Guide For Orlando - Vacation Rentals in Near East Side

4BR Old Town Chicago Loft | Walk to Wells St From US $920
         

10.0 (122 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Chicago Quick Stay From US $130
         

6.3 (47 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Internet
The Sono Chicago From US $471
         

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10.0 (526 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
3 BD condo near to downtown, Gold Coast and Michigan Avenue. From US $303
         

Magic Factory Loft 2West From US $618
         

10.0 (200 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Large 4BR/3BA Safe Old Town Location Walk Everywhere From US $1,467
         

10.0 (75 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Luxury Places to Stay in Near East Side

Over 3949+ Luxury Places to Stay in or Near Near East Side
: The Wolcott : Modern Elegance at Its Finest From US $3,490
         

9.4 (14 Reviews)
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area

Top-Rated Vacation Rentals with a Pool in Near East Side

Over 1140+ Top-Rated Vacation Rentals with a Pool in or Near Near East Side
Luxury Designer Penthouse Combo West | Gold Coast From US $1,954
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Chic 1-bedroom condo in the heart of Chicago, next to Mag Mile From US $147
         

New Luxury 3 Bdr Apt in Chicago C9 From US $1,516
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pool
3BR Luxury Modern Apartment From US $454
         

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10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
Level Chicago Old Town From US $270
         

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10.0 (1 Review)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Chicago Cityview Chic - Gold Coast/River North From US $199
         

Pet-Friendly Vacation Rentals in Near East Side

Over 1744+ Pet-Friendly Vacation Rentals in or Near Near East Side
Luxury House in the heart of Old Town with Parking From US $1,950
         

10.0 (57 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
InterContinental Chicago Magnificent Mile by IHG From US $292
         

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9.2 (3122 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Spacious 4BR Central Apartment w/Skyline Views From US $985
         

10.0 (21 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Luxury SOHO Styled Two-Level Townhouse - Old Town From US $1,087
         

10.0 (19 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Dtown Penthouse 3bd VIEWS+Parking +Gym+Pool From US $875
         

10.0 (13 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
West Loop Living – Bright 1BR From US $315
         

10.0 (11 Reviews)
Apartment
  • Pet Friendly
  • TV
  • Security/Safety

Large Vacation Homes & Villas in Near East Side

Over 479+ Large Vacation Homes & Villas in or Near Near East Side
The Orleans Floor 3 Private rooftop deck From US $1,599
         

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10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Security/Safety
Modern 3 BR Apt - 5 Mins to Downtown Sleeps 10 From US $309
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Modern West Loop Gem-City Views & Prime Location 6 From US $1,014
         

10.0 (22 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Security/Safety
Luxury Loft Collection 903 - Terrace - River North From US $1,016
         

10.0 (7 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Modern West Loop Gem-City Views & Prime Location 3 From US $813
         

10.0 (7 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Modern West Loop Gem-City Views & Prime Location 4 From US $810
         

10.0 (7 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible

Wheelchair Accessible Vacation Homes in Near East Side

Over 2567+ Wheelchair Accessible Vacation Homes in or Near Near East Side
Modern River West 2BR with W&D by Zencity From US $77
         

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10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
Villa D' Citta From US $336
         

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9.4 (121 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Luxury Loft Collection COMBO 01/02 | Terrace From US $1,454
         

10.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Spacious 3BR · Bronzeville/South Loop · Sleeps 8 From US $845
         

Luxury Designer Apartment 802| Gold Coast/Old Town From US $687
         

10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Near East Side Vacation Rentals and Airbnb Places to Stay Under $200

Over 1161+ Near East Side Vacation Rentals and Airbnb Places to Stay Under $200
Modern River West 2BR with W&D by Zencity From US $76
         

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9.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Wheelchair Accessible
  • Internet
Chicago Parthenon Hostel From US $170
         

8.2 (475 Reviews)
Hostel
  • Air Conditioner
  • Security/Safety
  • Wellness Facilities
Serene Loop 1BR w/Gym, Roof & Lounge, same block as L, by Blueground From US $96
         

Instantly Bookable Vacation Homes in Near East Side

Over 2497+ Instantly Bookable Vacation Homes in or Near Near East Side
Twice as Nice: Chic 2BR Stay with Style & Space From US $266
         

9.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Gorgeous 3BR River North Condo - Free Parking From US $857
         

10.0 (37 Reviews)
Condo
  • Air Conditioner
  • TV
  • Security/Safety
Spacious 5BR Chicago Suite Near McCormick Place & Soldier Field From US $548
         

8.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Trendy West Town Flat - 2 bed/1.5 bath with parking From US $339
         

Luxury Modern home minutes from Downtown Chicago From US $555
         

10.0 (21 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Spacious loft in the heart of West Town, Noble Square Chicago From US $220
         

10.0 (19 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Security/Safety

About Near East Side Vacation Rentals

With more than 3958 Near East Side vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Guidefororlando and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Near East Side.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Guidefororlando Near East Side, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Near East Side. Places to stay near Near East Side are 773.68 ft² on average, with prices averaging US $474 a night.

Guidefororlando makes it easy and safe to find and compare vacation rentals in Near East Side with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Near East Side

Type Count
Holiday Apartments 2579
Hotels 722
Vacation Homes 420
Resorts 9
B&B 7
Hostels 6
Villas 4
Others 2
Cabin Rentals 1

Use these Quick Filters to Find a Vacation Rental in Near East Side

Pro Tip: Guidefororlando makes it easy to compare the best listings on Guidefororlando homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Guidefororlando homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Near East Side.

Weather in Near East Side

View the weather forecast for Near East Side before booking your Near East Side Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Complexes around Near East Side, IL


Near East Side Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Near East Side?
How many vacation rentals are available in Near East Side?

Currently, the total number of properties listed in 2026 is over 3958 in the Near East Side area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Near East Side.