Book Holiday Homes in Cumberland Center

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Featured Holiday Homes in Cumberland Center

Sunny Modern Oasis in Portland’s Trendy East End

Sunny Modern Oasis in Portland’s Trendy East End

Portland ME
With a stay at this vacation home, you'll be centrally located in Portland, within a 10-minute drive of Maine Mall and Casco Bay.
Opens in a new windowSunny Modern Oasis in Portland’s Trendy East End
Fantastic Waterfront Views

Fantastic Waterfront Views

Phippsburg ME
The price is AU$566 per night from 5 Jan to 6 Jan
AU$566
5 Jan - 6 Jan 2026
includes taxes & fees
With a stay at this vacation home in Phippsburg (West Point), you'll be within a 15-minute drive of Casco Bay and Popham Beach State Park.
Opens in a new windowFantastic Waterfront Views
Waterfront, dog-friendly home on 12+ acres with dock, hot tub & sunset views

Waterfront, dog-friendly home on 12+ acres with dock, hot tub & sunset views

Poland ME
Located in Poland, this vacation home is on the waterfront, within a 15-minute drive of Tripp Pond and The Willows Flea Market.
Opens in a new windowWaterfront, dog-friendly home on 12+ acres with dock, hot tub & sunset views
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Large, light filled 4 bedroom house - walk to ocean and ferry

Large, light filled 4 bedroom house - walk to ocean and ferry

Peaks Island ME
With a stay at this vacation home in Peaks Island, you'll be by the ocean, just a 1-minute walk from Casco Bay and 6 minutes by foot from Richard Boyd Art ...
Opens in a new windowLarge, light filled 4 bedroom house - walk to ocean and ferry
Bright & breezy beach house w/ private backyard, central AC, & relaxing hot tub

Bright & breezy beach house w/ private backyard, central AC, & relaxing hot tub

Old Orchard Beach ME
With a stay at this vacation home, you'll be centrally located in Old Orchard Beach, within a 10-minute drive of Engine and Harmon Historical Museum.
Opens in a new windowBright & breezy beach house w/ private backyard, central AC, & relaxing hot tub
The Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach

The Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach

Old Orchard Beach ME
The price is AU$717 per night from 15 Dec to 16 Dec
AU$717
15 Dec - 16 Dec
includes taxes & fees
With a stay at this vacation home in Old Orchard Beach, you'll be within a 10-minute drive of Engine and Harmon Historical Museum.
Opens in a new windowThe Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach
Beautiful house on the Harpswell Peninsula over looking Casco Bay

Beautiful house on the Harpswell Peninsula over looking Casco Bay

Harpswell ME
With a stay at this vacation home in Harpswell, you'll be by the ocean, just steps from Casco Bay and a 4-minute drive from Mitchell Field.
Opens in a new windowBeautiful house on the Harpswell Peninsula over looking Casco Bay
Private 3BR waterfront home, hot tub, pool table, sandy beach, BBQ, w/d, wifi

Private 3BR waterfront home, hot tub, pool table, sandy beach, BBQ, w/d, wifi

Scarborough ME
With a stay at this vacation home in Scarborough, you'll be on the waterfront, within a 10-minute drive of Maine Mall and Nonesuch River Golf Club.
Opens in a new windowPrivate 3BR waterfront home, hot tub, pool table, sandy beach, BBQ, w/d, wifi
Spectacular Oceanfront Estate with Beautiful Sunsets on 8 acres

Spectacular Oceanfront Estate with Beautiful Sunsets on 8 acres

Harpswell ME
With a stay at this vacation home in Harpswell, you'll be on the waterfront, just steps from Casco Bay and a 5-minute drive from Lower Goose Island.
Opens in a new windowSpectacular Oceanfront Estate with Beautiful Sunsets on 8 acres
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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.

Cumberland Center Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Cumberland Center vacation homes are the perfect way for you to wing it.

Holiday houses in Cumberland Center let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Cumberland Center in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Cumberland Center adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Cumberland Center with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Cumberland Center vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Cumberland Center Holiday Homes essential information

Accommodation
764 Holiday Homes
Lowest Price
AU$109
Highest Price
AU$717
Popular accommodation
Sunny Modern Oasis in Portland’s Trendy East End, Fantastic Waterfront Views, Waterfront, dog-friendly home on 12+ acres with dock, hot tub & sunset views, Large, light filled 4 bedroom house - walk to ocean and ferry, Bright & breezy beach house w/ private backyard, central AC, & relaxing hot tub, The Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach, Beautiful house on the Harpswell Peninsula over looking Casco Bay, Private 3BR waterfront home, hot tub, pool table, sandy beach, BBQ, w/d, wifi, Spectacular Oceanfront Estate with Beautiful Sunsets on 8 acres

Top trending hotels in Cumberland Center

Tru by Hilton Portland Airport Area

Tru by Hilton Portland Airport Area

2.5 out of 5
369 Maine Mall Road South Portland ME
Fully refundableReserve now, pay when you stay
The price is AU$109 per night from 11 Jan to 12 Jan
AU$109
11 Jan - 12 Jan 2026
includes taxes & fees
When you stay at Tru by Hilton Portland Airport Area in South Portland, you'll be near the airport, just steps from Maine Mall and a 3-minute drive from Nonesuch ...
Opens in a new windowTru by Hilton Portland Airport Area
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is AU$241 per night from 16 Dec to 17 Dec
AU$241
16 Dec - 17 Dec
includes taxes & fees
With a stay at Portland Harbor Hotel, you'll be centrally located in Portland, within a 10-minute drive of Maine Mall and Casco Bay.
Opens in a new windowPortland Harbor Hotel
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
With a stay at Portland Regency Hotel & Spa, you'll be centrally located in Portland, within a 10-minute drive of Maine Mall and Casco Bay.
Opens in a new windowPortland Regency Hotel & Spa
Save an average of 15% on thousands of hotels when you're signed in
Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4 out of 5
9 Center Street Portland ME
Fully refundableReserve now, pay when you stay
The price is AU$203 per night from 22 Dec to 23 Dec
AU$203
22 Dec - 23 Dec
includes taxes & fees
With a stay at Canopy by Hilton Portland Waterfront in Portland (Downtown Portland), you'll be within a 10-minute drive of Maine Mall and Casco Bay.
Opens in a new windowCanopy by Hilton Portland Waterfront
Don't see what you're looking for?
See all available properties in Cumberland Center
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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.

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^Subject to availability and chosen travel dates.