Downtown Portland holiday homes

We found 231 holiday rentals — enter your dates for availability
Discover a selection of 16 apartments, 13 flats and other holiday rentals in Downtown Portland that are perfect for your trip. Whether you’re staying in a holiday home with family, friends or just your furry companion, you'll find the best amenities for hanging out with the people that matter most, which might include air conditioning and a pool. At the end of the day, you'll be able to choose a property to rent for everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Downtown Portland

Showing deals for:18 Dec - 25 Dec

Interior
Outdoor dining
Private kitchen
Exterior detail
Exceptional
(43 reviews)

Modern & Sunny House Steps from the Promenade.

Portland

8% off
NZ$4,921
for 7 nights, 1 home
NZ$703 per night
includes taxes & fees
Modern & Sunny House Steps from the Promenade.
Lobby can be accessed from Patton Ct or Exchange St. Door code will be provided.
Large open concept living space with tall sloped celling and a loft.
Oven, Keurig, microwave, fridge, toaster, and dishwasher.
View from inside unit.
Exceptional
(7 reviews)

Exchange Street Skylight Loft

Portland

8% off
NZ$4,889
for 7 nights, 1 apartment
NZ$698 per night
includes taxes & fees
Exchange Street Skylight Loft
Private kitchen
Living area
Interior
Off-street parking behind building dedicated to this unit only.
Exceptional
(41 reviews)

Eastbayside/Munjoy - Charming Downtown Escape

Portland

7% off
NZ$3,343
for 7 nights, 1 apartment
NZ$478 per night
includes taxes & fees
Eastbayside/Munjoy - Charming Downtown Escape
Dining
Interior
Living area
Exterior detail
Exceptional
(99 reviews)

2 Bedroom Apartment Unit In Portland's Historic West End Neighborhood

Portland

8% off
NZ$3,533
for 7 nights, 1 apartment
NZ$505 per night
includes taxes & fees
2 Bedroom Apartment Unit In Portland's Historic West End Neighborhood
Private kitchen
Smalls! A short walk from the house.
Room
Dining
Exceptional
(23 reviews)

West End Bright Spot with Parking.

Portland

8% off
NZ$2,509
for 7 nights, 1 apartment
NZ$358 per night
includes taxes & fees
West End Bright Spot with Parking.
Scales! The best spot in town for a delish dinner.
Tour the Victorian Mansion at the bottom of the street.
Interior
Pocket doors pull out from the walls separating the livingroom and bedroom.
Exceptional
(63 reviews)

Historic Home in the West End. Private Parking.

Portland

8% off
NZ$3,141
for 7 nights, 1 apartment
NZ$449 per night
includes taxes & fees
Historic Home in the West End. Private Parking.
Living area
Private kitchen
Dining
Room
Exceptional
(14 reviews)

Harborview - Curated East End Escape w/ Parking

Portland

8% off
NZ$9,067
for 7 nights, 1 apartment
NZ$1,295 per night
includes taxes & fees
Harborview - Curated East End Escape w/ Parking
Dining
Interior
Interior
Room
Exceptional
(22 reviews)

West End's Diamond in the Rough 2-bedroom Apartment with Parking & WiFi

Portland

8% off
NZ$5,554
for 7 nights, 1 apartment
NZ$793 per night
includes taxes & fees
West End's Diamond in the Rough 2-bedroom Apartment with Parking & WiFi
Walnut topped kitchenette counter with coffee maker.
Interior
Interior
Room
Exceptional
(43 reviews)

Fresh East End Apartment Walkable to Downtown Portland

Portland

8% off
NZ$5,283
for 7 nights, 1 apartment
NZ$755 per night
includes taxes & fees
Fresh East End Apartment Walkable to Downtown Portland
Discover Victoria Mansion at the bottom of the street.
Scales in the Old Port for the best seafood
The State Theater is a 5 minute walk away.
Interior
Exceptional
(53 reviews)

