Cumberland Foreside Holiday Rentals

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Holiday Rentals in Cumberland Foreside

Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)
Third-party on-site parking

Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)

9.8 out of 10, Exceptional, (115)
"Very relaxing getaway."
Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)
Sensational House on Sebago Lake, Raymond, ME
Interior

Sensational House on Sebago Lake, Raymond, ME

9.8 out of 10, Exceptional, (43)
"Great property located on an amazing lake sebago great amenities."
Sensational House on Sebago Lake, Raymond, ME
Gorgeous ocean-front home with stunning beach views
On the beach

Gorgeous ocean-front home with stunning beach views

9.6 out of 10, Exceptional, (98)
"Great oceanfront location for a relaxing girls getaway. We enjoyed walking the beach and collecting shells. Great location to start from to see other cities in the area. Best part was watching the sunrise in the morning from the balcony. "
Gorgeous ocean-front home with stunning beach views
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
Interior

Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist

10.0 out of 10, Exceptional, (35)
"Beautiful place , had everything you need . Very comfortable bed . Great shower & Kitchen . Also a great location! "
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
Fridge, microwave, oven, stovetop

Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants

9.8 out of 10, Exceptional, (99)
"Property was as described, communication was easy and fast, property was clean, spacious, and felt homey. We will be back! "
The price is AU$827
includes taxes & fees
11 Dec - 12 Dec
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
Cozy, Elegant and Bright 2 bed in the East End
Fridge, microwave, oven, stovetop

Cozy, Elegant and Bright 2 bed in the East End

9.6 out of 10, Exceptional, (35)
"Fabulous location for us as it’s just 1/2 block from our son’s apartment. So close to Casco Bay and the Portland Port area. Walkable to restaurants and shopping. Nice sunny apartment! "
The price is AU$572
includes taxes & fees
11 Dec - 12 Dec
Cozy, Elegant and Bright 2 bed in the East End
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
Fridge, microwave, oven, stovetop

Spacious & Sunny 4 Bedroom Close to Downtown, hot tub

9.2 out of 10, Wonderful, (30)
"We had a great time. Nate made check in/check out very easy and the location is great. Would recommend staying here!"
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
Charming Cottage Steps to Pine Point Bch - 1 mile OOB outside Scarborough w/ AC
1 bedroom, free WiFi, bed sheets

Charming Cottage Steps to Pine Point Bch - 1 mile OOB outside Scarborough w/ AC

9.6 out of 10, Exceptional, (26)
"Repeat visit. Short walk to beach. Convenient to stores if you want to shop. Cottage comfortable. We’ll be back!"
Charming Cottage Steps to Pine Point Bch - 1 mile OOB outside Scarborough w/ AC
Come enjoy 7 miles of beaches in sunny OOB in this 2 bedroom condo.
Beach nearby, beach towels

Come enjoy 7 miles of beaches in sunny OOB in this 2 bedroom condo.

7.4 out of 10, Good, (26)
"The location was amazing! Walking distance to the pier, and right by the beach! We enjoyed that it was far enough down from the pier that the beach was a bit less crowded but we were still able to walk downtown. The accommodations are very cute and rustic. Some things could use attention, like paint touch ups and the patio table needs replacing… however these were minor issues and we will be back! "
Come enjoy 7 miles of beaches in sunny OOB in this 2 bedroom condo.
Oceanfront Condo! Spectacular Views From Private Large Balcony
On the beach

Oceanfront Condo! Spectacular Views From Private Large Balcony

9.0 out of 10, Wonderful, (122)
"The condo was a little out dated but the balcony and the views of the sunrise can’t be beat!"
The price is AU$477
includes taxes & fees
11 Dec - 12 Dec
Oceanfront Condo! Spectacular Views From Private Large Balcony
Little Miss Cottages
Property grounds

Little Miss Cottages

2.5 star property
8.4 out of 10, Very good, (82)
"We stayed because they accept pets. Good place the 24/7 laundry was useable but not everything working"
Little Miss Cottages
100 feet from the ocean 3 bedroom cottage 420 friendly
Interior

100 feet from the ocean 3 bedroom cottage 420 friendly

8.6 out of 10, Excellent, (16)
"Owner should get new cleaners. House smelled like dog urine. Bathroom smelled like human urine. Had to clean floors and bathroom…lots of dirt…not sure the last time floors were I’m mopped. Dog hair on sheets. Beds were not comfortable so be prepared. Parking is a challenge. One paid parking spot in front ($36/day). Can park super close to house for 2nd spot. Owner not very responsive. Had to constantly message for arrival info and didn’t get it until 10 mins after checkin time. No instructions...
100 feet from the ocean 3 bedroom cottage 420 friendly
Dog-friendly cottage with deck & porch - walk to the beach, pier & town
Beach nearby

Dog-friendly cottage with deck & porch - walk to the beach, pier & town

8.2 out of 10, Very good, (12)
"We enjoyed our brief stay"
Dog-friendly cottage with deck & porch - walk to the beach, pier & town
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
Terrace/patio

