Cumberland County Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Top cities in Cumberland County

Portland Head Light showing rocky coastline, general coastal views and a sunset
Vacation RentalsVacation Rentals
Vacation RentalsVacation Rentals

Portland

Portland
Brunswick showing a church or cathedral and flowers
Vacation RentalsVacation Rentals
Vacation RentalsVacation Rentals

Brunswick

Brunswick
Bridgton
Vacation RentalsVacation Rentals
Vacation RentalsVacation Rentals

Bridgton

Bridgton

Cumberland County Vacation Rentals

The Weldon Hotel

The Weldon Hotel

4.5 out of 5
54 York St Portland ME
Free Cancellation
Reserve now, pay when you stay
$312 nightly
The price is $334 total per night
$334 total
Dec 29 - Dec 30
Total with taxes and fees
A 24-hour gym and free WiFi in public areas are features at The Weldon Hotel. Self parking is available for USD 40 per night. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls.
Kitchen
Washer
Charming Studio apartment with WiFi, AC in welcoming Portland

Charming Studio apartment with WiFi, AC in welcoming Portland

Portland ME
$198 nightly
The price is $215 total per night
$215 total
Dec 22 - Dec 23
Total with taxes and fees
This apartment is a smoke-free apartment building.
Air conditioning
Sebago Lake Cottage on Raymond Cape

Sebago Lake Cottage on Raymond Cape

Raymond ME
This cabin is a smoke-free cabin.
Kitchen
Air conditioning
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 ME
Guests staying at this vacation home have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
HomeAwhile

HomeAwhile

3.5 out of 5
205 Southborough Drive Scarborough ME
HomeAwhile features free WiFi in public areas and laundry facilities. Free parking is available if you drive. Friendly staff can provide front-desk service during limited hours, and also offer advice about sightseeing.
Kitchen
Pet friendly
WATERFRONT ON PETTENGILL POND

WATERFRONT ON PETTENGILL POND

WINDHAM ME
Guests of this cottage enjoy access to a water park, laundry facilities, and barbecue grills. This smoke-free cottage also has a garden.
Kitchen
Washer
New Well Built Elegant Home on the Water 2 miles to Freeport, 9 to Portland!

New Well Built Elegant Home on the Water 2 miles to Freeport, 9 to Portland!

South Freeeport ME
Guests staying at this vacation home have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
City Amenities, Casco Bay Sunrises and Natural Beauty

City Amenities, Casco Bay Sunrises and Natural Beauty

Portland ME
$235 nightly
The price is $256 total per night
$256 total
Dec 21 - Dec 22
Total with taxes and fees
Guests staying at this condo have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Spacious 4-bedroom house located in the heart of Portland, ME.

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

Portland ME
$777 nightly
The price is $846 total per night
$846 total
Dec 21 - Dec 22
Total with taxes and fees
At this vacation home, guests have access to features like laundry facilities.
Washer
Dryer
Private Entrance Residential Portland

Private Entrance Residential Portland

Portland ME
At this apartment, guests have access to features like laundry facilities.
Kitchen
Washer
Studio Unit Walkable Everywhere

Studio Unit Walkable Everywhere

Portland ME
$138 nightly
The price is $140 total per night
$140 total
Dec 21 - Dec 22
Total with taxes and fees
This apartment is a smoke-free apartment building.
Pet friendly
Air conditioning
1 room luxury ocean front studio cottage

1 room luxury ocean front studio cottage

Harpswell ME
Guests staying at this apartment have access to a garden and barbecue grills.
THE LILLIPAD.Off-grid A frame. Sebago lake region!

