in Maine.

Portland Headlight; Cape Elizabeth, Maine; USA

Frequently asked questions

How much are vacation packages to Cumberland County?

$717 is all you'll need for a memorable break in Cumberland County. Bundle your flights and hotel into a Travelocity package and see how much the savings pile up. With such good prices, you'll want to start packing your bags now!

Where can I get the best vacation package deals for Cumberland County?

Look no further than Travelocity. With as many as 400 airlines and 1,000,000 properties across the globe, it's a breeze to find a Cumberland County package deal that satisfies your wanderlust.

Why should I purchase my Cumberland County vacation package via Travelocity?

Travel should be about making cherished new memories and forgetting all your worries — which is why we provide you with a friendly team of customer service experts available 24/7 should you need them. On top of that, our Price Match Guarantee ensures you'll always get the best deal available on our superb range of getaway packages. So what are you waiting for? There's no time like the present to secure the vacation of a lifetime.

Will I save money on my Cumberland County car rental if I combine it with a hotel or flight?

Bundling your bookings into a Cumberland County vacation package will certainly save you money. You can book a car and flight; a car, flight and hotel; or a hotel and car. You won't find a better way to discover the greater Cumberland County region than with your own set of wheels. You can also add experiences and tours to your Travelocity package.

Which airport is best for Cumberland County?

Take your pick of Portland Intl. Jetport Airport (PWM) or Augusta State Airport (AUG). They are the main airports for those traveling to and from Cumberland County.

What is there to do in Cumberland County?

Cumberland County has hidden surprises around every corner, however ensure you get to Portland Museum of Art and University of Southern Maine while you're in town. These two attractions are very popular with visitors to the region.

Where to stay in Cumberland County: Best areas for travelers

Portland: The Press Hotel, Marriott Autograph Collection, the Holiday Inn Portland-By the Bay and the Portland Harbor Hotel are just a few of the terrific hotels here. After a good night's sleep, roll out of bed with all the energy you need to check out Portland Head Light and other big attractions around you.
Standish: The first thing to add to your Standish package is a good hotel. We'd recommend starting with the Frye Island Outstanding Waterfront Property and the Sebago Lake Waterfront Close To Portland. When putting together your to-do list here, Sebago Lake is a must-see.