Best Vacation Homes in Englewood
New
Apartment
10.0(1 Review)
3 Bedrooms
1 Bath
3 Guests
1600 ft²
Balcony/Terrace
Kitchen
Air Conditioner
Internet
US $162/Night
7 Nights - US $1,137
Apartment
10.0(5 Reviews)
3 Bedrooms
2 Baths
6 Guests
1496.18 ft²
Parking- Air Conditioner
- Internet
Child Friendly
US $686/Night
7 Nights - US $4,800
US $450/Night
7 Nights - US $3,150
House
9.8(7 Reviews)
4 Bedrooms
3 Baths
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $707/Night
7 Nights - US $4,949
Apartment
10.0(2 Reviews)
4 Bedrooms
3 Baths
8 Guests
2497.23 ft²
Hot Tub- Parking
- Air Conditioner
- Internet
US $405/Night
7 Nights - US $2,835
New
Apartment
8.0(13 Reviews)
1 Bedroom
1 Bath
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $197/Night
7 Nights - US $1,382
New
Apartment
3 Bedrooms
2 Baths
8 Guests
- Air Conditioner
- Internet
Pet Friendly- Child Friendly
US $323/Night
7 Nights - US $2,261
New
House
5 Bedrooms
1 Bath
9 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $117/Night
7 Nights - US $817
Englewood Luxury Rentals
Hotel
8.9(209 Reviews)
4 Baths
349.83 ft²
EV Charge Station- Parking
- Balcony/Terrace
- Air Conditioner
US $2,333/Night
7 Nights - US $16,331
New
House
5 Bedrooms
3 Baths
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $2,202/Night
7 Nights - US $15,413
House
5 Bedrooms
4 Baths
12 Guests
4004.17 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $1,539/Night
7 Nights - US $10,771
Apartment
5.7(4 Reviews)
4 Bedrooms
1 Bath
12 Guests
1097.92 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $1,000/Night
7 Nights - US $7,000
Apartment
9.7(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
1496.18 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $870/Night
7 Nights - US $6,090
House
10.0(20 Reviews)
5 Bedrooms
4 Baths
8 Guests
Ocean View- Balcony/Terrace
View- Kitchen
US $761/Night
7 Nights - US $5,325
House
9.2(22 Reviews)
6 Bedrooms
5 Baths
15 Guests
3600 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $722/Night
7 Nights - US $5,056
House
10.0(25 Reviews)
4 Bedrooms
3 Baths
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $714/Night
7 Nights - US $4,996
Englewood Pet Friendly Vacation Rentals
New
Condo
10.0(12 Reviews)
2 Bedrooms
2 Baths
6 Guests
1000 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $322/Night
7 Nights - US $2,256
Apartment
9.7(18 Reviews)
2 Bedrooms
2 Baths
8 Guests
1001.04 ft²
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $299/Night
7 Nights - US $2,093
Condo
1 Bedroom
1 Bath
- Kitchen
- Internet
- Pet Friendly
- Child Friendly
US $180/Night
7 Nights - US $1,259
Apartment
10.0(3 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $263/Night
7 Nights - US $1,844
Apartment
9.0(5 Reviews)
2 Bedrooms
1 Bath
5 Guests
796.53 ft²
- Parking
- View
- Air Conditioner
- Internet
US $183/Night
7 Nights - US $1,281
House
10.0(3 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $236/Night
7 Nights - US $1,653
Apartment
9.4(3 Reviews)
2 Bedrooms
1 Bath
4 Guests
700 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $250/Night
7 Nights - US $1,751
Apartment
7.4(3 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $223/Night
7 Nights - US $1,563
Englewood Large Vacation Homes
Apartment
1 Bedroom
1 Bath
16 Guests
- Air Conditioner
- Child Friendly
Security/Safety
US $173/Night
7 Nights - US $1,209
Apartment
10.0(1 Review)
6 Bedrooms
3 Baths
9 Guests
2098.96 ft²
Breakfast- Parking
- Balcony/Terrace
- Kitchen
US $377/Night
7 Nights - US $2,639
House
10.0(2 Reviews)
5 Bedrooms
2 Baths
18 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $476/Night
7 Nights - US $3,332
House
9.7(6 Reviews)
5 Bedrooms
3 Baths
12 Guests
1496.18 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $629/Night
7 Nights - US $4,404
Apartment
9.8(6 Reviews)
4 Bedrooms
2 Baths
10 Guests
1850 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $672/Night
7 Nights - US $4,701
House
9.2(14 Reviews)
3 Bedrooms
2 Baths
12 Guests
Oceanfront- Parking
- Ocean View
- Balcony/Terrace
US $677/Night
7 Nights - US $4,742
Apartment
8.8(10 Reviews)
3 Bedrooms
3 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $370/Night
7 Nights - US $2,593
Apartment
8.8(3 Reviews)
5 Bedrooms
3 Baths
12 Guests
2085 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $496/Night
7 Nights - US $3,472
Why Choose Rent By Owner for your Englewood 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 Englewood Vacation Rentals
Where are the best neighborhoods to stay in Englewood?
