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Holiday Rentals in Cumberland

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Our top choices for Cumberland holiday rentals

1. Heated Game Room, Coastal Maine Cape Sleeps 10

Heated Game Room, Coastal Maine Cape Sleeps 10
Yarmouth
10.0 out of 10, Exceptional, (4 reviews)
"What a great place to stay! The home is very clean and very quiet. Our host was very responsive to any questions we had. We would book this one over and over again."
United States
Michelle T.
The price is €826
includes taxes & fees
16 Nov - 17 Nov
Heated Game Room, Coastal Maine Cape Sleeps 10

2. Cabin w/ bath + kitchenette | Hot tub add-on - 03

Cabin w/ bath + kitchenette | Hot tub add-on - 03
Freeport
9.8 out of 10, Exceptional, (10 reviews)
"A lovely glamping facility with several different types of structure in a quiet, wooded area just a couple miles from downtown Freeport. They've built a beautiful spa with sauna, cold plunge, hot tub, and soaking pool, the unit we stayed in was bright and airy, had an outdoor fire pit. We stayed three nights, will definitely stop here again!"
United States
Kirt v.
The price is €296
includes taxes & fees
17 Nov - 18 Nov
Cabin w/ bath + kitchenette | Hot tub add-on - 03

3. Highland Lake House - Epic Lake Views, Easy Lake Access, Fully Appointed Home!

Highland Lake House - Epic Lake Views, Easy Lake Access, Fully Appointed Home!
Windham
9.8 out of 10, Exceptional, (43 reviews)
"Beautiful location and property! "
United States
Michael S.
The price is €604
includes taxes & fees
19 Nov - 20 Nov
Highland Lake House - Epic Lake Views, Easy Lake Access, Fully Appointed Home!

4. Modern dome w/ full bath | Hot tub add-on - 04

Modern dome w/ full bath | Hot tub add-on - 04
Freeport
10.0 out of 10, Exceptional, (5 reviews)
"Pet friendly and the experience is just amazing. Thank you for having us! "
United States
Rene B.
The price is €406
includes taxes & fees
17 Nov - 18 Nov
Modern dome w/ full bath | Hot tub add-on - 04

5. Fully Updated Airy Historic Home in South Freeport

Fully Updated Airy Historic Home in South Freeport
Freeport
10.0 out of 10, Exceptional, (1 review)
"Great property well kept and close to everything we wanted to do"
United States
boodu
The price is €414
includes taxes & fees
13 Nov - 14 Nov
Fully Updated Airy Historic Home in South Freeport

6. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (131 reviews)
"It was so spacious, kitchen area was well kept and they have QR codes to help travels understand how to use certain things"
United States
Branden
The price is €252
includes taxes & fees
3 Dec - 4 Dec
The Weldon Hotel

7. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (19 reviews)
"Truly a wonderful place with an unbeatable location. Highly recommend for a visit to Portland."
United States
Eric
The price is €363
includes taxes & fees
13 Dec - 14 Dec
Evalina Hotel

8. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
The price is €313
includes taxes & fees
13 Nov - 14 Nov
Quiet Spot in lovely Freeport neighborhood

9. Sunlit cabin w/ full bath | Hot tub add-on - 20

Sunlit cabin w/ full bath | Hot tub add-on - 20
Freeport
10.0 out of 10, Exceptional, (1 review)
The price is €298
includes taxes & fees
17 Nov - 18 Nov
Sunlit cabin w/ full bath | Hot tub add-on - 20

10. Great suburban location close to town!

Great suburban location close to town!
Deering Center
9.4 out of 10, Exceptional, (6 reviews)
"We were staying here for the sake of being able to see a show at Good Theater. The theater itself ended up being within walking distance, and same for a few different places to eat! This worked out great for our plans :)"
United States
Kaley
The price is €62
includes taxes & fees
16 Nov - 17 Nov
Great suburban location close to town!

11. Modern cabin w/ full bath | Hot tub add-on - 19

Modern cabin w/ full bath | Hot tub add-on - 19
Freeport
10.0 out of 10, Exceptional, (5 reviews)
"Great place, the Desert of Maine campground. The entire cabin was spotless. Great communication from the host, Doug. So wonderful for pets also. Quiet, clean & perfect. 5 stars. What a wonderful stay! If you are looking for a beautiful and peaceful get away, this is the place for you! You will not be disappointed. Doug is an awesome host!"
United States
Kim L.
The price is €298
includes taxes & fees
17 Nov - 18 Nov
Modern cabin w/ full bath | Hot tub add-on - 19

12. Portland 1-bedroom with enclosed porch & parking

Portland 1-bedroom with enclosed porch & parking
Deering Center
7.8 out of 10, Good, (19 reviews)
"Easy to get to, and a great night's sleep.Want to stay in Portland but in a quiet neighborhood?-Grab this spot!"
United States
Cricket C.
The price is €65
includes taxes & fees
15 Nov - 16 Nov
Portland 1-bedroom with enclosed porch & parking

13. 2-bedroom apartment in Portland, ME with WiFi, AC. Enjoy your stay!

