Portland holiday homes

We found 1,437 holiday rentals — enter your dates for availability
Discover a selection of 89 homes, 168 apartments and other holiday rentals in Portland that are perfect for your trip. Whether you're travelling with your children and pets, with friends or just your children, holiday rentals have the amenities that you expect for your stay, including parking and a TV. No matter what you're looking for, you'll be able to choose a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Portland

Showing deals for:30 Oct - 6 Nov

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Why visit Portland

  • Coastal charm: Portland enchants with its blend of urban vibrancy and scenic beaches, perfect for a relaxed seaside escape.
  • Historic allure: The city boasts rich history, featuring preserved historic houses and an iconic lighthouse that captures its maritime legacy.
  • Vibrant waterfront: Explore a lively waterfront with delightful local eateries and shops, offering a taste of Portland’s dynamic culture.
  • Family-friendly parks: Enjoy scenic parks and outdoor activities ideal for both families and solo travellers.
  • Inviting community: Experience the warm, welcoming atmosphere that makes Portland a memorable and unique holiday destination.

Top attractions in and around Portland

Portland, Maine offers a blend of outdoor charm and rich history. Visitors can enjoy scenic beaches, explore historic houses, and marvel at a historic lighthouse. Ideal for families and solo travellers alike, the city provides an array of cultural, beach, and outdoor experiences, ensuring a well-rounded holiday experience.

  • East End Beach: A picturesque seaside spot in Portland that offers a relaxed coastal vibe with soft sands and gentle waves, perfect for a leisurely stroll or a sunny day by the water.
  • Victoria Mansion: An exquisite historic house in Portland showcasing rich cultural heritage with ornate interiors and period charm, ideal for history buffs and architecture enthusiasts.
  • Willard Beach: Located 3km from Portland, this beach provides a refreshing escape with its inviting waters and scenic coastal views for a delightful day out.

Things to do recommended for couples

For a romantic getaway in Portland, explore the charming Old Port district, with its cobblestone streets and quaint shops. Enjoy a sunset sail on Casco Bay or indulge in a candlelit dinner at a waterfront restaurant, savouring fresh seafood while taking in stunning views of the harbour.

Things to do recommended for families

Families will love exploring the interactive exhibits at the Children's Museum & Theatre of Maine, or enjoying a scenic ferry ride to Peaks Island for a day of biking and beach fun. Don't miss the Portland Head Light for stunning views and a picnic.

Things to do recommended for groups

Experience the thrill of racing at Beech Ridge Motor Speedway, located 11km from Portland. It offers an exhilarating atmosphere perfect for group adventures. Enjoy the excitement of motor racing while soaking in the vibrant local sports culture.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Portland

When planning your trip—whether you're travelling with a group, family, pets, or seeking longer stays—be sure to apply the appropriate filters to align with your priorities. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Portland with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor areas for group get-togethers. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Portland with young kids: Travelling with young children can present some challenges. It's important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Portland: For many, a family holiday isn’t complete without their furry friend joining in. If that’s you, explore Vrbo properties welcoming pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring everyone feels at home.
  • Planning for a long term stay visiting Portland: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay in and around Portland

Portland, Maine, offers a delightful blend of urban charm and coastal beauty, making it a perfect holiday destination. Explore the lively waterfront, where local eateries and shops abound, or meander through downtown to experience its vibrant culture. Families can enjoy scenic parks and outdoor activities, while the friendly atmosphere invites visitors to connect with the community. With its unique vibe and stunning scenery, Portland promises an unforgettable getaway in coastal Maine.

