Boystown Vacation Rentals & Ski-in/Ski-out Homes
Apartment
10.0Exceptional
(176 Reviews)
2 Bedrooms
1 Bath
6 Guests
1000 ft²
Parking
Balcony/Terrace
Kitchen
Air Conditioner
US $391/Night
7 Nights - US $2,737
Apartment
- Chicago
- ·
- Lake View East
- 0.30 mi to center
10.0Exceptional
(14 Reviews)
1 Bedroom
1 Bath
2 Guests
699.65 ft²
Internet
Child Friendly
US $256/Night
7 Nights - US $1,792
Bed & Breakfast
10.0Exceptional
(566 Reviews)
1 Bedroom
1 Bath
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $224/Night
7 Nights - US $1,570
Apartment
- Chicago
- ·
- North Center
- 0.68 mi to center
10.0Exceptional
(157 Reviews)
2 Bedrooms
1 Bath
6 Guests
1000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $273/Night
7 Nights - US $1,909
Apartment
10.0Exceptional
(12 Reviews)
1 Bedroom
1 Bath
4 Guests
452.08 ft²
Private Pool
Oceanfront
Breakfast- Parking
US $208/Night
7 Nights - US $1,456
Apartment
- Chicago
- ·
- Roscoe Village
- 0.17 mi to center
10.0Exceptional
(103 Reviews)
2 Bedrooms
1 Bath
6 Guests
1200 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $349/Night
7 Nights - US $2,441
Apartment
10.0Exceptional
(92 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $151/Night
7 Nights - US $1,057
Apartment
- Chicago
- ·
- Sheffield Neighbors
- 0.18 mi to center
10.0Exceptional
(89 Reviews)
1 Bedroom
1 Bath
4 Guests
800 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $310/Night
7 Nights - US $2,168
Apartment
10.0Exceptional
(74 Reviews)
2 Bedrooms
2 Baths
4 Guests
1500 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $220/Night
7 Nights - US $1,543
Luxury Places to Stay in Boystown
Over 1758+ Luxury Places to Stay in or Near Boystown
Bed & Breakfast
- Chicago
- ·
- East Village
- 0.24 mi to center
8 Bedrooms
8 Baths
16 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $4,197/Night
7 Nights - US $29,376
House
- Chicago
- ·
- Gold Coast
- 0.29 mi to center
10.0Exceptional
(41 Reviews)
5 Bedrooms
5 Baths
14 Guests
7000 ft²
- Parking
Ocean View- Balcony/Terrace
View
US $3,761/Night
7 Nights - US $26,329
House
- Chicago
- ·
- Gold Coast
- 0.27 mi to center
6 Bedrooms
5 Baths
26 Guests
4294.8 ft²
Private Beach- Breakfast
EV Charge Station- Parking
US $3,466/Night
7 Nights - US $24,260
House
9.4Exceptional
(16 Reviews)
4 Bedrooms
6 Baths
12 Guests
6000 ft²
Hot Tub- Parking
- Balcony/Terrace
- Kitchen
US $3,382/Night
7 Nights - US $23,675
Hotel
- Chicago
- ·
- Near North Side
- 0.30 mi to center
2 Baths
1575 ft²
- Private Pool
- Parking
Pool- Kitchen
US $3,261/Night
7 Nights - US $22,829
House
- Chicago
- ·
- Gold Coast
- 0.19 mi to center
12 Bedrooms
7 Baths
23 Guests
5005.22 ft²
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $3,043/Night
7 Nights - US $21,299
New
House
- Chicago
- ·
- North Center
- 0.7 mi to center
6 Bedrooms
4 Baths
16 Guests
6000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $2,783/Night
7 Nights - US $19,481
Apartment
10.0Exceptional
(15 Reviews)
4 Bedrooms
4 Baths
10 Guests
2500 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $2,626/Night
7 Nights - US $18,380
House
- Chicago
- ·
- Gold Coast
- 0.19 mi to center
5.0Average
(1 Review)
8 Bedrooms
4 Baths
15 Guests
2002.09 ft²
- Parking
- Air Conditioner
- Internet
Sports/Activities
US $2,491/Night
7 Nights - US $17,436
Top-Rated Vacation Rentals with a Pool in Boystown
Over 109+ Top-Rated Vacation Rentals with a Pool in or Near Boystown
Hotel
10.0Exceptional
(9 Reviews)
1 Bath
- Pool
- Kitchen
- Air Conditioner
- Internet
US $281/Night
7 Nights - US $1,964
Apartment
- Chicago
- ·
- River North
- 0.81 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
1105 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $440/Night
7 Nights - US $3,077
Apartment
- Chicago
- ·
- River North
- 0.81 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
1100 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $431/Night
7 Nights - US $3,017
Hotel
- Chicago
- ·
- Near North Side
- 0.30 mi to center
10.0Exceptional
(1 Review)
1 Bath
900 ft²
- Private Pool
- Parking
- Pool
- Kitchen
US $597/Night
7 Nights - US $4,177
Hotel
- Chicago
- ·
- Near North Side
- 0.30 mi to center
10.0Exceptional
(1 Review)
1 Bath
710 ft²
- Private Pool
- Parking
- Pool
- Kitchen
US $430/Night
7 Nights - US $3,010
Hotel
- Chicago
- ·
- Near North Side
- 0.31 mi to center
10.0Exceptional
(1 Review)
4 Baths
771.41 ft²
- Hot Tub
- EV Charge Station
- Parking
- Pool
US $270/Night
7 Nights - US $1,890
Bed & Breakfast
- Chicago
- ·
- Roscoe Village
