
Vacation rentals in Oswego
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Top-rated vacation rentals in Oswego
Guests agree: these stays are highly rated for location, cleanliness, and more.

Spacious Historic Home in Downtown Plainfield
This stylish home is half a block from all the downtown restaurants, coffee shops, bakery, and a park/splash pad for kids and pet lovers. The home offers more than enough space with 3 bedrooms and 3 separate sitting rooms along with a dining room. The master bedroom even has it's own dressing room and coffee bar to make for some private morning coffee time. There are plenty of places to take walks near by. There is also an escape room venue and awe throwing at the end of the block. Enjoy!

Peaceful Private Coach-House in St. Charles
Enjoy our cozy and peaceful Coach-house , private entrance with everything you need for a wonderful stay. Newly renovated and updated throughout. Queen bed with mattress topper, studio area includes Smart TV, water station, Keurig coffee machine and quick-set lock. Even though you are less than a mile from downtown St. Charles and 4 miles to the Geneva train station you have a private area. You may see deer out your window overlooking the pool and tennis. Not suitable for children or pets.

Immaculate*1MiTrain*1GWifi*King*ParkFree*FullKitch
Popular, 2BR/1BA Garden unit. Near downtown Geneva. Hotel Baker 3mi, Equestrian Center 9mi, walk to Fox River Bike Trail, cinemas, bars. Metra Train (1 mi), restaurants, golf, shopping. New cookware, Keurig, kitchen appliances, French press, rice cooker, Insta pot, blender. Bike path 3 blocks. External security cameras at door & public coin laundry area. This unit contains a smoke detector, motion sensor and decibel monitoring device. Guests under 25+ yrs require owner approval.

AT YOUR SERVICE! Downtown Aurora River Facing Gem
Welcome to your cozy retreat in the heart of Downtown Aurora! This charming 1-bedroom apartment is perfect for up to 2 guests and offers a peaceful river view. The unit is complete with a full kitchen & is pet-friendly. Located steps from Hollywood Casino, Paramount Theatre, RiverEdge Park, and the scenic Riverwalk, you'll have easy access to local attractions. Stroll to restaurants, shops, and entertainment, making this the perfect base for exploring all that Downtown Aurora has to offer.

Nice, Private Ranch Home
Nice private ranch home in a quiet neighborhood. Fox River and the river bike trail are only 3 minutes away, Rush Copley Medical Center, lots of shopping and dining options within minutes, Phillips park zoo, and water park very close, major roadways to Chicago. 10 min, from downtown Aurora where you can find the Hollywood Casino, Paramount theatre, many shopping stores and you can enjoy a walk along the Fox river, Fox valley mall and the Chicago premium outlets mall are only 20min away.

Penthouse In The Historic Hobbs
Experience luxury and historic charm at the Penthouse in the Historic Hobbs. Built in 1892, and restored in 2023, this new one bedroom corner unit offers a panoramic view of the Aurora skyline. Cook a delicious meal in the fully stocked kitchen. Dine at the bespoke table in the window bay under the iconic onion dome. Relax on the cozy sofa and enjoy a movie on the big screen TV. Rest in the plush king-sized bed. This urban retreat is near coffee, shopping, art and entertainment.

Cozy 4-bedroom ranch - minutes from everything
Relax and have fun with the whole family at this peaceful place to stay. It is located within walking distance from US Route 34 in the middle of shopping centers such as Meijer, Jewels, Target, Walmart, great restaurants, bars, entertainment, hair and nail salons, gas stations, etc. There are 5 beds (1 king and 4 queens plus a queen-size air mattress and a twin pull-out bed) and 3 couches waiting for their guests. The house is cleaned and sanitized before every reservation.

