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Holiday Rentals in Cumberland County

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Featured Holiday Rentals in Cumberland County

Exterior
Sebago Lake Cottage on Raymond Cape

Sebago Lake Cottage on Raymond Cape

Raymond
10.0 out of 10, Exceptional, (48)
"We loved this cabin! A stone throw from the lake. Private and quiet. "
United States
Kathy K.
Sebago Lake Cottage on Raymond Cape
On the beach
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

Bailey Island
10.0 out of 10, Exceptional, (234)
"Tremendous stay, great property and host."
United States
Curtis G.
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
Property grounds
WATERFRONT ON PETTENGILL POND

WATERFRONT ON PETTENGILL POND

WINDHAM
9.6 out of 10, Exceptional, (4)
"My kids and I loved our stay at the pond. We enjoyed kayaking and floating in the peaceful setting. "
United States
Darby F.
WATERFRONT ON PETTENGILL POND
Interior
Spacious 4-bedroom house located in the heart of Portland, ME.

Spacious 4-bedroom house located in the heart of Portland, ME.

Munjoy Hill
9.8 out of 10, Exceptional, (6)
"Great place great location. "
United States
Chris f.
The price is €737
includes taxes & fees
7 Dec - 8 Dec
Spacious 4-bedroom house located in the heart of Portland, ME.
Fridge, microwave, oven, stovetop
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

East Deering
10.0 out of 10, Exceptional, (66)
"Nice stay. Good amenities. "
United States
Laura H.
The price is €947
includes taxes & fees
7 Dec - 8 Dec
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
Fridge, microwave, oven, stovetop
Private Entrance Residential Portland

Private Entrance Residential Portland

Deering Center
9.2 out of 10, Wonderful, (5)
"Great location for seeing the Portland Head Lighthouse. Comfortable bed."
United States
Michelle S.
Private Entrance Residential Portland
Fridge, microwave, oven, stovetop
1 room luxury ocean front studio cottage

1 room luxury ocean front studio cottage

Harpswell
9.6 out of 10, Exceptional, (171)
"Very clean beautiful view we definitely enjoyed ourselves "
United States
Ilona F.
1 room luxury ocean front studio cottage
Property grounds
Bright and Fresh Back Cove4 Bedroom, Sleeps 8. Airmatress for additional 2.

Bright and Fresh Back Cove4 Bedroom, Sleeps 8. Airmatress for additional 2.

Back Cove
9.6 out of 10, Exceptional, (72)
"The house is great and just outside of downtown, perfect location. The check-in and checkout processes were easy and simple! We really enjoyed our stay"
United States
matt m.
Bright and Fresh Back Cove4 Bedroom, Sleeps 8. Airmatress for additional 2.
Exterior
Charming lakefront cottage with a dock, WiFi, & washer/dryer - dogs welcome

Charming lakefront cottage with a dock, WiFi, & washer/dryer - dogs welcome

Windham
8.8 out of 10, Excellent, (48)
"Was great spot!"
United States
Nora O.
Charming lakefront cottage with a dock, WiFi, & washer/dryer - dogs welcome
1 bedroom, bed sheets
Studio Unit Walkable Everywhere

Studio Unit Walkable Everywhere

West Bayside
5.8 out of 10, (7)
"We didn't stay there at all. Canceled reservation "
United States
Dianne
The price is €124
includes taxes & fees
16 Dec - 17 Dec
Studio Unit Walkable Everywhere
Property grounds
THE LILLIPAD.Off-grid A frame. Sebago lake region!

THE LILLIPAD.Off-grid A frame. Sebago lake region!

