Photo by Karen Rinaldo-green

Oakdale holiday lettings

We found 142 holiday rentals — enter your dates for availability

Discover a selection of 20 apartments and other holiday rentals in Oakdale that are perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday rentals have the amenities that you need and want for your stay, which might include a garden and Wi-Fi. Whatever you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Oakdale

Showing deals for:7 Nov - 14 Nov
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Why visit Oakdale

  • Charming neighbourhood: Oakdale offers a delightful mix of community spirit and picturesque surroundings, perfect for exploration.
  • Rich cultural experiences: Discover historic houses and local colleges that highlight the area's history and heritage.
  • Family-friendly attractions: Enjoy a variety of activities suitable for all ages, ensuring a fun experience for families.
  • Outdoor pursuits: Take advantage of the beautiful parks and recreational spaces for activities like walking and picnicking.
  • Varied accommodation options: Choose from charming vacation homes, cosy cottages, and stylish condos for a comfortable stay.

Popular types of accommodation around Oakdale

If you're contemplating a getaway in Oakdale, rest assured, we have a variety of delightful options for you. The most sought-after types of accommodation include charming houses, cosy cottages, and stylish condos. Whether you're searching for a holiday retreat in Oakdale Portland or a serene vacation home, our platform offers transparency and savings, ensuring a memorable stay in this picturesque locale.

  • Houses: The top choice for visitors in Oakdale, these homes offer ample space and a homely atmosphere, perfect for families or groups.
  • Cottages: Quaint and charming, cottages provide a delightful retreat, ideal for those seeking a peaceful getaway.
  • Condos: A convenient option, condos offer modern amenities and a community feel, suitable for couples or small families.
  • Apartments: Versatile and often centrally located, apartments are a fantastic choice for those wanting easy access to local attractions.
  • Cabins: Rustic and cosy, cabins are perfect for nature enthusiasts looking to escape into the great outdoors.**

Top attractions in and around Oakdale

Oakdale, Portland, Maine, offers a delightful mix of outdoor activities, family-friendly attractions, and cultural experiences. Visitors can explore notable sites such as historic houses, colleges, and entertainment venues, making it ideal for those seeking a vibrant city atmosphere. Whether you're interested in history or simply enjoying time with loved ones, Oakdale provides a rich tapestry of experiences to make your holiday memorable.

  • University of Southern Maine: A historic institution rich in culture, the University of Southern Maine offers picturesque grounds and vibrant academic life, perfect for a leisurely stroll and immersion in local education and arts.
  • Portland Museum of Art: Located a mile from Oakdale, this art museum showcases an impressive collection of American, European, and contemporary art, providing a deep cultural experience and inspiration for art enthusiasts.
  • Cross Insurance Arena: This lively entertainment venue hosts various events, from concerts to sports, creating a family-friendly atmosphere where visitors can enjoy thrilling performances and community spirit.

Things to do recommended for couples

For a romantic getaway in Oakdale, explore the vibrant atmosphere at Thompson's Point with live music, indulge in luxury at the Portland Club, or embark on an adventurous water sports experience with Capt Lyman Stuart. Each offers a unique charm for couples to enjoy together.

Things to do recommended for families

Families visiting Oakdale can enjoy a game at Hadlock Field, just 186m away, or have a thrilling time at Bayside Bowl, 559m away. Don't miss the Southworth Planetarium nearby for an entertaining and educational experience suitable for all ages.

Things to do recommended for groups

Groups visiting Oakdale can enjoy shopping at the Maine Mall, just 1.9km away, immerse themselves in culture and entertainment at the State Theatre, only 621m from Oakdale, and unwind with a round of golf at Sable Oaks Golf Course, also 1.9km away.

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

If you're travelling with a group, family, or pets, or if you're seeking longer stays, it's important to apply the appropriate filters to meet your needs. Here are some helpful booking tips for using Vrbo.

  • Traveling to Oakdale with a group: Think about how many bedrooms you require, as well as additional features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Oakdale with young kids: Travelling with young children can present its difficulties. 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 attractions that are friendly for families.
  • Taking your pets with you to Oakdale: For many, a family holiday isn’t truly fulfilled without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at ease.
  • Planning for a long term stay visiting Oakdale: If you’re in search of holiday rentals offering special rates for stays of a month or more, you’ve come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include preferences such as a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Oakdale

Oakdale, a charming neighbourhood in Portland, Maine, offers a delightful blend of outdoor activities, cultural experiences, and family-friendly attractions. Visitors can explore the vibrant atmosphere of nearby cities, enjoy the friendly community, and discover romantic spots perfect for couples. With a variety of vacation rentals available, Oakdale serves as an ideal base for your adventures in the picturesque Bayside area and beyond, ensuring a memorable holiday for all.

  • Portland: Located a mere mile from Oakdale, Portland is a vibrant city known for its stunning outdoor experiences and scenic beauty. Visitors flock to Portland for family-friendly activities and the chance to explore its rich cultural scene. The city is home to a variety of venues including theatres and an arena entertainment facility, as well as a bustling shopping mall. Nature enthusiasts will appreciate the nearby beaches and serene lake areas, perfect for leisurely strolls or picnics with loved ones.
  • South Portland: Situated two miles from Oakdale, South Portland offers a delightful mix of family-friendly attractions and a city-themed atmosphere. This city is ideal for those who enjoy shopping, with a range of shopping centres and malls at your disposal. It's also a notable educational hub, making it suitable for families and business travellers alike. The local beaches and lakes provide ample opportunities for relaxation and recreation, ensuring a fulfilling experience for all visitors.
  • Downtown Portland: Just 1.6km away from Oakdale, Downtown Portland is a lively neighbourhood that promises a variety of experiences, from family outings to romantic getaways. The area is bustling with activities, including theatres and music concerts that cater to diverse tastes. Visitors can enjoy the picturesque beaches and family-friendly lakes within the vicinity, making it an ideal spot for both relaxation and entertainment amidst a charming urban backdrop.

