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.

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Top guest favorite
A spacious bedroom features a queen bed dressed in crisp white linens, accompanied by decorative pillows. Soft lighting is provided by a bedside lamp, while an accent rug adds warmth to the wood floor. A built-in shelf displays various decorative items.
Guest suite in Saint Charles
5 out of 5 average rating, 300 reviews

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.

Guest favorite
A modern kitchen features dark cabinetry complemented by granite countertops. Stainless steel appliances, including a refrigerator and stove, are present. Two bar stools with circular bases are positioned near the countertop. Pendant lights hang above the island, adding functional illumination to the space.
Apartment in Aurora
4.84 out of 5 average rating, 98 reviews

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.

Guest favorite
A single-story ranch home is presented with a dark blue exterior and white shutters. A neatly trimmed lawn and concrete pathway lead to the front door. Flanking the entrance, small shrubs add greenery, while a tall evergreen tree stands nearby.
Home in Montgomery
4.87 out of 5 average rating, 155 reviews

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.

Top guest favorite
A bedroom features hand-painted floral murals on the walls, complemented by light-colored curtains framing a window. A spacious bed with white linens is centered on a patterned floor. A cozy sitting area with a dark wicker chair adds to the comfort of the space.
Home in Geneva
4.95 out of 5 average rating, 120 reviews

The Secret Garden

Summer is COOLER in Geneva! Located just 3 blocks from shops and restaurants in beautiful, downtown Geneva. Our space can sleep up to 4 comfortably. We offer amazing amenities like plush bed & linens, array of coffee and teas and goodies, 50" flat screen smart tv for watching movies after a day of fun in Geneva. Beautiful bath equipped with everything, including homemade salt scrub. A secure, separate entrance to come & go. It is a basement soace so ceilings are lower than average home.

Top guest favorite
A spacious living area features a corner sectional sofa with soft cushioning and a cozy throw. Large windows provide natural light and city views. A simple coffee table sits in front, with light-colored carpet underfoot, enhancing the comfortable atmosphere.
Apartment in Aurora
4.98 out of 5 average rating, 197 reviews

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.

Guest favorite
A spacious room is highlighted by a patterned bedspread on a comfortable bed, with a wooden headboard. A flat-screen television is mounted on the wall, and a small kitchen area with bar stools is visible. Natural light enters through a window, enhancing the inviting space.
Guesthouse in Oswego
4.91 out of 5 average rating, 107 reviews

The Loft-Rustic Retreat and Sauna

This unique space features a beautiful relaxing yard space and easy walking distance to downtown Oswego.. If you need a place to work quietly or stay overnight this is the ideal location to get rest and relaxation, as well as, enjoy the local tranquilities. Antique shopping, River adventures, Bike trails, and more! The Fox River Trail is a few blocks from the Loft and goes North all of the way up to Algonquin. Along the trail is the River where you can tube, kayak, canoe, fish…

Superhost
A light-filled living area is presented with a soft blue couch and a glass coffee table atop a textured rug. A comfortable armchair complements the seating arrangement. French doors lead to an outdoor deck, enhancing the connection with nature.
Townhouse in Yorkville
4.79 out of 5 average rating, 154 reviews

Riverfront Townhome in Downtown Yorkville

➢ Everything is sanitized/washed/cleaned after every guest ➢ Right on Fox river ➢ Raging Waves Waterpark - 4.1mi ➢ Yak Shack (Canoe & kayak rental) - 0.8mi ➢ Saw Wee Kee Park - 6mi ➢ Fast, Dedicated Wifi ➢ Free parking in attached garage for 2 compact-size cars + additional free parking onsite. ➢ 3 Smart TVs (Living Room, Bedrooms) ➢ Fully equipped + stocked kitchen / bathroom / laundry ➢ Located Downtown Yorkville ➢ Pack 'n Play ➢ High chair ➢ Kurig coffee maker ➢ King size beds

Guest favorite
A spacious living room features a large sectional sofa and two blue upholstered chairs, arranged around a black coffee table on a light area rug. A flat-screen TV is mounted on the wall, flanked by shelves with decorative items. Natural light enters through large windows with sheer curtains.
Home in Oswego
4.9 out of 5 average rating, 136 reviews

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.

Guest favorite
The cottage exterior is surrounded by lush green grass and mature trees, providing a peaceful setting. A pathway leads to the inviting porch with pleasant lighting. The sunset casts a warm glow, enhancing the tranquil atmosphere of the setting.
Home in Big Rock
5 out of 5 average rating, 18 reviews

Riverside Cottage

Peaceful two bedroom cottage newly refurbished. Plenty of outdoor space, woods streams and walking trails nearby. Tucked out of the way of busy roads or city life but only a short drive to all the amenities of civilization. Keep an eye out for deer, ducks, beavers, hawks and other scenic wildlife out the back window/patio. There’s even a couple bald eagles that live nearby. Consider a longer stay to take advantage of discounts on 2, 4 or 7 night stays

Top guest favorite
A functional kitchen area features wooden cabinetry and modern appliances. Ample countertop space is complemented by tile flooring. A small dining table with chairs is positioned near a window, allowing natural light to illuminate the space. A doorway leads to a cozy bedroom.
Guest suite in Oswego
4.96 out of 5 average rating, 72 reviews

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!

Top guest favorite
A tranquil lake scene is depicted, featuring autumnal trees reflecting vibrant hues of yellow, orange, and red in still water. The grassy shoreline enhances the serene environment, while neighboring greenery contributes to the picturesque landscape.
Guest suite in Naperville
4.96 out of 5 average rating, 473 reviews

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.

Guest favorite
A cozy living area is presented, featuring a comfortable sofa with decorative cushions and a matching ottoman. Two lamps provide soft lighting, and a large mirror reflects the space. A textured area rug defines the seating arrangement, with stair access visible in the background.
Apartment in Downtown Naperville
4.87 out of 5 average rating, 180 reviews

Comforts of home in downtown Naperville

Cozy 1 bedroom garden level apartment located in downtown Naperville. Short walking distance to great shopping and many fine restaurants. Also short walking distance to train which goes directly to Chicago. Parking is available for 1 car in driveway. Professionally cleaned after every guest visit, as well as free cleaning offered for stays of two weeks or longer.

Popular amenities for Oswego vacation rentals

When is the best time to visit Oswego?

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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 free parking, over 10 homes with air conditioning, 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.

Quick stats about vacation rentals in Oswego

  • Total vacation rentals

    Explore 30 vacation rentals in Oswego

  • Nightly prices starting at

    Oswego vacation rentals start at ﺩ.ﺇ147 per night before taxes and fees

  • Verified guest reviews

    Over 1,530 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Oswego vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Oswego rentals

  • 4.8 Average rating

    Oswego stays are highly rated by guests—averaging 4.8 out of 5!

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