Best Vacation Homes in Boystown
New
House
4 Bedrooms
2 Baths
12 Guests
Fireplace/Heating
Air Conditioner
Internet
Child Friendly
R12,942/Night
7 Nights - R90,588
Apartment
10.0(14 Reviews)
1 Bedroom
1 Bath
2 Guests
699.65 ft²
- Internet
- Child Friendly
R4,319/Night
7 Nights - R30,230
Bed & Breakfast
10.0(511 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
Balcony/Terrace
Parking- Air Conditioner
R3,149/Night
7 Nights - R22,048
New
House
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
R6,451/Night
7 Nights - R45,159
Apartment
10.0(12 Reviews)
1 Bedroom
1 Bath
4 Guests
452.08 ft²
Private Pool
Oceanfront- Fireplace/Heating
Pool
R1,974/Night
7 Nights - R13,816
Apartment
10.0(203 Reviews)
2 Bedrooms
1 Bath
4 Guests
900 ft²
- Fireplace/Heating
- Balcony/Terrace
Kitchen- Parking
R4,865/Night
7 Nights - R34,059
Apartment
10.0(169 Reviews)
2 Bedrooms
1 Bath
6 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly- Kitchen
R5,637/Night
7 Nights - R39,457
Apartment
10.0(134 Reviews)
2 Bedrooms
1 Bath
6 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R4,194/Night
7 Nights - R29,353
Boystown Luxury Rentals
Bed & Breakfast
8 Bedrooms
8 Baths
16 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
R85,406/Night
7 Nights - R597,848
House
4 Bedrooms
2 Baths
10 Guests
2497.23 ft²
- Parking
- Internet
- Child Friendly
Security/Safety
R63,863/Night
7 Nights - R447,036
House
9.4(14 Reviews)
4 Bedrooms
6 Baths
12 Guests
6000 ft²
Hot Tub- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R59,167/Night
7 Nights - R414,175
House
6 Bedrooms
5 Baths
26 Guests
4294.8 ft²
Private Beach- Fireplace/Heating
Ocean View- Balcony/Terrace
R58,463/Night
7 Nights - R409,249
House
10.0(1 Review)
4 Bedrooms
3 Baths
10 Guests
5000 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
View
R53,252/Night
7 Nights - R372,761
House
10.0(33 Reviews)
5 Bedrooms
5 Baths
14 Guests
7000 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R50,654/Night
7 Nights - R354,576
Hotel
2 Baths
1575 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Kitchen
R49,223/Night
7 Nights - R344,555
House
1 Bedroom
4 Baths
15 Guests
2002.09 ft²
- Fireplace/Heating
- Parking
- Air Conditioner
- Internet
R42,018/Night
7 Nights - R294,133
Boystown Pet Friendly Vacation Rentals
Apartment
10.0(97 Reviews)
2 Bedrooms
1 Bath
6 Guests
1200 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R5,362/Night
7 Nights - R37,534
Apartment
10.0(8 Reviews)
2 Bedrooms
1 Bath
4 Guests
914.93 ft²
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
R10,432/Night
7 Nights - R73,027
Bed & Breakfast
7.8(641 Reviews)
1 Bedroom
1 Bath
- Pet Friendly
- Parking
- Internet
- Security/Safety
R2,592/Night
7 Nights - R18,134
Apartment
10.0(76 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R4,185/Night
7 Nights - R29,302
Apartment
10.0(8 Reviews)
1 Bedroom
1 Bath
2 Guests
495.14 ft²
- Pet Friendly
- Parking
- Air Conditioner
- Internet
R3,155/Night
7 Nights - R22,082
Apartment
10.0(65 Reviews)
2 Bedrooms
2 Baths
4 Guests
1500 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
R6,794/Night
7 Nights - R47,555
Apartment
10.0(53 Reviews)
1 Bedroom
1 Bath
2 Guests
441 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R4,842/Night
7 Nights - R33,890
Apartment
10.0(24 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Internet
R7,165/Night
7 Nights - R50,152
Boystown Large Vacation Homes
Apartment
10.0(8 Reviews)
2 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
R10,054/Night
7 Nights - R70,379
Apartment
10.0(4 Reviews)
4 Bedrooms
2 Baths
10 Guests
1205.56 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
R6,973/Night
7 Nights - R48,803
Apartment
9.2(9 Reviews)
2 Bedrooms
2 Baths
14 Guests
800 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
R9,390/Night
7 Nights - R65,723
Apartment
10.0(3 Reviews)
6 Bedrooms
2 Baths
20 Guests
3498.27 ft²
- Private Beach
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R10,881/Night
7 Nights - R76,165
Apartment
9.2(5 Reviews)
2 Bedrooms
1 Bath
10 Guests
969 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R5,749/Night
7 Nights - R40,233
Apartment
10.0(199 Reviews)
3 Bedrooms
2 Baths
10 Guests
1800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R10,906/Night
7 Nights - R76,350
House
10.0(136 Reviews)
4 Bedrooms
3 Baths
12 Guests
2700 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R16,392/Night
7 Nights - R114,745
Apartment
10.0(120 Reviews)
4 Bedrooms
3 Baths
15 Guests
1850 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R18,176/Night
7 Nights - R127,228
Why Choose Rent By Owner for your Boystown Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Popular Areas for Boystown Vacation Rentals
Where are the best neighborhoods to stay in Boystown?