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

10.0 out of 10, Exceptional, (99)
"This property is stunning, and the view is spectacular. If this were my house, I’d never leave! We had a fabulous time. "
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
Cottages by the Sea #1 | Private Beach | Steps to Sand | Bayley Vacation Rentals
On the beach

Cottages by the Sea #1 | Private Beach | Steps to Sand | Bayley Vacation Rentals

10.0 out of 10, Exceptional, (6)
"We had a wonderful stay - myself, my husband and my 6,4, and 2 year old children all enjoyed our time at the beach. We could have done without the harassment of the old lady from cottage 4 (owner perhaps?) telling us to get out at 10am. We were packing the car at 10:02 and trying to get the kids in - we were not in the cottage anymore everything was out. We left the property 10:11am. Her nagging and threats of charging extra were completely unnecessary. It was too bad to have to leave on...
Cottages by the Sea #1 | Private Beach | Steps to Sand | Bayley Vacation Rentals
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
Fridge, microwave, oven, stovetop

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

9.0 out of 10, Wonderful, (27)
"Cute place - makes very good use of the space. It was comfortable and very conveniently located to everything we wanted to do. We have a few suggestions but overall very happy, had a wonderful time, and the ultimate compliment - we look forward to staying there again. "
The price is AU$598
includes taxes & fees
1 Dec - 2 Dec
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
Spacious 3BR, 12-Min to OOB Beach & Pier, Sleeps 8
Smart TV

Spacious 3BR, 12-Min to OOB Beach & Pier, Sleeps 8

9.0 out of 10, Wonderful, (2)
"Our stay at the property was great."
Spacious 3BR, 12-Min to OOB Beach & Pier, Sleeps 8
Glorious getaway on Portland's Eastern Promenade.
Property grounds

Glorious getaway on Portland's Eastern Promenade.

10.0 out of 10, Exceptional, (139)
"Nice and spacious 2 bedroom unit steps from the promenade. Jennifer was very helpful and accommodating. Easy check in and plenty of parking. Amazing central location. "
The price is AU$478
includes taxes & fees
16 Dec - 17 Dec
Glorious getaway on Portland's Eastern Promenade.
NEW TO THE MARKET - 1 block from the beach!
Beach nearby

NEW TO THE MARKET - 1 block from the beach!

10.0 out of 10, Exceptional, (18)
"Close walk to beach restaraunts and pier very nice inside"
NEW TO THE MARKET - 1 block from the beach!
Escape to the Beach! Cozy Condo in downtown OOB.
Beach nearby

Escape to the Beach! Cozy Condo in downtown OOB.

9.6 out of 10, Exceptional, (21)
"Cute little condo within a short walk from everything. Quiet and clean. Would recommend!"
The price is AU$380
includes taxes & fees
24 Dec - 25 Dec
Escape to the Beach! Cozy Condo in downtown OOB.
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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Other types of properties in Cumberland Foreside you may be interested in

La Quinta Inn & Suites by Wyndham Portland
Exterior

La Quinta Inn & Suites by Wyndham Portland

2.5 star property
9.0 out of 10, Wonderful, (2054)
"Different area for a motel. "
The price is AU$137
includes taxes & fees
1 Dec - 2 Dec
La Quinta Inn & Suites by Wyndham Portland
Casco Bay Hotel, Ascend Hotel Collection
Lobby

Casco Bay Hotel, Ascend Hotel Collection

3.5 star property
8.4 out of 10, Very good, (2375)
"I like most everything about this place and have stayed several times. The only flaws: the rooms often smell very strongly of air freshener, including the pillows. Bring your own pillow! And there is often no dark roast k-cups. Bring your own dark roast K-cups. And finally, they used to have a wonderful coffee maker downstairs, but the machine has been broken for months. Now it's brewed ahead and can be weak. "
The price is AU$120
includes taxes & fees
16 Dec - 17 Dec
Casco Bay Hotel, Ascend Hotel Collection
Portland Harbor Hotel
Honeymoon Suite, 1 King Bed

Portland Harbor Hotel

4.0 star property
9.2 out of 10, Wonderful, (1436)
"Friendly and professional staff. Room spacious with lovely view. Walkable to dining and shopping. Thank you. Travel well. "
The price is AU$273
includes taxes & fees
1 Dec - 2 Dec
Portland Harbor Hotel
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Frequently asked questions

Can I find a holiday rental in Cumberland Foreside?

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

Spacious & Sunny 4 Bedroom Close to Downtown, hot tub: This holiday home rental outside of Cumberland Foreside is located in the city centre, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

How many holiday rentals are there in Cumberland Foreside?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Cumberland Foreside stay.

What can I see and do in Cumberland Foreside?

While exploring the area, visit family-friendly sights like Maine Narrow Gauge Railroad Company and Museum, or get outside and enjoy nature at Sturdivant Island. In the wider area, you’ll find Eastern Promenade and East End Beach.

What are holiday rentals like in Cumberland Foreside?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Cumberland Foreside. Holiday rentals offer amenities like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great option for a family trip or a small group gathering.