Charming West End Hideaway. Private Parking

Portland

8% off
NZ$3,373
for 7 nights, 1 apartment
NZ$482 per night
includes taxes & fees
Charming West End Hideaway. Private Parking

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Why visit Downtown Portland

  • Stunning waterfront views: Downtown Portland boasts picturesque coastal scenery, perfect for leisurely strolls along the water.
  • Historic charm: Explore the neighbourhood's rich history through its beautifully preserved houses and iconic lighthouses.
  • Vibrant local culture: Enjoy the lively atmosphere filled with local art, music, and friendly faces that characterise the area.
  • Delicious dining: Savor a variety of culinary delights at charming eateries offering fresh, local seafood and other regional cuisines.
  • Outdoor adventures: Take advantage of scenic parks and recreational activities ideal for families and nature lovers.

Top attractions near Downtown Portland

Downtown Portland is a vibrant neighbourhood offering a mix of cultural and outdoor experiences perfect for families and beach lovers. Enjoy exploring historic houses and lighthouses, along with scenic coastal views and outdoor adventures that truly capture the local charm. It’s an ideal destination for travellers seeking a blend of history, culture, and nature in a relaxed urban setting.

  • East End Beach: A lovely sandy spot perfect for relaxing and soaking up the sun, East End Beach offers stunning views of Casco Bay, making it an ideal place for a leisurely stroll or a picnic.
  • Victoria Mansion: This exquisite historic house showcases opulent architecture and stunning interiors, reflecting the grandeur of the 19th century. A visit here immerses you in the rich cultural heritage of Portland.
  • Willard Beach: Known for its tranquil atmosphere, Willard Beach is a fantastic place for beachcombing and enjoying picturesque sunsets, perfect for a peaceful getaway.

Things to do recommended for couples

Downtown Portland is perfect for a romantic getaway. Enjoy a leisurely stroll along the picturesque waterfront, explore charming local shops, or share a cozy meal at a waterfront restaurant. Don’t miss a sunset cruise for breathtaking views of the harbour and city skyline.

Things to do recommended for families

Families visiting Downtown Portland can explore the fascinating Children's Museum & Theatre of Maine, enjoy the scenic waterfront at the Eastern Promenade, and experience hands-on exhibits at the Maine Discovery Museum, all within a short walk from each other, making for a delightful family adventure.

Things to do recommended for groups

Groups visiting Downtown Portland, Maine can enjoy the thrill of Beech Ridge Motor Speedway, just 11km away, where adrenaline-pumping motor racing takes centre stage. It's a fantastic spot for those seeking adventure and a vibrant atmosphere.

*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 around Downtown Portland

Whether you're travelling with a group, as a family, with your pets, or seeking extended stays, be sure to filter by your key priorities. Here are some Vrbo booking tips for you.

  • Traveling to Downtown 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 gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Downtown Portland with young kids: Traveling with little ones can be a challenge. You must prioritise their comfort and safety, ensuring they have age-appropriate facilities, like a private swimming pool where available. It’s also wise to consider how close you are to attractions that are family-friendly.
  • Taking your pets with you to Downtown Portland: For many families, a holiday isn’t truly complete without their furry companion. If that resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that your four-legged friend feels just as comfortable as you do.
  • Planning for a long term stay visiting Downtown Portland: If you're after holiday rentals that offer deals for month-long or longer stays, you've come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Also, think about including options like a parking bay, a well-equipped kitchen, or your own private pool in your search.

Where to stay near Downtown Portland

Downtown Portland, Maine, is a vibrant neighbourhood perfect for exploring with family and friends. With its walkable streets, you'll uncover stunning waterfront views, charming boutiques, and delightful eateries. The urban atmosphere is enriched by local art, culture, and friendly faces. Enjoy scenic parks and waterfront strolls, making it an ideal destination for outdoor adventures. Experience the best of urban life while soaking in the unique charm that makes Downtown Portland a must-visit location.

