Cumberland County Vacation Rentals - HolidayHomes base64Hash Cumberland County Vacation Rentals - HolidayHomes

Cumberland County Vacation Rentals

Browse 4,344 available vacation homes and compared across 16 trusted partners

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Top-Rated Vacation rentals in Cumberland County

Book the highest-rated Cumberland County vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

House Bailey Island
Panoramic Oceanfront Views Of Garrison Cove, Wills Gut And Casco Bay
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House Saco
Gorgeous and Unique New England Beach House: Panoramic Views of Saco Bay!
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Cabin Sebago
Beachfront Sebago Cottage w/ Deck + Grill!
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House Frye Island
House with patio, pool & grill
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House Casco
Serenity - Stunning Sebago Lake scenery
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House Cape Elizabeth
Atlantic Ocean Views, Private Beach. Newly Built Home Close To Portland, Maine!
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House Standish
Expansive Upscale Retreat on 2 Acres with Sebago Beach Access, Canal Dock, A/C
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House Casco
Private setting Sparkling Lake Sebago. Newly Renovated spring 2025.
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House Harpswell
Vacation home with grill & terrace
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House Harrison
Crystal Lake House W/ Private Beach Lake Access
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Cabin Standish
Cottage with BBQ, garden & patio | Nature view
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Cabin Harpswell
Family-friendly nice cottage with yard & patio
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House Bridgton
Cozy Summer Getaway with Lake Beach and Boating Access
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House Casco
House with terrace, grill & garden | Nature view | Suitable for remote work
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House Casco
Vacation home with yard, terrace & grill | Nature view
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Top 15 most Recommended Vacation Rentals in Cumberland County

Discover your ideal Cumberland County vacation rental with real-time comparisons of 4,344 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

Cabin Casco
Cabin ∙ 6 guests ∙ 3 bedrooms

60 m² Cabin

Casco, Cumberland County, Maine, United States
This cozy cabin in Casco accommodates 6 guests and features a fireplace for a warm, inviting atmosphere.
from $325
per night
(22)
View deal
Cabin Standish
Cabin ∙ 7 guests ∙ 3 bedrooms

88 m² Cabin

Standish, Cumberland County, Maine, United States
This cozy cabin in Standish accommodates 7 guests and features a beautiful lakeview for a perfect getaway.
from $217
per night
(73)
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House Peaks Island
8 guests ∙ 3 bedrooms

House

Peaks Island, Portland, Cumberland County
This house rental in Peaks Island accommodates 8 guests and features a family-friendly yard for outdoor activities.
from $313
per night
(65)
View deal
Condo West End
Condo ∙ 8 guests ∙ 3 bedrooms

121 m² Condo

West End, Portland, Cumberland County
This spacious West End condo accommodates 8 guests and features family-friendly amenities for a comfortable stay.
from $165
per night
(87)
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House North Deering
House ∙ 10 guests ∙ 4 bedrooms

269 m² House

North Deering, Portland, Cumberland County
Spacious house rental in North Deering for 10 guests featuring a cozy fireplace and a large yard for outdoor activities.
from $548
per night
(7)
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House Pine Point
House ∙ 12 guests ∙ 5 bedrooms

206 m² House

Pine Point, Scarborough, Cumberland County
Spacious house rental in Pine Point accommodates 12 guests and features a family-friendly kitchen perfect for gatherings.
from $477
per night
(170)
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Cabin Harpswell
Cabin ∙ 7 guests ∙ 4 bedrooms

149 m² Cabin

Harpswell, Cumberland County, Maine, United States
This cozy cabin in Harpswell accommodates 7 guests and features a charming fireplace for a warm and inviting atmosphere.
from $300
per night
(61)
View deal
House Raymond
House ∙ 8 guests ∙ 3 bedrooms

149 m² House

Raymond, Cumberland County, Maine, United States
This house rental in Raymond accommodates 8 guests and features waterfront access for a perfect getaway.
from $548
per night
(38)
View deal
House Raymond
House ∙ 20 guests ∙ 6 bedrooms

325 m² House

Raymond, Cumberland County, Maine, United States
Spacious house rental in Raymond for 20 guests featuring a family-friendly kitchen and ample parking.
from $1,001
per night
(9)
View deal

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