Book Exclusive Cumberland County Vacation Packages

Choose one or more items to build your trip:

Search vacation packages deals in Cumberland County's top destinations

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

Portland

Vacations
Portland
A brick building with green shutters, a tree with red leaves, and a street with people walking.

Freeport

Vacations
Freeport

Cumberland County flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was CA $1,451, price is now CA $1,092 per person
CA $1,092
per person
Aug 21 - Aug 24
found 18 hours ago
Roundtrip flight included
Montreal (YUL) to Boston (BOS)
Book a stay at this beach guesthouse in Dennis Port. Enjoy free WiFi, free parking, and a private beach. Popular attractions West Dennis Beach and Cape Cod Inflatable Park are located nearby.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,385, price is now CA $1,451 per person
CA $1,451
per person
Sep 4 - Sep 7
found 12 hours ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the room service in our reviews. Popular attractions New England Aquarium and Boston Harbor are located nearby.
Good Hotels Boston

Good Hotels Boston

2 out of 5
South End
Price was CA $1,688, price is now CA $1,187 per person
CA $1,187
per person
Sep 4 - Sep 7
found 12 hours ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
Stay at this hotel in Boston. Enjoy free WiFi, laundry facilities, and bathrobes. Popular attractions Copley Square and Fenway Park are located nearby.
The Cape Club Resort

The Cape Club Resort

2 out of 5
Price was CA $2,372, price is now CA $1,707 per person
CA $1,707
per person
Aug 23 - Aug 29
found 9 hours ago
Roundtrip flight included
Montreal (YUL) to Boston (BOS)
Book a stay at this golf hotel in East Falmouth. Enjoy free WiFi, free parking, and a golf course. Popular attractions Old Silver Beach and Francis A. Crane Wildlife Management Area are located nearby.
Sea Crest Beach Resort

Sea Crest Beach Resort

3.5 out of 5
Price was CA $2,516, price is now CA $1,872 per person
CA $1,872
per person
Aug 23 - Aug 29
found 9 hours ago
Roundtrip flight included
Montreal (YUL) to Boston (BOS)
Book a stay at this beach hotel in North Falmouth. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Old Silver Beach and Southwest Beach are located nearby.

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
The price is CA $225 per night
CA $225
CA $249 total
Jul 12 - Jul 13
includes taxes & fees
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Thompson's Point and State Theatre are located nearby.
Pool
Breakfast included
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Free cancellation
Reserve now, pay when you stay
The price is CA $508 per night
CA $508
CA $616 total
Jul 26 - Jul 27
includes taxes & fees
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Casco Bay Lines Ferry Terminal and State Theatre are located nearby.
Pet-friendly
Free WiFi
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
Free cancellation
The price is CA $341 per night
CA $341
CA $416 total
Jul 12 - Jul 13
includes taxes & fees
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Cross Insurance Arena and State Theatre are located nearby.
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
The price is CA $346 per night
CA $346
CA $382 total
Jul 12 - Jul 13
includes taxes & fees
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Casco Bay Lines Ferry Terminal and State Theatre are located nearby.
Hot tub
Spa
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
The price is CA $324 per night
CA $324
CA $358 total
Aug 2 - Aug 3
includes taxes & fees
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions State Theatre and Casco Bay Lines Ferry Terminal are located nearby.
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St Portland ME
The price is CA $396 per night
CA $396
CA $438 total
Jul 26 - Jul 27
includes taxes & fees
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions State Theatre and Casco Bay Lines Ferry Terminal are located nearby.
Don't see what you're looking for?
See all available properties in Cumberland County
View all properties
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 multi-story brick building with a large arched window and a sign that reads "STATE".

State Theatre

8.8/10 (392 reviews)
You can make plans for a show at State Theatre during your trip to Portland. Experience the area's acclaimed theater scene and entertainment choices.
See properties

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?
CA $1,092 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.