Cumberland Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Cumberland vacation rentals

Deluxe Suite, 1 King Bed | Living area | LCD TV, Netflix, streaming services, music library
The Weldon Hotel

Aparthotel in Downtown Portland

The Weldon Hotel
4.5 star property
9.8 out of 10, Exceptional, (89)
"Loved this place and would definitely stay here next time we go back."
United States
Eleni
$328 nightly
The price is $351
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Weldon Hotel
Exterior
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach

Apartment in Brunswick

Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
10.0 out of 10, Exceptional, (144)
"Lovely space, comfortable bed, very convenient to downtown Brunswick."
United States
Kimberly G.
$110 nightly
The price is $120
Dec 22 - Dec 23
Total with taxes and fees
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
Fridge, microwave, oven, stovetop
Pine Point Beach private, quaint, charming studio.

Apartment in Blue Point

Pine Point Beach private, quaint, charming studio.
2.0 star property
10.0 out of 10, Exceptional, (24)
"Sweet place! "
United States
Lisa G.
$182 nightly
The price is $198
Dec 12 - Dec 13
Total with taxes and fees
Pine Point Beach private, quaint, charming studio.
Smart TV
Beautiful 1st Floor Apartment & Amazing Shower

Apartment in Parkside

Beautiful 1st Floor Apartment & Amazing Shower
9.0 out of 10, Wonderful, (26)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
$144 nightly
The price is $157
Dec 14 - Dec 15
Total with taxes and fees
Beautiful 1st Floor Apartment & Amazing Shower
Private kitchen
Classic New England 1st Floor 3 BR Downtown Brunswick

Apartment in Brunswick

Classic New England 1st Floor 3 BR Downtown Brunswick
9.6 out of 10, Exceptional, (9)
"We had a good time in Brunswick.... great location and jumping off point to explore."
United States
Karin S.
$310 nightly
The price is $338
Dec 15 - Dec 16
Total with taxes and fees
Classic New England 1st Floor 3 BR Downtown Brunswick
2 bedrooms, WiFi, bed sheets
Large, luxurious geodesic dome - 04

Cabin in Freeport

Large, luxurious geodesic dome - 04
10.0 out of 10, Exceptional, (1)
$226 nightly
The price is $246
Dec 15 - Dec 16
Total with taxes and fees
Large, luxurious geodesic dome - 04
Interior
Adorable Portland getaway on the Eastern Promenade

Apartment in Munjoy Hill

Adorable Portland getaway on the Eastern Promenade
9.6 out of 10, Exceptional, (127)
"Very convenient location. Comfortable accommodation! I would stay here again. "
United States
Cynthia W.
$162 nightly
The price is $177
Dec 14 - Dec 15
Total with taxes and fees
Adorable Portland getaway on the Eastern Promenade
Dining
Sunny Spot with Private Parking.

Apartment in Knightville

Sunny Spot with Private Parking.
2.0 star property
9.8 out of 10, Exceptional, (24)
"Cute property.. also really suitable for long stay as the amenities were complete and near groceries and some restaurants and cafes.. convenient!"
United States
Giana
$180 nightly
The price is $196
Dec 17 - Dec 18
Total with taxes and fees
Sunny Spot with Private Parking.
Outdoor dining
Camp Forever cottage

Vacation Home in Harpswell

Camp Forever cottage
9.6 out of 10, Exceptional, (58)
"Most enjoyed vacation this year.Location was beautiful. "
United States
Debra S.
$333 nightly
The price is $363
Dec 31 - Jan 1, 2026
Total with taxes and fees
Camp Forever cottage
Outdoor dining
Vacation Creation Downtown Brunswick 2King Beds

Apartment in Brunswick

Vacation Creation Downtown Brunswick 2King Beds
9.6 out of 10, Exceptional, (18)
"Stayed here while visiting Bowdoin. Great place!"
United States
Deborah B.
$293 nightly
The price is $319
Dec 15 - Dec 16
Total with taxes and fees
Vacation Creation Downtown Brunswick 2King Beds
TV, books
Back Cove Gem ★ 5 Min to Old Port ★ Bright and New

Apartment in Oakdale

Back Cove Gem ★ 5 Min to Old Port ★ Bright and New
10.0 out of 10, Exceptional, (43)
"Very clean, updated, safe and comfortable! Great location for exploring Portland. "
United States
Eden R.
Back Cove Gem ★ 5 Min to Old Port ★ Bright and New
Exterior detail
West End Bright Spot with Parking.

