Best Vacation Homes in Old Town Triangle
Apartment
9.8(6 Reviews)
2 Bedrooms
2 Baths
6 Guests
Fireplace/Heating
Pet Friendly
Kitchen
Air Conditioner
US $540/Night
7 Nights - US $3,779
Apartment
10.0(1 Review)
2 Bedrooms
1 Bath
5 Guests
947.22 ft²
- Fireplace/Heating
- Air Conditioner
Internet
Child Friendly
US $90/Night
7 Nights - US $630
Bed & Breakfast
10.0(517 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
Balcony/Terrace
Parking- Air Conditioner
US $339/Night
7 Nights - US $2,375
Condo
Walk to Lincoln Park, North Avenue Beach, and Second City! Lovely Old Town Charm! by AllSet Turnover
9.4(27 Reviews)
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $447/Night
7 Nights - US $3,130
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $371/Night
7 Nights - US $2,598
Condo
9.0(25 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $621/Night
7 Nights - US $4,347
Apartment
8.8(5 Reviews)
2 Bedrooms
1 Bath
5 Guests
950 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $371/Night
7 Nights - US $2,597
House
8.4(43 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $622/Night
7 Nights - US $4,353
Old Town Triangle Luxury Rentals
Condo
9.6(4 Reviews)
8 Bedrooms
4 Baths
16 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $1,690/Night
7 Nights - US $11,830
House
10.0(14 Reviews)
6 Bedrooms
6 Baths
32 Guests
4000 ft²
Hot Tub- Fireplace/Heating
Ocean View- Balcony/Terrace
US $1,644/Night
7 Nights - US $11,508
House
10.0(57 Reviews)
5 Bedrooms
7 Baths
12 Guests
6200 ft²
Spa- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,580/Night
7 Nights - US $11,060
Apartment
10.0(75 Reviews)
4 Bedrooms
3 Baths
15 Guests
2500 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $1,467/Night
7 Nights - US $10,272
House
9.6(5 Reviews)
4 Bedrooms
4 Baths
18 Guests
3003.13 ft²
- Spa
- Fireplace/Heating
- Balcony/Terrace
View
US $1,199/Night
7 Nights - US $8,393
House
8.3(3 Reviews)
5 Bedrooms
4 Baths
22 Guests
3003.13 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
Breakfast
US $1,191/Night
7 Nights - US $8,335
House
10.0(19 Reviews)
3 Bedrooms
3 Baths
14 Guests
2400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $1,087/Night
7 Nights - US $7,606
House
9.8(27 Reviews)
4 Bedrooms
3 Baths
12 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,084/Night
7 Nights - US $7,586
Old Town Triangle Pet Friendly Vacation Rentals
House
10.0(5 Reviews)
3 Bedrooms
2 Baths
14 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $542/Night
7 Nights - US $3,792
House
9.5(30 Reviews)
4 Bedrooms
3 Baths
14 Guests
1496.18 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Breakfast
US $852/Night
7 Nights - US $5,966
House
9.8(140 Reviews)
3 Bedrooms
2 Baths
6 Guests
2000 ft²
Oceanfront- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $447/Night
7 Nights - US $3,126
House
4.0(2 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $878/Night
7 Nights - US $6,148
House
9.8(109 Reviews)
4 Bedrooms
4 Baths
18 Guests
3000 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,017/Night
7 Nights - US $7,117
House
9.4(113 Reviews)
5 Bedrooms
3 Baths
22 Guests
3000 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $899/Night
7 Nights - US $6,294
House
9.2(71 Reviews)
4 Bedrooms
2 Baths
14 Guests
1500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $777/Night
7 Nights - US $5,442
House
8.4(21 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $810/Night
7 Nights - US $5,671
Old Town Triangle Large Vacation Homes
Apartment
10.0(7 Reviews)
6 Bedrooms
3 Baths
12 Guests
3000 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $1,001/Night
7 Nights - US $7,008
Bed & Breakfast
9.3(345 Reviews)
11 Bedrooms
10 Baths
29 Guests
319.33 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $366/Night
7 Nights - US $2,562
Apartment
10.0(38 Reviews)
4 Bedrooms
2 Baths
13 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $881/Night
7 Nights - US $6,165
House
8.8(12 Reviews)
1 Bedroom
2 Baths
14 Guests
1194.79 ft²
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $1,030/Night
7 Nights - US $7,210
Apartment
9.8(15 Reviews)
4 Bedrooms
1 Bath
12 Guests
21528 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $714/Night
7 Nights - US $4,997
House
5 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $1,248/Night
7 Nights - US $8,735
Condo
9.8(31 Reviews)
3 Bedrooms
2 Baths
10 Guests
2400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $539/Night
7 Nights - US $3,773
House
4.8(5 Reviews)
4 Bedrooms
3 Baths
10 Guests
- Air Conditioner
- Child Friendly
Laundry
Bedding/Linens
US $814/Night
7 Nights - US $5,698
Why Choose Rent By Owner for your Old Town Triangle 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 Old Town Triangle Vacation Rentals
Where are the best neighborhoods to stay in Old Town Triangle?