  • Downtown Portland: Nestled in the heart of Portland, Downtown Portland offers a vibrant blend of urban energy and scenic beauty. Visitors are drawn to its outdoor and family-friendly attractions, with ample opportunities to enjoy the nearby beach, family beach, and lake. The area boasts a variety of entertainment options, including a bustling arena and expansive shopping centres, making it a versatile destination for leisure and exploration.
  • Oakdale: Located in the vicinity of Portland, Oakdale is a charming neighbourhood that caters to those seeking an outdoor escape with a touch of romance. Its picturesque setting is enhanced by scenic views and access to landmarks such as the beach, lake, and family beach. The area also offers cultural experiences through music concerts and educational venues, as well as inviting trails for a leisurely stroll.
  • Ferry Village: Just 1.6km away from Portland, Ferry Village is a delightful neighbourhood that combines beachside charm with a rich outdoor experience. It is renowned for its serene beaches and scenic vistas, with attractions including a historic lighthouse and a family beach. Travellers can also enjoy educational facilities, golf, and arena entertainment, ensuring a well-rounded visit filled with both relaxation and activity.

Best time to go to Portland

If you're planning a trip to Portland, it's a good idea to check both the weather and property rates. The warmest month is July.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January26.1°F (-3.3°C)Light RainMostly Sunny
February27.0°F (-2.8°C)Light RainMostly Sunny
March33.4°F (0.8°C)Light RainMostly Sunny
April43.9°F (6.6°C)Light RainMostly Sunny
May54.0°F (12.2°C)Light RainMostly Sunny
June61.9°F (16.6°C)Light RainMostly Sunny
July68.9°F (20.5°C)Light RainMostly Sunny
August68.5°F (20.3°C)Light RainMostly Sunny
September62.2°F (16.8°C)Light RainMostly Sunny
October52.2°F (11.2°C)Light RainMostly Sunny
November41.2°F (5.1°C)Light RainMostly Sunny
December32.9°F (0.5°C)Light RainMostly Sunny

Booking with Vrbo is a breeze

If you want to save on your next adventure, try being flexible with your travel dates since prices do vary. Additionally, booking a longer stay can often result in significant savings. To locate the perfect Vrbo property within your budget, simply use our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a handy space to organise your journeys—be it starting afresh, picking up where you last left off, or simply viewing and managing your plans. You can easily find properties that you’ve either saved or booked, neatly sorted under Potential, Upcoming, or Current Trips. To get started with your Trip Boards, visit: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

Delight in the waterfront landscape of Portland

Enjoy the area's live music, museums and theatre scene with a rental holiday home in Portland. This cosmopolitan city attracts visitors thanks to its seafood restaurants and shopping. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around Portland

Do you want to discover attractions to visit during your stay? Venture out of your holiday home and experience everything that makes Portland a fun spot to go on holiday. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Aquaboggan Water Park (10.8 mi / 17.3 km)
  • Pirate's Cove (12 mi / 19.3 km)
  • Funtown Splashtown USA (12.7 mi / 20.5 km)
  • Old Orchard Beach Parasail (15.1 mi / 24.2 km)
  • Happy Wheels Skate Center (4.2 mi / 6.7 km)
  • Len Libby Chocolates (7.6 mi / 12.3 km)

Exploring the natural features in Portland

Whether you're an adventurous traveller or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Portland. Here are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Eastern Promenade (0.8 mi / 1.3 km)
  • East End Beach (0.9 mi / 1.4 km)
  • Willard Beach (1.8 mi / 2.9 km)
  • Thompson's Point (2 mi / 3.2 km)
  • Sand Beach (2.2 mi / 3.5 km)
  • Higgins Beach (7 mi / 11.2 km)

Travelling to and around Portland

Fly into Portland, ME (PWM-Portland Intl. Jetport), the closest airport, located 2.9 mi (4.7 km) from the city centre. If you're unable to find a flight that fits your schedule, you could also fly into Auburn, ME (LEW-Auburn - Lewiston Municipal), which is 26.8 mi (43.2 km) away.

If you prefer train travel, the main station is Portland Transportation Center.