2-bedroom apartment in Portland, ME with WiFi, AC. Enjoy your stay!
Munjoy Hill
8.8 out of 10, Excellent, (3 reviews)
"Was right in the area we wanted and in a nice neighborhood. Would def stay again!"
United States
Amalia C.
The price is €309
includes taxes & fees
13 Nov - 14 Nov
2-bedroom apartment in Portland, ME with WiFi, AC. Enjoy your stay!

14. New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10

New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
North Deering
9.4 out of 10, Exceptional, (17 reviews)
"The house was perfect for our week in Portland. New, great features in the home, lovely backyard and close to everything Portland"
United States
Patrick J.
The price is €688
includes taxes & fees
22 Nov - 23 Nov
New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10

15. Stargazing dome w/ full bath | Hot tub add-on - 02

Stargazing dome w/ full bath | Hot tub add-on - 02
Freeport
10.0 out of 10, Exceptional, (1 review)
"Doug our host always was ready to answer any questions we had and we loved his sense of humor "
United States
Alice A.
The price is €403
includes taxes & fees
17 Nov - 18 Nov
Stargazing dome w/ full bath | Hot tub add-on - 02

16. Glamping cabin w/ full bath | Hot tub add-on - 21

Glamping cabin w/ full bath | Hot tub add-on - 21
Freeport
10.0 out of 10, Exceptional, (1 review)
The price is €298
includes taxes & fees
17 Nov - 18 Nov
Glamping cabin w/ full bath | Hot tub add-on - 21

17. Studio Apartment in Freeport

Studio Apartment in Freeport
Freeport
10.0 out of 10, Exceptional, (4 reviews)
"The bed was the most comfortable I have ever slept on! Lovely large warm open room. I appreciated the coffee/tea options, and the condiments in the fridge. There was a white noise machine in the room though we did not use it."
United States
Susan S.
The price is €137
includes taxes & fees
16 Nov - 17 Nov
Studio Apartment in Freeport

18. Glamping cabin w/ kitchen | Hot tub add-on - 17

Glamping cabin w/ kitchen | Hot tub add-on - 17
Freeport
10.0 out of 10, Exceptional, (3 reviews)
"Awesome camping in a great, quiet campground. The staff is very responsive and all the little details make this place special."
United States
Miranda K.
The price is €304
includes taxes & fees
17 Nov - 18 Nov
Glamping cabin w/ kitchen | Hot tub add-on - 17

19. 22-ft dome w/ star loft | Hot tub add-on - 07

22-ft dome w/ star loft | Hot tub add-on - 07
Freeport
10.0 out of 10, Exceptional, (1 review)
"Fun place with all amenities. Had an excellent time!"
United States
Andrew L.
The price is €406
includes taxes & fees
17 Nov - 18 Nov
22-ft dome w/ star loft | Hot tub add-on - 07

20. 22-ft stargazing loft dome | Hot tub add-on - 08

22-ft stargazing loft dome | Hot tub add-on - 08
Freeport
10.0 out of 10, Exceptional, (1 review)
"Overall, great experience and love to visit this place with my extended families!!"
United States
Hrishi K.
The price is €406
includes taxes & fees
17 Nov - 18 Nov
22-ft stargazing loft dome | Hot tub add-on - 08
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 Hotel Reviews

Find out more about Cumberland

Everything you need to know about Cumberland 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 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Cumberland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cumberland. 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 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 holiday rentals we have selected for you start as low as €110 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Cumberland rentals

At Expedia, we put the best Cumberland 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 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 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. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Cumberland?

Yes, there are holiday rentals in Cumberland close to Greely Center for the Arts, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Cumberland has to offer?

Charming 110-year former Inn 10' from the Ocean!: This holiday home rental outside of Cumberland is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

What’s there to see and do in Cumberland?

Explore the area and family-friendly sights such as Portland Observatory, or get out into nature at a spot like Casco Bay. Greely Center for the Arts and Desert of Maine are a couple of places you'll find in the wider area.

What’s a holiday rental in Cumberland like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Cumberland. Holiday rentals offer amenities like laundry facilities and kitchens so you'll have everything you need. If you're concerned about a sanitised environment, a holiday rental can provide a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for small groups.