Book Exclusive Cumberland County Vacation Packages

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Search vacation packages deals in Cumberland County's top destinations

Portland

Vacations
Portland

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 $2,444, price is now CA $1,618 per person
CA $1,618
per person
Aug 1 - Aug 7
found 1 day 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 Sea Street Beach and Pleasant Road Beach are located nearby.
Sea Crest Beach Resort

Sea Crest Beach Resort

3.5 out of 5
Price was CA $4,347, price is now CA $2,900 per person
CA $2,900
per person
Aug 1 - Aug 7
found 1 day 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 Cataumet Arts Center are located nearby.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $5,473, price is now CA $3,685 per person
CA $3,685
per person
Aug 16 - Aug 23
found 21 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) 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.
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $3,654, price is now CA $2,497 per person
CA $2,497
per person
Aug 3 - Aug 7
just found
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Price was CA $2,845, price is now CA $1,953 per person
CA $1,953
per person
Aug 16 - Aug 23
found 21 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy a rooftop terrace, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Copley Square and Boston Common are located nearby.

Top Cumberland County hotels deals

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 $295 per night
CA $295
CA $379 total
May 31 - Jun 1
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 Thompson's Point and Cross Insurance Arena 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 $266 per night
CA $266
CA $294 total
May 31 - Jun 1
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 Thompson's Point and Maine Mall are located nearby.
Hot tub
Spa
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 $236 per night
CA $236
CA $299 total
May 31 - Jun 1
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 Thompson's Point and Maine Mall are located nearby.
Pet-friendly
Free WiFi
HomeAwhile

HomeAwhile

2 out of 5
205 Southborough Drive Scarborough ME
The price is CA $163 per night
CA $163
CA $178 total
May 28 - May 29
includes taxes & fees
Stay at this hotel in Scarborough. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Maine Mall and Thompson's Point are located nearby.
Pet-friendly
Parking included
Inn at St John Portland In-Town

Inn at St John Portland In-Town

2.5 out of 5
939 Congress St Portland ME
The price is CA $187 per night
CA $187
CA $204 total
May 28 - May 29
includes taxes & fees
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Thompson's Point and Hadlock Field are located nearby.
Breakfast included
Pet-friendly
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 $148 per night
CA $148
CA $164 total
May 28 - May 29
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 Maine Mall are located nearby.
Pool
Breakfast included
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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

Portland Head Lighthouse at Cape Elizabeth, Maine, USA.
Portland Head Light, is a historic lighthouse in Cape Elizabeth, Maine.
Portland Head Light, is a historic lighthouse in Cape Elizabeth, Maine.
Portland Head Light, is a historic lighthouse in Cape Elizabeth, Maine.
Portland Head Light, lighthouse

Frequently asked questions

How much are vacation packages to Cumberland County?
CA $1,618 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.