Holiday Homes in Portland

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Featured Holiday Homes in Portland and around

Historic West End Neighborhood
Exterior
Historic West End Neighborhood
10.0 out of 10, Exceptional, 102 reviews
"We were in Portland for our daughter’s grad school graduation, and our accommodations were perfect. Jim was an awesome host! Thank you so much for the use of you home."
Historic West End Neighborhood
Beautiful, single story ranch. Next to city park with ocean view!
Fireplace
Beautiful, single story ranch. Next to city park with ocean view!
10.0 out of 10, Exceptional, 1 review
"Beautiful spot in Portland with plenty of space for 6 adults. Ken could not have been nicer. He was in touch and available for questions all weekend."
Beautiful, single story ranch. Next to city park with ocean view!
Elegant condo - walk to Portland's best restaurants & Old Port
Fridge, microwave, oven, stovetop
Elegant condo - walk to Portland's best restaurants & Old Port
9.4 out of 10, Exceptional, 48 reviews
"My two sisters and I loved everything about the place especially the kitchen and the temperature control via AC or heat. The only concern about the place is that it took 1-3 tries each time we had to unlock the front door by code. There was supposed to be music to help but couldn't really hear anything. May need some attention but have to admit we never alerted anyone at the time thinking it was related to our ineptitude! I tried to do this review on the Vacasa site but the page never came up...
The price is €469
per night
23 Jul - 24 Jul
Elegant condo - walk to Portland's best restaurants & Old Port
Convenient Portland home 3 miles from Downtown
Fridge, microwave, oven, stovetop
Convenient Portland home 3 miles from Downtown
10.0 out of 10, Exceptional, 11 reviews
"Good place for staying near the university with a family. Simple kitchen utensils. Clean rooms and bathroom. Any questions addressed promptly. Would stay again."
The price is €655
per night
30 Jun - 1 Jul
Convenient Portland home 3 miles from Downtown
Willard Beach Neighborhood-Close to all Southern Maine has to offer!
Beach nearby
Willard Beach Neighborhood-Close to all Southern Maine has to offer!
9.8 out of 10, Exceptional, 60 reviews
"Listing is spot on, loved our stay!"
Willard Beach Neighborhood-Close to all Southern Maine has to offer!
Nature with in-town living that feels a world away. May-June-July special!!!
Property grounds
Nature with in-town living that feels a world away. May-June-July special!!!
8.8 out of 10, Excellent, 13 reviews
"this house was nice but could use some attention in the kitchen. it was a bit dirty and cluttered. also the walk way into the house had over grown bushes that you hit when you walked to the door. overall i would probably stay again in hopes these minor issues were resolved!"
Nature with in-town living that feels a world away. May-June-July special!!!
Luxurious island home on the water, 30 minute ferry ride from Portland Maine
Terrace/patio
Luxurious island home on the water, 30 minute ferry ride from Portland Maine
Luxurious island home on the water, 30 minute ferry ride from Portland Maine
Charming 110-year former Inn 10' from the Ocean!
Property grounds
Charming 110-year former Inn 10' from the Ocean!
9.8 out of 10, Exceptional, 101 reviews
"Perfect location. House could not be closer to the beach. You have your own large private balcony directly on the beach. Short drive to downtown Porland. There are a few close places to walk to also. We spent every night and morning on the balcony watching the boats go by and dogs playing on the beach early morning and nights. "
Charming 110-year former Inn 10' from the Ocean!
Rent a room in the gorgeous Holt House
Exterior
Rent a room in the gorgeous Holt House
8.4 out of 10, Very good, 19 reviews
"It was a great trip up to Portland and the property met our needs."
Rent a room in the gorgeous Holt House
5 Star Back Cove Hide-Away<br>1 bedroom Back Cove apartment with water views!
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, 119 reviews
"We needed a comfortable place to stop on a long drive to Canada. The place was very comfortable and the owner communicated in very clear and helpful ways. I needed an extra half hour at check out due to a work commitment. She was accommodating, WiFi worked great and I was able to engage without worry. Will definitely seek to stay again as 1 1/2 days in Portland wasn’t quite enough to truly enjoy the area."
5 Star Back Cove Hide-Away<br>1 bedroom Back Cove apartment with water views!
Modern & Sunny House Steps from the Promenade. Private Parking!
Property grounds
Modern & Sunny House Steps from the Promenade. Private Parking!
10.0 out of 10, Exceptional, 11 reviews
"We enjoyed our time on Cumberland Ave. It was walking distance to fun bars and restaurants. The rooms were comfy. We had everything we needed! Thank you for a wonderful stay!"
The price is €744
per night
18 Jul - 19 Jul
Modern & Sunny House Steps from the Promenade. Private Parking!
Sunny Modern Oasis in Portland’s Trendy East End
Fridge, microwave, oven, stovetop
Sunny Modern Oasis in Portland’s Trendy East End
10.0 out of 10, Exceptional, 41 reviews
"Rode up with the wife for a long bday weekend and the property and location were perfect. Mark is a great hose and gave us some awesome local recommendations. Really clean, comfortable and modern apartment for a refreshing getaway! Would definitely rent again."
Sunny Modern Oasis in Portland’s Trendy East End
"Glamp" out near downtown Portland w/outdoor patio, fire pit & outdoor shower!
Property grounds
"Glamp" out near downtown Portland w/outdoor patio, fire pit & outdoor shower!
9.2 out of 10, Wonderful, 9 reviews
"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!
FunJoy Hill - The Perfect Location!
Fridge, microwave, oven, stovetop
FunJoy Hill - The Perfect Location!
9.8 out of 10, Exceptional, 10 reviews
"Great location. Easy to find. We had a great time"
FunJoy Hill - The Perfect Location!
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
Fridge, microwave, oven, stovetop
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
9.4 out of 10, Exceptional, 24 reviews
"Stayed here for a guys weekend in June. Home was spacious, clean, and a ton of fun. Close enough to downtown that taxis are cheap, but within reasonable walking distance that we walked back multiple times. Hot tub was clean and worked great. Highly recommend"
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
The Globe House on Munjoy Hill - Amazing Sunsets - Walk to Breweries
Fridge, microwave, oven, stovetop
The Globe House on Munjoy Hill - Amazing Sunsets - Walk to Breweries
10.0 out of 10, Exceptional, 57 reviews
"We came for a friends weekend, and we had a great time! The location cannot be beat and the house was clean and as described in the listing."
The price is €643
per night
5 Jul - 6 Jul
The Globe House on Munjoy Hill - Amazing Sunsets - Walk to Breweries
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Interior
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
8.8 out of 10, Excellent, 50 reviews
"The property was easy to access. It had a full kitchen, dining room, and nice-sized shaded backyard. It is in a quiet neighborhood. It was a nice crash pad for a getaway weekend."
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Rent a room in the gorgeous Holt House
Exterior
Rent a room in the gorgeous Holt House
7.8 out of 10, Good, 12 reviews
"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
Prime City Living Townhouse
Fridge, microwave, oven, stovetop
Prime City Living Townhouse
5.4 out of 10, 3 reviews
"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!"
Prime City Living Townhouse
Munjoy Hill hideaway with fireplace & AC - walk to dining & Eastern Promenade
1 bedroom, Internet, bed sheets
Munjoy Hill hideaway with fireplace & AC - walk to dining & Eastern Promenade
9.2 out of 10, Wonderful, 10 reviews
"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
Don't see what you're looking for?
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

