Discover a selection of 2,500 vacation rentals in Cumberland County, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $119 per night, and houses and cabins are popular options for a stay in Cumberland County. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Cumberland County
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What are the top vacation rentals in Cumberland County?

From lavish houses to rustic cottages, Vrbo has properties to suit every taste and budget. Here are some of the top vacation rentals in Cumberland County:

  • "Henry” Penthouse Suite: Amazing Views": If you're after a comfy space in Downtown Portland, unpack your bags here. It offers 2 bedrooms and quality amenities including internet services and a wood stove.
  • "Chic One Bedroom Apartment In Portland's Arts District": Put your bags down and your weary feet up at this popular getaway in Parkside. It features 1 bedroom, a living room, golf and more.

For even more great options, use the search bar at the top of the page to find the perfect Cumberland County vacation rental for you.

What are the best tiny house vacation rentals in Cumberland County?

Punching way above its weight when it comes to charm and innovation, a tiny house vacation rental in Cumberland County promises big adventure. Power down all your tech and switch your focus to Mother Nature at one of these fun-sized stays:

  • Look forward to a simpler way of living at "A Place To Be Tiny Home On The Back 40 Acres Farm". Amenities at this retreat in Mount Vernon include a nearby river and a nearby beach.
  • "Custom Built Tiny Home/cabin In The Switzerland Of Maine - Jackman" has many conveniences, including a hair dryer and a restaurant dining guide. Located in Jackman, you'll be able to live large in this small but cleverly designed abode.

Can I find log cabins to rent in Cumberland County?

There's something delightfully cozy about curling up in a log cabin with a cup of coffee and a good book. Leave the hustle and bustle of life behind and spend a few nights or longer at one of these log cabins in Cumberland County:

  • If you'd like to go kayaking or water skiing while you're in Cumberland County, "Year Round Log Cabin Built In 1989 On Long Lake - 2" in Harrison will be a great choice.
  • Another fabulous option is "Cozy Log Cabin - Walking Distance To Morse Mountain And 3 Miles From Popham Beach". With fun activities such as surfing and boogie boarding and kayaking close by, this Phippsburg hideaway will be perfect if you love the outdoors.

What are the top-rated vacation rentals for weekend getaways in Cumberland County?

Got limited time but still want to get away? A weekend break will be just what you need. Reserve a couple of nights at one of these top-rated rentals and get ready for good food, sleep-ins and relaxation:

  • "Maine Oceanfront Home" - Located in Cumberland County, this getaway offers its guests handy extras including a kitchen and heating.
  • "Private Waterfront <5 Min To Shawnee Peak And Town. Dock" - This is another top pick with all the ingredients that make for a delightful weekend away. Make use of an oven and a microwave oven at this Cumberland County rental property.

Can I find studio apartments for rent in Cumberland County?

Forget about the standard hotel room and choose one of our studio apartments in Cumberland County. Here's where you can hole up in your own pad and enjoy your next bucket-list destination like a local:

  • Settle in and make yourself comfortable at "Chic One Bedroom Apartment In Portland's Arts District", situated in Parkside. There are loads of amenities to make use of here, including a kitchen and a washing machine.
  • With lots of character and promising more privacy than a big hotel, "Historic Condo With Casco Bay Views" is another favorite. It's located in Munjoy Hill and features nearby museums and a hair dryer.

Can I find short term rentals in Cumberland County?

Cumberland County has short-term rentals to suit all budgets and tastes. Spend your mini break in an affordable cabin, a luxurious condo or whatever else you like. Below are a couple of popular options to consider:

  • Stay close to central Cumberland County and spend your days checking out the sights from "Maine Oceanfront Home". Along with its handy location, this retreat has everything you need to make your visit relaxed and stress-free.
  • Otherwise, bunk down for a few days at "Private Waterfront <5 Min To Shawnee Peak And Town. Dock" and discover the best of Cumberland County. This property also caters to short-term guests and is a good choice if you love to be near the action.

What are the best romantic weekend getaways in Cumberland County?

Whether you've been with each other for a month, a decade or forever, there's nothing like a romantic weekend getaway to stoke passions. If you're searching for a dreamy place to spend a couple of days with your boo, you'll fall headfirst for these escapes:

  • "Henry” Penthouse Suite: Amazing Views" in Downtown Portland was just made for lurrrve. This retreat is full of nice touches, including winery tours and a nearby bay.
  • Another attractive option is "Chic One Bedroom Apartment In Portland's Arts District" in Parkside. Enjoy perks here including a nearby bay and winery tours, as well as each other's company.

What are the best houses for rent with a pool in Cumberland County?

In Cumberland County, there are plenty of house rentals where a pool day can be every day. Having a splashing great time will be your highest priority at one of these top-rated properties:

  • The pool at "Entire House - Three Suites - Conferences" will add another level of fun to your adventure. Located in Westbrook, this rental house also comes with a kitchen and a dishwasher.
  • Kick back by the water while the kids paddle around at "Maine Getaway: Bright Beautiful Back Cove House Near Woodfords Corner And Old Port". This property in Back Cove comes with a range of features to keep your crew nice and comfortable, such as a TV and childrens activities.

What are the best large family vacation rentals in Cumberland County?

At Vrbo, we have properties that are large enough to fit the extended branches of your family tree. And if you'd prefer not to invite everybody, just spread out and enjoy the extra space! Check out these large family vacation rentals in Cumberland County:

  • For style, function and size, you can't go past "Maine Oceanfront Home". Situated in Cumberland County, this vacation property offers 4 bedrooms and handy amenities like a TV and towels. It can comfortably fit up to 11 guests.
  • "New Well Built Elegant Home On The Water 2 Miles To Freeport" in Freeport is another appealing option. It can accommodate up to 12 guests and has 6 bedrooms. A porch and a dishwasher will help keep your crew happy and comfortable.

Bust out of the house and head to Children's Museum of Maine — one of Cumberland County's finest family-friendly attractions. Portland Observatory and Fort Williams Park are also a must while you're in the area.

Can I find family cabin rentals in Cumberland County?

Reserving a cabin in Cumberland County is an ideal way to spend quality time with the family. Consider these amazing options:

  • "Country Cottage With Gardens" - Located in Brooksville, this charming retreat features handy amenities such as a video library and a microwave oven.
  • "Pine Grove Cottages: Cottage 3: Studio Cottage" - Amenities like a fridge and a separate dining area also make this a favorite with families. Head to this Hammett's Crossing property and enjoy some time in Mother Nature.

For more options, use the search bar at the top of the page and adjust the filters to find the Cumberland County vacation rental that's perfect for your needs.

Explore destinations around Cumberland County

Casco
425 vacation rentals
Bridgton
470 vacation rentals
Portland
707 vacation rentals
Harpswell
335 vacation rentals
Naples
455 vacation rentals
Bailey Island
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Raymond
414 vacation rentals
Peaks Island
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Windham
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Harrison
249 vacation rentals
Standish
372 vacation rentals
Freeport
710 vacation rentals
Scarborough
772 vacation rentals
Orrs Island
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Sebago
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Westbrook
251 vacation rentals
Brunswick
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Cape Elizabeth
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Yarmouth
683 vacation rentals
Gray
239 vacation rentals