Book Holiday Homes in Cumberland Foreside

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Cumberland Foreside

 Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

Old Orchard Beach
With a stay at this vacation home in Old Orchard Beach, you'll be within a 5-minute drive of Old Orchard Beach and Old Orchard Beach Pier.
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
NEW! Coveside! Designer decor, waterfront, AC, 2 Bedroom in Harpswell.

NEW! Coveside! Designer decor, waterfront, AC, 2 Bedroom in Harpswell.

Harpswell
Located in Harpswell, this vacation home is by the ocean, a 1-minute drive from Casco Bay and 9 minutes from Paddleworks.
NEW! Coveside! Designer decor, waterfront, AC, 2 Bedroom in Harpswell.
Sunny Modern Oasis in Portland’s Trendy East End

Sunny Modern Oasis in Portland’s Trendy East End

Portland
With a stay at this vacation home, you'll be centrally located in Portland, within a 10-minute drive of Thompson's Point and Maine Mall.
Sunny Modern Oasis in Portland’s Trendy East End
Save an average of 15% on thousands of hotels when you're signed in
Elegant and efficient Island home 4 miles from downtown Portland

Elegant and efficient Island home 4 miles from downtown Portland

Portland
With a stay at this vacation home in Portland, you'll be steps from Casco Bay and a 3-minute drive from Little Diamond Island.
Elegant and efficient Island home 4 miles from downtown Portland
Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.

Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.

2 out of 5
Portland
With a stay at this vacation home, you'll be centrally located in Portland, within a 15-minute drive of Thompson's Point and Maine Mall.
Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.
Quaint Cottage Vacation

Quaint Cottage Vacation

Old Orchard Beach
With a stay at this vacation home in Old Orchard Beach, you'll be by the sea, a 3-minute walk from Old Orchard Beach and 11 minutes by foot from Old Orchard ...
Quaint Cottage Vacation
Charming 110-year former Inn 10' from the Ocean!

Charming 110-year former Inn 10' from the Ocean!

South Portland
With a stay at this vacation home in South Portland (Willard Beach), you'll be within a 15-minute drive of Thompson's Point and Maine Mall.
Charming 110-year former Inn 10' from the Ocean!
Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!

Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!

Cumberland
With a stay at this vacation home, you'll be centrally located in Cumberland Center, within a 15-minute drive of Thompson's Point and LL Bean Flagship ...
Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!
Luxurious Penthouse with Modern Design in Downtown

Luxurious Penthouse with Modern Design in Downtown

Portland
Located in Portland (Downtown Portland), this vacation home is within a 10-minute drive of Thompson's Point and Maine Mall.
Luxurious Penthouse with Modern Design in Downtown
Don't see what you're looking for?
See all available properties in Cumberland Foreside
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.

Cumberland Foreside 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 Foreside vacation homes are the perfect way for you to wing it.

Holiday houses in Cumberland Foreside 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 Foreside 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 Foreside adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Cumberland Foreside 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 Foreside 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 Foreside Holiday Homes essential information

Accommodation
688 Holiday Homes
Lowest Price
AU$180
Highest Price
AU$260
Popular accommodation
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach, NEW! Coveside! Designer decor, waterfront, AC, 2 Bedroom in Harpswell., Sunny Modern Oasis in Portland’s Trendy East End, Elegant and efficient Island home 4 miles from downtown Portland, Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN., Quaint Cottage Vacation, Charming 110-year former Inn 10' from the Ocean!, Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!, Luxurious Penthouse with Modern Design in Downtown

Top trending hotels in Cumberland Foreside

Days Inn by Wyndham Airport/Maine Mall

Days Inn by Wyndham Airport/Maine Mall

2 out of 5
461 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$185 per night from 24 Aug to 25 Aug
AU$185
24 Aug - 25 Aug
includes taxes & fees
When you stay at Days Inn by Wyndham Airport/Maine Mall in South Portland, you'll be in a shopping district, a 2-minute drive from Maine Mall and 8 minutes from ...
Days Inn by Wyndham Airport/Maine Mall
Germaine Inn South Portland

Germaine Inn South Portland

2 out of 5
675 Main Street I-95, Rt 1-I95 ex 45-I295 Ex 3, South Portland, ME
Fully refundable
The price is AU$180 per night from 12 Aug to 13 Aug
AU$180
12 Aug - 13 Aug
includes taxes & fees
With a stay at Germaine Inn South Portland in South Portland, you'll be a 4-minute drive from Maine Mall and 6 minutes from Thompson's Point.
Germaine Inn South Portland
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
155 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$225 per night from 1 Sept to 2 Sept
AU$225
1 Sept - 2 Sept
includes taxes & fees
Located in Portland (Nasons Corner), Ramada Plaza by Wyndham Portland is within a 10-minute drive of Maine Mall and Thompson's Point.
Ramada Plaza by Wyndham Portland
Save an average of 15% on thousands of hotels when you're signed in
Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$260 per night from 18 Aug to 19 Aug
AU$260
18 Aug - 19 Aug
includes taxes & fees
With a stay at Clarion Hotel Portland in Portland, you'll be near the airport, within a 15-minute walk of Thompson's Point and Portland Exposition Building.
Clarion Hotel Portland
Don't see what you're looking for?
See all available properties in Cumberland Foreside
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.