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.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was $1,490, price is now $683 per person
$683
per person
Oct 19 - Oct 23
found 14 hours ago
Roundtrip flight included
Tampa (TPA) 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.
Iris Hotel Boston

Iris Hotel Boston

4 out of 5
Coolidge Corner
Save 100% on your flight
Price was $2,435, price is now $1,449 per person
$1,449
per person
Sep 23 - Sep 30
found 9 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Boston (BOS)
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 computer station, dry cleaning, and luggage storage are also on offer.
The Godfrey Hotel Boston

The Godfrey Hotel Boston

4 out of 5
Downtown Boston
Save 100% on your flight
Price was $2,170, price is now $1,388 per person
$1,388
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Boston (BOS)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Valet parking, a business center, and a coffee shop are also offered.
Furnished Apartment Near Longwood

Furnished Apartment Near Longwood

3 out of 5
Coolidge Corner
Save 100% on your flight
Price was $2,747, price is now $1,770 per person
$1,770
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to Boston (BOS)
This apartment features a virtual front desk. Take advantage of the self parking.
Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Save 100% on your flight
Price was $2,798, price is now $1,851 per person
$1,851
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, laundry service, and valet parking. There's a 24-hour gym on site, and laundry facilities and concierge services are also offered.

Top Cumberland County hotels deals

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
$254 nightly
The price is $281 total per night
$281 total
Aug 30 - Aug 31
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
Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

3 out of 5
81 Riverside St Portland ME
Free Cancellation
Reserve now, pay when you stay
$111 nightly
The price is $123 total per night
$123 total
Sep 1 - Sep 2
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
Hot Tub
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Free Cancellation
$131 nightly
The price is $145 total per night
$145 total
Sep 1 - Sep 2
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
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
Free Cancellation
$300 nightly
The price is $332 total per night
$332 total
Aug 30 - Aug 31
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.
Pet friendly
Free WiFi
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Free Cancellation
Reserve now, pay when you stay
$394 nightly
The price is $435 total per night
$435 total
Aug 30 - Aug 31
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
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
$269 nightly
The price is $298 total per night
$298 total
Aug 30 - Aug 31
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
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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.

Stay near popular Cumberland County attractions

A building with 'L.L. Bean Inc.' signage, a large boot sculpture, and outdoor seating.

LL Bean Flagship Store

9.2/10 (1,289 reviews)
During your trip to Freeport, you can enjoy retail therapy at LL Bean Flagship Store. Stroll along the area's waterfront or simply enjoy its seafood restaurants.
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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?
$683 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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