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Hotel In Greenville - Vacation Rentals in Uptown

The Guesthouse Hotel From US $252
         

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9.5 (180 Reviews)
Hotel
The Guesthouse Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

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Luxury Places to Stay in Uptown

Over 94+ Luxury Places to Stay in or Near Uptown
Massive Queen Anne Mansion for your whole family to stay! From US $1,480
         

10.0 (4 Reviews)
House
Massive Queen Anne Mansion for your whole family to stay!
  • Air Conditioner
  • Parking
  • Pet Friendly

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-Lovely 5BD/3BR/3Parking on premises/Sleeps 14 guests/Andersonville From US $1,120
         

10.0 (6 Reviews)
Apartment
-Lovely 5BD/3BR/3Parking on premises/Sleeps 14 guests/Andersonville
  • Air Conditioner
  • Parking
  • Pet Friendly

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Ultra-modern 4BR/2.5BA Uptown/Edgewater duplex, featuring a rooftop deck with fire pit and easy access to the lake, dining, shopping, and Chicago’s cultural highlights. From US $959
         

10.0 (2 Reviews)
Apartment
Ultra-modern 4BR/2.5BA Uptown/Edgewater duplex, featuring a rooftop deck with fire pit and easy access to the lake, dining, shopping, and Chicago’s cultural highlights.
  • Air Conditioner
  • Parking
  • Pet Friendly

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The Velvet Manor Luxe 3BR Jacuzzi Garage From US $781
         

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10.0 (1 Review)
Apartment
The Velvet Manor Luxe 3BR Jacuzzi Garage
  • Air Conditioner
  • Parking
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Majestic Modern Style Beach Front Rooftop WFH Gym From US $747
         

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New
Apartment
Majestic Modern Style Beach Front Rooftop WFH Gym
  • Air Conditioner
  • Pet Friendly
  • View

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Spacious 4-bedroom apartment with WiFi, AC in brilliant Chicago From US $740
         

10.0 (12 Reviews)
Apartment
Spacious 4-bedroom apartment with WiFi, AC in brilliant Chicago
  • Air Conditioner
  • Parking
  • Pet Friendly

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Stay at The Velvet Manor, a beautifully designed 3BR home just steps from Andersonville's vibrant Clark Street. Enjoy spacious living, a chef's kitchen, dedicated office, Jacuzzi tub, outdoor area, and garage parking. From US $683
         

New
Apartment
Stay at The Velvet Manor, a beautifully designed 3BR home just steps from Andersonville's vibrant Clark Street. Enjoy spacious living, a chef's kitchen, dedicated office, Jacuzzi tub, outdoor area, and garage parking.
  • Air Conditioner
  • Parking
  • Pet Friendly

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Chic Vintage Stay w/Private Balcony – Walk to Argyle Redline, Lake, Dining From US $627
         

10.0 (2 Reviews)
House
Chic Vintage Stay w/Private Balcony – Walk to Argyle Redline, Lake, Dining
  • Air Conditioner
  • TV
  • View

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Top-Rated Vacation Rentals with a Pool in Uptown

Over 16+ Top-Rated Vacation Rentals with a Pool in or Near Uptown
Newly Renovated 1 BR in Art Deco Architectural Gem, Steps to L & Free Parking From US $175
         

10.0 (14 Reviews)
Apartment
Newly Renovated 1 BR in Art Deco Architectural Gem, Steps to L & Free Parking
  • Air Conditioner
  • Parking
  • Pool

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Uptown Gem From US $117
         

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10.0 (12 Reviews)
Apartment
Uptown Gem
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  • Parking
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Uptown 1BR w Gym Rooftop Pool 2 blocks to L CHI-383 From US $242
         

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New
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Uptown 1BR w Gym Rooftop Pool 2 blocks to L CHI-383
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  • Pet Friendly
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Dreamy Uptown 1BR w/Gym, Rooftop Pool, 2 blocks to L, by Blueground From US $133
         

New
Apartment
Dreamy Uptown 1BR w/Gym, Rooftop Pool, 2 blocks to L, by Blueground
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  • Pet Friendly
  • Pool

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Beautiful Uptown 1BR w/Gym, Rooftop Pool, 2 blocks to L, by Blueground From US $132
         

New
Apartment
Beautiful Uptown 1BR w/Gym, Rooftop Pool, 2 blocks to L, by Blueground
  • Air Conditioner
  • Pet Friendly
  • Pool

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Uptown studio apartment with breathing views From US $208
         

10.0 (19 Reviews)
Apartment
Uptown studio apartment with breathing views
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1bedroom condo with fitness room fabulous view literally steps away from Beach From US $227
         

New
Condo
1bedroom condo with fitness room fabulous view literally steps away from Beach
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  • Parking
  • Pool

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Bright Uptown 1BR w/ Gym w/ Boxing Ring, nr Red Line, by Blueground From US $206
         

New
Apartment
Bright Uptown 1BR w/ Gym w/ Boxing Ring, nr Red Line, by Blueground
  • Air Conditioner
  • Pet Friendly
  • Pool

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Pet-Friendly Vacation Rentals in Uptown

