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

Cumberland County flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Pier 7 Condominiums

Pier 7 Condominiums

2 out of 5
Bass River
Price was CA $1,359, price is now CA $936 per person
CA $936
per person
Sep 26 - Oct 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) 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.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,444, price is now CA $1,572 per person
CA $1,572
per person
Oct 29 - Nov 1
found 4 hours ago
Roundtrip flight included
Ottawa (YOW) 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 Faneuil Hall Marketplace are located nearby.
Luxury Apartments by Hyatus at Boston Everett

Luxury Apartments by Hyatus at Boston Everett

5 out of 5
Price was CA $2,057, price is now CA $1,374 per person
CA $1,374
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
Book a stay at this luxury apartment in Everett. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Encore Boston Harbor and TD Garden are located nearby.
Chatham Bars Inn

Chatham Bars Inn

5 out of 5
Price was CA $6,485, price is now CA $4,357 per person
CA $4,357
per person
Oct 7 - Oct 12
found 7 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
Book a stay at this luxury resort in Chatham. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Chatham Seaside Links and Mayo House are located nearby.
The Cove at Yarmouth by Westgate Resorts

The Cove at Yarmouth by Westgate Resorts

3 out of 5
Price was CA $2,001, price is now CA $1,388 per person
CA $1,388
per person
Oct 7 - Oct 12
found 7 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
Book a stay at this spa aparthotel in West Yarmouth. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Hyannis Harbor and Cape Cod Inflatable Park are located nearby.

Top Cumberland County hotels deals

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 $163 per night
CA $163
CA $180 total
Aug 31 - Sep 1
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 Maine Mall are located nearby.
Pool
Hot tub
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 $153 per night
CA $153
CA $169 total
Sep 15 - Sep 16
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 Maine Mall and Thompson's Point are located nearby.
Pool
Hot tub
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 $350 per night
CA $350
CA $387 total
Aug 30 - Aug 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 State Theatre and Thompson's Point are located nearby.
Hot tub
Spa
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 $350 per night
CA $350
CA $387 total
Sep 20 - Sep 21
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 Thompson's Point and Portland Head Light are located nearby.
Spa
Pet-friendly
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 $378 per night
CA $378
CA $471 total
Aug 30 - Aug 31
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 Maine Mall and Cross Insurance Arena are located nearby.
Pet-friendly
Free WiFi
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
The price is CA $261 per night
CA $261
CA $289 total
Sep 7 - Sep 8
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 Thompson's Point and Portland Head Light are located nearby.
Pool
Free airport shuttle
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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.
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 $936 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.