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Cumberland Vacation Rentals

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Cumberland vacation rentals

A backyard with a wooden deck, a small staircase, and a wooden fence.

1. 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
$68 nightly
The price is $68
Nov 16 - Nov 17
Total with taxes and fees
Great suburban location close to town!
A modern interior with a dining area, a living room, and a kitchen.

2. 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.
$135 nightly
The price is $142
Nov 16 - Nov 17
Total with taxes and fees
Studio Apartment in Freeport
A living room with a sofa, armchair, and glass coffee table. There are two lamps on side tables and a window with curtains.

3. 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.
$71 nightly
The price is $72
Nov 15 - Nov 16
Total with taxes and fees
Portland 1-bedroom with enclosed porch & parking
A cabin with two chairs facing a fire pit, surrounded by trees.

4. 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.
$269 nightly
The price is $294
Nov 15 - Nov 16
Total with taxes and fees
Cabin w/ bath + kitchenette | Hot tub add-on - 03
A dining area with a wooden table and chairs, a red sofa, and a small round table with a decorative plate.

5. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
$330 nightly
The price is $342
Nov 15 - Nov 16
Total with taxes and fees
Quiet Spot in lovely Freeport neighborhood
A living room with a sofa, armchair, wooden coffee table, and a potted plant.

6. 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
$423 nightly
The price is $461
Nov 15 - Nov 16
Total with taxes and fees
Fully Updated Airy Historic Home in South Freeport
A bedroom with a wooden bed, a nightstand, a bench, a chair, and a ceiling with a light fixture.

7. Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.2 out of 10, Very good, (27 reviews)
"Location was convenient to everything and building was super secure."
United States
Rose
$121 nightly
The price is $122
Nov 19 - Nov 20
Total with taxes and fees
Studio Apartment near downtown Walkable!
A kitchen with wooden cabinets, a stainless steel sink, and a potted plant.

8. Bright & Spacious Apartment with Amazing Shower

Bright & Spacious Apartment with Amazing Shower
Parkside
8.6 out of 10, Excellent, (29 reviews)
"Lovely apartment, in a pristine location. Very spacious and comfortable all around. Highly recommended this place for your next stay in Portland, Maine!"
United States
Gintare V.
$126 nightly
The price is $137
Nov 17 - Nov 18
Total with taxes and fees
Bright & Spacious Apartment with Amazing Shower
A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.

9. 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
$252 nightly
The price is $268
Dec 1 - Dec 2
Total with taxes and fees
The Weldon Hotel
A living room with a sofa, armchairs, a coffee table, and a potted plant.

10. Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
8.6 out of 10, Excellent, (35 reviews)
"Good price, decent location, clean, and affordable"
United States
Chloe C.
$128 nightly
The price is $139
Nov 18 - Nov 19
Total with taxes and fees
Beautiful 1st Floor Apartment & Amazing Shower
A cabin with a fire pit and outdoor seating.

11. 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)
$269 nightly
The price is $294
Nov 15 - Nov 16
Total with taxes and fees
Glamping cabin w/ full bath | Hot tub add-on - 21
A kitchen with wooden cabinets, a stainless steel dishwasher, a coffee maker, and a potted plant.

12. Cozy Two Bedroom on Munjoy Hill

Cozy Two Bedroom on Munjoy Hill
Munjoy Hill
$194 nightly
The price is $210
Nov 16 - Nov 17
Total with taxes and fees
Cozy Two Bedroom on Munjoy Hill
A covered porch with a view of a lake and trees.

13. 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.
$609 nightly
The price is $664
Nov 21 - Nov 22
Total with taxes and fees
Highland Lake House - Epic Lake Views, Easy Lake Access, Fully Appointed Home!
A kitchen with a wooden countertop, a black kettle, a vase with flowers, and a small wire basket.

14. Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland

Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland
Munjoy Hill
9.4 out of 10, Exceptional, (32 reviews)
"Everything you need, very clean, close to the water and easily walkable to many things. Would definitely stay again!"
United States
Ryan B.
$192 nightly
The price is $209
Nov 16 - Nov 17
Total with taxes and fees
Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland
A brick wall with a logo and the text 'THE SEND BREWING CO.'

15. Sunny Spot with Private Parking

Sunny Spot with Private Parking
Knightville
9.8 out of 10, Exceptional, (38 reviews)
"Great property. Cute place. Note that there are very steep steps to get into the place, which is a conveyed attic."
United States
Greg Z.
$181 nightly
The price is $198
Nov 15 - Nov 16
Total with taxes and fees
Sunny Spot with Private Parking
A multi-story building with a stone facade, large windows, and a corner entrance.

16. 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
$358 nightly
The price is $390
Dec 14 - Dec 15
Total with taxes and fees
Evalina Hotel
A spacious living room with a sofa, ottoman, and coffee table, a dining area with chairs, and a kitchen with cabinets and appliances.

17. 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.
$839 nightly
The price is $915
Nov 16 - Nov 17
Total with taxes and fees
Heated Game Room, Coastal Maine Cape Sleeps 10
A brick wall with a logo and the text 'THE SEND BREWING CO.'

18. Peaceful & minutes from Old Port w/private parking

Peaceful & minutes from Old Port w/private parking
Knightville
9.8 out of 10, Exceptional, (14 reviews)
"Cute, convenient spot!"
United States
Kelly S.
$215 nightly
The price is $235
Nov 15 - Nov 16
Total with taxes and fees
Peaceful & minutes from Old Port w/private parking
A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

19. 1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port

1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port
West End
8.6 out of 10, Excellent, (64 reviews)
"Nice place, good location and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
$306 nightly
The price is $333
Nov 16 - Nov 17
Total with taxes and fees
1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port
A narrow pathway leading to a wooden house with a porch, surrounded by lush greenery and trees.

20. King Size Bed ♦ West End Studio ♦ Walk to Old Port

King Size Bed ♦ West End Studio ♦ Walk to Old Port
West End
9.6 out of 10, Exceptional, (4 reviews)
"Super clean. Exactly as advertised. Perfect location in a quiet neighborhood on the West End."
United States
Maureen R.
$204 nightly
The price is $222
Nov 17 - Nov 18
Total with taxes and fees
King Size Bed ♦ West End Studio ♦ Walk to Old Port
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

Portland Harbor Hotel

Portland Harbor Hotel

10/10 Excellent
"Old hotel recently updated. Great location in Old Port in walking distance of restaurants and shop. Very helpful staff. Easy valet parking. They charge a resort fee but you get it back as credit to use for breakfast or at the bar. Great outdoor patio area with gas fire pit. Great vibe for adult travelers."
Eric 2-night trip
Posted 5 hours ago
Portland Harbor Hotel

Find out more about Cumberland

Everything you need to know about Cumberland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cumberland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cumberland vacation 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 low season months. For more hustle and bustle, you may prefer to visit Cumberland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $111 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Cumberland rentals

At Expedia, we put the best Cumberland vacation 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 vacation.

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 vacation rentals in Cumberland?

Yes, there are vacation rentals in Cumberland close to Greely Center for the Arts, or you can choose a more secluded option if you want a relaxing stay.

What's the top vacation rental that Cumberland has to offer?

Charming 110-year former Inn 10' from the Ocean!: This vacation home rental near Cumberland is located on the beach and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation 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 larger area.

What’s a vacation rental in Cumberland like?

Vacation rentals are private properties you can book for several days or longer in Cumberland. Vacation rentals offer extras such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a clean environment, vacation rentals can offer a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for family gatherings.