Book Exclusive Cumberland County Vacation Packages

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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.
Inn at Diamond Cove

Inn at Diamond Cove

3.5 out of 5
Price was CA $1,198, price is now CA $850 per person
CA $850
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, 2 restaurants, and a marina. Our guests praise the helpful staff in our reviews. Popular attractions Casco Bay Lines Ferry Terminal and Cross Insurance Arena are located nearby.
Pier 7 Condominiums

Pier 7 Condominiums

2 out of 5
Bass River
Price was CA $2,231, price is now CA $1,602 per person
CA $1,602
per person
Sep 5 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Abbotsford (YXX) to Boston (BOS)
Stay at this hotel in South Yarmouth. Enjoy free WiFi, free parking, and a picnic area. Popular attractions Cape Cod Inflatable Park and West Dennis Beach are located nearby.
The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was CA $1,425, price is now CA $1,032 per person
CA $1,032
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
Stay at this hotel in Ogunquit. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Ogunquit Beach and Marginal Way are located nearby.
The Charles Hotel

The Charles Hotel

5 out of 5
West Cambridge
Price was CA $2,014, price is now CA $1,473 per person
CA $1,473
per person
Oct 2 - Oct 5
found 22 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Boston (BOS)
Book a stay at this luxury hotel in Cambridge. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Harvard Square and Fenway Park are located nearby.
Good Hotels Boston

Good Hotels Boston

2 out of 5
South End
Price was CA $1,978, price is now CA $1,455 per person
CA $1,455
per person
Oct 1 - Oct 4
found 2 hours ago
Roundtrip flight included
Toronto (YYZ) 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.

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
The price is CA $359 per night
CA $359
CA $397 total
Aug 23 - Aug 24
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 Cross Insurance Arena are located nearby.
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
The price is CA $224 per night
CA $224
CA $248 total
Aug 16 - Aug 17
includes taxes & fees
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.
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
The price is CA $209 per night
CA $209
CA $231 total
Aug 3 - Aug 4
includes taxes & fees
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Thompson's Point and State Theatre are located nearby.
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
Reserve now, pay when you stay
The price is CA $402 per night
CA $402
CA $484 total
Aug 23 - Aug 24
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 Casco Bay Lines Ferry Terminal and Cross Insurance Arena are located nearby.
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 $507 per night
CA $507
CA $615 total
Aug 23 - Aug 24
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 Cross Insurance Arena and Casco Bay Lines Ferry Terminal 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
The price is CA $430 per night
CA $430
CA $476 total
Jul 30 - Jul 31
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 Cross Insurance Arena are located nearby.
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 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.
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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?
CA $850 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.