Cumberland County Holiday Rentals

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Top Holiday Rentals Destinations in Cumberland County

2 Bedroom Apartment on Top Floor in Portland's West End
Terrace/patio
2 Bedroom Apartment on Top Floor in Portland's West End
9.8 out of 10, Exceptional, 41 reviews
"WOW! What an adorable 2 bedroom with everything you could possibly need! Very clean with a great ambiance! Check-in was a breeze upon arrival. Comes with a parking spot! A great location with so many good coffee shops and restaurants nearby, and a walkable distance down to the pier and shopping. Megan and Jason were so easy to work with and terrific welcoming hosts! They made you feel at home and were super helpful! When we make it back to Maine, we will be staying here again! Thank you! :)"
The price is AU$850
includes taxes & fees
9 June - 10 June
2 Bedroom Apartment on Top Floor in Portland's West End
Rent a room in the gorgeous Holt House
Exterior
Rent a room in the gorgeous Holt House
8.4 out of 10, Very good, 19 reviews
"It was a great trip up to Portland and the property met our needs."
Rent a room in the gorgeous Holt House
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
Property grounds
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
10.0 out of 10, Exceptional, 18 reviews
"Apartment was in a great location, Close enough for walking to most of the Portland attractions and was well clipped and comfortable inside. Private deck on the roof was a great perk."
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
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Completely remodeled 2 bedroom apartment in Portland's West End
Exterior
Completely remodeled 2 bedroom apartment in Portland's West End
10.0 out of 10, Exceptional, 35 reviews
"We very much enjoyed our stay at this location. The stairs were a bit scary, but with the light on, you'll be fine. :) Cozy spot for the three of us, well appointed and in a fantastic area. Very walkable, even down to the wharf. We are from a very non-walkable area, so it was amazing to see all the activity and places we could go just walking a bit. We enjoyed our first time in Maine, and can't wait to get back for a longer trip. Thanks to the hosts!"
The price is AU$696
includes taxes & fees
13 June - 14 June
Completely remodeled 2 bedroom apartment in Portland's West End
GREAT Newly Renovated Sebago Lake- short walk to Nason`s beach🏠🏖🚗
Beach
GREAT Newly Renovated Sebago Lake- short walk to Nason`s beach🏠🏖🚗
10.0 out of 10, Exceptional, 62 reviews
"Great cottage Road was busy There was alcohol left in the fridge. I am an alcoholic in recovery. I was not tempted but was a little off putting. Would go back definitely 💯"
GREAT Newly Renovated Sebago Lake- short walk to Nason`s beach🏠🏖🚗
Lakefront home with sunrise views, private dock, kayaks, paddle boards, WFH desk
Exterior
Lakefront home with sunrise views, private dock, kayaks, paddle boards, WFH desk
9.2 out of 10, Wonderful, 17 reviews
"The place was clean, beautiful, and centrally located to shops, restaurants and bars. It was tucked away and quiet right on the lake. Would highly recommend!"
Lakefront home with sunrise views, private dock, kayaks, paddle boards, WFH desk
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
Exterior
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
10.0 out of 10, Exceptional, 93 reviews
"Susan Jeff are obviously seasoned and experienced hosts. Their impeccable attention to details is amazing! Susan greeted us Briefly and warmly, and then left us to ourselves. The apartment in their home in a newer, upscale development was very clean and spacious. They had left us little gifts each day and a helpful binder with suggestions for local restaurants and things to do. Very quiet neighborhood, but 5-10 minutes away from restaurants and shopping."
The price is AU$247
includes taxes & fees
3 June - 4 June
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
Cozy 2 bedroom new apartment
Property grounds
Cozy 2 bedroom new apartment
10.0 out of 10, Exceptional, 1 review
"This in-town apartment was perfectly located. It was spacious and all amenities were as described or better. A visitor could not ask for a nicer more comfortable place to stay or a more caring host."
Cozy 2 bedroom new apartment
Vacation Creation Downtown Brunswick 2King Beds
Property grounds
Vacation Creation Downtown Brunswick 2King Beds
9.4 out of 10, Exceptional, 13 reviews
"Everything was very clean and just as described. The hosts were very hospitable and responded quickly with everything. Will definitely book again"
The price is AU$820
includes taxes & fees
3 June - 4 June
Vacation Creation Downtown Brunswick 2King Beds
Contemporary Comfort: Game Room & Portland Access
Fridge, microwave, oven, stovetop
Contemporary Comfort: Game Room & Portland Access
Contemporary Comfort: Game Room & Portland Access
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
