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

Cumberland County Vacation Rentals

Browse 4,415 available vacation homes and compared across 13 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 Saco
Gorgeous and Unique New England Beach House: Panoramic Views of Saco Bay!
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House Naples
Sebago Waterfront Naples Maine--Dog Friendly-Sleeps 10
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House Frye Island
House with patio, pool & grill
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Cabin Standish
Authentic with Luxury Amenities With 250 Ft Of Private Sandy Frontage On Sebago
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House Cape Elizabeth
Atlantic Ocean Views, Private Beach. Newly Built Home Close To Portland, Maine!
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House Raymond
Sebago Lake Retreat with Private Beach
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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 Sebago
5 bdrm Lakefront, Sebago Lake, 100ft of Sandy Beach, Winter seasonal rates avail.
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House Harpswell
Oceanfront 4 bed, 3 bath colonial beach home, right on Casco Bay!
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House Harpswell
Unique Waterfront Experience
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House Harpswell
Vacation home with grill & terrace
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House Raymond
Sebago Lake Camp Sandy Beach Jordan Bay Raymond MaineRental Saturday-Saturday
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House Sebago
Ski Shawnee Peak & Sunday River, beautifully newly renovated vacation home.
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House Standish
PRIME TIME - JULY 2 WeeksSAVE 15%/WEEK IF booked by 4/31/2026Up to 10 people
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House Harpswell
Charming summer cottage with all the comforts of home. Fabulous covered porch overlooking Card Cove!
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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 4,415 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Bridgton
House ∙ 8 guests ∙ 3 bedrooms

112 m² House

Bridgton, Cumberland County, Maine, United States
This house rental in Bridgton accommodates 8 guests and features a cozy fireplace for relaxing evenings.
from $180
per night
(89)
View deal
House New Gloucester
House ∙ 6 guests ∙ 3 bedrooms

93 m² House

New Gloucester, Cumberland County, Maine, United States
This house rental in New Gloucester accommodates 6 guests and features a family-friendly yard perfect for outdoor activities.
from $228
per night
(94)
View deal
House Saco
House ∙ 8 guests ∙ 3 bedrooms

139 m² House

Saco, Scarborough Town, Cumberland County
This house rental in Saco accommodates 8 guests and features a family-friendly kitchen and a spacious yard.
from $271
per night
(23)
View deal
House Harpswell
House ∙ 15 guests ∙ 7 bedrooms

223 m² House

Harpswell, Cumberland County, Maine, United States
This house rental in Harpswell accommodates 15 guests and features a spacious yard perfect for family gatherings.
from $586
per night
(103)
View deal
House Bridgton
House ∙ 2 guests ∙ 3 bedrooms

209 m² House

Bridgton, Cumberland County, Maine, United States
This cozy house rental in Bridgton accommodates 2 guests and features a charming fireplace for a warm and inviting atmosphere.
from $145
per night
(22)
View deal
House Peaks Island
8 guests ∙ 3 bedrooms

House

Peaks Island, Portland, Cumberland County
This house rental on Peaks Island accommodates 8 guests and features a spacious yard for outdoor enjoyment.
from $549
per night
(8)
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Cabin Bridgton
Cabin ∙ 8 guests ∙ 3 bedrooms

139 m² Cabin

Bridgton, Cumberland County, Maine, United States
This cozy cabin in Bridgton accommodates 8 guests and features a welcoming fireplace for a perfect family getaway.
from $366
per night
(6)
View deal
Cabin Gray
Cabin ∙ 13 guests ∙ 4 bedrooms

179 m² Cabin

Gray, Cumberland County, Maine, United States
This spacious cabin in Gray accommodates 13 guests and features a cozy fireplace for a perfect family getaway.
from $318
per night
(7)
View deal
House Gray
6 guests ∙ 3 bedrooms

House

Gray, Cumberland County, Maine, United States
This house rental in Gray accommodates 6 guests and features a spacious yard perfect for family-friendly activities.
from $180
per night
(61)
View deal

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