Photo by Marc Maheu

Oakland vacation rentals

We found 181 vacation rentals — enter your dates for availability

Select from 25 homes, 14 cottages, and other vacation rentals in Oakland to find one that's perfect for your trip. Whether you're traveling with family, friends, or just your furry companion, vacation rentals have the best amenities for spending time at your vacation home, which might include hot tub and a washer and dryer. No matter what you're looking for, you'll be sure to find a rental to meet everyone's needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Oakland

Showing deals for:Aug 1 - Aug 8
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Choose a vacation 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 vacation rentals feature full kitchens and laundry facilities.

Activities and attractions in Oakland

Are you hoping to discover top things to see and do in the area? Venture out of your cozy vacation rental and check out everything that makes Oakland a fun spot to vacation. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • 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)
  • Tree Spirits (1.4 mi / 2.3 km)
  • Natanis Golf Course (8.8 mi / 14.2 km)

Exploring the natural features in Oakland

Whether you're looking for adventure or just want to appreciate the scenery, Oakland is a great place to get out in nature. These are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city center:

  • 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 center. If you can't find a flight that works for your travel itinerary, you might consider flying 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 vacation rental?
Rome is one of the more desirable neighborhoods where you’ll find a vacation home in Oakland. Browse our range of comfy stays and then get out and experience this destination like a local.
What is the most popular type of vacation rental accommodation in Oakland?
Cottages are the most popular type of vacation rental in Oakland, according to our data. Even if you’ve got something bigger or smaller in mind, Vrbo has vacation homes in many shapes and sizes. Browse our options to find your perfect Oakland pad.
How much does it cost to rent a vacation rental in Oakland?
A range of things can affect the price of a vacation rental in Oakland, like the time of year, property type and length of stay. But, all Vrbo homes have one thing in common — incredible value. Simply add your travel dates to find your perfect match.
How much does it cost to rent a beach house in Oakland?
The average price for a vacation home close to the beach in Oakland will depend on when you’ll be there and the size and style of property you’re searching for. You can easily find prices on Vrbo by entering your preferred travel dates and destination. Then use the filters to pick the number of bedrooms and amenities important to you, such as WiFi, a pool and air conditioning.
Are there pet-friendly vacation rentals in Oakland?
With 40 properties that welcome pets, your little buddy can join in on your Oakland vacation. Use the filter tool to search our pet-friendly vacation rentals and find a pad that’ll set tails wagging on Vrbo.
Can I rent a house with a pool in Oakland?
Add an extra layer of fun to your getaway by booking your family into one of the three houses with a private pool in Oakland. Use our search filter to find properties with pools on Vrbo, then spend your days playing and splashing in a swimming pool that’s exclusively for you.
What are popular rental amenities in Oakland?
Some of the most popular rental amenities guests are looking for in Oakland include a garden, a water view and ski-in/ski-out facilities. Whether you’re traveling with family, buddies or even pets, Vrbo vacation properties provide the best amenities for ultimate relaxation with your loved ones.
Are there large group vacation rentals in Oakland?
With six vacation rentals that can host 10 or more people in Oakland, there’s no need to keep anyone off the invite list. From vacations with the extended family to special events like birthday and Christmas parties, Vrbo can help you find a large group rental to match the occasion.
Are there vacation rentals in Oakland that welcome kids?
Gather your whole family for a memorable adventure in Oakland at one of our 40 family-friendly vacation properties. A lot of these stays come with conveniences that are just perfect for getaways with children, like kitchens, extra bedrooms and pools. Just click on the “Properties good for families” filter box and select your favorite.
Are there one-bedroom vacation rentals in Oakland?
Yes, there are three one-bedroom properties in Oakland to select from. A one-bedroom vacation home is a great option if it’s just the two of you or if you’re vacationing solo. Toss in more convenience, space and privacy compared to a regular hotel, and you’re bound to have a memorable getaway.
Can I find two-bedroom vacation rentals in Oakland?
Gather your loved ones and relax in total privacy and comfort in one of the nine two-bedroom vacation properties Oakland has to offer.
Are there vacation rentals with WiFi in Oakland?
Oakland has 14 vacation rentals with WiFi, so you’ll be able to stay connected while on vacation. Simply check the “WiFi” box in our handy search filter for a list of properties with this feature. From streaming movies with the family to updating your social media, these Vrbo homes will keep you online.
How can I find vacation rentals with air conditioning in Oakland?
You’ll have a choice of 15 Vrbo vacation rentals with air conditioning in Oakland offering that cooling breeze and extra touch of comfort. Enter your preferred dates of travel and then use our handy filters to find properties with air conditioning.
How old do you have to be to rent a vacation rental in Oakland?
You’ll need to check with the Oakland vacation home you want on Vrbo as age restrictions differ. However, it’s typically 16, 18 or 21.
How long can I rent a vacation rental in Oakland for?
The amount of time you can rent an Oakland vacation rental for varies depending on the property. Just put in your travel dates to view options offering longer term stays. They come with the things you need to make your extended getaway more convenient and enjoyable, such as air conditioning and kitchens. Some properties might also offer weekly or monthly discounts, so you can stick around for longer for less.
Does Vrbo offer discounts for vacation homes in Oakland?
In Oakland, you’ll find some fantastic discounts and deals for weekly and monthly discounts on vacation rentals, as well as newly listed homes on Vrbo. Whether you’re planning a mini vacay or a few weeks away, we have plenty of options to suit your needs and budget.

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