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

Standish ME
This cabin is a smoke-free cabin.
Kitchen
Pet friendly
Updated Long Island Maine Cottage

Updated Long Island Maine Cottage

Long Island ME
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Back yard paradise

Back yard paradise

Portland ME
This vacation home offers a water park, an outdoor pool, and laundry facilities. Additional amenities include barbecue grills and a garden.
Pool
Kitchen
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

Portland ME
$1,074 nightly
The price is $1,171 total per night
$1,171 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Guests staying at this vacation home enjoy a hot tub, laundry facilities, and a garden. This family-friendly vacation home also has barbecue grills.
Hot Tub
Kitchen
Charming 2-bedroom house with AC, WiFi in lovely Falmouth

Charming 2-bedroom house with AC, WiFi in lovely Falmouth

Falmouth ME
At this vacation home, guests have access to features like laundry facilities.
Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade

Portland ME
$149 nightly
The price is $162 total per night
$162 total
Dec 21 - Dec 22
Total with taxes and fees
At this apartment, guests enjoy features like tennis courts.
Kitchen
Free WiFi
Don't see what you're looking for?
See all available properties in Cumberland County
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.

Hotel Options in Cumberland County

    Portland Regency Hotel & Spa

    Portland Regency Hotel & Spa

    20 Milk Street Portland ME
    $134 nightly
    The price is $148 total per night from Dec 22 to Dec 23
    $148 total
    Dec 22 - Dec 23
    Total with taxes and fees
    9.4/10 Exceptional! (1,550 reviews)
    Portland Harbor Hotel

    Portland Harbor Hotel

    468 Fore Street Portland ME
    $124 nightly
    The price is $137 total per night from Dec 23 to Dec 24
    $137 total
    Dec 23 - Dec 24
    Total with taxes and fees
    9.2/10 Wonderful! (1,712 reviews)
    The Westin Portland Harborview

    The Westin Portland Harborview

    157 High St Portland ME
    $89 nightly
    The price is $98 total per night from Jan 5 to Jan 6
    $98 total
    Jan 5 - Jan 6, 2026
    Total with taxes and fees
    8.8/10 Excellent! (1,001 reviews)

Orbitz makes it easy to find vacation rentals in Cumberland County 

🏠 What is the best price for a Cumberland County vacation rental?


Cumberland County rentals range between $98 and $1,171 per night. At Orbitz, we have a vacation rental for every budget.


🏠 What types of vacation rentals in Cumberland County can I rent?


Choose from apartments to beautifully decorated vacation homes, condo resorts or even B&Bs or motels for your next Cumberland County getaway. Orbitz filters your search results so you can find the best Cumberland County vacation rental for you. We have tons of options.


🏠 Are cancellations free on Cumberland County vacation rentals with Orbitz?


You may be able to cancel or amend your Cumberland County vacation rental booking free of charge before a pre-agreed deadline. Make sure to check the terms of cancellation before you book—so you know exactly where you stand. 


🏠 How do I find the best vacation rental deals in Cumberland County?


Enter your travel dates, and we’ll do the rest. You can then browse our exciting deals and all the tempting vacation rentals we have on offer in Cumberland County by filtering your search by amenities, prices, and property types and look at customers ratings to help you pick.


🏠 How do I cancel my vacation rental booking through Orbitz


Vacation rentals have slightly different rules to other bookings on Orbitz. Usually, you need to contact your property manager, you may be able to get a full refund before the cancellation date. Click My TripsOpens in a new window on your Orbitz account page to find the right information contact. If you need more help, visit our Customer ServiceOpens in a new window page. 


🏠 What are the advantages of booking a vacation rental in Cumberland County?


When you book a Cumberland County vacation rental, you have the privacy of home and can add on those luxury amenities of a hotel. Filter your vacation rental results to find a place with a hot tub or pool, games rooms or large patio with a barbecue. With so much choice on offer, it’s easy to plan the perfect trip with Orbitz. 


🏠 Where can I find vacation rentals in Cumberland County?


Escape back to nature and check out some of the smaller towns. You’ll find great vacation rentals right across Cumberland County—with plenty of hidden gems. We also have plenty of inventory in Cumberland County main cities and near popular attraction spots.


🏠 Why should I book my Cumberland County vacation rental with Orbitz?


At Orbitz, we search the market for the best accommodation, flights, and car rental deals, so you don’t have to. We’ll help you build your dream Cumberland County vacation. With plenty of vacation rentals on offer, you can be sure to find the one that’s right for you in just a few clicks. 


More to Explore