Holiday Homes in Cumberland Foreside

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Featured Holiday Homes in Cumberland Foreside

New Well Built Elegant Home on the Water 2 miles to Freeport, 9 to Portland!

9.8 out of 10, Exceptional, (174)
"We all had a great time staying here. It was so clean and spacious and comfortable. Beautiful views. Easy in and out. We will come back again if we are coming back this way. Loved it!! Very relaxing. Thank you for a great weekend away!!"
New Well Built Elegant Home on the Water 2 miles to Freeport, 9 to Portland!

Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough

2.0 star property
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough

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

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

Beautiful Combo Home Located in Downtown Portland - Close to the Beach

8.8 out of 10, Excellent, (15)
"Convenient to walking to town , great restaurants in the area for breakfast & dinner, house was perfect, comfortable, well maintained great off street parking and had everything we could ever had needed."
Beautiful Combo Home Located in Downtown Portland - Close to the Beach

Modern, Luxury Lakefront Home on Crescent Lake, Maine

10.0 out of 10, Exceptional, (103)
"Well equipped and well maintained, very comfortable and peaceful. We had a great stay!"
Modern, Luxury Lakefront Home on Crescent Lake, Maine

Lofty cottage

9.4 out of 10, Exceptional, (39)
"We really enjoyed our time here has a beautiful view of the ocean. Had all the things needed to kayak and go out on the water. Nice and secluded. Had a fire pit, which was lovely to turn on In the evening. Would recommend this place and stay again"
The price is AU$571
includes taxes & fees
30 Nov - 1 Dec
Lofty cottage

Charming ocean-view cottage just 10 minutes from downtown Freeport shops

2.0 star property
Charming ocean-view cottage just 10 minutes from downtown Freeport shops

3 Story Historic Landmark - Walk to All! West End, Dog-Friendly, 2 King Beds

8.4 out of 10, Very good, (6)
"We booked Nick’s place for myself, husband, 3 year old & my in-laws before we all left Portland. We were able to get an early check in, which was great because I felt horrible with a migraine & the heat was unbearable. The home has a lot of character. I would stay there again!"
The price is AU$1,161
includes taxes & fees
1 Dec - 2 Dec
3 Story Historic Landmark - Walk to All! West End, Dog-Friendly, 2 King Beds

Rise & Shine on Sebago Lake

9.8 out of 10, Exceptional, (8)
"We wanted a place for extended family to be together for a family wedding at Caswell Farms There was room for everyone and a wonderful Lake Sebago view from multiple rooms We enjoyed kayaking, hot tub, wonderful kitchen amenities for a lobster boil Conveniently located to stores and restaurants Wonderful home and memories made!! Attentive hosts and maintenance staff Loved it!"
Rise & Shine on Sebago Lake

Shady Potts Point Cottage Cooled by Ocean Breezes

9.6 out of 10, Exceptional, (77)
"Great stay in very clean house in a very quiet ocean side community. Perfect getaway!"
Shady Potts Point Cottage Cooled by Ocean Breezes

Lakeside Living w\sandy beach, gas fireplace -easy 25 minute commute to Portland

10.0 out of 10, Exceptional, (23)
"My family of three really enjoyed our stay! My 5 year old enjoyed playing with the different toys and puzzles at the house. Photos are accurate and the beds were very comfortable. The kitchen was well stocked for making meals. My son liked having his own room and bathroom upstairs. We spent a lot of time outside and had several fires! Visited Pineland Farms (loved seeing the cows up close!) and the Maine Wildlife Park (1000 ft from the house). Also loved that it was dog friendly so our pup...
Lakeside Living w\sandy beach, gas fireplace -easy 25 minute commute to Portland

Enjoy Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

9.8 out of 10, Exceptional, (68)
"Great house very comfortable and well appointed. Very roomy for our entire family. Nice to have en suite bathrooms with all the bedrooms. The host was very good with communication. Located on a busy road and the driveway is on a curve which made it a little challenging entering and exiting the property. "
Enjoy Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

Spectacular Waterfront Retreat Close To Portland!

10.0 out of 10, Exceptional, (46)
"Spent 2 glorious fall weeks at this West Bath property. This older, well updated house nicely accommodated the two of us. It was very comfortable and clean. We had everything we needed. There were plenty of dishes and flatware. We cooked in for most meals. There are black out curtains in the main bedroom, so you can really sleep in if you want to! We did! The backyard views are wonderful. Jennie’s Nubble has an active eagles nest. Lobster boats and sail boats were frequently in the area. The...
Spectacular Waterfront Retreat Close To Portland!

beautiful home away from home in Orchard Beach

7.8 out of 10, Good, (9)
"Wonderful!..we all had our own comfy bedrooms…The kitchen was fully stocked with everything you might need..Loved the back porch with tv and couches..Big back yard with fire pit which we used twice.Ahmad even gave us the wood.Very clean…and the air conditioning was greatly appreciated.Ahmad was the perfect host. Warning…..owner has a dog on the premises if you’re bringing a pet…and watch out…the hot water is scalding!.If you’re looking for a vacation home near the beach but in a quiet area,this...
beautiful home away from home in Orchard Beach

Cottage by the Sea - Steps to Crescent Beach, a Quick Drive to Portland

10.0 out of 10, Exceptional, (19)
"Our stay was memorable and so enjoyable. There were 5 of us, 4 adults and 1 child. The location is in a nice little neighborhood, only steps from Crescent Beach. We could sit on our deck and see the ocean and sleep by the sounds of the waves. This property has so much to offer with three bedrooms, one of which is downstairs for this older stair challenged lady. It has three parking spots and a lovely fenced yard for the kids to play in. The cottage was very clean and the owner has it stocked...
Cottage by the Sea - Steps to Crescent Beach, a Quick Drive to Portland

New Listing - Private Oceanfront Property on Peaks Island, Maine - Sleeps 10

9.6 out of 10, Exceptional, (7)
"Cute place with nice amenities. Friendly and responsive host. Love Peak's Island! Nice relaxing location. Great for walking and biking."
New Listing - Private Oceanfront Property on Peaks Island, Maine - Sleeps 10

Blue Lobster! 2-bedroom house with Heat, AC, Deck and Seasonal Dock in Harpswell

2.0 star property
9.6 out of 10, Exceptional, (11)
"We very much enjoyed our stay at the Blue Lobster! We were in town visiting our student at Bowdoin and found this property to be a lovely vacation spot a reasonable distance from campus. The house sits on a beautiful spot on the water and had everything we needed for our stay. We will return!"
Blue Lobster! 2-bedroom house with Heat, AC, Deck and Seasonal Dock in Harpswell

Modern Comfort: Game Room & Access to Portland

2.0 star property
9.4 out of 10, Exceptional, (3)
"Very nice."
Modern Comfort: Game Room & Access to Portland

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
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 property types in Cumberland Foreside

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

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

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
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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