When choosing where to stay in Chicago’s Old Town Triangle, you’ll find a neighborhood rich in charm and vibrant local culture. This area offers a variety of appealing options for those seeking a convenient and authentic experience in the Windy City. Carefully selecting your vacation rentals here allows you to enjoy easy access to the neighborhood's unique character while benefiting from the dependable and seamless booking experience that trustworthy accommodations provide. Whether you're exploring the historic streets or simply soaking in the lively atmosphere, Old Town Triangle makes for an ideal base for your Chicago adventure.
Downtown Chicago
Staying near the heart of the city places you close to vibrant attractions and world-class amenities, making it an ideal choice for exploring Chicago's dynamic urban scene.
View 1317+ Rentals in Downtown ChicagoLincoln Park
This neighborhood offers a blend of natural beauty and lively city life, providing a peaceful yet engaging environment just minutes from the area's top cultural destinations.
View 131+ Rentals in Lincoln ParkBest Times to Visit Old Town Triangle
When should you plan your Vacation Rentals stay?
Choosing the right time to visit this charming destination can enhance your experience, as seasonal changes and local events influence the best periods for booking exceptional vacation rentals in the area.
Peak Season Highlights
Summer (June to August)
During the summer months, this area experiences warm weather and lively outdoor events, making it an ideal time to explore local attractions and enjoy pleasant daytime temperatures.
Average Temperature Daytime: 80°F - 85°F - Nighttime: 65°F - 70°F
Fall (September to November)
Fall brings cooler temperatures and vibrant foliage, perfect for leisurely strolls through this destination's charming streets and cultural activities.
Average Temperature Daytime: 70°F - 75°F - Nighttime: 55°F - 60°F
Off-Season Highlights
Winter (December to February)
The winter months see fewer visitors as colder weather settles in, offering a peaceful atmosphere and lower prices for your stay here.
Average Temperature Daytime: 30°F - 40°F - Nighttime: 20°F - 30°F
Spring (March to May)
Early spring features mild weather and blooming gardens, providing a quieter time to experience the region’s local charm before the summer rush begins.
Average Temperature Daytime: 50°F - 60°F - Nighttime: 40°F - 50°F
Weekly Weather Forecast for Old Town Triangle
How to Book Your Old Town Triangle 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 Old Town Triangle
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 a private outdoor patio or garden space to relax and unwind after exploring the area.
- Take advantage of on-site outdoor seating areas perfect for dining al fresco in the vibrant neighborhood.
- Make the most of shared courtyards or communal gardens commonly available in properties here.
- Benefit from convenient parking options with dedicated outdoor parking spaces or garages.
- Utilize outdoor grilling facilities to host barbecues during your stay in this lively part of the city.
- Relax on balconies or terraces that overlook the charming streets of this historic district.
- Access bike storage or rental options ideal for exploring the surrounding region on two wheels.
Top Attractions Around Old Town Triangle
What attractions are nearby?
In this vibrant area, you can enjoy a variety of activities nearby, including exploring charming shops, indulging in local dining experiences, and discovering cultural events—all just moments from your vacation rentals in Old Town Triangle, Chicago.
Family Activities
- Chicago History Museum: Dive into the rich history of the city through interactive exhibits and family-friendly activities in this renowned museum located in the area.
- Oz Park: Enjoy a relaxing day outdoors at this scenic park featuring whimsical Oz-themed sculptures that captivate children and adults alike.
- Cabbage Patch Kids Market & Cafe: Explore local artisan crafts and indulge in kid-friendly treats within walking distance, making it a perfect stop for families exploring here.
- Old Town Art Center: Participate in creative workshops and discover local art in a welcoming environment designed for family engagement in this lively neighborhood.
Adult Activities
- Art Institute of Chicago Tours: Explore world-renowned artworks and enjoy exclusive access to inspiring exhibitions in this cultural landmark.