Discover the vibrant neighborhood of Boystown in Chicago, Illinois, a lively area known for its welcoming atmosphere and rich cultural history. Staying in this dynamic part of the city provides easy access to local events, diverse dining options, and a friendly community spirit. Whether you're seeking a lively nightlife or a quiet retreat, neighborhoods within Boystown offer a range of vacation rentals that cater to various preferences. Enjoy the authentic Chicago experience by choosing a strategic location in this prominent neighborhood, where comfort and convenience meet seamlessly for your upcoming visit.
Lakeview
In this vibrant area of Chicago, you'll find a lively atmosphere filled with diverse dining, entertainment, and nightlife options. Staying here offers convenient access to the city's main attractions while providing a comfortable base for exploring the region.
View 246+ Rentals in LakeviewLake View East
This sought-after neighborhood boasts a dynamic local scene with a variety of shops and cafes nearby, making it an ideal spot for experiencing the authentic charm of the city. Here, you can enjoy the convenience of being close to key destinations while relaxing in well-appointed vacation rentals.
View 64+ Rentals in Lake View EastBest Times to Visit Boystown
When should you plan your Vacation Rentals stay?
Choosing the ideal time to visit helps you experience this vibrant neighborhood at its best, whether you're seeking lively festivals or a quieter escape in this destination’s charming surroundings.
Peak Season Highlights
Summer (June to August)
During the warmest months, this destination experiences lively street festivals and outdoor events, making it an ideal time to stay in vacation rentals that offer vibrant city experiences.
Average Temperature Daytime: 78°F to 85°F - Nighttime: 65°F to 70°F
Fall (September to November)
Fall brings colorful foliage and a festive atmosphere, attracting visitors who want to enjoy the region’s mild weather while exploring local culture from their comfortable vacation rentals.
Average Temperature Daytime: 68°F to 75°F - Nighttime: 55°F to 60°F
Off-Season Highlights
Winter (December to February)
With colder temperatures, this time of year offers fewer crowds and better deals on vacation rentals, perfect for those seeking a quieter visit amid the winter charm of the area.
Average Temperature Daytime: 30°F to 40°F - Nighttime: 20°F to 30°F
Early Spring (March to April)
As the season transitions, the region sees fewer tourists. Vacation rentals often provide more availability and affordability, ideal for visitors looking to avoid peak crowds.
Average Temperature Daytime: 45°F to 55°F - Nighttime: 35°F to 45°F
Weekly Weather Forecast for Boystown
How to Book Your Boystown Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Boystown
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy access to a private outdoor patio or balcony for relaxing in the fresh air.
- Take advantage of communal gardens or green spaces nearby for outdoor activities.
- Make use of on-site grilling facilities for outdoor cooking experiences.
- Benefit from designated outdoor parking areas to conveniently explore the city.
- Discover outdoor seating areas for dining al fresco with friends or family.
- Access bicycle rentals or bike storage to explore the surrounding neighborhood.
- Relax in outdoor lounging zones that provide a comfortable space to unwind outdoors.
Top Attractions Around Boystown
What attractions are nearby?
Within this vibrant neighborhood, you can enjoy a variety of nearby activities, including exploring lively entertainment venues, dining at diverse restaurants, and experiencing the local culture that makes the area a unique destination for your stay.
Family Activities
- Lincoln Park Zoo: Enjoy a day exploring one of Chicago's most beloved free attractions, perfect for family members of all ages to observe animals in naturalistic habitats.
- Chicago Children's Museum: Engage your children's curiosity and creativity through interactive exhibits designed to inspire learning and fun here in the area.
Spend time outdoors with picnics and sports activities in this scenic urban park, offering a lively atmosphere for families to relax and play. - Lakefront Trail: Take a family stroll or bike ride along the picturesque lakeside path that offers stunning views of Lake Michigan and access to various beaches and parks in the region.
Adult Activities
- Exploring Boystown's vibrant nightlife: Immerse yourself in the lively bars, LGBTQ+ friendly venues, and entertainment options that make this area a hub for fun and community engagement.
- Dining at renowned restaurants: Savor diverse culinary experiences at some of the region’s most popular eateries, known for their welcoming atmospheres and eclectic menus.
- Enjoying cultural events and festivals: Attend local pride celebrations and seasonal festivals that highlight the area's rich history and vibrant culture, perfect for memorable experiences.
- Shopping in boutique stores and local markets: Browse unique shops and artisan markets that showcase the area's creative spirit and offer one-of-a-kind souvenirs.
