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Cumberland County Accommodation: Most Popular Cities to Stay

Portland Head Light showing a lighthouse, general coastal views and rugged coastline
Holiday RentalsHoliday Rentals

Portland

Portland
Holiday RentalsHoliday Rentals

Bridgton

Bridgton

Top Holiday Rentals in Cumberland County

Our top choices for Cumberland County holiday rentals

The Weldon Hotel
Deluxe Suite, 1 King Bed | Living area | LCD TV, Netflix, streaming services, music library

The Weldon Hotel

4.5 star property
9.8 out of 10, Exceptional, (78)
"Absolutely beautiful place to stay. "
The price is £309
includes taxes & fees
1 Oct - 2 Oct
The Weldon Hotel
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
On the beach

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

10.0 out of 10, Exceptional, (226)
"Beautiful views, very clean and enjoyed the oceanside vibe both inside and out! Easy walk to general store and walkable to Giant Stairs trail and Cedar Beach."
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
Romantic getaway for 2 couple date's in July just opened up
Exterior

Romantic getaway for 2 couple date's in July just opened up

10.0 out of 10, Exceptional, (310)
"Place is beautiful and well crafted with a perfect nature setting"
Romantic getaway for 2 couple date's in July just opened up
Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.
1 bedroom, in-room safe, free WiFi, bed sheets

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

2.0 star property
10.0 out of 10, Exceptional, (2)
"The property was as described, clean, and in a quiet neighborhood. Conveniently located to many local attractions. Check in and check out process was smooth. Overall enjoyed my stay very much. "
Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.
Full sized home
Interior

Full sized home

9.8 out of 10, Exceptional, (39)
"The house was lovely. Very comfortable place. Within 15- 20 mins to a store or restaurants."
The price is £270
includes taxes & fees
13 Oct - 14 Oct
Full sized home
Private Lakefront Estate with 180 Degree Views
Property grounds

Private Lakefront Estate with 180 Degree Views

10.0 out of 10, Exceptional, (6)
Private Lakefront Estate with 180 Degree Views
Studio Unit Walkable Everywhere
1 bedroom, bed sheets

Studio Unit Walkable Everywhere

6.0 out of 10, (3)
"Great, comfortable place to stay. The location is super walkable. There are several bars/restaurants very close, and other areas are close enlighten to walk to as well (I.e. Congress Street). Commercial is a bit of a walk, but if you’re like us and love to walk a new area. It’s not that far. The bed is comfortable and the place was very clean. Communication was great. We would stay here again!"
The price is £135
includes taxes & fees
16 Sept - 17 Sept
Studio Unit Walkable Everywhere
In-town no frills 2 bedroom apt
TV

In-town no frills 2 bedroom apt

7.8 out of 10, Good, (9)
"The Apt is very old but nice. Wasn’t aware of stairs as we were on the 3rd floor and had to go up very narrow stairs with no hand rails. The outdoors had bums sitting around and people across the street partying and coming up to us . Didn’t feel safe and would never have kids here. The place was nice to lay your head down but that’s it"
The price is £136
includes taxes & fees
21 Sept - 22 Sept
In-town no frills 2 bedroom apt
Private Entrance Residential Portland
Fridge, microwave, oven, stovetop

Private Entrance Residential Portland

9.0 out of 10, Wonderful, (4)
"Check in was simple. Quaint place. "
The price is £135
includes taxes & fees
28 Sept - 29 Sept
Private Entrance Residential Portland
Ocean view Victorian
Exterior

Ocean view Victorian

9.8 out of 10, Exceptional, (95)
"Great space and awesome location!!! Would highly recommend! "
Ocean view Victorian
Serenity - Stunning Sebago Lake scenery
Interior

Serenity - Stunning Sebago Lake scenery

10.0 out of 10, Exceptional, (46)
"Nice house , nice host , everything was great!"
Serenity - Stunning Sebago Lake scenery
Spacious Historic Home | 7BR West End for Groups
Marina

