Cumberland County Vacation Packages 2026 from $911

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.

Hotel Ivy Boston Common

Bay Village

Save 100% on your flight

$911

per person

Jul 17 - Jul 23

found 22 hours ago

Roundtrip flight included

Dallas (DAL) to Boston (BOS)

Free WiFi in public areas, luggage storage, and a safe deposit box are available at this hotel. There's locker space and multilingual staff can provide around-the-clock assistance.

The Langham, Boston

Downtown Boston

Save 100% on your flight

$1,171

per person

Jun 10 - Jun 13

found 11 hours ago

Roundtrip non-stop flight included

Dallas (DAL) 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.

The Inn at Hastings Park, Relais & Chateaux - Boston

Save 100% on your flight

$1,895

per person

Jun 10 - Jun 17

found 1 day ago

Roundtrip flight included

Phoenix (PHX) to Boston (BOS)

A restaurant and a bar/lounge are featured at this hotel. A terrace, limo/town car service, and a snack bar/deli are also on offer.

Meadowmere Resort

Save 100% on your flight

$1,008

per person

Jul 10 - Jul 14

found 3 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Portland (PWM)

This smoke-free hotel features 2 hot tubs, an indoor pool, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and free perks like continental breakfast and free self parking.

By the Sea Guests Bed & Breakfast & Suites

$915

per person

Jul 19 - Jul 25

found 14 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Boston (BOS)

This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.

Top Cumberland County hotels deals

Portland Harbor Hotel

468 Fore Street Portland ME

Free Cancellation

Reserve now, pay when you stay

$212 nightly

$235 total

May 3 - May 4

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

Cambria Hotel Portland Downtown-Old Port

25 HANCOCK STREET Portland ME

Free Cancellation

$163 nightly

$181 total

May 3 - May 4

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 Regency Hotel & Spa

20 Milk Street Portland ME

$161 nightly

$178 total

May 26 - May 27

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.

Hot Tub

Spa

HomeAwhile

205 Southborough Drive Scarborough ME

Free Cancellation

Reserve now, pay when you stay

$125 nightly

$136 total

May 27 - May 28

Total with taxes and fees

This aparthotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Laundry facilities are provided for your convenience.

Kitchen

Pet friendly

Holiday Inn Portland-By the Bay by IHG

88 Spring St Portland ME

Free Cancellation

$118 nightly

$131 total

May 11 - May 12

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

Hyatt Place Portland Downtown - Old Port Square

433 Fore St Portland ME

Free Cancellation

Reserve now, pay when you stay

$134 nightly

$148 total

May 3 - May 4

Total with taxes and fees

This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Valet parking, a coffee shop, and a snack bar/deli are also offered.

Free airport shuttle

Pet friendly

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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.

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Frequently asked questions

How much are vacation packages to Cumberland County?

$911 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.