- Coffee Tasting at Local Cafés: Savor expertly brewed coffees at the area's charming cafés, perfect for a relaxing break during your stay.
- Shopping in Boutique Stores: Discover unique fashion and handcrafted goods in the neighborhood’s boutique shops, ideal for leisurely afternoons.
- Walking Historic Streets: Stroll through tree-lined avenues filled with historic architecture that beautifully showcases the region’s rich heritage.
Other Places to Stay in Old Town Triangle, IL
Second City
Chicago History Museum
Park West
Old Town
Old Town Triangle Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Dining and Shops: Take advantage of the charming eateries and boutique shops that line the streets, immersing yourself in the authentic neighborhood atmosphere.
- Visit Iconic Neighborhood Events: Check the local calendar for any festivals or community gatherings to experience the area's vibrant culture during your stay.
- Discover Nearby Parks and Green Spaces: Enjoy the outdoor tranquility by visiting parks within walking distance, perfect for relaxing or picnicking in this scenic region.
- Utilize Public Transportation Options: Make use of convenient transit services to effortlessly explore the broader city while avoiding the hassle of driving in this bustling destination.
Transportation Options
- Chicago Transit Authority (CTA) Trains: The CTA Blue and Brown Lines provide quick and convenient access from the area to downtown Chicago and other neighborhoods.
- Bus Services: Multiple bus routes operate through here, making it easy to reach key attractions and amenities within the city without a car.
- Divvy Bike Rentals: You can rent bikes easily from nearby stations to explore the region at your own pace along scenic streets and trails.
- Taxi and Rideshare Services: Reliable options like taxis and rideshare apps are readily available for comfortable and direct transportation around here and beyond.
Local Customs Options
- Historic Preservation:** Respect for the area's architecture and history is a key aspect of local customs, so you’ll find residents value maintaining the charm of their neighborhood.
- Greeting Etiquette:** Warm and friendly greetings are common here, reflecting the community’s welcoming spirit whenever you interact with locals.
- Dining Etiquette:** When enjoying meals at local eateries, it's customary to be courteous and patient, especially during busy hours in this vibrant part of the city.
- Community Engagement:** Participating in neighborhood events or supporting local businesses demonstrates appreciation for the close-knit community here.
Old Town Triangle Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Old Town Triangle?
There are a lot of options in Old Town Triangle. If you plan on staying in the Old Town Triangle area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Old Town Triangle:
- The Sono Chicago
- Large 4BR/3BA Safe Old Town Location Walk Everywhere
- Luxury House in the heart of Old Town with Parking
- Luxury SOHO Styled Two-Level Townhouse - Old Town
- THE COMPOUND Large Exquisite House Private Yard 'Best Location' Well Appointed
- GROUP LUX in Old Town/Gold Coast (+private roof)
- Ideal Group Getaway: Prime Location, Parking, Backyard, Sunroom & Pet-Friendly
- Walk to Lincoln Park, North Avenue Beach, and Second City! Lovely Old Town Charm! condo
- MTM Fully Furnished Rental in Old Town - 2 beds
- A home away from home!
2. Which vacation homes in Old Town Triangle are best for families?
If you are looking for a family-friendly vacation home in Old Town Triangle, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Old Town Triangle:
3. How many Rentbyowner vacation rentals are available in Old Town Triangle?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 84 in the Old Town Triangle 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 Old Town Triangle.
4. What is the cancellation policy for a vacation rental in Old Town Triangle, Chicago?
Cancellation policies vary by property. You should review the specific listing details or contact the host directly to understand the terms regarding cancellations, refunds, and any applicable fees.
5. Are there any additional fees I should be aware of when booking a vacation rental here?
Additional fees such as cleaning, service charges, or taxes may apply depending on the listing. It’s recommended to check the detailed listing information or communicate with the property owner for clarity on any extra costs.
6. How do I confirm my reservation at a vacation rental in this region?
Reservation confirmation typically occurs after you complete the booking process and receive a confirmation email. Be sure to read the listing instructions carefully, and reach out to the host if you need further assistance.
7. Can I modify or cancel my booking once it's confirmed?
Modifications or cancellations are subject to the host’s policies outlined in the listing. Review these policies before booking and contact the host directly if you need to make changes or cancel your reservation.
8. What amenities are usually included in vacation rentals in this area?
Amenities vary between properties, but common features include Wi-Fi, kitchen facilities, and laundry services. For specific amenities, always check the detailed property description or contact the owner directly.