Over 45+ Pet-Friendly Vacation Rentals in or Near Uptown
W3 - Spacious 2BR Apt + Free On-site Parking From US $248
         

10.0 (67 Reviews)
Apartment
W3 - Spacious 2BR Apt + Free On-site Parking
  • Air Conditioner
  • Parking
  • Pet Friendly

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Designer 3BR with Balcony & Elevator on Clark! apts From US $376
         

New
Apartment
Designer 3BR with Balcony & Elevator on Clark! apts
  • Air Conditioner
  • Parking
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Artistic Loft Rooftop | 13 mins DT | 4 mins Lake From US $152
         

10.0 (58 Reviews)
Apartment
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
  • Air Conditioner
  • Pet Friendly
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PET FRIENDLY! Desirable Sheridan Park is a Safe, Vibrant, and Welcoming Area you are Sure to Love by AllSet Turnover From US $355
         

9.4 (12 Reviews)
Apartment
PET FRIENDLY! Desirable Sheridan Park is a Safe, Vibrant, and Welcoming Area you are Sure to Love by AllSet Turnover
  • Air Conditioner
  • Pet Friendly
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Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake From US $327
         

9.2 (25 Reviews)
Apartment
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
  • Air Conditioner
  • Pet Friendly
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Sheridan Park Stunner! No Matter if You Are in Town for Business or Fun This Property Has You Covered by AllSet Turnover From US $356
         

9.0 (15 Reviews)
Apartment
Sheridan Park Stunner! No Matter if You Are in Town for Business or Fun This Property Has You Covered by AllSet Turnover
  • Air Conditioner
  • Pet Friendly
  • TV

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Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake From US $266
         

8.8 (18 Reviews)
Apartment
Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake
  • Air Conditioner
  • Pet Friendly
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Elegant Style Loft Montrose|13 mins DT|4 mins Lake From US $222
         

8.4 (10 Reviews)
Apartment
Elegant Style Loft Montrose|13 mins DT|4 mins Lake
  • Air Conditioner
  • Pet Friendly
  • TV

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Large Vacation Homes & Villas in Uptown

Over 4+ Large Vacation Homes & Villas in or Near Uptown
2 Bedroom Unit in Uptown Chicago From US $262
         

New
Apartment
2 Bedroom Unit in Uptown Chicago
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Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake! From US $1,321
         

10.0 (139 Reviews)
House
Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Pet Friendly! Can You Smell the Popcorn and Peanuts? One Mile from Wrigley Field and Room for All the Super Fans! by RedAwning From US $853
         

10.0 (1 Review)
House
Pet Friendly! Can You Smell the Popcorn and Peanuts? One Mile from Wrigley Field and Room for All the Super Fans! by RedAwning
  • Air Conditioner
  • Parking
  • Pet Friendly

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Gorgeous Wrigley Greystone From US $217
         

8.4 (38 Reviews)
Condo
Gorgeous Wrigley Greystone
  • Air Conditioner
  • Parking
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Wheelchair Accessible Vacation Homes in Uptown

Over 18+ Wheelchair Accessible Vacation Homes in or Near Uptown
Chic apartment in marvelous Chicago with WiFi, AC From US $267
         

10.0 (10 Reviews)
Apartment
Chic apartment in marvelous Chicago with WiFi, AC
  • Air Conditioner
  • Parking
  • TV

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Elegant Style Loft Montrose Beach Rooftop WFH Gym From US $282
         

9.4 (20 Reviews)
Apartment
Elegant Style Loft Montrose Beach Rooftop WFH Gym
  • Air Conditioner
  • Pet Friendly
  • TV

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Sunny Modern Loft Montrose Beach Rooftop WFH Gym From US $188
         

9.4 (13 Reviews)
Apartment
Sunny Modern Loft Montrose Beach Rooftop WFH Gym
  • Air Conditioner
  • Pet Friendly
  • TV

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Majestic Modern Style|13 mins DT|4 mins Lake From US $180
         

9.4 (13 Reviews)
Apartment
Majestic Modern Style|13 mins DT|4 mins Lake
  • Air Conditioner
  • Pet Friendly
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Barsala l Bright Studio with full kitchen From US $241
         

New
House
Barsala l Bright Studio with full kitchen
  • Air Conditioner
  • Pet Friendly
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Bright Uptown 1BR w/ W/D & Roof, near Aragon Ballroom, by Blueground From US $179
         

New
Apartment
Bright Uptown 1BR w/ W/D & Roof, near Aragon Ballroom, by Blueground
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  • Pet Friendly
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Lovely Uptown 1BR w/Gym w/Boxing Ring, close to Beach, by Blueground From US $147
         

New
Apartment
Lovely Uptown 1BR w/Gym w/Boxing Ring, close to Beach, by Blueground
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  • Pet Friendly
  • Pool

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Amazing Uptown 1BR w/ Roof & W/D, 1 block to Red Line, by Blueground From US $140
         

New
Apartment
Amazing Uptown 1BR w/ Roof & W/D, 1 block to Red Line, by Blueground
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  • Pet Friendly
  • TV

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Uptown Vacation Rentals and Airbnb Places to Stay Under $200

