Holiday Homes in Portland

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Featured Holiday Homes in Portland

Exterior
Rent a room in the gorgeous Holt House
8.4 out of 10, Very good, (19)
"It was a great trip up to Portland and the property met our needs."
Rent a room in the gorgeous Holt House
Private kitchen
Elegant condo - walk to Portland's best restaurants & Old Port
9.4 out of 10, Exceptional, (45)
"The kitchen was very well equipped. Living room was so cozy with the fire. Bed was super comfortable. The unit has really tall ceilings and is cozy. Only issue was the dog upstairs. They kept barking and whining."
Elegant condo - walk to Portland's best restaurants & Old Port
Interior
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
8.8 out of 10, Excellent, (48)
"This was a great old townhouse. Great parking and very clean. Easy walk to attractions and a charming neighborhood bar just around the corner. "
The price is NZ$406
per night
28 May - 29 May
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
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Fridge, microwave, oven, stovetop
Convenient Portland home 3 miles from Downtown
10.0 out of 10, Exceptional, (8)
"The house was spotless and comfortable. We arrived in the middle of a snowstorm, and it was great to have the one-car attached garage, a heating system that worked well, someone who plowed the driveway and shoveled the snow shortly after we arrived, and a comfortable hot shower. Grocery stores and restaurants are nearby. Beds are comfortable, and there is a lot of closet space and drawer space. We would stay here again."
The price is NZ$1,126
per night
29 May - 30 May
Convenient Portland home 3 miles from Downtown
Fridge, microwave, oven, stovetop
5 Star Back Cove Hide-Away<br>1 bedroom Back Cove apartment with water views!
10.0 out of 10, Exceptional, (115)
"Perfect little place just outside of downtown, very convenient to everything. Very clean & nicely decorated. Exactly as shown. Excellent communication from host, easy check in. Will def re-book if/when we return to Portland!"
5 Star Back Cove Hide-Away<br>1 bedroom Back Cove apartment with water views!
Property grounds
Charming 110-year former Inn 10' from the Ocean!
9.8 out of 10, Exceptional, (99)
"Lovely home in a beautiful location. Very welcoming, cozy, and friendly. Easy check-in and check-out process. The owner was very accommodating and helpful. Made amazing memories and look forward to returning soon. Thank you so much!"
Charming 110-year former Inn 10' from the Ocean!
Private kitchen
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
9.4 out of 10, Exceptional, (23)
"This property was perfect for our group of 10 girls!!! It was much bigger than I was even anticipating, beautiful home and very clean. *Very* safe and nice neighborhood, which was incredibly important for us girls. The hot tub was the best part and the fireplace was great too. No complaints with our stay at all, though I wish it was a walking distance to downtown. It was about a 10 minute car ride so we ubered for our stay which worked out pretty good and was still cheap! The host lives upstairs...
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
Fridge, microwave, oven, stovetop
The Globe House on Munjoy Hill - Amazing Sunsets - Walk to Breweries
10.0 out of 10, Exceptional, (52)
"Artfully decorated and located walking distance to restaurants and parks. This was the perfect place for me and friends to visit around the table, watch a hockey game on TV, walk to restaurants, heat up take out, and was close to site seeing museums and light houses. The host was quickly available for suggestions. Check in and out was simple."
The Globe House on Munjoy Hill - Amazing Sunsets - Walk to Breweries
Exterior
Rent a room in the gorgeous Holt House
7.8 out of 10, Good, (12)
"This was such a cool house to stay in. The host was very responsive and the check in/out process couldn't have been easier."
Rent a room in the gorgeous Holt House
1 bedroom, Internet, bed sheets
Munjoy Hill hideaway with fireplace & AC - walk to dining & Eastern Promenade
9.2 out of 10, Wonderful, (10)
"We stayed a few nights in November while in town for a wedding. The apartment was just as pictured and described, with extra blankets and such for warming up. I had an issue with the fireplace in the bedroom not coming on. I contacted the property manager who reached out to the owner and someone was there to fix it within an hour. Only other negative was the hot water in the shower didn’t last very long. Otherwise, I’d was very cozy and comfortable, very quiet at night. The apartment is close...
Munjoy Hill hideaway with fireplace & AC - walk to dining & Eastern Promenade
Property grounds
Modern & Sunny House Steps from the Promenade. Private Parking!
10.0 out of 10, Exceptional, (9)
"We just loved this place! Off street parking is a big plus!! We were able to sit out on the back deck all afternoon one day!! We walked all over the place. Great location!! We would stay here again."
The price is NZ$933
per night
10 Jun - 11 Jun
Modern & Sunny House Steps from the Promenade. Private Parking!
