Holiday Rentals 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

Holiday Rentals in Portland

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
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 €372
includes taxes & fees
23 Nov - 24 Nov
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
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 €295
includes taxes & fees
9 Dec - 10 Dec
Glorious getaway on Portland's Eastern Promenade.
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, (56)
"We really enjoyed this home and the location. The upgrades were beautiful and the restaurants nearby were amazing. When we checked out and took out our trash the outside bin had a lock on it so our only issue was not being able to access that but that wasn’t anyone’s fault. "
The price is €412
includes taxes & fees
2 Dec - 3 Dec
Elegant condo - walk to Portland's best restaurants & Old Port
Rent a room in the gorgeous Holt House
Exterior
Rent a room in the gorgeous Holt House
8.2 out of 10, Very good, (22)
"We loved staying at the Holt House. It's a truly beautiful building. It's like staying in a hotel from another era. The room was beautifully decorated with victorian decor and we loved it. It was also handy to have access to a full kitchen on the first floor where we washed some of our dishes. Overall, it was a cozy and quiet place to stay."
Rent a room in the gorgeous Holt House
The Globe House on Munjoy Hill - Walk to Breweries - monthly Dec-May
Fridge, microwave, oven, stovetop
The Globe House on Munjoy Hill - Walk to Breweries - monthly Dec-May
10.0 out of 10, Exceptional, (74)
"The Globe House was a wonderful Plato spend a couple of days while exploring Portland. The house itself was immaculate and well appointed, with extra touches that put it a step above: the fresh scent from a diffuser welcomed us, a complimentary bottle of wine awaited us in the refrigerator, and luxe amenities like L’Occitane moisturizer were provided. Great location with easily walkable and excellent restaurants. Our hosts left a fabulous “guide to Portland” for us, with many of their favorite...
The Globe House on Munjoy Hill - Walk to Breweries - monthly Dec-May
Inviting apartment with full kitchen, porch, convenient location, & fast WiFi
2 bedrooms, Internet, bed sheets
Inviting apartment with full kitchen, porch, convenient location, & fast WiFi
7.4 out of 10, Good, (20)
"After a bit of confusion getting into the house, we found a nice, very well lit, spacious home with lots of windows. The beds were pretty comfy. The location was great, easy walk to the state theater, easy to walk to lots of cool bars and restaurants. The harbor and that touristy area were about 20 to 25 minute walk away, which was lovely in the nice weather. Overall, it Served well, for four people wanting to explore Portland. "
Inviting apartment with full kitchen, porch, convenient location, & fast WiFi
Adorable Portland getaway on the Eastern Promenade
Interior
Adorable Portland getaway on the Eastern Promenade
9.8 out of 10, Exceptional, (90)
"We really enjoyed our stay. This little third floor walk up was a perfect place for my husband and I to explore Portland. It is homey and comfortable and spotless. If you have any issues with mobility you should look elsewhere, but that is disclosed in the listing. The last set of stairs are very steep, but we found it charming. I highly recommend this rental. Well done! "
The price is €198
includes taxes & fees
24 Nov - 25 Nov
Adorable Portland getaway on the Eastern Promenade
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Interior
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
8.6 out of 10, Excellent, (55)
"The property is an older triplex, interior is nice. Neighborhood is quiet. Close to historic wharf area. Easy to walk to local restaurants and sites. I had my dog with me and appreciated the back yard. Of note, there is no washer/dryer in the unit. No dishwasher, but this wasn't a problem. Parking is limited to on-street and would be an issue if more than one car required space. The only bathroom and both bedrooms are on the second floor and might be a consideration for anyone with mobility...
The price is €308
includes taxes & fees
24 Nov - 25 Nov
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Quintessential Maine Beach Cottage
Property grounds
Quintessential Maine Beach Cottage
10.0 out of 10, Exceptional, (105)
"Great spot, the dog loved it too"
Quintessential Maine Beach Cottage
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)
Historic Kennebunkport home only 0.3 miles to Dock Square
Fridge, microwave, oven, stovetop
Historic Kennebunkport home only 0.3 miles to Dock Square
10.0 out of 10, Exceptional, (57)
"Cute and cozy antique home within walking distance to downtown Kennebunkport. We had three girls staying there for a girls weekend, and even though the house can sleep more than that, I think it would have felt cramped, so keep that in mind. The host was very responsive to our communications. The house was super clean and she included a bunch of nice little *sweet* touches throughout :-)"
The price is €606
includes taxes & fees
15 Dec - 16 Dec
Historic Kennebunkport home only 0.3 miles to Dock Square
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
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 €296
includes taxes & fees
25 Nov - 26 Nov
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
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.
Don't see what you're looking for?
See all available properties in Portland
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other types of properties in Portland 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, (2017)
"I enjoyed my stay, room was quiet, slept well 4 nights!!! Only downside was skimpy breakfast compared to la quinta in Harrisburg earlier on our trip."
The price is €86
includes taxes & fees
2 Dec - 3 Dec
La Quinta Inn & Suites by Wyndham Portland
Portland Harbor Hotel
Honeymoon Suite, 1 King Bed
Portland Harbor Hotel
4.0 star property
9.2 out of 10, Wonderful, (1400)
"The hotel is wonderful. They seemed very short on staff. Coffee and tea stations were sparsely stocked. Always out of coffee. The menu for dinner at the restaurant could be greatly improved and have a few more offerings. The breakfast staff was inexperienced and very understaffed. Other than that everything was great, as usual"
The price is €167
includes taxes & fees
2 Dec - 3 Dec
Portland Harbor Hotel
Canopy by Hilton Portland Waterfront
Bar (on property)
Canopy by Hilton Portland Waterfront
4.0 star property
9.4 out of 10, Exceptional, (837)
"Staff was awesome, property was in excellent condition, check in and out couldn't have been easier. Had a little trouble with the light switches in the room, but may have been operator error."
The price is €120
includes taxes & fees
3 Dec - 4 Dec
Canopy by Hilton Portland Waterfront
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.

Frequently asked questions

Can I find a holiday rental in Portland?

Yes, there are holiday rentals in Portland close to Maine Narrow Gauge Railroad Company and Museum, or you can select a more secluded option if you're looking for a relaxing stay. Tourists who visit Portland speak highly of the bustling port and array of shops. The acclaimed theatre scene and great live music are some other things you might like to check out during your trip.

What are some of the best holiday rentals that Portland has to offer?

Spacious & Sunny 4 Bedroom Close to Downtown, hot tub: This highly rated holiday home rental in Portland 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. Some other homes for rent in Portland include Elegant condo - walk to Portland's best restaurants & Old Port and Rent a room in the gorgeous Holt House.

How many holiday rentals are there in Portland?

Choose from 113 Expedia holiday rentals in Portland for a memorable holiday.

What can I see and do in Portland?

Maine Narrow Gauge Railroad Company and Museum and Bayside Bowl are a couple of the family-friendly sights, whereas cultural attractions include Merrill Auditorium and Wadsworth-Longfellow House. While here, Fore Street Gallery and Casco Bay Lines Ferry Terminal are other places worth a visit.

What are holiday rentals like in Portland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Portland. Holiday rentals provide amenities like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from shared hotel lifts and busy front desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for small groups.