Spacious Historic Home | 7BR West End for Groups

10.0 out of 10, Exceptional, (6)
"Seven of us stayed at this beautiful home in a perfect location by the Western Promenade. Everyone had a comfortable bed, bathrooms and showers were plentiful, and the kitchen was perfectly appointed. Both cars we had fit into the garage (an added luxury). The beds were very comfortable and had soft sheets and fluffy towels. We loved every minute of our stay and made great use of the family room. Can't thank our hosts enough...very easy to work with and I would certainly rent from them again...
The price is £1,209
includes taxes & fees
15 Sept - 16 Sept
Spacious Historic Home | 7BR West End for Groups
Private Contemporary Artist's Tree House on two acres with perennial gardens.
Outdoor spa tub

Private Contemporary Artist's Tree House on two acres with perennial gardens.

10.0 out of 10, Exceptional, (48)
"Beautiful, fun space. Very comfortable, and accommodating. Great location and hosts!"
Private Contemporary Artist's Tree House on two acres with perennial gardens.
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (62)
"Very clean, lots of room for gathering. Perfect location on a quiet street with great views of the lake. Plenty of towels, bedding, water, etc. Would come back!"
The price is £835
includes taxes & fees
16 Sept - 17 Sept
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
Elegant and efficient Island home 4 miles from downtown Portland
Outdoor dining

Elegant and efficient Island home 4 miles from downtown Portland

9.0 out of 10, Wonderful, (2)
"An ideal home away from home at our most favorite place in Maine. Plenty of extra touches to make guests feel welcome and comfortable. Owner is quick to respond to any questions, and went well above-and-beyond to help us out when we experienced an unforeseen situation. I am so very grateful! I hope we can book this wonderful home again next summer. Thank you!"
Elegant and efficient Island home 4 miles from downtown Portland
Luxury on Back Cove - Three Gables
Fridge, microwave, oven, stovetop

Luxury on Back Cove - Three Gables

10.0 out of 10, Exceptional, (4)
"GoodLocation, very clean. Would stay again "
The price is £427
includes taxes & fees
28 Sept - 29 Sept
Luxury on Back Cove - Three Gables
Updated Long Island Maine Cottage
Fridge, oven, stovetop, coffee/tea maker

Updated Long Island Maine Cottage

10.0 out of 10, Exceptional, (6)
"Great location. Comfortable living room. Well stocked kitchen. Great communication with owner."
Updated Long Island Maine Cottage
Charming Studio apartment with WiFi, AC in welcoming Portland
Interior

Charming Studio apartment with WiFi, AC in welcoming Portland

9.8 out of 10, Exceptional, (7)
"This was a great stay through and through. Excellent condition, very responsive before and during the stay, and a great location. 10/10 will recommend to anyone staying in Portland! "
The price is £174
includes taxes & fees
22 Sept - 23 Sept
Charming Studio apartment with WiFi, AC in welcoming Portland
City Amenities, Casco Bay Sunrises and Natural Beauty
Interior

City Amenities, Casco Bay Sunrises and Natural Beauty

9.8 out of 10, Exceptional, (115)
"We enjoyed our stay here. Property manager was great. House as advertised. The traffic was a little much but otherwise no issues at all."
The price is £328
includes taxes & fees
15 Oct - 16 Oct
City Amenities, Casco Bay Sunrises and Natural Beauty
Walkable near downtown 1 Bedroom
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils

Walkable near downtown 1 Bedroom

6.0 out of 10, (1)
The price is £154
includes taxes & fees
15 Sept - 16 Sept
Walkable near downtown 1 Bedroom
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

Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

10/10 Excellent
"Great "
Earl 2-night trip
Posted 5 days ago
Canopy by Hilton Portland Waterfront

Find out more about Cumberland County

Find out more about Cumberland County

Everything you need to know about Cumberland County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cumberland County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cumberland County holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Cumberland County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cumberland County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cumberland County holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cumberland County holiday rentals we have selected for you start as low as £135 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Cumberland County rentals

At Expedia, we put the best Cumberland County holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Cumberland County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cumberland County holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cumberland County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.