Discover the vibrant neighborhoods of Englewood, Chicago, Illinois, where each area offers a unique blend of community charm and local character. When choosing your stay, consider the different neighborhoods that provide convenient access to the city's attractions while offering authentic Chicago experiences. Whether you're seeking a lively atmosphere or a quieter retreat, Englewood's diverse neighborhoods ensure you'll find the perfect location for your vacation rental. Trust in reliable and seamless booking options to make your trip to Englewood memorable and stress-free, allowing you to focus on enjoying all that this dynamic area has to offer.
Greater Grand Crossing
This neighborhood offers a vibrant local atmosphere with easy access to the broader attractions of Chicago, making it an ideal choice for those seeking authentic city living. Staying here places you close to diverse dining and shopping options, enriching your experience in the region.
View 605+ Rentals in Greater Grand CrossingFuller Park
Known for its peaceful residential streets and green spaces, this area provides a quiet retreat while still being conveniently connected to the city's main attractions. It’s perfect if you prefer a relaxed environment during your stay in the region.
View 796+ Rentals in Fuller ParkBack of the Yards
With its historical ties to Chicago’s industrial past, this neighborhood offers an authentic urban experience, ideal for travelers interested in exploring the city’s rich heritage. Choosing accommodations here allows you to enjoy convenient access to local landmarks and community events.
View 390+ Rentals in Back of the YardsNew City
This lively district features a mix of cultural influences and modern amenities, making it a dynamic base for exploring all that the area has to offer. Staying in New City ensures you're close to diverse entertainment options and local hotspots, enhancing your visit.
View 427+ Rentals in New CityBest Times to Visit Englewood
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit will enhance your experience in this vibrant area, allowing you to enjoy its unique charm and local atmosphere at the best moments of the year.
Peak Season Highlights
Summer (June to August)
During the summer months, the region experiences warm weather that attracts travelers looking to enjoy outdoor activities and events.
Average Temperature Daytime: around 80-85°F - Nighttime: around 65-70°F
Fall (September to November)
Autumn offers mild temperatures and vibrant foliage, making it an ideal time for exploring local sights and enjoying seasonal festivals.
Average Temperature Daytime: around 70-75°F - Nighttime: around 55-60°F
Off-Season Highlights
Winter (December to February)
The winter months tend to be colder and quieter, providing a peaceful setting for those seeking a more relaxed visit.
Average Temperature Daytime: around 35-45°F - Nighttime: around 25-35°F
Spring (March to May)
Early spring sees fewer visitors, with cooler temperatures gradually warming up as nature begins to bloom in this area.
Average Temperature Daytime: around 50-60°F - Nighttime: around 40-45°F
Weekly Weather Forecast for Englewood
How to Book Your Englewood 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 Englewood
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
- Private outdoor patios or decks for relaxing and enjoying the fresh air
- Well-maintained gardens or landscaped yards to explore and unwind
- Outdoor dining areas equipped with tables and seating for al fresco meals
- Access to nearby parks or green spaces for outdoor activities
- Barbecue grills available for cookouts and gatherings in the open air
- Comfortable outdoor furniture designed for lounging and socializing
- Secure fencing around the property to ensure privacy and safety during outdoor activities
Top Attractions Around Englewood
What attractions are nearby?
In this vibrant area, you can enjoy a variety of nearby activities that showcase the local culture and community spirit, making it an ideal destination to explore while staying in your comfortable vacation rentals.
Family Activities
- Chicago Bird Collision Monitors: Enjoy a family-friendly visit to this engaging conservation program dedicated to protecting local bird populations in the area around Englewood.
- The Garfield Park Conservatory: Explore lush plant collections and interactive exhibits at this popular indoor botanical garden, perfect for a day of learning and fun for all ages in the region.
- Local Lakefront Parks: Spend quality time outdoors by visiting nearby parks along Lake Michigan, offering playgrounds, picnic areas, and scenic views ideal for family relaxation.
- Historic Englewood Community Tours: Discover the area's rich history on guided tours that showcase its vibrant cultural heritage and urban development stories tailored for family exploration.
Adult Activities
- Arts and Cultural Experience: Explore local galleries and art centers that showcase the vibrant creative scene unique to this part of Chicago.
- Historic Neighborhood Tours: Discover the rich history of Englewood through guided walking tours that highlight its cultural landmarks and heritage sites.
