Deals on vacations and trips to Cumberland County

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A lighthouse, a white house with a red roof, and rocky coastline at sunset.

Portland

Vacations
Portland

Cumberland County flight + hotel vacation packages

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

Castle Manor Inn

2.5 out of 5
Save 100% on your flight
Price was $470, price is now $324 per person
$324
per person
Sep 3 - Sep 6
found 11 hours ago
Roundtrip flight included
Raleigh (RDU) to Boston (BOS)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a picnic area are also on offer.
The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

3 out of 5
Save 100% on your flight
Price was $5,744, price is now $3,791 per person
$3,791
per person
Aug 5 - Aug 10
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Boston (BOS)
A private beach and a hot tub are featured at this guesthouse. Enjoy a day at the beach kayaking, or relax with sun loungers. WiFi in public areas is free.
Hotel UMass

Hotel UMass

2.5 out of 5
Save 100% on your flight
Price was $960, price is now $634 per person
$634
per person
Sep 5 - Sep 12
found 1 day ago
Roundtrip flight included
Raleigh (RDU) to Boston (BOS)
This hotel features 5 coffee shops/cafes and a bar/lounge. Enjoy a meal from the restaurant and perks like free continental breakfast and free WiFi. Self parking, a snack bar/deli, and a lobby fireplace are also offered.
Good Hotels Boston

Good Hotels Boston

2 out of 5
South End
Save 100% on your flight
Price was $2,107, price is now $1,468 per person
$1,468
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Express check-in, express check-out, and luggage storage are available at this hotel. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. Laundry facilities and a virtual front desk are also provided.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $2,381, price is now $1,673 per person
$1,673
per person
Aug 4 - Aug 8
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Boston (BOS)
A marina, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the indoor pool and perks like free WiFi.

Top Cumberland County hotels deals

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

3 out of 5
340 Park Ave Portland ME
Free Cancellation
Reserve now, pay when you stay
$134 nightly
The price is $148 total per night
$148 total
Jul 1 - Jul 2
Total with taxes and fees
This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Enjoy the free on-the-go breakfast each morning.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Free Cancellation
Reserve now, pay when you stay
$349 nightly
The price is $386 total per night
$386 total
Jul 5 - Jul 6
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.
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
Free Cancellation
$275 nightly
The price is $304 total per night
$304 total
Jul 5 - Jul 6
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, free WiFi in public areas, and valet parking. A safe deposit box is provided and the front desk is staffed around-the-clock.
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
Free Cancellation
Reserve now, pay when you stay
$255 nightly
The price is $282 total per night
$282 total
Jul 5 - Jul 6
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

Holiday Inn Portland-By the Bay by IHG

4 out of 5
88 Spring St Portland ME
Free Cancellation
$190 nightly
The price is $210 total per night
$210 total
Jul 5 - Jul 6
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.
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St Portland ME
Free Cancellation
Reserve now, pay when you stay
$237 nightly
The price is $262 total per night
$262 total
Jul 6 - Jul 7
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.
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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

A coastal lighthouse with red-roofed houses, rocky shoreline, and the ocean.
A lighthouse on a rocky outcrop with a red-roofed building nearby, a clear blue sky, and the ocean in the background.
A lighthouse, a red-roofed house, and rocky coastline.
A lighthouse, rocky coastline, and a house by the sea.
A lighthouse, rocky shoreline, and a house by the sea.

Frequently asked questions

How much are vacation packages to Cumberland County?
$324 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

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