Portland holiday rentals

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Booking Insights
Recommended by KAYAK

Best Portland holiday rentals

Most recommended holiday rentals in Portland

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Island View House Bnb Self Check-In - Portland - Building
Island View House Bnb Self Check-In
Portland, ME, United States
Parking
Free Wi-Fi
Air conditioning
Back Cove Views - Portland - Bedroom
Back Cove Views
Portland, ME, United States
Free Wi-Fi
Air conditioning
East End Annex - Portland - Bedroom
East End Annex
Portland, ME, United States
Air conditioning
Beautiful 1st Floor Apartment & Amazing Shower - Portland - Living room
Free Wi-Fi
Air conditioning
Bright & Spacious Apartment with Amazing Shower - Portland - Dining room
Free Wi-Fi
Air conditioning
Rosemont 1st Fl: 2BR: Sunny Spacious Convenient - Portland - Living room
Free Wi-Fi
Air conditioning
Ocean view Victorian - Portland - Building
Ocean view Victorian
Portland, ME, United States
Free Wi-Fi
Air conditioning
Pearl of Portland - Portland - Kitchen
Pearl of Portland
Portland, ME, United States
Free Wi-Fi
Air conditioning
Simple & Convenient Downtown Living - Portland
Simple & Convenient Downtown Living
Portland, ME, United States
6.8Okay(10)
Apartment
Parking
Free Wi-Fi
Air conditioning
The Downtown Downeast Room - Portland
The Downtown Downeast Room
Portland, ME, United States
5.5Fair(3)
Apartment
Free Wi-Fi
Air conditioning
3rd Floor Furnished Apt Downtown Portland - Portland
3rd Floor Furnished Apt Downtown Portland
Portland, ME, United States
6.7Okay(2)
Apartment
Parking
Free Wi-Fi
Air conditioning
The Brew House - 2nd Floor Private Apartment - Portland
Parking
Free Wi-Fi
Air conditioning
House Island Private Residence - Watchhouse - Portland
House Island Private Residence - Watchhouse
Portland, ME, United States
House
Free Wi-Fi
Air conditioning
Booking Insights

KAYAK’s insights for holiday rentals in Portland

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Portland with confidence.

What is the cheapest day of the week to book a vacation rental in Portland?

Wednesday offers the lowest rates in Portland, with an average nightly price of £175. The highest prices are found on Thursday, with average rates at £410.

How early should you book a vacation rental in Portland?

Book at least 24 days before your stay begins to get the best price for your Portland vacation rental.

KAYAK's top tips for finding Portland holiday rental deals

  • If you want to enjoy some local history on your trip, you should look for Portland holiday rentals that are in the centre of the city, where many of the main attractions are. For example, West End Retreat @ The Arts District is located a short walk from Victoria Mansion, which is a popular historical landmark.
  • For those that want to enjoy some of the best food that the city has to offer, you should look for Portland holiday rentals that are near East Bayside. For instance, Panoramic Water, Island & City Views W/Private Roof Deck is located only a short distance from popular eateries like Chong Tu Bot and Terlingua.
  • If want to enjoy a holiday by the coast, you should look for Portland house rentals that are close to the beach. For example, Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants is only about a 10min walk to East End Beach, which is a calm beach that offers a range of activities.
  • To make the most of the hiking trails that are in the city, you should look for Portland holiday rentals in the East End. For example, if you stayed at Enjoy Portland With Family or Friends, you would be close to popular walks like the Eastern Promenade Trail.
  • If you are looking to hire a car during your visit to Portland, you should look for properties that provide you with parking areas. For instance, Adorable Portland Getaway on the Eastern Promenade typically provides parking spaces to its guests.
  • Hot tub, pool, pet friendly, and beachfront are the most popular holiday rental property amenities in Portland
  • Holiday rentals in Portland are around 65% more expensive than hotels on average. Search here to compare prices for all accommodation types in Portland.
  • The best holiday rental properties in Portland are Private Rooftop Deck!/Artsy Apt/Old Port Arts Dist (10.0, 32 reviews), Chic One Bedroom Apartment In Portland's Arts District (9.9, 74), and Sunny Modern Oasis in Portland’s Trendy East End (9.9, 53), based on ratings and reviews from real travellers.
  • Holiday rentals are a popular choice for both long and short-term stays. KAYAK users usually book their holiday rental in Portland for 4 days.

FAQs when booking a holiday home in Portland

  • What types of holiday rentals are available in Portland?

    There are loads of different property types that you can make your holiday home in Portland. You’ll find apartments, cabins, campgrounds, caravan parks, chalets, condos, cottages, houses, campsites, lodges and luxury tents.

  • Are there any pet-friendly holiday rentals in Portland?

    There are a number of dog and pet-friendly Portland holiday rentals, with around 7% allowing you to bring your pet along with you.

  • How much is a holiday rental in Portland for tonight?

    In the last 72 hours, users have found Portland holiday rentals for tonight for as low as £101. Search here for similar prices

  • How can I find holiday rentals near me in Portland?

    Take a look at our holiday rentals map to find the best holiday rental homes near you.

  • What are the benefits of a self-catered property?

    When you’re in the U.S. you will find that there are many great places to eat, but it can be expensive to eat out every day. If you get a self-catered property, you’ll have the option to dine in whenever you fancy. For example, Glorious Getaway On Portland's Eastern Promenade provides facilities like an oven and cooktop, so you can cook as much as you like. There is also a range of shops nearby, where you can pick up fresh ingredients for your stay.

  • Where is best to stay in Portland for nightlife?

    If you want to go to the best bars and pubs, you should look for accommodation that’s in the centre of the city. For example, Bright & Spacious Apartment with Amazing Shower is only a short distance from popular establishments like Blackstones and The Jewel Box.

  • What options are there for Portland properties that have swimming pools?

    If you want to swim but prefer to avoid the sea, you will be pleased to know that there are properties that have pools. For example, Close To Downtown With Hot Tub! has an outdoor pool for its guests as well as a spa for you to use.

  • Where is best to stay to be close to the airport?

    If you want to be close to Portland International Jetport (PWM), then you should stay close to Highway 95, so you’ll be close to the terminal. For example, Beautifully Spacious with Charm is about a 12min drive from the airport.

Where to stay in Portland?

Our map will help you find the perfect place to stay in Portland by showing you the exact location of each holiday rental.