Apartment in West End

West End Bright Spot with Parking.
10.0 out of 10, Exceptional, (16)
"Super cute spot! Wonderful girls weekend!"
United States
Diana M.
$219 nightly
The price is $239
Jan 11 - Jan 12, 2026
Total with taxes and fees
West End Bright Spot with Parking.
Fridge, microwave, oven, stovetop
2King Bed BR Private Apt Downtown Brunswick

Apartment in Brunswick

2King Bed BR Private Apt Downtown Brunswick
8.4 out of 10, Very Good, (10)
"Small place in a great location. Easily walk to several shops and restaurants. "
United States
Jillian B.
$216 nightly
The price is $235
Dec 17 - Dec 18
Total with taxes and fees
2King Bed BR Private Apt Downtown Brunswick
Outdoor dining
Waterfront Access with Kayaks, Private Deck and a Firepit

Cabin in Gray

Waterfront Access with Kayaks, Private Deck and a Firepit
2.0 star property
10.0 out of 10, Exceptional, (3)
" The place was wonderful!! Very peaceful and beautiful!! "
United States
Anonymous traveler
$633 nightly
The price is $697
Dec 15 - Dec 16
Total with taxes and fees
Waterfront Access with Kayaks, Private Deck and a Firepit
TV
Lofty Ambition | Stunning West End Rooftop Retreat

Apartment in Parkside

Lofty Ambition | Stunning West End Rooftop Retreat
8.8 out of 10, Excellent, (5)
"Loved the loft. Clean and comfortable. Would stay here again. "
United States
Belinda C.
$306 nightly
The price is $333
Dec 16 - Dec 17
Total with taxes and fees
Lofty Ambition | Stunning West End Rooftop Retreat
1 bedroom, desk, free WiFi, bed sheets
Spacious Studio Near Sebago Lake

Apartment in Windham

Spacious Studio Near Sebago Lake
2.0 star property
10.0 out of 10, Exceptional, (2)
"Host was very welcoming and check in was simple "
United States
Michael C.
$112 nightly
The price is $122
Dec 14 - Dec 15
Total with taxes and fees
Spacious Studio Near Sebago Lake
Fridge, microwave, oven, stovetop
Whispering Pine 3BR 2Bath In Central Brunswick& Topsham

Apartment in Topsham

Whispering Pine 3BR 2Bath In Central Brunswick& Topsham
9.6 out of 10, Exceptional, (5)
"A perfect place for corporate housing. Close to the center of Topsham and Brunswick. Great amenities and fully furnished to make you feel at home. Thank you!"
United States
Kim A.
$310 nightly
The price is $313
Dec 14 - Dec 15
Total with taxes and fees
Whispering Pine 3BR 2Bath In Central Brunswick& Topsham
Private kitchen
Classic New England Waterfront

Vacation Home in Harpswell

Classic New England Waterfront
10.0 out of 10, Exceptional, (2)
"Great property"
United States
Scott D.
$650 nightly
The price is $709
Dec 14 - Dec 15
Total with taxes and fees
Classic New England Waterfront
TV
Cozy 1-bedroom apartment in awesome Portland with WiFi, AC

Apartment in Parkside

Cozy 1-bedroom apartment in awesome Portland with WiFi, AC
8.0 out of 10, Very Good, (4)
"Everything was perfect."
United States
Edward J.
$136 nightly
The price is $148
Dec 21 - Dec 22
Total with taxes and fees
Cozy 1-bedroom apartment in awesome Portland with WiFi, AC
TV
In-town no frills 2 bedroom apt

Apartment in West Bayside

In-town no frills 2 bedroom apt
8.6 out of 10, Excellent, (16)
"Host was very accommodating. Apartment worked well for. Description accurate. Would stay again."
United Kingdom
Martha F.
$154 nightly
The price is $156
Dec 14 - Dec 15
Total with taxes and fees
In-town no frills 2 bedroom apt
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

Hampton Inn Portland Downtown - Waterfront

Hampton Inn Portland Downtown - Waterfront

10/10 Excellent
"clean room, digital key wonderful, good breakfast selection, staff very accommodating. Pool water very, very cloudy (negative)"
geraldine 3-night trip
Posted 2 days ago
Hampton Inn Portland Downtown - Waterfront

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 $135 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.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Cumberland?

Yes, there are vacation rentals close to well known attractions in Cumberland, or you can select a more remote option if you'd like a relaxing place to stay.

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

Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough: This vacation home rental near Cumberland is on the beach and equipped with air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

What’s there to see and do in Cumberland?

Explore the area and family-friendly sights such as Maine Narrow Gauge Railroad Company and Museum, or get out into nature at a spot like Casco Bay. Desert of Maine and University of New England 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.