Private kitchen
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
9.8 out of 10, Exceptional, 89 reviews
"Six of us stayed for our daughter's graduation. Nicely appointed property! We were able to walk to dinner, and it was a short drive to our other activities. Highly recommend!"
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
Back Cove Charmer Close to Everything
Property grounds
Back Cove Charmer Close to Everything
9.2 out of 10, Wonderful, 72 reviews
"There was dirty dishes left in the dishwasher, the TV and internet didn’t work and the host didn’t get back to us very fast, the floor was dirty, but overall it was a good place to stay for a few days."
Back Cove Charmer Close to Everything
Elegant condo - walk to Portland's best restaurants & Old Port
Private kitchen
Elegant condo - walk to Portland's best restaurants & Old Port
9.4 out of 10, Exceptional, 45 reviews
"The kitchen was very well equipped. Living room was so cozy with the fire. Bed was super comfortable. The unit has really tall ceilings and is cozy. Only issue was the dog upstairs. They kept barking and whining."
The price is AU$714
includes taxes & fees
3 June - 4 June
Elegant condo - walk to Portland's best restaurants & Old Port
Inviting apartment with full kitchen, porch, convenient location, & fast WiFi
2 bedrooms, cots/infant beds, Internet, bed sheets
Inviting apartment with full kitchen, porch, convenient location, & fast WiFi
7.2 out of 10, Good, 7 reviews
"This home was clean, bright and comfortable. Great location, no issues. Would definitely stay here again."
Inviting apartment with full kitchen, porch, convenient location, & fast WiFi
Cozy, Elegant and Bright 2 bed in the East End
Fridge, microwave, oven, stovetop
Cozy, Elegant and Bright 2 bed in the East End
10.0 out of 10, Exceptional, 27 reviews
"Host was responsive, directions were very clear, home was clean and comfortable place to stay."
The price is AU$557
includes taxes & fees
17 June - 18 June
Cozy, Elegant and Bright 2 bed in the East End
Rent a room in the gorgeous Holt House
Exterior
Rent a room in the gorgeous Holt House
7.8 out of 10, Good, 12 reviews
"This was such a cool house to stay in. The host was very responsive and the check in/out process couldn't have been easier."
Rent a room in the gorgeous Holt House
Walk Everywhere! Entire Downtown Apt - "La Maison"
Property grounds
Walk Everywhere! Entire Downtown Apt - "La Maison"
10.0 out of 10, Exceptional, 6 reviews
"This place was huge, lots of room!"
The price is AU$659
includes taxes & fees
12 June - 13 June
Walk Everywhere! Entire Downtown Apt - "La Maison"
Highland Lakefront Cabin
Highland Lakefront Cabin
9.0 out of 10, Wonderful, 65 reviews
"We had a very nice stay and enjoyed both the cottage and property. It was a bit rainy, so we didn't get a chance to enjoy the fire pit area, but it looked great. There are a few places that could use some updates, but this is a true lake cottage, so it's really like elevated camping."
Highland Lakefront Cabin
5 Star Back Cove Hide-Away<br>1 bedroom Back Cove apartment with water views!
Fridge, microwave, oven, stovetop
5 Star Back Cove Hide-Away<br>1 bedroom Back Cove apartment with water views!
10.0 out of 10, Exceptional, 117 reviews
"We had a wonderful stay. The property was beautiful and the hosts were very accommodating. They always made sure we had everything we needed. We could not have asked for a more comfortable stay in such a beautiful neighborhood. If we travel that way in the future, we will definitely try to stay again. Thank you."
5 Star Back Cove Hide-Away<br>1 bedroom Back Cove apartment with water views!
Cozy Lakeside Studio w/ Private Swimming Area
Beach nearby
Cozy Lakeside Studio w/ Private Swimming Area
10.0 out of 10, Exceptional, 2 reviews
"Beautiful views nice and quiet little getaway"
Cozy Lakeside Studio w/ Private Swimming Area
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See all available properties in Cumberland County
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.

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, 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 depend 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 chosen for you start as low as AU$247 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. 

Cumberland County Holiday Home Travel Info

Holiday homes
78
Popular accommodation
Cumberland County private holiday homes
Known landmarks
State Theatre, Shawnee Peak and Higgins Beach
International airport
Portland, ME (PWM-Portland Intl. Jetport)

Recent reviews in Cumberland County
Expedia verified reviews

AC Hotel by Marriott Portland Downtown/Waterfront, ME

AC Hotel by Marriott Portland Downtown/Waterfront, ME

5/5 Excellent
"Nice stay"
A verified traveller stayed at AC Hotel by Marriott Portland Downtown/Waterfront, ME
Posted 1 day ago
AC Hotel by Marriott Portland Downtown/Waterfront, ME