Photo by Marc Maheu

Oakland holiday rentals

We found 179 holiday rentals — enter your dates for availability

Select from 25 homes, 14 cottages and other holiday rentals in Oakland to find one that's perfect for your trip. Whether you're travelling with a group or just with your pet, holiday rentals have the best amenities for spending time at your holiday home, which might include a garden and hot tub. At the end of the day, you're sure to find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Find spaces that suit your style

  • 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

Choose a holiday rental for your Oakland getaway

Enjoy the monuments and other features of Oakland. This city is well-known for its shopping and restaurants. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in Oakland

Are you looking for top things to see and do in the city? Venture out of your cosy holiday rental and experience everything that makes Oakland a fun spot to go on holiday. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Augusta Country Club (16.9 mi / 27.2 km)
  • Belgrade Lakes Golf (8.1 mi / 13 km)
  • Samantha Smith (15.7 mi / 25.3 km)
  • Titcomb Mountain Ski Area (23.2 mi / 37.4 km)
  • Spruce Mountain Jay (24.2 mi / 39 km)
  • Wilson Lake Country Club (26.3 mi / 42.3 km)

Exploring the natural features in Oakland

Whether you're an adventurous traveller or just want to take in the scenery, Oakland is a great place to get outside. These are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Kennebec River (4.8 mi / 7.7 km)
  • Belgrade Lakes Chain (5.9 mi / 9.6 km)
  • Kennebec River Rail Trail (16 mi / 25.7 km)
  • Capitol Park (16.4 mi / 26.4 km)
  • Cobbosseecontee Lake (22.7 mi / 36.5 km)
  • Wilson Lake (26.3 mi / 42.3 km)

How to get to and around Oakland

Fly into Waterville, ME (WVL-Robert Lafleur), the closest airport, located 2.1 mi (3.4 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Augusta, ME (AUG-Augusta State), which is 15.8 mi (25.4 km) away.

Frequently asked questions

What is the best area to stay in Oakland when booking a holiday home?
If you’re planning a getaway to Oakland, Rome is one of the most popular locations to stay. Whether you want a cottage, chalet or another property style, you’ll always have the whole place to yourself.
What is the most popular type of holiday home accommodation in Oakland?
According to our data, houses are the most desirable type of property in Oakland. But that goes without saying, everyone’s idea of an epic trip isn’t the same. Stayz has holiday homes with every size, shape and budget in mind, and we’ll help you discover the perfect match.
How much does it cost to rent a holiday home in Oakland?
Property type, season and length of stay are some things that can affect the price of a holiday home. Simply add your dates of travel to find your ideal match. From comfy cottages to expansive luxury villas, all Stayz holiday homes offer incredible value.
How much does it cost to rent a beach house in Oakland?
When you travel and the style and size of the property will determine the cost of your beachside stay. Type in your Oakland travel dates to view your options on Stayz. Can’t live without a hot tub, or maybe a private pool? Use the filters to pick the features and amenities you want.
Are there pet-friendly holiday homes in Oakland?
With 39 holiday homes that host pets, your furry little friend can join you on your Oakland holiday. Use the filter tool to browse our pet-friendly holiday homes and find your pawfect holiday home on Stayz.
Can I rent a house with a pool in Oakland?
Add another level of fun to your holiday by booking one of the two houses with a private pool in Oakland. Use our search filter to find the kind of property you want on Stayz, and then spend leisurely days splashing around in a swimming pool that’s just for you.
What are popular home amenities in Oakland?
Some of the most popular home amenities people are looking for in Oakland are a nearby waterfront, a sauna and a fireplace. Whether you’re on the road with family, your besties or even pets, Stayz holiday homes include the best amenities for beginning new traditions with the people you cherish the most.
Are there large group holiday homes in Oakland?
Choose from seven holiday homes in Oakland that can sleep 10 or more guests. Whether you’re planning a holiday with extended family or an event like an anniversary, there’s plenty of space to get your loved ones together under one roof.
Are there holiday homes in Oakland that welcome kids?
Oakland has 39 family-friendly holiday homes to pick from. And securing a stay that welcomes youngsters is super easy with Stayz’s “Properties good for families” filter. As well as having the whole place to yourselves, you’ll also get access to perks and conveniences such as multiple bedrooms, kitchens and yards.
What are the top attractions for families in Oakland?
Keep the kids busy at these popular family-friendly attractions in Oakland:

  • First Congregational Church
  • Belgrade Lakes Chain
  • Fort Halifax

Are there one-bedroom holiday homes in Oakland?
Yes, Oakland has three one-bedroom homes on offer. Usually situated in popular spots because of their compact size, a one-bedroom holiday property is ideal if you’re travelling with a pal or your partner. And with plenty of home comforts like kitchens and more privacy than a standard hotel, you’ll be able to kick back and relax while exploring this top destination.
Can I find two-bedroom holiday homes in Oakland?
Take off with your besties and experience complete comfort and privacy in one of the nine two-bedroom holiday homes Oakland has to offer.
Are there holiday homes with WiFi in Oakland?
Oakland has 12 holiday homes with WiFi, so you can stay connected while on holiday. Simply check the “WiFi” box in our handy search filter to find the perfect property. From streaming TV shows with the family to posting pics on social media, these Stayz homes make it easy to go online.
How can I find holiday homes with air conditioning in Oakland?
Select your dates and then make use of the filters to look for holiday homes with ac in Oakland on Stayz. With 14 air-conditioned properties available, you can look forward to a comfortable and cool stay.
How old do you have to be to rent a holiday home in Oakland?
The minimum age allowed can differ between properties on Stayz, so be sure to check the rules of the holiday home in Oakland you want. But typically, it’s 16, 18 or 21.
How long can I rent a holiday home in Oakland for?
The length of time you can book a holiday home in Oakland is up to the property. Simply enter your chosen travel dates to view a list of options offering extended stays. With lots of amenities such as full kitchens and air conditioning, as well as some offering discounted weekly or monthly prices, you’re sure to discover the perfect place to call your home away from home in Oakland.

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