Naperville/Aurora | Fenced Yard!
Our 3bd, 1.5ba house is perfect for a group of friends or family looking for a clean place in a safe neighborhood on the Naperville/Aurora border. There is plenty of space for 9 people to sleep comfortably (5 beds & a couple comfy couches), as well as 3 smart TVs, a gas grill & large, private, fully-fenced yard (including outdoor games), a desk space, & much more. Enjoy close access to main roads & many restaurants, stores, parks, & other places of need!

Quaint Oswego Downtown Bungalow
Enjoy Staying at this Downtown Oswego Charming Bungalow . Downtown Oswego .3 M Event Centers Venue 5126 - 2 M Norfolk Farm Weddings - 6.2 M Ashley Farm Events - 6.7 M Bear Cave Lake Events 4.4 M Fox River Trail - .4 M River Edge Park - 6.2 Miles Caterpillar Corporate - Montgomery 2.5 M (Interns/Rotations Welcome) Hospitals within 14 Miles Travel Clinicians Welcome! Rush-Copley Hospital Edwards Hospital Mercy Hospital Delnor Hospital

1 Bed w/ Full Kitchen A Mile From Downtown Oswego
Enjoy a stay within walking distance of 3 parks and about a mile from downtown Oswego and its quaint shopping area. Nestled in the middle of a great neighborhood, you'll feel safe and be able to enjoy a quick getaway or an extended stay. If you're interested in visiting Chicago, we're close enough for day trips to the city (about 45 miles) but far enough to save some money. You'll definitely have a great time here!

Quaint Batavia Coach House
The Coach House is located behind our house. It is a private and separate little house. It is located close to the river path and lots of restaurants. The upstairs is one big room that has 1 queen and 2 twin beds. The upstairs also has a full bath. The TV in main living area on first floor is not hooked up to cable, but you can log into all of your apps and have access to news via YouTube TV, Netflix, Prime etc.

Cozy Lakeview Studio with Private Access
Enjoy luxury and comfort in this cozy lakefront studio with a private entrance, attached to a home where the friendly hosts reside. The studio offers a plush queen bed, a kitchenette with a mini fridge, microwave, induction cooktop, and a full bathroom. Located in one of Naperville’s safest neighborhoods, it’s just moments from cafes, restaurants, markets, and a biking trail, with easy access to I-88.
Popular amenities for Oswego vacation rentals
Other great vacation rentals in Oswego

Private room in Elgin w/ Amenities & Hot Tub

Close to Riverwalk | Indoor Pool + Free Breakfast

A Touch of Country in the Burbs #2

Cozy Room

Aurora House • Room # 2 (Queen Bed)

Beautiful Home 1 Mile from Downtown

Room within a Cozy Cottage

E. Quiet room short - long term.
Frequently Asked Questions
Are there vacation rentals with a dedicated workspace in Oswego?
Yes! Work meets play with ease at over 20 vacation rentals in Oswego featuring dedicated workspaces. Stay connected and productive in your home away from home.
What are the most popular amenities for House Rentals in Oswego?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with a kitchen, over 10 homes with air conditioning, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there family-friendly vacation rentals in Oswego?
Oswego has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Oswego have wifi?
Absolutely! We offer over 10 house rentals with wifi in Oswego. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Oswego have free parking?
Absolutely! We offer over 10 house rentals with free parking in Oswego. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Oswego have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Oswego. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Oswego?
Four-legged friends are welcome in Oswego. Choose from more than 10 vacation rentals for guests traveling with pets.
How much does it cost to stay in house rentals in Oswego?
Experience the best of Oswego with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Destinations to explore
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- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Grant Park
- Navy Pier
- 875 North Michigan Avenue
- Humboldt Park
- Soldier Field
- Shedd Aquarium
- Guaranteed Rate Field
- The Field Museum
- Matthiessen State Park
- Wicker Park
- Oak Street Beach
- Lincoln Park Zoo
- Garfield Park Conservatory
- Frank Lloyd Wright Home and Studio
- Brookfield Zoo
- Museum of Science and Industry
- Willis Tower
- The 606
- Naval Station Great Lakes
- University of Chicago




