Best Vacation Homes in Boystown
12 Guests
4 Bedrooms
2 Bathrooms
Group Friendly
House
- Fireplace/Heating
- Air Conditioner
- Internet
AU $1,006/Night
For 7 Nights AU $7,046
699.65 ft²
2 Guests
1 Bedroom
1 Bathroom
Apartment
- Internet
- Child Friendly
AU $359/Night
For 7 Nights AU $2,515
1 Bedroom
1 Bathroom
Couples Retreat
Bed & Breakfast
- Fireplace/Heating
- Balcony/Terrace
- Parking
AU $196/Night
For 7 Nights AU $1,372
8 Guests
3 Bedrooms
2 Bathrooms
Group Friendly
House
- Fireplace/Heating
- Air Conditioner
- Internet
AU $404/Night
For 7 Nights AU $2,825
452.08 ft²
4 Guests
1 Bedroom
1 Bathroom
Apartment
- Private Pool
- Oceanfront
- Fireplace/Heating
AU $164/Night
For 7 Nights AU $1,149
900 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
AU $395/Night
For 7 Nights AU $2,766
1000 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
AU $505/Night
For 7 Nights AU $3,533
1000 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
AU $329/Night
For 7 Nights AU $2,306
Boystown Luxury Rentals
7000 ft²
14 Guests
5 Bedrooms
5 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
AU $6,401/Night
For 7 Nights AU $44,810
2497.23 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Free Cancellation
House
- Parking
- Internet
- Child Friendly
AU $5,312/Night
For 7 Nights AU $37,187
6000 ft²
16 Guests
4 Bedrooms
6 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
AU $4,992/Night
For 7 Nights AU $34,945
4294.8 ft²
26 Guests
6 Bedrooms
5 Bathrooms
House
- Private Beach
- Fireplace/Heating
- Ocean View
AU $4,863/Night
For 7 Nights AU $34,044
5000 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
AU $4,430/Night
For 7 Nights AU $31,008
10 Guests
4 Bedrooms
2 Bathrooms
Group Friendly
Apartment
- Fireplace/Heating
- Air Conditioner
- Internet
AU $3,687/Night
For 7 Nights AU $25,811
1575 ft²
2 Bathrooms
Family Friendly
Hotel
- Private Pool
- Fireplace/Heating
- Pool
AU $3,605/Night
For 7 Nights AU $25,238
3200 ft²
12 Guests
6 Bedrooms
4 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
AU $3,485/Night
For 7 Nights AU $24,395
Boystown Pet Friendly Vacation Rentals
1200 ft²
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
Apartment
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
AU $441/Night
For 7 Nights AU $3,089
495.14 ft²
2 Guests
1 Bedroom
1 Bathroom
Apartment
- Pet Friendly
- Parking
- Air Conditioner
AU $262/Night
For 7 Nights AU $1,837
1 Bedroom
1 Bathroom
Couples Retreat
Bed & Breakfast
- Pet Friendly
- Parking
- Internet
AU $161/Night
For 7 Nights AU $1,128
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
AU $346/Night
For 7 Nights AU $2,423
3498.27 ft²
20 Guests
6 Bedrooms
2 Bathrooms
Apartment
- Private Beach
- Fireplace/Heating
- Ocean View
AU $905/Night
For 7 Nights AU $6,336
1500 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
AU $613/Night
For 7 Nights AU $4,290
1000 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Ocean View
AU $777/Night
For 7 Nights AU $5,442
441 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Ocean View
AU $389/Night
For 7 Nights AU $2,722
Boystown Large Vacation Homes
10 Guests
2 Bedrooms
2 Bathrooms
Apartment
- Fireplace/Heating
- Air Conditioner
- Internet
AU $812/Night
For 7 Nights AU $5,685
1205.56 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Free Cancellation
Apartment
- Fireplace/Heating
- Pet Friendly
- Parking
AU $580/Night
For 7 Nights AU $4,060
800 ft²
14 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
AU $1,050/Night
For 7 Nights AU $7,349
2497.23 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Free Cancellation
Apartment
- Parking
- Air Conditioner
- Internet
AU $2,619/Night
For 7 Nights AU $18,337
969 ft²
10 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
AU $392/Night
For 7 Nights AU $2,745
1800 ft²
10 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
AU $888/Night
For 7 Nights AU $6,218
2700 ft²
12 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
AU $1,364/Night
For 7 Nights AU $9,545
1850 ft²
15 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
AU $1,370/Night
For 7 Nights AU $9,589
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 250+ 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 59+ 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 1712 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
450 ft²
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- Balcony/Terrace
AU $809/Night
For 7 Nights AU $5,661
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Kitchen
AU $791/Night
For 7 Nights AU $5,535
900 ft²
1 Bathroom
Family Friendly
Hotel
- Private Pool
- Fireplace/Heating
- Pool
AU $1,156/Night
For 7 Nights AU $8,091
710 ft²
1 Bathroom
Family Friendly
Hotel
- Private Pool
- Fireplace/Heating
- Pool
AU $820/Night
For 7 Nights AU $5,739
AU $379/Night
For 7 Nights AU $2,652
650 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Bed & Breakfast
- Fireplace/Heating
- Pool
- Balcony/Terrace
AU $586/Night
For 7 Nights AU $4,103
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
AU $752/Night
For 7 Nights AU $5,264
AU $500/Night
For 7 Nights AU $3,497