Fridge, microwave, oven, stovetop
Munjoy Hill- Immaculately restored antique 1874 New Englander with private patio
10.0 out of 10, Exceptional, (8)
"We loved our stay and great house for my family to stay in. Christine was very responsive to my questions/emails. I would highly recommend this house!"
Munjoy Hill- Immaculately restored antique 1874 New Englander with private patio
Interior
Exquisite home with fireplace, pool table, washer/dryer & sleek kitchen
8.0 out of 10, Very good, (1)
"We enjoyed our stay at this aptly described "chic west end retreat," and could appreciate the way the owners breathed life into a charming 19th-century property. The home was comfortable, artful, clean, and full of amenities. The only aspect related to our stay that was less than stellar was dealing with Vrbo/Vacasa personnel. In fact, the customer service provided by Vrbo/Vacasa was abysmal, and I often wondering if there was an actual human responding to me or if there was a bot generating...
Exquisite home with fireplace, pool table, washer/dryer & sleek kitchen
Fridge, microwave, oven, stovetop
Beautiful Combo Home Located in Downtown Portland - Close to the Beach
8.8 out of 10, Excellent, (13)
"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
Property grounds
Pet friendly cape, close proximity to downtown, shops, walking trails and I95!
Pet friendly cape, close proximity to downtown, shops, walking trails and I95!
Property grounds
Historic Bakery House on Great Diamond Island with Lots of Charm
9.0 out of 10, Wonderful, (2)
"This was a terrific VRBO for a family gathering. Spacious, attractive convenient, located in the middle of a converted military base that offers many communal facilities that most VRBOs lack. Beautiful manicured lawns and easily walkable, with quick ferry service to Portland, Me. Only hitch, we couldn't find the thermostat, so a late September stay was a bit cool."
Historic Bakery House on Great Diamond Island with Lots of Charm
Property grounds
"Glamp" out near downtown Portland w/outdoor patio, fire pit & outdoor shower!
9.2 out of 10, Wonderful, (9)
"This was a great spot to stay for a guys weekend. Location is a short drive to Old Port where we spent most of our time. When we weren't out and about the backyard with a fire pit and corn hole boards was perfect for hanging out. Ryan was great and responsive."
"Glamp" out near downtown Portland w/outdoor patio, fire pit & outdoor shower!
Fridge, microwave, oven, stovetop
FunJoy Hill - The Perfect Location!
9.8 out of 10, Exceptional, (10)
"Great location. Easy to find. We had a great time"
FunJoy Hill - The Perfect Location!
Fridge, microwave, oven, stovetop
Prime City Living Townhouse
6.0 out of 10, (2)
"My family and I have started the tradition of spending a weekend in Portland to visit the city and the surrounding ski area. This apartment and location made our trip so effortless and enjoyable. It's within steps of one of our favorite coffee places, Tandem, and a walk to all of the excellent shopping on Congress St. Our host couldn't have been more accommodating and helpful. We look forward to returning soon!"
The price is NZ$1,095
per night
27 May - 28 May
Prime City Living Townhouse
Property grounds
Upscale large 3 bedroom within walking distance to everything!
10.0 out of 10, Exceptional, (7)
"Cozy second floor apartment was clean and nicely located with some restaurants nearby (great ice cream/slush across the street) and a 15-20 minute walk to the heart of downtown Portland. Perfect for a weekend getaway."
The price is NZ$2,509
per night
23 Jun - 24 Jun
Upscale large 3 bedroom within walking distance to everything!
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See all available properties in Portland
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.

Other property types in Portland

Exterior
Rent a room in the gorgeous Holt House
8.4 out of 10, Very good, (19)
"It was a great trip up to Portland and the property met our needs."
Rent a room in the gorgeous Holt House
2 bedrooms, cots/infant beds, Internet, bed sheets
Inviting apartment with full kitchen, porch, convenient location, & fast WiFi
7.0 out of 10, Good, (6)
"This home was clean, bright and comfortable. Great location, no issues. Would definitely stay here again."
Inviting apartment with full kitchen, porch, convenient location, & fast WiFi
Property grounds
Glorious getaway on Portland's Eastern Promenade.
10.0 out of 10, Exceptional, (124)
"We really enjoyed our stay. We loved being able to walk to the Eastern Promenade. The beds, including the sofa bed were very comfortable. Very cute and cozy There are stairs to enter the building for anyone with mobility issues. If you are unfamiliar with older buildings, the radiators do make some noise while heating in the winter."
The price is NZ$747
per night
27 May - 28 May
Glorious getaway on Portland's Eastern Promenade.
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.

Portland Holiday Homes information

Number of reviews
448
Accommodation
68 Holiday Homes
Lowest Price
NZ$406
Highest Price
NZ$1,126

Recent Reviews in Portland
Expedia verified reviews