Maimon Beach - Vacation Rentals in West Town

3 BD condo near to downtown, Gold Coast and Michigan Avenue. From US $454
         

Chicago Quick Stay From US $130
         

6.3 (47 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Internet
Wicker Park Inn From US $247
         

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9.0 (261 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
NEW LUXURY PENTHOUSE CONDO From US $604
         

10.0 (204 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
NEW LUXURY CONDO WITH PATIO DECK From US $392
         

10.0 (193 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Private Historic Coach House Wicker Park From US $401
         

10.0 (69 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Luxury Places to Stay in West Town

Over 616+ Luxury Places to Stay in or Near West Town
Unique Luxury Fulton Market Penthouse - Sleeps 32 From US $3,663
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
: The Wolcott : Modern Elegance at Its Finest From US $3,543
         

9.4 (14 Reviews)
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area
3 Flat Building Downtown - With Private Patios From US $2,412
         

New
Apartment
  • Air Conditioner
  • Parking
  • Security/Safety
Stunning 5BR Home in Heart of Chicago with 2 Rooftops From US $2,234
         

Wicker Park Entire House, Private Yard and Parking From US $2,006
         

10.0 (15 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
The Golden Arm From US $1,996
         

8.6 (56 Reviews)
Hotel
  • Air Conditioner
  • View
  • Balcony/Terrace

Top-Rated Vacation Rentals with a Pool in West Town

Over 26+ Top-Rated Vacation Rentals with a Pool in or Near West Town
BlueJay/Unique One Bedroom Full of Amazing Art From US $230
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pool
iKlektik House/Robin From US $225
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pool
iKlektik House Chicago From US $237
         

9.8 (24 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
The Robey, Chicago, a Member of Design Hotels From US $214
         

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9.2 (1002 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
The Robey, Chicago, a Member of Design Hotels From US $423
         

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8.6 (293 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in West Town

Over 199+ Pet-Friendly Vacation Rentals in or Near West Town
Large Chicago 3BR/3BA Sleeps 7 Near Downtown From US $812
         

10.0 (34 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Wicker Park 1-BR Walk to Train & Grocery Easy Downtown Access From US $187
         

10.0 (8 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Art Villa From US $1,030
         

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10.0 (2 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • Designated Smoking Area
Vital Urban: Spa Inspired Retreat From US $617
         

10.0 (11 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Relax with family in a super deluxe single family home. West town. From US $1,139
         

Large Vacation Homes & Villas in West Town

Over 109+ Large Vacation Homes & Villas in or Near West Town
Spacious 4-Level/4-Bedroom Townhouse in West Loop From US $1,381
         

NEW! Spacious Art Deco Modern 5 BD/3BA Condo From US $580
         

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10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Balcony/Terrace
2 Suites, 2 Floors in Downtown Chicago From US $493
         

10.0 (5 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Designer Apt, Billiards, Private Patio, 1 Parking From US $613
         

10.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Spacious 5-bedroom house great for large groups From US $716
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
4 BR | Pool Table, 2 Decks + Fire Pit, Free Street Parking and W/D From US $1,125
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
LUX 3-Level Chicago Home +garage & patio From US $784
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area

Wheelchair Accessible Vacation Homes in West Town

Over 99+ Wheelchair Accessible Vacation Homes in or Near West Town
The Cornerstone - Designer 4BR Flat in Bucktown/WP From US $1,000
         

10.0 (11 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
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
Cabin 105 by 747 Lofts From US $253
         

10.0 (1 Review)
Apartment
  • Wheelchair Accessible
  • Accessibility
  • Security/Safety
1 Garage Parking/Skyline Rooftop/PingPong/Balcony From US $541
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Private Balcony, 1 Garage Parking, Sleeps 8! From US $449
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Downtown Chicago Retreat 2BD/2BA Views+Gym+Rooftop From US $668
         

Luxury Fulton Market Penthouse Amazing City Views From US $1,409
         

9.6 (27 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Blueground | West Town, view, nr Chicago River From US $284
         

West Town Vacation Rentals and Airbnb Places to Stay Under $200

Over 178+ West Town 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
Hyatt Place Chicago/Wicker Park From US $175
         

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9.4 (1003 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Flexhome Ukrainian Village 2BR Walkable + Private Balcony From US $179
         

9.6 (11 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Balcony/Terrace
Flexhome East Village Modern 2BR Quiet Street From US $189
         

9.6 (8 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Flexhome Wicker Park Stylish 2BR Sleeps 6 From US $167
         

9.6 (4 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Flexhome Ukrainian Village 2BR Convenient Walkability From US $180
         

8.2 (10 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

Instantly Bookable Vacation Homes in West Town

Over 290+ Instantly Bookable Vacation Homes in or Near West Town
Spacious & private! Free parking! Great location! From US $210
         

10.0 (34 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Trendy West Town Flat - 2 bed/1.5 bath with parking From US $339
         

Spacious loft in the heart of West Town, Noble Square Chicago From US $220
         

10.0 (14 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Security/Safety
3BD West Town Gem: Explore the Windy City in Style From US $628
         

About West Town Vacation Rentals

With more than 625 West Town vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Maimonbeach 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 West Town.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Maimonbeach West Town, 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 West Town. Places to stay near West Town are 940.96 ft² on average, with prices averaging $452 a night.

Maimonbeach makes it easy and safe to find and compare vacation rentals in West Town 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 West Town

Type Count
Holiday Apartments 411
Vacation Homes 118
Hotels with Suites 16
B&B 3
Villas 3
Hostels 1
Others 1

Use these Quick Filters to Find a Vacation Rental in West Town

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

Weather in West Town

View the weather forecast for West Town before booking your West Town 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

West Town Vacation Rental Frequently Asked Questions

What are the top vacation rentals in West Town?
How many vacation rentals are available in West Town?

Currently, the total number of properties listed in 2026 is over 625 in the West Town area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in West Town.