- Local Dining Experiences: Savor authentic regional cuisine at popular eateries and hidden gems in this area known for its diverse food scene.
- Parks and Outdoor Recreation: Relax or get active in nearby parks offering scenic views, walking trails, and outdoor activities perfect for unwinding in the region.
Other Places to Stay in Englewood, IL
St. Bernard Hospital
South Englewood
Englewood Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Dining Options: Take time to enjoy the area's diverse eateries to experience the authentic flavors unique to this vibrant destination.
- Plan Your Transportation: Familiarize yourself with public transit or nearby parking to effortlessly navigate and make the most of your stay in this region.
- Visit Nearby Neighborhoods: Spent some time exploring surrounding neighborhoods to discover hidden gems and gain a richer understanding of the local culture.
- Schedule Cultural Activities: Incorporate visits to community events or local galleries to immerse yourself in the area's artistic and cultural scene.
Transportation Options
- Chicago Transit Authority (CTA) Train: The CTA train system provides quick and reliable access to downtown Chicago and surrounding neighborhoods from your vacation rental in the area.
- Bus Services: Local bus routes operated by the CTA offer convenient transportation options for exploring here and reaching various destinations within the region.
- Ride-Sharing Services: Popular ride-sharing apps like Uber and Lyft are readily available, offering flexible and direct travel within this destination and nearby locations.
- Driving and Car Rentals: If you prefer autonomy, renting a car or using your own vehicle allows for easy exploration of the broader region at your own pace.
Local Customs Options
- Respect for Local History: You’ll find that residents value engaging with the area's rich history through community events and local museums, creating an authentic experience during your stay.
- Community Celebrations: Participating in neighborhood festivals and parades showcases the pride here and offers an excellent way to immerse yourself in the local culture.
- Dining Etiquette: When exploring here, it’s customary to enjoy soul food and regional specialties, embracing the culinary traditions that are central to the community’s identity.
- Public Courtesy: Politeness and respectful interactions are highly appreciated by locals, making your engagement during visits smooth and welcoming.
Frequently Asked Questions About Englewood?
1. What are the top vacation rentals in Englewood?
There are a lot of options in Englewood. If you plan on staying in the Englewood area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Englewood:
- Luxury Hyde Park Haven- Perfect for families and digital nomads. Pet Friendly.
- Gorgeous historic mansion on UChicago campus. Renovation with original detail.
- Modern Apt Near U of Chicago!
- Spacious 3BR on UChicago Campus & Hospitals Free Street Parking
- The En Bronze ~ 7mins To Dining & Downtown Chicago
- The Brown House - A luxurious UChicago Campus stay
- Lux New Hyde Park Apt by U Chicago, Museum of Science & Industry w/Peloton
- Spacious unit in historic gem
- High-end 2Bdrm Garden Apt. Where Comfort Meets Style
- Luxe Loft vibe –4BR/3BA Apt– King Suite-11 minutes from downtown-Families-Groups
2. Which vacation homes in Englewood are best for families?
If you are looking for a family-friendly vacation home in Englewood, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Englewood:
3. How many Rentbyowner vacation rentals are available in Englewood?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 471 in the Englewood 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 Englewood.
4. What is the cancellation policy for vacation rentals in Englewood, Chicago?
Cancellation policies vary by listing, so it’s important to review the specific terms outlined in the property description or contact the host directly to understand the refund options and deadlines.
5. How do I confirm my booking in this Chicago neighborhood?
Booking confirmation typically occurs once you complete the reservation process and receive a confirmation email from the host. Be sure to check your inbox and contact the host if you have any questions about your reservation.
6. Are there any house rules I should be aware of when staying in this area?
Each vacation rental has its own set of house rules which are detailed in the listing. It’s advisable to read these carefully before booking to ensure a smooth and enjoyable stay.
7. What amenities can I expect at vacation rentals near Chicago's Englewood area?
Amenities vary by property but often include essentials like Wi-Fi, kitchen access, and parking. For specific features, refer to the property listing or reach out directly to the host for clarification.
8. How close is the rental to local public transportation options in Chicago's Englewood neighborhood?
Location details regarding proximity to public transportation are listed in the property description. Contact the host if you need more precise information to plan your travel around the city efficiently.
Englewood Top Rated Vacation Rentals
House
8.3(12 Reviews)
6 Bedrooms
5 Baths
15 Guests
3196.88 ft²
- Parking
Pool- Balcony/Terrace
- View
US $657/Night
7 Nights - US $4,597
House
4 Bedrooms
3 Baths
10 Guests
- Breakfast
- Pool
- Air Conditioner
- Internet
US $988/Night
7 Nights - US $6,916
Apartment
1 Bedroom
1 Bath
2 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $213/Night
7 Nights - US $1,494