  • Portland: Portland, Maine, is a vibrant coastal city offering a delightful blend of outdoor activities and urban charm. Located right in the heart of the city, Downtown Portland is renowned for its stunning waterfront views, beautiful beaches, and family-friendly attractions. Visitors can enjoy thrilling arena entertainment, captivating theatre performances, and live music concerts throughout the year. The picturesque local landmarks, including scenic beaches and tranquil lakes, provide ample opportunities for relaxation and recreation, making it a perfect destination for outdoor enthusiasts and families alike.
  • Ferry Village: Just 1km from Downtown Portland, Ferry Village is a charming neighbourhood known for its inviting beaches and stunning coastal scenery. It is an ideal spot for those seeking outdoor adventures and picturesque views. The area features various venues for education and golf, as well as an arena entertainment facility for sports and events. Visitors can explore local attractions, including a historic lighthouse and beautiful family beaches, making it a great choice for a leisurely day out by the water.
  • Oakdale: Oakdale, located 2km from Downtown Portland, is a lovely neighbourhood that offers a romantic atmosphere and scenic outdoor experiences. It is perfect for couples and nature lovers who enjoy music concerts and educational activities. The area provides access to beautiful trails, along with nearby beaches and lakes that invite visitors to immerse themselves in nature. Whether you're strolling hand in hand or exploring the local scenery, Oakdale is a delightful escape from the hustle and bustle of city life.

Best time to go to Downtown Portland

If you're planning a trip to Downtown 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

Are you keen to save on your next adventure? Being flexible with your travel dates can really help, as prices can vary quite a bit. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, feel free to use our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a handy platform for you to plan new adventures, easily resume your previous arrangements, or manage your travel itinerary. You can find your saved or booked properties neatly sorted into categories such as Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

When is the best time to visit Downtown Portland for a holiday rental?
July marks the peak season for visiting Downtown Portland, where visitors can enjoy the vibrant setting and a lot of outdoor experiences. From July to September, the city comes alive with an array of festivals, events, and an abundance of opportunities for sightseeing along the picturesque waterfront.During this time, the weather is typically warm and pleasant, with temperatures averaging between 20 and 30 degrees Celsius. This creates ideal conditions for exploring the city's renowned food scene, visiting local markets, or simply soaking in the sun at one of the many parks.For those looking for a more budget-friendly option, consider planning your trip in May. This month offers a quieter experience with fewer crowds, allowing you to fully appreciate the beauty of spring blooms and enjoy leisurely walks through the charming streets. Plus, you can still partake in delightful local events and enjoy the city's culinary delights without the peak season bustle.Ultimately, your ideal time to visit Downtown Portland will hinge on whether you wish to immerse yourself in the lively option of summer or prefer a more relaxed experience during the spring.
What are the top attractions in Downtown Portland, Maine, United States of America?
In Downtown Portland, Maine, visitors can enjoy a vibrant mix of attractions and experiences. The Old Port district is renowned for its cobblestone streets, historic buildings, and a variety of boutique shops and restaurants. Here, you can explore the bustling waterfront and indulge in fresh seafood at local eateries. The Portland Head Light, located a short drive away in Cape Elizabeth, is a must-see lighthouse offering stunning coastal views.The Arts District, home to the Portland Museum of Art, showcases an impressive collection of American and European art, making it a great stop for culture enthusiasts. Nearby, the historic State Theatre hosts various live performances and events.For those interested in local history, the Wadsworth-Longfellow House offers a glimpse into the life of the famous poet Henry Wadsworth Longfellow. Additionally, the Eastern Promenade provides picturesque walking trails along the waterfront, ideal for enjoying the scenic beauty of Casco Bay.
Are all fees included in the Downtown Portland holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Downtown Portland holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Downtown Portland with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Downtown Portland holiday homes?
You can find great discounts on holiday homes in Downtown Portland on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Downtown Portland holiday home booking on Bookabach?
To find Downtown Portland holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Downtown Portland?
A long-stay holiday home in Downtown Portland is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Downtown Portland holiday home?
Book your Downtown Portland holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Downtown Portland?
Prices for holiday homes in Downtown Portland vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Downtown Portland to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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