- 0.04 mi to center
9.8Exceptional
(110 Reviews)
1 Bedroom
1 Bath
2 Guests
650 ft²
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $430/Night
7 Nights - US $3,011
Hotel
9.6Exceptional
(7 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $263/Night
7 Nights - US $1,838
Hotel
- Chicago
- ·
- Wicker Park
- 0.14 mi to center
9.2Exceptional
(1001 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
Spa
US $273/Night
7 Nights - US $1,914
Pet-Friendly Vacation Rentals in Boystown
Over 708+ Pet-Friendly Vacation Rentals in or Near Boystown
Apartment
10.0Exceptional
(59 Reviews)
1 Bedroom
1 Bath
2 Guests
441 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $267/Night
7 Nights - US $1,871
Apartment
- Chicago
- ·
- Wrigleyville
- 0.22 mi to center
10.0Exceptional
(5 Reviews)
4 Bedrooms
2 Baths
10 Guests
1205.56 ft²
- Parking
- Air Conditioner
- Internet
Pet Friendly
US $462/Night
7 Nights - US $3,235
Bed & Breakfast
8.0Excellent
(682 Reviews)
1 Bedroom
1 Bath
- Parking
- Internet
- Pet Friendly
Security/Safety
US $159/Night
7 Nights - US $1,112
Apartment
- Chicago
- ·
- Irving Park East
- 0.23 mi to center
10.0Exceptional
(29 Reviews)
2 Bedrooms
1 Bath
6 Guests
900 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $265/Night
7 Nights - US $1,853
Apartment
- Chicago
- ·
- Lake View East
- 0.18 mi to center
10.0Exceptional
(4 Reviews)
6 Bedrooms
2 Baths
20 Guests
3498.27 ft²
- Private Beach
- EV Charge Station
- Parking
- Ocean View
US $482/Night
7 Nights - US $3,371
House
- Chicago
- ·
- Wicker Park
- 0.45 mi to center
10.0Exceptional
(13 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Parking
- Spa
- Balcony/Terrace
US $634/Night
7 Nights - US $4,440
Apartment
- Chicago
- ·
- Old Town Triangle
- 0.14 mi to center
10.0Exceptional
(11 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $302/Night
7 Nights - US $2,111
Apartment
10.0Exceptional
(7 Reviews)
1 Bedroom
1 Bath
6 Guests
900 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $408/Night
7 Nights - US $2,859
Apartment
- Chicago
- ·
- Irving Park East
- 0.16 mi to center
10.0Exceptional
(6 Reviews)
1 Bedroom
1 Bath
4 Guests
592 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $282/Night
7 Nights - US $1,977
Large Vacation Homes & Villas in Boystown
Over 276+ Large Vacation Homes & Villas in or Near Boystown
New
Apartment
- Chicago
- ·
- West Bucktown
- 0.32 mi to center
9.8Exceptional
(14 Reviews)
2 Bedrooms
2 Baths
10 Guests
- Air Conditioner
- Internet
- Child Friendly
Laundry
US $577/Night
7 Nights - US $4,042
House
- Chicago
- ·
- River North
- 0.78 mi to center
10.0Exceptional
(3 Reviews)
10 Bedrooms
3 Baths
10 Guests
1205.56 ft²
- Balcony/Terrace
- Air Conditioner
- Internet
- Child Friendly
US $307/Night
7 Nights - US $2,147
Villa
9.6Exceptional
(13 Reviews)
1 Bedroom
6 Baths
16 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $619/Night
7 Nights - US $4,334
Apartment
- Chicago
- ·
- Wrigleyville
- 0.20 mi to center
10.0Exceptional
(2 Reviews)
5 Bedrooms
3 Baths
10 Guests
2497.23 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $799/Night
7 Nights - US $5,594
Apartment
9.6Exceptional
(11 Reviews)
2 Bedrooms
1 Bath
10 Guests
1000 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $630/Night
7 Nights - US $4,413
Apartment
- Chicago
- ·
- Gold Coast
- 0.27 mi to center
9.2Exceptional
(10 Reviews)
2 Bedrooms
2 Baths
14 Guests
800 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $434/Night
7 Nights - US $3,036
Apartment
- Chicago
- ·
- Sheridan Park
- 0.17 mi to center
2 Bedrooms
2 Baths
11 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $172/Night
7 Nights - US $1,202
Condo
10.0Exceptional
(136 Reviews)
3 Bedrooms
3 Baths
10 Guests
2200 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $452/Night
7 Nights - US $3,161
Apartment
- Chicago
- ·
- River North
- 0.64 mi to center
10.0Exceptional
(126 Reviews)
4 Bedrooms
3 Baths
15 Guests
1850 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $694/Night
7 Nights - US $4,858
Wheelchair Accessible Vacation Homes in Boystown
Over 339+ Wheelchair Accessible Vacation Homes in or Near Boystown
Apartment
- Chicago
- ·
- Lake View East
- 0.13 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
500 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $171/Night
7 Nights - US $1,199
Bed & Breakfast
9.5Exceptional
(161 Reviews)
11 Bedrooms
11 Baths
30 Guests
190.81 ft²
- Breakfast
- EV Charge Station
- Parking
- Spa
US $296/Night
7 Nights - US $2,074
Bed & Breakfast
