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Cumberland Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Cumberland vacation rentals

A living room with a sofa, armchair, and glass coffee table. There are two lamps on side tables and a window with curtains.

1. Portland 1-bedroom with enclosed porch & parking

Portland 1-bedroom with enclosed porch & parking
Deering Center
8.0 out of 10, Very good, (14 reviews)
"This was a great place to stay. Easy to get to all of our destinations. Place was clean and comfortable. Would stay here again. "
United States
Ameleah B.
$109 nightly
The price is $111
Oct 5 - Oct 6
Total with taxes and fees
Portland 1-bedroom with enclosed porch & parking
A cabin with a fire pit and outdoor seating.

2. Glamping cabin w/ full bath + spa access - 21

Glamping cabin w/ full bath + spa access - 21
Freeport
10.0 out of 10, Exceptional, (1 review)
$319 nightly
The price is $348
Oct 4 - Oct 5
Total with taxes and fees
Glamping cabin w/ full bath + spa access - 21
A bedroom with a bed, a nightstand, a lamp, a door, and a staircase.

3. Great suburban location close to town!

Great suburban location close to town!
Deering Center
10.0 out of 10, Exceptional, (1 review)
"Small but cozy space, well kept, good value for the price and has all the amenities you could expect. Would be happy to stay here again."
United States
Peter H.
$95 nightly
The price is $97
Oct 25 - Oct 26
Total with taxes and fees
Great suburban location close to town!
A cabin with two chairs facing a fire pit, surrounded by trees.

4. Modern cabin w/ full bath & kitchenette - 03

Modern cabin w/ full bath & kitchenette - 03
Freeport
10.0 out of 10, Exceptional, (8 reviews)
"Easy check in process. More than clean, it looked brand new. Overall a great stay. Kitchen was well stocked with plates, utensils, and cookware. "
United States
Michael H.
$319 nightly
The price is $348
Oct 4 - Oct 5
Total with taxes and fees
Modern cabin w/ full bath & kitchenette - 03
A spacious living room with a sofa, ottoman, and coffee table, a dining area with chairs, and a kitchen with cabinets and appliances.

5. Luxe 5 Bed/ 3 Bath with Game Room & AC

Luxe 5 Bed/ 3 Bath with Game Room & AC
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.
$872 nightly
The price is $951
Sep 30 - Oct 1
Total with taxes and fees
Luxe 5 Bed/ 3 Bath with Game Room & AC
A dining area with a wooden table, two chairs, and a window with a view of trees.

6. Cozy 1 BR ADU | Private Access | Projector Theater

Cozy 1 BR ADU | Private Access | Projector Theater
Windham
10.0 out of 10, Exceptional, (5 reviews)
"Very clean! Small space (no microwave) pet friendly and very accommodating to our travel needs!"
United States
Traci P.
$427 nightly
The price is $465
Oct 27 - Oct 28
Total with taxes and fees
Cozy 1 BR ADU | Private Access | Projector Theater
A kitchen with a wooden countertop, a black kettle, a vase with flowers, and a small wire basket.

7. Charming Studio apartment with WiFi, AC in welcoming Portland

Charming Studio apartment with WiFi, AC in welcoming Portland
Munjoy Hill
9.6 out of 10, Exceptional, (29 reviews)
"Loved this spot and would stay again. Had everything you needed and a great location. Cute little attic spot but nice and cool."
United States
Emily N.
$228 nightly
The price is $249
Oct 20 - Oct 21
Total with taxes and fees
Charming Studio apartment with WiFi, AC in welcoming Portland
A street lined with buildings, one with a red door and a sign that reads "MINATO".

8. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (149 reviews)
"Owner was so accommodating!"
United States
Kiernan
$252 nightly
The price is $275
Oct 20 - Oct 21
Total with taxes and fees
Adorable Portland getaway on the Eastern Promenade
A living room with a sofa, armchairs, a coffee table, and a potted plant.

9. Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
9.0 out of 10, Wonderful, (32 reviews)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
$189 nightly
The price is $206
Oct 7 - Oct 8
Total with taxes and fees
Beautiful 1st Floor Apartment & Amazing Shower
A two-story house with a covered porch, a garage, and a front yard with potted plants.