Best time to go to Oakdale

If you're planning a trip to Oakdale, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like January to March tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January26.1°F (-3.3°C)Light RainMostly SunnyLowSlightly Low
February27.0°F (-2.8°C)Light RainMostly SunnyLowSlightly Low
March33.4°F (0.8°C)Light RainMostly SunnyLowSlightly Low
April43.9°F (6.6°C)Light RainMostly SunnyAverageAverage
May54.0°F (12.2°C)Light RainMostly SunnyAverageAverage
June61.9°F (16.6°C)Light RainMostly SunnyHighSlightly High
July68.9°F (20.5°C)Light RainMostly SunnyHighSlightly High
August68.5°F (20.3°C)Light RainMostly SunnyHighSlightly High
September62.2°F (16.8°C)Light RainMostly SunnyAverageAverage
October52.2°F (11.2°C)Light RainMostly SunnyAverageAverage
November41.2°F (5.1°C)Light RainMostly SunnyAverageAverage
December32.9°F (0.5°C)Light RainMostly SunnyAverageAverage

Booking with Vrbo is a breeze

Are you hoping to save on your upcoming holiday? Consider being flexible with your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To discover the perfect Vrbo property that fits your budget, utilise our filters to sort by price, location, and type of accommodation.

Vrbo Trips: Planning made easy

Vrbo's Trip Board offers a handy platform for you to organise new trips, resume your planning, or review your existing itineraries. You'll find your saved or booked properties neatly arranged under Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply head over to: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of holiday rental accommodation in Oakdale?
According to our data, apartments are considered the most popular type of holiday rental in Oakdale. But having said that, everyone's idea of an epic stay will differ. Vrbo has holiday homes in a variety of shapes and sizes, and we'll help you to find your perfect match.
How much does it cost to rent a holiday rental in Oakdale?
The average price for a holiday rental in Oakdale can vary depending on factors such as property type, length of stay and season. Whether you're thinking about a sprawling villa with a pool or a comfy cabin just enough for two, just add your travel dates to discover stays that offer great value.
How much does it cost to rent a beach house in Oakdale?
Prices for beach houses in Oakdale can differ depending on the size and style of the property and when you plan to travel. All you need to do is enter your travel dates into Vrbo and the number of guests to view your holiday rental options and prices. From there you can use our filters to narrow down your search by amenities, ratings, nearby activities and more.
Are there pet-friendly holiday rentals in Oakdale?
Pack a bone and a squeezy toy for the pooch in your life because Oakdale has eight holiday rentals that put out the welcome mat to pets. Let your four-legged pal have fun with the family at one of our pet-friendly holiday rentals on Vrbo. Simply enter your travel dates then check the "Pets allowed" filter box.
What are popular rental amenities in Oakdale?
Some of the most popular rental amenities guests are looking for in Oakdale are an electric car charging station, a firepit and a barbecue grill. Whether you're on the road with your besties, family or even pets, Vrbo holiday properties come with the best amenities for ultimate relaxation with the people you cherish the most.
Are there large group holiday rentals in Oakdale?
You'll discover four holiday homes in Oakdale that can host 10 or more guests. Whether you're planning a family holiday or a celebration like an anniversary, there's enough space to get your loved ones together under the same roof.
Are there holiday rentals in Oakdale that welcome kids?
Oakdale has eight family-friendly holiday rentals. And discovering a stay that welcomes little ones is simple with Vrbo's "Properties good for families" filter. On top of having the whole place to yourselves, you'll have access to amenities and perks like dining rooms, kitchens and pools.
What are the top attractions for families in Oakdale?
There are lots of wonderful things to see and do with the family in Oakdale, including:

  • East End Beach
  • Sand Beach
  • Portland Observatory

Are there holiday rentals with WiFi in Oakdale?
You'll have a choice of six holiday rentals with WiFi in Oakdale. If you want to disconnect from daily life on your escape, but still need to be connected to the web, these properties are for you. Narrow your search by applying the WiFi filter on Vrbo.
How can I find holiday rentals with air conditioning in Oakdale?
Work out your travel dates and then use our filters to locate holiday rentals with ac in Oakdale on Vrbo. With eight air-conditioned properties to choose from here, you can enjoy a cool and comfortable stay.
How old do you have to be to rent a holiday rental in Oakdale?
The minimum age is generally 16, 18 or 21. It can vary from property to property on Vrbo, so check the rules of your preferred Oakdale holiday home before you book.
How long can I rent a holiday rental in Oakdale for?
The amount of time you can book an Oakdale holiday home for differs depending on the property. Just tap in your travel dates to see available options offering longer term stays. They have all you need to make your extended getaway more comfortable and enjoyable, like air conditioning and kitchens. Some properties might also offer weekly or monthly discounts, so you can hang around longer for less.

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