- Chicago
- ·
- Lincoln Park
- 0.23 mi to center
9.4Exceptional
(127 Reviews)
1 Bedroom
1 Bath
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
US $296/Night
7 Nights - US $2,070
Apartment
- Chicago
- ·
- Near North Side
- 0.34 mi to center
9.8Exceptional
(17 Reviews)
2 Bedrooms
2 Baths
8 Guests
1200 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $330/Night
7 Nights - US $2,311
Apartment
- Chicago
- ·
- Ravenswood
- 0.45 mi to center
8.2Excellent
(6 Reviews)
1 Bedroom
1 Bath
2 Guests
602.78 ft²
- Air Conditioner
- Internet
Wheelchair Accessible
US $57/Night
7 Nights - US $399
Apartment
- Chicago
- ·
- Near North Side
- 0.35 mi to center
9.6Exceptional
(8 Reviews)
2 Bedrooms
2 Baths
8 Guests
1200 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $308/Night
7 Nights - US $2,159
Apartment
- Chicago
- ·
- Near North Side
- 0.35 mi to center
9.6Exceptional
(7 Reviews)
2 Bedrooms
2 Baths
8 Guests
1200 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $326/Night
7 Nights - US $2,280
House
- Chicago
- ·
- River North
- 0.79 mi to center
9.4Exceptional
(3 Reviews)
1 Bedroom
1 Bath
4 Guests
700 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $405/Night
7 Nights - US $2,833
Apartment
8.8Fabulous
(19 Reviews)
1 Bedroom
1 Bath
2 Guests
441 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $189/Night
7 Nights - US $1,326
Boystown Resorts and Airbnb Homes Under $200
Over 552+ Boystown Resorts and Airbnb Homes Under $200
Apartment
10.0Exceptional
(64 Reviews)
1 Bedroom
1 Bath
3 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $160/Night
7 Nights - US $1,118
Apartment
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
5 Guests
947.22 ft²
- View
- Air Conditioner
- Internet
- Child Friendly
US $90/Night
7 Nights - US $630
Apartment
- Chicago
- ·
- Ravenswood
- 0.35 mi to center
10.0Exceptional
(9 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $181/Night
7 Nights - US $1,268
House
9.9Exceptional
(7 Reviews)
1 Bedroom
1 Bath
4 Guests
850.35 ft²
- Parking
- Air Conditioner
- Internet
- Laundry
US $160/Night
7 Nights - US $1,118
House
- Chicago
- ·
- Irving Park East
- 0.29 mi to center
10.0Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $141/Night
7 Nights - US $985
Apartment
- Chicago
- ·
- Sheffield and DePaul
- 0.17 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $141/Night
7 Nights - US $986
House
- Chicago
- ·
- Roscoe Village
- 0.21 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
900 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $137/Night
7 Nights - US $961
Apartment
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
4 Guests
1000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $195/Night
7 Nights - US $1,364
Instantly Bookable Vacation Homes in Boystown
Over 1039+ Instantly Bookable Vacation Homes in or Near Boystown
Condo
10.0Exceptional
(68 Reviews)
2 Bedrooms
2 Baths
5 Guests
1200 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $274/Night
7 Nights - US $1,916
Apartment
- Chicago
- ·
- Sheffield and DePaul
- 0.16 mi to center
2 Bedrooms
1 Bath
6 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $820/Night
7 Nights - US $5,741
Apartment
- Chicago
- ·
- North Center
- 0.08 mi to center
10.0Exceptional
(62 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $492/Night
7 Nights - US $3,442
Apartment
10.0Exceptional
(58 Reviews)
2 Bedrooms
1 Bath
5 Guests
900 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $487/Night
7 Nights - US $3,407
Apartment
- Chicago
- ·
- Wrigleyville
- 0.16 mi to center
10.0Exceptional
(55 Reviews)
2 Bedrooms
2 Baths
4 Guests
1000 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $674/Night
7 Nights - US $4,721
Apartment
- Chicago
- ·
- Logan Square
- 0.43 mi to center
10.0Exceptional
(40 Reviews)
2 Bedrooms
1 Bath
5 Guests
750 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $415/Night
7 Nights - US $2,902
Condo
10.0Exceptional
(38 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $459/Night
7 Nights - US $3,216
New
Apartment
10.0Exceptional
(37 Reviews)
2 Bedrooms
2 Baths
4 Guests
800 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $328/Night
7 Nights - US $2,299
Condo
10.0Exceptional
(36 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $322/Night
7 Nights - US $2,254
Book a Last Minute Place to Stay in Boystown
About Boystown Vacation Rentals
Explore over 1767 vacation rentals in Boystown with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in Boystown for more space and value.