Over 30+ Uptown Vacation Rentals and Airbnb Places to Stay Under $200
The Bright Retreat in Andersonville From US $194
         

9.8 (74 Reviews)
Condo
The Bright Retreat in Andersonville
  • Air Conditioner
  • Parking
  • TV

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Chic Chicago Apartment about 1 Mi to Wrigley Field! From US $133
         

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9.8 (6 Reviews)
Apartment
Chic Chicago Apartment about 1 Mi to Wrigley Field!
  • Air Conditioner
  • Parking
  • Accessibility

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Elite Studio Apartment in Uptown near Shops From US $94
         

10.0 (5 Reviews)
Apartment
Elite Studio Apartment in Uptown near Shops
  • Air Conditioner
  • Pet Friendly
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Montrose Studio:Your Uptown Base From US $155
         

9.8 (7 Reviews)
Apartment
Montrose Studio:Your Uptown Base
  • Pet Friendly
  • TV
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Nice & Comfy Uptown Studio Apt near Shops & Dining From US $94
         

8.0 (7 Reviews)
Apartment
Nice & Comfy Uptown Studio Apt near Shops & Dining
  • Air Conditioner
  • Pet Friendly
  • TV

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Uptown NEW and MODERN 1BR Wrigleyville area PRIME From US $178
         

5.0 (1 Review)
Apartment
Uptown NEW and MODERN 1BR Wrigleyville area PRIME
  • Air Conditioner
  • Bedding/Linens
  • Internet

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PRIVATE Boho vintage condo with sunrooms and plants in Historic Andersonville From US $121
         

4.5 (2 Reviews)
Condo
PRIVATE Boho vintage condo with sunrooms and plants in Historic Andersonville
  • Air Conditioner
  • TV
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Landing at Platform 4611 - 1 Bedroom in Uptown From US $155
         

New
Apartment
Landing at Platform 4611 - 1 Bedroom in Uptown
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Instantly Bookable Vacation Homes in Uptown

Over 24+ Instantly Bookable Vacation Homes in or Near Uptown
Music-Inspired 2BR Garden Flat in Historic Uptown Near Legendary Music Venues From US $228
         

10.0 (6 Reviews)
Apartment
Music-Inspired 2BR Garden Flat in Historic Uptown Near Legendary Music Venues
  • Air Conditioner
  • TV
  • Security/Safety

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Chicago Gem: Wrigley - Lakefront - Red Line Train From US $295
         

10.0 (3 Reviews)
Condo
Chicago Gem: Wrigley - Lakefront - Red Line Train
  • Air Conditioner
  • Parking
  • TV

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The Shingle Life near Wrigley From US $229
         

10.0 (1 Review)
Apartment
The Shingle Life near Wrigley
  • Air Conditioner
  • TV
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A Hand-some Place Near Wrigley From US $218
         

10.0 (1 Review)
Apartment
A Hand-some Place Near Wrigley
  • Air Conditioner
  • TV
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Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover From US $215
         

9.8 (37 Reviews)
Condo
Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover
  • Air Conditioner
  • TV
  • Security/Safety

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Inviting Stylish Home with Covered Patio From US $222
         

9.4 (10 Reviews)
House
Inviting Stylish Home with Covered Patio
  • Air Conditioner
  • Parking
  • TV

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Walk to Wrigley! Spacious 3BR in the Heart of Chicago From US $346
         

9.4 (3 Reviews)
Apartment
Walk to Wrigley! Spacious 3BR in the Heart of Chicago
  • Air Conditioner
  • TV
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Toad Hall near Wrigley From US $266
         

New
Apartment
Toad Hall near Wrigley
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About Uptown Vacation Rentals

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Hotelingreenville Uptown, 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 Uptown. Places to stay near Uptown are 1001.04 ft² on average, with prices averaging US $252 a night.

Hotelingreenville makes it easy and safe to find and compare vacation rentals in Uptown 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 Uptown

Type Count
Hotels 1

Use these Quick Filters to Find a Vacation Rental in Uptown

★ Pro Tip: Hotelingreenville makes it easy to compare the best listings on Hotelingreenville homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Hotelingreenville 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 Uptown.

Weather in Uptown

View the weather forecast for Uptown before booking your Uptown 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

Other Places to Stay Near Uptown, IL


Sheridan Park 1,303 Properties Graceland Cemetery 1,273 Properties Buena Park 1,255 Properties Our Lady of Lourdes Church 1,244 Properties About Face Theater 1,212 Properties Essanay Studios 1,204 Properties Pegasus Players 1,202 Properties Riviera Theatre 1,202 Properties Methodist Hospital of Chicago 1,192 Properties Aragon Ballroom 1,186 Properties Aragon Entertainment Center 1,181 Properties Hutchinson Street District 1,159 Properties

Complexes around Uptown, IL


Wells Apartments St Chicago 3 Properties

Uptown Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Uptown?

There are a lot of options in Uptown. If you plan on staying in the Uptown area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Uptown:

How many vacation rentals are available in Uptown?

Currently, the total number of properties listed in 2026 is over 1 in the Uptown area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Uptown.