Other Places to Stay in Boystown, IL
Our Lady of Mount Carmel Church
Flashy Trash
Boystown Travel Tips
How Can You Make the Most of Your Stay?
- Explore local dining and entertainment: Take advantage of the vibrant food scene and lively nightlife that make this area a favorite spot for visitors seeking authentic Chicago experiences.
- Plan ahead for popular attractions: While you won't find traditional tourist hotspots, scheduling your activities in advance ensures you enjoy the region’s best-kept secrets without missing out.
- Use public transportation or walk: Make the most of the area's walkability and transit options to easily access nearby neighborhoods and maximize your time exploring.
- Choose centrally located vacation rentals: Selecting accommodations near the heart of this neighborhood offers convenience and immersion into its unique local culture, enriching your stay.
Transportation Options
- Chicago Transit Authority (CTA) Train: The CTA train system offers convenient and affordable access to the area, making it easy to explore Chicago from your vacation rental.
- Bus Services: Local bus routes provide flexible transportation options throughout the region, connecting you directly to popular destinations nearby.
- Divvy Bike Share: With the bike-sharing program, you can enjoy a scenic ride around the neighborhood and neighboring districts at your own pace.
- Taxis and Rideshares: Taxis and rideshare services like Uber and Lyft offer quick and reliable door-to-door transportation within the city, ideal for spontaneous trips or late-night outings.
Local Customs Options
- Respectful LGBTQ+ Etiquette: Embrace the area's welcoming spirit by being openly respectful and supportive of local LGBTQ+ customs when visiting this vibrant neighborhood.
- Celebration of Diversity: Participate in or observe the colorful parades and community events that highlight the region's rich cultural diversity and inclusive traditions.
- Friendly Social Norms: Engage with residents and fellow visitors through friendly gestures and polite conversation, reflecting the area's open-minded atmosphere.
- Casual Street Style: Dress comfortably yet stylishly, aligning with the relaxed and expressive fashion often seen in the local scene here.
Frequently Asked Questions About Boystown?
1. What are the top vacation rentals in Boystown?
There are a lot of options in Boystown. If you plan on staying in the Boystown area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Boystown:
- The Sono Chicago
- Roscoe Village Inn -Guesthouse - Walk to Chicago's Wrigley Field
- Great Location-Beautiful Friendly Andersonville Neighborhood
- Magic Factory Loft 2West
- Single Family Home! Sleeps 8 Lincoln Park/Lakeview
- Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood
- Amazing Lincoln Park Rowhouse - Perfect for Groups, Reunions and Cubs Games!
- North Center - Modern, Safe, Family-Friendly, Solar-Powered Apartment
- 4BR Old Town Chicago Loft | Walk to Wells St
- Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field
2. How many vacation rentals have private pools in Boystown?
There are 6 vacation rentals with private pools near Boystown. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Boystown are best for families?
If you are looking for a family-friendly vacation home in Boystown, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Boystown:
4. How many Rentbyowner vacation rentals are available in Boystown?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 1737 in the Boystown area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Boystown.
5. What is the cancellation policy for vacation rentals in this area?
Cancellation policies can vary depending on the property owner. To ensure you understand the specific terms, please review the cancellation details listed on the property page or contact the owner directly before booking.
6. Are there any additional fees I should be aware of when booking here?
Additional fees such as cleaning fees, service charges, or security deposits are typically outlined in the property listing. Be sure to read the full description and fee details to avoid surprises during your booking process.
7. How do I confirm my reservation for a vacation rental in this destination?
Reservations are usually confirmed once you complete the booking process and receive a confirmation email. For any questions about your booking status, contacting the property owner or support team can provide further assistance.
8. What amenities are commonly available in vacation rentals here?
Most properties offer amenities like Wi-Fi, kitchen facilities, air conditioning, and laundry services. Specific amenities are listed on each property's page, so reviewing those details will help you find the best fit for your needs.
9. Is it possible to communicate directly with the property owner before booking?
Yes, many listings include options to message the owner directly. This is a good way to ask specific questions about the property, availability, or special requests before finalizing your booking.
Boystown Top Rated Vacation Rentals
Apartment
10.0(14 Reviews)
1 Bedroom
1 Bath
3 Guests
450 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
R9,219/Night
7 Nights - R64,542
Hotel
10.0(9 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Kitchen
- Air Conditioner
R9,504/Night
7 Nights - R66,533
Hotel
10.0(1 Review)
1 Bath
900 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Kitchen
R13,499/Night
7 Nights - R94,485
Hotel
10.0(1 Review)
1 Bath
710 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Kitchen
R9,993/Night
7 Nights - R69,957
R4,555/Night
7 Nights - R31,883
Bed & Breakfast
9.8(100 Reviews)
1 Bedroom
1 Bath
2 Guests
650 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
R7,046/Night
7 Nights - R49,326
Hotel
9.6(7 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
R9,039/Night
7 Nights - R63,277
R6,538/Night
7 Nights - R45,766