In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in Boystown. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Boystown tailored to your preferences. On average, these rentals offer 789.84 ft² of space, and are priced at an average of US $476 per night.
SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Boystown at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.
Show more
Show less
Top Types of Ski Accommodations in Boystown
| Type | Count |
|---|---|
| Holiday Apartments | 1176 |
| Vacation Homes | 298 |
| B&B | 26 |
| Villas | 3 |
| Cottages | 2 |
| Others | 2 |
Use these Quick Filters to Find a Vacation Rental in Boystown
★ Pro Tip: Discover Your Ideal Vacation Rental in Boystown with SunSki Resorts™. Compare a diverse array of properties, including RBO homes, vacation rentals, cottages, cabins, and more. Utilize our advanced filters to search by location, amenities, and price. Book with confidence and enjoy savings of up to 40-60% compared to a hotel stay. Create unforgettable memories with SunSki Resorts™.
Weather in Boystown, IL
View the weather forecast for Boystown before booking your Boystown 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 in Boystown, IL
Frequently Asked Questions About Boystown?
What are the top vacation rentals in Boystown?
When organizing your trip to Boystown, don't miss the chance to explore the top-rated vacation rentals in the vicinity. With a plethora of options available, you're bound to discover the ideal accommodation for your stay in Boystown. Peruse our collection of highly-rated properties and secure your reservation today.
- The Sono Chicago
- Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood
- North Center - Modern, Safe, Family-Friendly, Solar-Powered Apartment
- Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field
- 4BR Old Town Chicago Loft | Walk to Wells St
- Dramatic Wrigley Loft +PRIVATE Rooftop, Center of Wrigley, Ranked GUEST FAVORITE
- Roscoe Village- Only steps to cute shops & dining! Sleeps 4-6
- Stylish, Inviting 2-BR near Logan Square and Wrigley Field
- Lincoln Park Light Filled Loft
- W3 - Spacious 2BR Apt + Free On-site Parking
How many vacation rentals have private pools in Boystown?
Uncover 6 vacation rentals boasting private pools near Boystown. Explore top-rated RBO homes offering access to a swimming pool:
- Experience Chic Old Town Living: Spacious Suites, Top Amenities & Iconic Locale
- The Hotel & Athletic Club at Midtown
- Live the Suite Life: Historic Old Town Chicago Stays with Modern Luxury & Style
- Experience the Suite Life in Chicago’s Iconic Old Town – Spacious Stays Await
Which vacation homes or resorts in Boystown are best for families?
Choose SunSki for a wide variety of vacation rentals, including family-friendly homes, ski cabins, cottages, and more in Boystown. Enjoy great views, locations and save money with SunSki Resorts.™
- Cute new Garden unit located between Andersonville and Lincoln Square , Chicago.
- Modern 3BR Apt in Boystown, 12-min walk to Wrigley - Stratford 1S
- Wrigleyville Inn
How many SunSkiResorts vacation rentals or resorts are available in Boystown?
Discover the ideal vacation rental in Boystown with SunSki Resorts™. We provide an extensive selection of over 1767 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Boystown.
Nearby Neighborhood (2)
| Neighborhood | Property Count |
|---|---|
| Lakeview Vacation Rentals in Chicago, Illinois | 225 |
| Lake View East Vacation Rentals in Chicago, Illinois | 47 |
Map