10. Large suite/private bath/private entrance on quiet street near Thomas Bay

Large suite/private bath/private entrance on quiet street near Thomas Bay
Brunswick
10.0 out of 10, Exceptional, (172 reviews)
"What a beautiful place to stay. Jeff and Susan made your stay a very special experience."
United States
DENESE
$149 nightly
The price is $162
Sep 30 - Oct 1
Total with taxes and fees
Large suite/private bath/private entrance on quiet street near Thomas Bay
A modern kitchen with white cabinets, a wooden dining table, and a vase with green leaves.

11. King Size Sun Rise Midcoast Lovely Stay

King Size Sun Rise Midcoast Lovely Stay
Topsham
9.6 out of 10, Exceptional, (18 reviews)
"Perfect for a my husband and I. Close to everything!"
United States
Tabcline S.
$245 nightly
The price is $247
Sep 30 - Oct 1
Total with taxes and fees
King Size Sun Rise Midcoast Lovely Stay
A dining table with chairs, a potted plant, and decorative items.

12. Willard Beach–Apartment Near Portland & Parks

Willard Beach–Apartment Near Portland & Parks
Willard Beach
10.0 out of 10, Exceptional, (8 reviews)
"Excellent in every way."
United States
Robert B.
$295 nightly
The price is $322
Oct 27 - Oct 28
Total with taxes and fees
Willard Beach–Apartment Near Portland & Parks
A spacious living room with large windows, a sofa, a chair, and a small table.

13. 1 Mi to Maine Street! Mcm-style Home in Brunswick

1 Mi to Maine Street! Mcm-style Home in Brunswick
3.0 star property
Brunswick
$249 nightly
The price is $271
Oct 20 - Oct 21
Total with taxes and fees
1 Mi to Maine Street! Mcm-style Home in Brunswick
A bedroom with a wooden bed, a nightstand, a bench, a chair, and a ceiling with a light fixture.

14. Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.4 out of 10, Very good, (19 reviews)
"I will admit the location and surrounding areas are a bit sketchy, but, once inside, we felt super secure. There are multiple doors and gates with locks to ensure safety. Place was clean and had everything we needed for a quick stay."
United States
Krysta
$159 nightly
The price is $161
Oct 6 - Oct 7
Total with taxes and fees
Studio Apartment near downtown Walkable!
A modern kitchen with a wooden countertop, a glass coffee table, and a built-in shelf with kitchenware.

15. Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
10.0 out of 10, Exceptional, (34 reviews)
"This is a perfect location. 6 minutes from downtown Portland. Secure, Clean and Jen was a Perfect and attentive host. It is a hidden Gem!"
United States
Irish D.
$282 nightly
The price is $307
Oct 5 - Oct 6
Total with taxes and fees
Sunny Spot with Private Parking.
A hallway leading to a living room with a sofa, a lamp, and a window.

16. The Coastal Connection

The Coastal Connection
Thorton Heights
7.2 out of 10, Good, (7 reviews)
"Very convenient, comfortable, and bright apartment. We appreciated that dogs were allowed as well."
United States
Sheryl S.
$282 nightly
The price is $308
Sep 30 - Oct 1
Total with taxes and fees
The Coastal Connection
A wooden deck with outdoor seating and string lights.

17. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (71 reviews)
"The house was lovely and well kept and in a great location."
United States
Angela M.
$319 nightly
The price is $347
Oct 5 - Oct 6
Total with taxes and fees
Full sized home
A modern house with a wooden exterior, a small garden, and a visible window.

18. Spacious and Contemporary Condo in the Heart of Portland - Close to Beach

Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
East Bayside
8.8 out of 10, Excellent, (40 reviews)
"Overall a pleasing stay."
United States
Mallory D.
$405 nightly
The price is $441
Oct 4 - Oct 5
Total with taxes and fees
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
A lakeside property with a deck, picnic table, and barbecue grill.

19. Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (68 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
$315 nightly
The price is $343
Oct 3 - Oct 4
Total with taxes and fees
Camp Forever cottage
A window with a view of a snowy landscape and bare trees.

20. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
$284 nightly
The price is $310
Oct 5 - Oct 6
Total with taxes and fees
Tranquility between the Lakes & Sea
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

Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

10/10 Excellent
"It was convenient"
Matthew 2-night trip
Posted 4 hours ago
Holiday Inn Portland-By the Bay by IHG

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 $161 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.