Cumberland Holiday Rentals

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Holiday Rentals in Cumberland

Camp Forever cottage

9.6 out of 10, Exceptional, (50)
"Great stay. My husband and I were there for 4 days. Peaceful and quiet. Lovely views. Just perfect for the two of us. Short drive to area sites, businesses and restaurants."
The price is AU$594
includes taxes & fees
24 July - 25 July
Camp Forever cottage

Centerview cottage

9.8 out of 10, Exceptional, (51)
"Very good people, excellent stay and we highly recommend this place, good home feeling and beautiful view"
Centerview cottage

The Harpswell House-Waterfront, SunRise, Big Yards, Classic & Luxury

The price is AU$2,708
includes taxes & fees
21 July - 22 July
The Harpswell House-Waterfront, SunRise, Big Yards, Classic & Luxury

Classic New England Waterfront

The price is AU$2,612
includes taxes & fees
20 July - 21 July
Classic New England Waterfront

Private Home w/ Office Year Round in town Brunswick next to Bowdoin

9.0 out of 10, Wonderful, (19)
"Nice place, I'd stay again!"
The price is AU$674
includes taxes & fees
22 July - 23 July
Private Home w/ Office Year Round in town Brunswick next to Bowdoin

Beautiful 3BR Home with Office in Town of Brunswick with King beds

9.0 out of 10, Wonderful, (4)
"Had a great stay here, the property was clean and came as advertised"
The price is AU$674
includes taxes & fees
29 July - 30 July
Beautiful 3BR Home with Office in Town of Brunswick with King beds

Waterfront Spacious Luxury Home, 5 min to LL Bean!

9.8 out of 10, Exceptional, (18)
"Great place. Gracious hosts. Warm and cozy space with plenty of room for everyone. "
The price is AU$1,313
includes taxes & fees
21 July - 22 July
Waterfront Spacious Luxury Home, 5 min to LL Bean!

Waterfront, Luxury, Spacious home in Freeport!

10.0 out of 10, Exceptional, (26)
"Great location - close to downtown Freeport. Beautiful property with plenty of comfortable sleeping options"
The price is AU$3,750
includes taxes & fees
27 July - 28 July
Waterfront, Luxury, Spacious home in Freeport!

Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport

10.0 out of 10, Exceptional, (4)
"We had a wonderful time in Freeport, getting some Christmas season shopping in and bring our 4 year old to the Sparkle weekend festivities. "
The price is AU$1,359
includes taxes & fees
27 July - 28 July
Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport

Absolutely Breathtaking Direct Oceanfront Cottage ~ Perfect Location!

9.8 out of 10, Exceptional, (31)
"I spent summers on Long Island in Casco Bay always dreaming of staying at Peak’s Island to see what all the hype was about… Well, it exceeded my expectations at this location! The communication with the owner, to the comfort of the cottage and view was priceless. We are already planning for next summer 😃"
The price is AU$1,914
includes taxes & fees
5 Aug - 6 Aug
Absolutely Breathtaking Direct Oceanfront Cottage ~ Perfect Location!

Modern Cottage with Peeks of Ocean Views

The price is AU$872
includes taxes & fees
13 Aug - 14 Aug
Modern Cottage with Peeks of Ocean Views

Willard Beach–Private Apt Near Portland & Parks

10.0 out of 10, Exceptional, (1)
"Cozy and clean place with a quick walk to the beach in beautiful neighborhood!"
The price is AU$504
includes taxes & fees
22 July - 23 July
Willard Beach–Private Apt Near Portland & Parks

Charming Studio apartment with WiFi, AC in welcoming Portland

10.0 out of 10, Exceptional, (2)
"This was a great stay through and through. Excellent condition, very responsive before and during the stay, and a great location. 10/10 will recommend to anyone staying in Portland! "
The price is AU$357
includes taxes & fees
18 Aug - 19 Aug
Charming Studio apartment with WiFi, AC in welcoming Portland

Charming 2-bedroom apartment with AC, WiFi in fabulous Portland

6.0 out of 10, (1)
"The location was very convenient. I missed the part that said it was on second floor with a curved stair case. The actual apartment was clean, but in need of a few repairs. "
The price is AU$642
includes taxes & fees
12 Aug - 13 Aug
Charming 2-bedroom apartment with AC, WiFi in fabulous Portland

Spacious 4-bedroom house located in the heart of Portland, ME.

The price is AU$1,413
includes taxes & fees
14 Aug - 15 Aug
Spacious 4-bedroom house located in the heart of Portland, ME.

Mint Ocean Promenade Condo, Steps to Old Port

The price is AU$653
includes taxes & fees
23 July - 24 July
Mint Ocean Promenade Condo, Steps to Old Port

Modern & Sunny House Steps from the Promenade. Private Parking!

10.0 out of 10, Exceptional, (29)
"This properly was perfectly suited for my wife and I, it is exactly as it is described. We were comfortable and enjoyed every minute at this property. We had to reschedule our flight which required us staying an extra night, Jennifer so graciously allowed us to stay another night. We would definitely stay here again if we ever return to Portland."
The price is AU$1,068
includes taxes & fees
23 July - 24 July
Modern & Sunny House Steps from the Promenade. Private Parking!

Elegant condo - walk to Portland's best restaurants & Old Port

9.4 out of 10, Exceptional, (62)
"Right off a Main Street with tons of food and drink options. Loved the area, felt safe and fun. Close to walking trails as well. Inside decor was nice. "
The price is AU$677
includes taxes & fees
28 July - 29 July
Elegant condo - walk to Portland's best restaurants & Old Port

The Globe House on Munjoy Hill - Walk to Breweries

10.0 out of 10, Exceptional, (79)
"Perfect location to take advantage of all the foodie places!! Place was clean and hosts were wonderful. "
The price is AU$1,060
includes taxes & fees
27 July - 28 July
The Globe House on Munjoy Hill - Walk to Breweries
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

Frequently asked questions

Are there holiday rentals in Cumberland?

Yes, there are holiday rentals close to the most popular sights in Cumberland, 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?

Cozy and Quiet Beautiful Home One Bedroom Private Bathroom in Portland Maine.: This holiday home rental outside of Cumberland is located on the beach, and offers a fireplace, air conditioning and a Smart TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave and an electric kettle.

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. Desert of Maine and University of New England 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.