Elegant condo - walk to Portland's best restaurants & Old Port
Fridge, microwave, oven, stovetop
Elegant condo - walk to Portland's best restaurants & Old Port
9.4 out of 10, Exceptional, 48 reviews
"My two sisters and I loved everything about the place especially the kitchen and the temperature control via AC or heat. The only concern about the place is that it took 1-3 tries each time we had to unlock the front door by code. There was supposed to be music to help but couldn't really hear anything. May need some attention but have to admit we never alerted anyone at the time thinking it was related to our ineptitude! I tried to do this review on the Vacasa site but the page never came up...
The price is €469
per night
23 Jul - 24 Jul
Elegant condo - walk to Portland's best restaurants & Old Port
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
8.8 out of 10, Excellent, 20 reviews
"Clean and easy to access, nice property for a short stay. Easy communication."
The price is €413
per night
1 Jul - 2 Jul
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
Rent a room in the gorgeous Holt House
Exterior
Rent a room in the gorgeous Holt House
8.4 out of 10, Very good, 19 reviews
"It was a great trip up to Portland and the property met our needs."
Rent a room in the gorgeous Holt House
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
657
Accommodation
73 Holiday Homes
Lowest Price
€469
Highest Price
€744

Recent Reviews in Portland
Expedia verified reviews

Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

5/5 Excellent
"I’d go back just for the pancakes. Everything was perfect & a short walk down to restaurants & downtown."
A verified traveller stayed at Cambria Hotel Portland Downtown-Old Port
Posted 2 days ago
Cambria Hotel Portland Downtown-Old Port