Destination guide

Explore the beachside setting in Oakland

The beaches and lake provide a pleasant backdrop to your holiday home in Oakland. Revered for its restaurants, skyscrapers and shopping, this city is both cosmopolitan and scenic. McCormick Place and Willis Tower are just a couple of the must-see attractions in the area. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.


Sightseeing in and around Oakland

Are you searching for top things to see and do while you're in town? Venture out of your holiday home and experience everything that makes Oakland a fun spot to go on holiday. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Skydeck Ledge (4.1 mi / 6.7 km)
  • Adler Planetarium and Astronomy Museum (2.9 mi / 4.7 km)
  • John G. Shedd Aquarium (3 mi / 4.8 km)
  • Navy Pier (4.7 mi / 7.6 km)
  • Lincoln Park Zoo (6.8 mi / 11 km)
  • Brookfield Zoo (11.9 mi / 19.2 km)
Natural highlights

Exploring the natural landscape of Oakland

Whether you're an outdoor enthusiast or just want to take in the scenery, you'll be sure to find the perfect setting for your holiday in Oakland. Here are some of the area’s most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Millennium Park (4.2 mi / 6.7 km)
  • Grant Park (3.5 mi / 5.7 km)
  • Lincoln Park (8.9 mi / 14.4 km)
  • Burnham Park (0.4 mi / 0.6 km)
  • Lake Meadows Park (1 mi / 1.6 km)
  • Lakefront Trail (1.2 mi / 2 km)
How to get there

Transport options to and around Oakland

Fly into Chicago, IL (MDW-Midway Intl.), the closest airport, located 7.5 mi (12.1 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to Chicago, IL (ORD-O'Hare Intl.), which is 18.8 mi (30.2 km) away.

How many holiday accommodation are available around Oakland?

Our 2019 accommodation listings offer a large selection of 29 holiday rentals around Oakland. From 13 Houses to 13 Condos/Apartments, find unique holiday homes for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay around Oakland is on Stayz.

What is the best area to stay when travelling to Oakland?

Whether you are travelling solo or with family and friends, here are the areas with the largest selection of holiday rentals for a long holiday or just a weekend break in Oakland:

  • Gold Coast: 220 holiday homes
  • Lincoln Park: 670 holiday homes
  • Sheffield Neighbors: 117 holiday homes
  • Rush & Division: 226 holiday homes
  • North Center: 190 holiday homes

For other neighbourhoods, please use our search bar to access the selection of holiday homes available.

What are the most popular points of interest and landmarks to stay near when travelling to Oakland?

Stayz offers a large selection of holiday homes near great places in Oakland. From Stayz travellers, the most popular points of interest to stay near are:

  • Swedish Covenant Hospital: 1,693 holiday rentals
  • Harvey 147th Street-Sibley Boulevard Station: 844 holiday rentals
  • Chicago 79th Street Station (Cheltenham): 1,666 holiday rentals
  • Orland Park 143rd Street Station: 311 holiday rentals
  • Chicago McCormick Place Station: 1,691 holiday rentals

But there are many other points of interest around Oakland listed on Stayz where you can find your place to stay. Please use our search bar to access the selection of holiday rentals available near the point of interest of your choice.

Can I rent Houses in Oakland?

Yes, of course. Stayz offers 13 Houses in Oakland. Our other popular types of Oakland holiday rentals include:

  • Condos/Apartments: 13 holiday houses
  • Townhouses: 2 holiday houses
  • Studios: 10 holiday houses

Can I find a holiday accommodation with internet/wifi in Oakland?

Yes, you can select your preferred holiday accommodation with internet/wifi among our 28 holiday homes with internet/wifi available in Oakland. Please use our search bar to access the selection of holiday rentals available.

    Explore destinations around Oakland

    1,208 holiday rentals
    327 holiday rentals
    Oak Park
    1,490 holiday rentals
    Forest Park
    1,370 holiday rentals
    279 holiday rentals
    189 holiday rentals
    Elmwood Park
    1,262 holiday rentals
    73 holiday rentals
    985 holiday rentals
    Oak Lawn
    176 holiday rentals
    Orland Park
    28 holiday rentals
    239 holiday rentals
    30 holiday rentals
    15 holiday rentals
    Des Plaines
    221 holiday rentals
    23 holiday rentals
    Franklin Park
    458 holiday rentals
    122 holiday rentals
    Blue Island
    96 holiday rentals
    92 holiday rentals