Discover a selection of 500 vacation rentals in Near East Side, Chicago that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $86 per night, and condos and houses are popular options for a stay in Near East Side. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Near East Side
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What are the top vacation rentals in or near Near East Side?

Whether you're searching for an intimate escape for you and your love or a sprawling house to fit friends and family, you'll find some top vacation rentals in and around Near East Side. Here are a couple to get you started:

  • Make the most of amenities including a microwave oven and lowered locks at "Luxury Loyola 3 Bedroom, 2 Bath". Located around 8 miles from Near East Side, this leading option has 3 bedrooms and good guest reviews.
  • Another enticing choice is "Wrigleyville | Chicago Guest House | Not Just A Vacation Rental", which is around 4 miles from Near East Side. With 3 bedrooms, golf and free toiletries, it has everything you need to keep you happy and comfortable.

For even more great options, use the search bar at the top of the page to find the perfect Near East Side vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in or near Near East Side?

Nothing beats squeezing in a quick break to dust away the cobwebs. Pack your carry-on bag and catch your breath at one of these top weekend getaways in and near Near East Side:

  • Located 1 mile to the northwest of central Near East Side, "53th Floor Magmile Penthouse - Views" is a good match for adventure lovers and nature fans. Get out and see nearby attractions, such as Ohio Street Beach and Lincoln Park. Then, try some activities like cycling or sailing.
  • "52nd Floor Magmile Penthouse - Views" is another great setting for a fun few days away. Around 1 mile northwest of Near East Side, use it as a base to do a little golf or fishing. Northerly Island Park and Kohl Children's Museum should also be on your to-do list if you stay here.

Can I find studio apartments for rent in and around Near East Side?

Studio apartments are hard to match when it comes to convenience and location. Get comfy in one of these studio apartments for rent in or near Near East Side and enjoy a taste of the local vibe and culture:

  • Toss your bags down and put your feet up at "52nd Floor Magmile Penthouse - Views". Amenities including a washing machine and concierge services will help you feel right at home here.
  • Another tempting choice is "51st Floor Magmile Penthouse - Views". Make use of a kitchen, an iron and ironing board and other conveniences during your stay.

There are loads of attractions around Near East Side to add to your itinerary. Nourish your inner culture vulture and visit Chicago Cultural Center and Theatre on the Lake.

Can I find short term rentals in or near Near East Side?

Every once in a while, you just need to get away from it all, even if it's only for a couple of days. Enjoy the perfect combination of relaxation and sightseeing at one of these short-term rentals in or around Near East Side:

  • Located close to the center of Near East Side, "51st Floor Magmile Penthouse - Views" is great for a whirlwind break. While you're in the area, be sure to visit top sights like Wrigley Field and McCormick Place.
  • "52th Floor Penthouse - Fireplace" is another appealing option. Consider adding Millennium Park and Willis Tower to your to-do list when you're ready to sightsee.

What are the best romantic weekend getaways in or near Near East Side?

Nothing says "I love you" like a romantic weekend escape. If you'd like to spend a couple of nights away with your sweetheart, we've got some romantic getaways in and around Near East Side that will whisk you off your feet:

  • Located around 8 miles from Near East Side, "Luxury Loyola 3 Bedroom, 2 Bath" is the perfect place for doting couples. Beauty services and a nearby marina are some of the many amenities you'll find here.
  • "Wrigleyville | Chicago Guest House | Not Just A Vacation Rental" is another wonderful option guaranteed to woo you. It's about 4 miles from Near East Side and comes with air conditioning and housekeeping services.

Are there mansions for rent in or near Near East Side?

Nothing says "best vacation ever" like staying in a mansion. Treat your loved ones to an unforgettable getaway at one of these mansions for rent in or near Near East Side:

  • Approximately 6 miles to the north of Near East Side is "Beautiful 9bedroom Mansion With 4 Parking Spots. Walk To Wrigley Field And Lake Michigan". As well as its grand design, you'll be impressed by its high-end amenities, such as a chef and a firepit.
  • Another great option is "Stone Mansion - 20 Free Parking Near Lake". Around 4 miles to the north of Near East Side, this sumptuous vacation rental gives you a taste of high-class living and offers a fireplace, golf and more.

What are the best houses for rent with a pool in or near Near East Side?

A pool is often a highlight of any good vacation. Enjoy hours of entertainment splashing about or simply kicking back by the water at one of these refreshing retreats in or near Near East Side:

  • Pack your swimsuit and goggles and enjoy a fun stay at "Wrigleyville | Chicago Guest House | Not Just A Vacation Rental". Other amenities here include a toaster and childrens activities.
  • Another popular option is "Stunning House In The Heart Of Old Town". There's loads to love about this retreat apart from its pool, such as free toiletries and a stair gate.

What are the best large family vacation rentals in or near Near East Side?

Whether your ideal escape is out in the country or down by the beach, you'll have a lot more fun if you share it with loved ones. Check out these large family vacation rentals in or near Near East Side and bring the entire crew along:

  • Invite your nearest and dearest to "Wrigleyville | Chicago Guest House | Not Just A Vacation Rental", which has 3 bedrooms sleeping up to 8 guests. This retreat is located 4 miles to the northwest of Near East Side and comes with amenities such as a dishwasher and a toaster.
  • "Views, Pool, Fireplace, Fitness Center" is also a top pick for families. It's around 1 mile to the northwest of Near East Side, has 3 bedrooms and accommodates up to 8 people. Handy amenities here include a swimming pool and a toaster.

If you want to sightsee, there are plenty of family-friendly attractions close by to put on your to-do list. Skydeck Ledge, Navy Pier and John G. Shedd Aquarium are great places to start.

What are the best large houses to rent with indoor pools in or near Near East Side?

Nothing says fancy-schmancy like having an indoor pool. Pack your swimwear and take a dip in the comfort and privacy of one of these spacious vacation homes in or near Near East Side:

  • Book a few days or more at "Cozy 4 Bedroom/2 Bath Cozy Home In East Glenview With Inground Pool" and spend lazy days poolside. This sprawling retreat has 4 bedrooms sleeping up to 7 guests along with many other quality amenities. A fireplace and a swimming pool are among them.
  • Besides its fancy indoor pool, "3b/2. 5ba Luxury Penthouse With Views" features a lake view and a sauna. It has 3 bedrooms that can accommodate up to 8 people, so you can bring the whole gang along.

If you're after more options, use the search bar at the top of the page and adjust the filters to find the Near East Side vacation rental that's perfect for your needs.

Are there one-bedroom vacation rentals in or near Near East Side?

There sure are. There are plenty of one-bedroom vacation rentals in or near Near East Side. If space is not a priority, one of these popular properties might be just the thing:

  • Great things come in little packages, and "52nd Floor Magmile Penthouse - Views" is a fabulous example of this. This one-bedroom property can be found in a handy central location and includes amenities like a swimming pool and a fireplace.
  • "51st Floor Magmile Penthouse - Views" is another lovely one-bedroom escape also close to the center. When you're not out exploring the area, enjoy a swimming pool and a fireplace.