Frequently asked questions

What is the best area to stay in Portland when booking a holiday home?
One of the more popular neighbourhoods to experience a holiday home in Portland is Downtown Portland. Base yourself here and you won't be too far from leading visitor attractions like Portland Museum of Art and Wadsworth-Longfellow House.
What is the most popular type of holiday home accommodation in Portland?
Apartments are the most popular style of holiday home in Portland, according to our data. Even if you've got a different idea about what you'd like, Bookabach has holiday homes in a variety of shapes and sizes. Compare our options to find your perfect match.
How much does it cost to rent a holiday home in Portland?
The average price for a holiday home in Portland is based on several factors, including season, property type and length of stay. Whether you prefer a sprawling villa with room to move around or a quaint cabin for just you and the kids, just enter your travel dates to discover some great-value stays.
How much does it cost to rent a beach house in Portland?
The average price for a holiday home by the beach in Portland will depend on when you're going and the style and size of property you're looking for. You can easily and quickly find prices on Bookabach by entering the dates you'll be travelling. Then use our filters to pick the number of bedrooms and amenities important to you, like WiFi, air conditioning and a pool.
Are there pet-friendly holiday homes in Portland?
Yes, there are. Take your pick of 189 holiday homes that allow pets in Portland on Bookabach. Our cuddly best friends need a getaway too, so simply use our search function for pet-friendly holiday homes to find a pad where your pup can get in on the fun.
Can I rent a house with a pool in Portland?
Mark the "pool" box in our handy filter tool and select from 17 houses with private pools in Portland on Bookabach. Morning soak, afternoon splash or midnight swim? How you spend your free time is up to you when your holiday home has a swimming pool.
What are popular home amenities in Portland?
When it comes to home amenities that people are searching for in Portland, mountain views, an electric car charging station and a garden rank highest. With Bookabach holiday homes, there are choices to match your taste and style, whether you're travelling with your partner, your family or even pets.
Are there large group holiday homes in Portland?
Portland has 17 holiday properties that can accommodate 10 or more people. These stays come with all the space you need to share good times with your favourite people.
Are there holiday homes in Portland that welcome kids?
Portland has 185 family-friendly holiday homes. And securing a stay that welcomes kiddos is a breeze with Bookabach's "Properties good for families" filter. As well as having the whole place to yourselves, you'll get access to conveniences and perks like bunk beds, kitchens and private pools.
What are the top attractions for families in Portland?
There are tons of exciting things to see and do with the family in Portland, including:

  • Higgins Beach
  • East End Beach
  • Pine Point Beach

Are there one-bedroom holiday homes in Portland?
You can choose from 65 one-bedroom homes in Portland. Whether you'd prefer a townhouse or a condo, our one-bedroom properties are perfect if you don't require a lot of space. One of the main perks of having your own digs? You'll never need to share your getaway with strangers.
Can I find two-bedroom holiday homes in Portland?
Take off with your loved ones and experience complete comfort and privacy in one of the 57 two-bedroom holiday homes Portland has to offer.
Are there holiday homes with WiFi in Portland?
Portland has 95 holiday homes with WiFi, so you can stay connected while you're on holiday. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming movies with the family to sending emails, these Bookabach homes make it a breeze to get online.
How can I find holiday homes with air conditioning in Portland?
You can pick from 161 holiday homes with air conditioning in Portland giving you that gentle, cool breeze and extra level of comfort. Simply enter your desired travel dates and then use our handy filter tool to help you book properties with air conditioning.
How old do you have to be to rent a holiday home in Portland?
It's a good idea to check with the Portland holiday home you want on Bookabach as the age limit varies. However, generally it's 16, 18 or 21.
How long can I rent a holiday home in Portland for?
The amount of time you can book a Portland holiday home for differs depending on the property. Simply tap in your preferred travel dates to see available options offering longer term stays. They include all you require to make your extended holiday more enjoyable and convenient, like laundries and air conditioning. Some Bookabach holiday homes may also offer weekly or monthly discounted prices, so you can stay longer for less money.