Holiday Rentals in Portland

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Check prices for these dates

In two weeks
5 Jun - 7 Jun
In two months
17 Jul - 19 Jul
In three months
14 Aug - 16 Aug
In four months
11 Sept - 13 Sept

Our top choices for Portland holiday rentals

Outdoor dining

Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.6 out of 10, Exceptional, (10 reviews)
"Great little place in south Portland! Close to many parks, lighthouses, and driving distance to downtown. Parking downtown and in the old port area can be tricky and expensive though. "
United States
Christopher R.
The price is €215
includes taxes & fees
20 May - 21 May
Peaceful & minutes from the Old Port with private parking
Living area

Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (1 review)
"Beautiful new boutique hotel in Portland! Easy access to the Old Port and everything Portland has to offer. Very quiet, clean and well appointed rooms. The kitchen makes all the difference, even for a short stay! We loved our visit so much that we've booked a second trip!"
United States
Allison
The price is €357
includes taxes & fees
27 May - 28 May
Evalina Hotel
TV

The Coastal Connection

The Coastal Connection
Thorton Heights
8.0 out of 10, Very good, (1 review)
"Nice clean apartment very updated in older building. 3 Units or so in this renovated house. So expect to hear your neighbors. Also the main road has a lot of traffic at every hour. Semis shake the house. "
United States
Benjamin
The price is €267
includes taxes & fees
20 May - 21 May
The Coastal Connection
Interior

Charming Studio apartment with WiFi, AC in welcoming Portland

Charming Studio apartment with WiFi, AC in welcoming Portland
Munjoy Hill
9.6 out of 10, Exceptional, (11 reviews)
"A great location and a comfortable place to stay!"
United States
Andrew K.
The price is €198
includes taxes & fees
20 May - 21 May
Charming Studio apartment with WiFi, AC in welcoming Portland
TV

Private Entrance Residential Portland

Private Entrance Residential Portland
Deering Center
8.8 out of 10, Excellent, (6 reviews)
"This was a great place to stay. Easy to get to all of our destinations. Place was clean and comfortable. Would stay here again. "
United States
Ameleah B.
The price is €147
includes taxes & fees
21 May - 22 May
Private Entrance Residential Portland
Private kitchen

1-bedroom hotel suites in Scarborough with essentially stocked kitchens.

1-bedroom hotel suites in Scarborough with essentially stocked kitchens.
South Portland
10.0 out of 10, Exceptional, (1 review)
"We really appreciated our stay!"
United States
Anonymous traveller
The price is €141
includes taxes & fees
21 May - 22 May
1-bedroom hotel suites in Scarborough with essentially stocked kitchens.
Exterior detail

Elegant condo - walk to Portland's best restaurants & Old Port

Elegant condo - walk to Portland's best restaurants & Old Port
East Bayside
9.4 out of 10, Exceptional, (78 reviews)
"Lovely unit. Very comfortable bed. Nice to have off street parking. Walkable to Old Port. Would def stay again. "
United States
Erin H.
Elegant condo - walk to Portland's best restaurants & Old Port
Interior

Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
9.8 out of 10, Exceptional, (25 reviews)
"Cute property.. also really suitable for long stay as the amenities were complete and near groceries and some restaurants and cafes.. convenient!"
United States
Giana
The price is €200
includes taxes & fees
20 May - 21 May
Sunny Spot with Private Parking.
Deluxe Suite, 1 King Bed | Private kitchen

The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (101 reviews)
"Lovely suite! Comfy king bed, everything spotless, Great location. Would stay here again"
United States
Roberta
The price is €245
includes taxes & fees
26 May - 27 May
The Weldon Hotel
Interior

East end. Walk to food, beer and downtown fun.

East end. Walk to food, beer and downtown fun.
Munjoy Hill
9.8 out of 10, Exceptional, (33 reviews)
"Clean, great location, excellent communication with host, perfectly furnished for our group"
United States
Elizabeth P.
East end. Walk to food, beer and downtown fun.
Property grounds

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

Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
East Bayside
8.8 out of 10, Excellent, (37 reviews)
"Overall a pleasing stay."
United States
Mallory D.
The price is €402
includes taxes & fees
20 May - 21 May
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
1 bedroom, WiFi, bed sheets

Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.4 out of 10, Very good, (7 reviews)
"Maine Oyster Company was a highlight of the trip! "
United Kingdom
Tyler P.
The price is €181
includes taxes & fees
31 May - 1 Jun
Studio Apartment near downtown Walkable!
1 bedroom, desk, iron/ironing board, free WiFi