Standish
9.8 out of 10, Exceptional, (7)
"Great view of the pond and nice accommodations for a single guest."
United States
Brian M.
THE LILLIPAD.Off-grid A frame. Sebago lake region!
Fridge, microwave, oven, stovetop
The Globe House on Munjoy Hill - Walk to Breweries

The Globe House on Munjoy Hill - Walk to Breweries

Munjoy Hill
10.0 out of 10, Exceptional, (93)
"Beautiful house in great area."
United States
Amber W.
The Globe House on Munjoy Hill - Walk to Breweries
Fridge, oven, stovetop, coffee/tea maker
Updated Long Island Maine Cottage

Updated Long Island Maine Cottage

Long Island
10.0 out of 10, Exceptional, (7)
"Great island house! Loved how stocked the kitchen was, we had comfortable beds and even beach chairs and cooler. We would definitely stay here again. "
United States
Serra C.
Updated Long Island Maine Cottage
Exterior
Romantic getaway for 2 PEAK fall foliage!!!

Romantic getaway for 2 PEAK fall foliage!!!

Naples
10.0 out of 10, Exceptional, (313)
"Perfect waterfront property. Not far from all the action in town. Has all the needed amenities to make this a memorable vacation we won't forget. "
United States
Owen E.
Romantic getaway for 2 PEAK fall foliage!!!
TV
In-town no frills 2 bedroom apt

In-town no frills 2 bedroom apt

West Bayside
8.6 out of 10, Excellent, (16)
"Host was very accommodating. Apartment worked well for. Description accurate. Would stay again."
United Kingdom
Martha F.
The price is €138
includes taxes & fees
16 Dec - 17 Dec
In-town no frills 2 bedroom apt
Exterior
Cozy, Elegant and Bright 2 bed in the East End

Cozy, Elegant and Bright 2 bed in the East End

Munjoy Hill
9.8 out of 10, Exceptional, (52)
"Excellent stay and location"
United States
David M.
The price is €324
includes taxes & fees
29 Dec - 30 Dec
Cozy, Elegant and Bright 2 bed in the East End
Outdoor dining
Knock on Wood | Airy Charm in Heart of Downtown

Knock on Wood | Airy Charm in Heart of Downtown

Parkside
8.8 out of 10, Excellent, (25)
"peaceful apartment. located near great restaurants. walk to town. "
United States
NATHAN F.
The price is €243
includes taxes & fees
8 Dec - 9 Dec
Knock on Wood | Airy Charm in Heart of Downtown
Beach
GREAT Newly Renovated Sebago Lake- short walk to Nason`s beach🏠🏖🚗

GREAT Newly Renovated Sebago Lake- short walk to Nason`s beach🏠🏖🚗

North Sebago
9.8 out of 10, Exceptional, (84)
"Easy check in and out. Cabin was clean. We liked being so close to the beach and a quick drive to Naples where there were restaurants."
United States
Kristina G.
GREAT Newly Renovated Sebago Lake- short walk to Nason`s beach🏠🏖🚗
Interior
Charming Studio apartment with WiFi, AC in welcoming Portland

Charming Studio apartment with WiFi, AC in welcoming Portland

Munjoy Hill
9.6 out of 10, Exceptional, (11)
"A great location and a comfortable place to stay!"
United States
Andrew K.
The price is €189
includes taxes & fees
7 Dec - 8 Dec
Charming Studio apartment with WiFi, AC in welcoming Portland
Outdoor dining
Beautiful Delightful 3BR Downtown Brunswick All King Beds

Beautiful Delightful 3BR Downtown Brunswick All King Beds

Brunswick
10.0 out of 10, Exceptional, (19)
"We only stayed 2 nights but really loved the central location. Very easy :) "
United States
Elizabeth A.
The price is €292
includes taxes & fees
15 Dec - 16 Dec
Beautiful Delightful 3BR Downtown Brunswick All King Beds
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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Top Cumberland County Hotel Reviews

Portland Harbor Hotel

Portland Harbor Hotel

10/10 Excellent
"Beautiful room, friendly staff, and perfect location."
Lisa 2-night trip
Posted 17 hours ago
Portland Harbor Hotel

Find out more about Cumberland County

Holiday Homes in Cumberland County

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