Charming West End Hideaway. Private Parking

Charming West End Hideaway. Private Parking
West End
10.0 out of 10, Exceptional, (51 reviews)
"Great stay in the heart of Portland, the bathtub was so good for a warming soak after a cool day of exploring the arts district! The host was very accommodating and we will be considering staying here again, for sure! "
United States
James S.
The price is €234
includes taxes & fees
27 May - 28 May
Charming West End Hideaway. Private Parking
Exterior detail

1200 Sq Ft ♦ West End Gem ♦ Perfect Location

1200 Sq Ft ♦ West End Gem ♦ Perfect Location
West End
9.4 out of 10, Exceptional, (100 reviews)
"Great location with easy parking"
United States
Lauren J.
1200 Sq Ft ♦ West End Gem ♦ Perfect Location
Interior

1200 sq ft ♦ West End Townhouse ♦ Perfect Location

1200 sq ft ♦ West End Townhouse ♦ Perfect Location
West End
8.4 out of 10, Very good, (59 reviews)
"Nice place. Good location."
United States
Rob M.
The price is €334
includes taxes & fees
7 Jun - 8 Jun
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Smart TV

Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
9.0 out of 10, Wonderful, (28 reviews)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
The price is €180
includes taxes & fees
25 May - 26 May
Beautiful 1st Floor Apartment & Amazing Shower
Smart TV

Willard Beach–Private Apt Near Portland & Parks

Willard Beach–Private Apt Near Portland & Parks
Willard Beach
10.0 out of 10, Exceptional, (5 reviews)
"Excellent in every way."
United States
Robert B.
The price is €257
includes taxes & fees
27 May - 28 May
Willard Beach–Private Apt Near Portland & Parks
Interior

NEW 1 BDR-Heart of Munjoy Hill

NEW 1 BDR-Heart of Munjoy Hill
Munjoy Hill
10.0 out of 10, Exceptional, (4 reviews)
"Great location within walking distance to activities, food, the bay, etc. "
United States
Anne D.
NEW 1 BDR-Heart of Munjoy Hill
Flat-screen TV, Netflix, books, streaming services

Walk to Old Port ♦ West End Condo ♦ Parking

Walk to Old Port ♦ West End Condo ♦ Parking
West End
9.6 out of 10, Exceptional, (83 reviews)
"Great location and very spacious! Easy commutation - must stay! "
United States
Courtney H.
The price is €314
includes taxes & fees
20 May - 21 May
Walk to Old Port ♦ West End Condo ♦ Parking
Exterior detail

Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (132 reviews)
"The host was very friendly and it was an easy apartment to check into. "
United States
Kendall M.
Adorable Portland getaway on the 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.
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Top Portland Hotel Reviews

Portland Harbor Hotel

Portland Harbor Hotel

6/10 Okay
"Location is fantastic and staff was friendly. The room and common areas were acceptably clean. The room was pretty basic and felt a little cramped but I could have booked a suite and didn’t. Some of the maintenance could have been done better, which would have been more fitting for a well restored building, but whatever. Unfortunately, we had a room facing Fore Street, which apparently doubles as the Portland Drag Strip on Friday and Saturday night. Super loud motorcycles and cars sped past, revving engines, well after midnight. No clue why the PPD tolerates this. As others have mentioned, the Resort Fee is silly. Basically, you get charged $35 per day but can get use of those funds if you eat, or drink in their restaurant. We were informed of this upon checking in but I saw no mention of it during the booking process, but perhaps I simply missed it. Several States have outlawed such practices, often referring to them as “predatory pricing” because they’re normally not clear at the time of booking (up-front). Not a huge deal, as we simply had a drink in the bar every day, but you just wouldn’t expect it from a hotel that’s this nice otherwise. It just feels a but slimy. I’ll stay elsewhere next time, simply due to the noise, but obviously that’s something they can’t control."
Chad 3-night trip
Posted 4 hours ago
Portland Harbor Hotel

Find out more about Portland

Everything you need to know about Portland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Portland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Portland holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Portland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Portland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Portland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Portland holiday rentals we have selected for you start as low as €141 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Portland rentals

At Expedia, we put the best Portland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Portland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Portland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Portland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Portland?

Yes, there are holiday rentals in Portland close to Bayside Bowl, 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?

Steps from Old Port. New, Beautifully Appointed Home. Sleeps up to 11.: This highly rated holiday home rental in Portland is located in the city centre, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. Our travellers also rate Cozy & Quiet Home in Portland, Maine 1Bedroom, Private Bathroom “No Kitchen” as a favourite home for rent in Portland.

How many holiday rentals are there in Portland?

Choose from 89 Expedia holiday rentals in Portland for a memorable holiday.

What can I see and do in Portland?

Bayside Bowl and Portland Observatory are a couple of the family-friendly sights, whereas cultural attractions include Merrill Auditorium and Portland Museum of Art. While here, Casco Bay Lines Ferry Terminal and Cross Insurance Arena 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.