Vacation rentals in Oswego

4.88 out of 5 average rating, 132 reviews

The interior of a large theater is showcased, featuring rows of red seats arranged in a sweeping curve. Ornate decorations adorn the walls, and a striking chandelier hangs from a vibrant ceiling, adding an element of grandeur to the space.

Home in Naperville

California King Bed | Fast Wi-Fi | 75" Smart TV

Our 3bd, 2.5ba house is perfect for a group of friends or family looking for a clean, modern place in a wonderful, quiet neighborhood. Built w/ cathedral ceilings, there is plenty of space for 10 people to sleep comfortably (6 beds & several comfy couches), as well as 3 smart TVs (w/ complimentary Hulu & Disney+), an indoor fireplace, a gas grill & large yard (including outdoor games), a desk space, & more. Enjoy close access to main roads & large stores (Costco, Walmart, hardware stores, etc.)!

4.98 out of 5 average rating, 197 reviews

A serene winter scene captures a waterfall cascading over rocks beneath a historic stone bridge. Surrounding trees are bare, and snow blankets the ground, creating a tranquil atmosphere. The water reflects the blue sky, while icicles hang from the rock formations along the stream.

Townhouse in Ottawa

Starved Rock Retreat w/hot tub & full-fenced yard!

Updated, 2-bedroom, 1 bathroom townhouse in a quiet neighborhood close to all amenities. This pet-friendly home features an open floor plan, deck with a year-round hot tub & seating area, along with a fully fenced-in yard. The main level also features a laundry room, two bedrooms (one room is an office/workout room) and full bathroom. Downtown Ottawa - 1.6 mile Starved Rock State Park - 14 mile Matthiessen State Park - 16 mile Buffalo Rock State Park - 5.8 mile Skydive Chicago - 4.7 mile

4.99 out of 5 average rating, 659 reviews

The exterior of the home features light-colored siding and red shutters, complemented by neatly trimmed shrubs. A stone pathway leads to a white front door, flanked by large windows that allow for ample natural light. Lush green grass surrounds the entrance.

Guest suite in Geneva

A Suite within a Cozy cottage in Geneva Illinois.

Cozy private suite in the lower level. Guests have the suite to themselves. The bathroom is adjacent to the room and is private. There is a small fridge, a coffee maker, and a microwave oven. We are in Geneva, Illinois. We are LGBTQ+friendly. Our space is ideal for shorter stays and visitors on the go . Not suitable for staycations. Quiet area. Hosts live on the upper level and guests pass through our space to get to the suite. In a bind we can accommodate a 3rd guest and a pet. Welcome.

4.86 out of 5 average rating, 125 reviews

An outdoor seating area features a circular firepit surrounded by sectional seating in bright red and dark wicker. A grassy yard extends beyond the patio, complemented by trees and a shed in the background. The sky is clear, enhancing the inviting outdoor space.

Home in Naperville

Dog Friendly Cozy North Naperville 3 BED/2 BA Home

Welcome to the Naperville Nest! Rare North Naperville opportunity to find a home suited for the whole family! Pets are more than welcome to enjoy the 1/2 acre fully fenced in yard. This is a a fully updated home minutes from Downtown Naperville, I-88 and many more exciting destinations in the Western Suburbs. You will feel at home whether you're inside or outside...each bedroom has it's own TV and the outdoor living includes natural gas firepit & grill/dining table...this home has it all!

4.87 out of 5 average rating, 140 reviews

The kitchen features dark wood cabinetry and a large marble-topped table, providing a functional space for meals. A black refrigerator stands beside a gas stove, while a mosaic tile backsplash adds texture. Kitchen utensils are neatly arranged on the countertop.

Home in Montgomery

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.

4.99 out of 5 average rating, 153 reviews

Apartment in Aurora

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.

4.91 out of 5 average rating, 106 reviews

A tall tree is viewed from below, showcasing a strong trunk with textured bark. Lush green leaves form a canopy that filters sunlight, creating a natural ceiling. The clear blue sky is visible through the branches, enhancing the outdoor ambiance.

Guesthouse in Oswego

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…

4.9 out of 5 average rating, 126 reviews

A spacious living area features polished wooden floors and large windows allowing natural light to illuminate the room. A light gray sofa is centered on a neutral area rug, accompanied by two blue accent chairs. A small side table and wall decor complete the inviting space.

Home in Oswego

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.

4.95 out of 5 average rating, 62 reviews

A private entrance to a residence is shown, featuring a white door with glass panels above the handle. The door is set against a light gray siding. A concrete step leads to the door, with a nearby exterior light fixture mounted on the wall.

Guest suite in Oswego

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!

4.92 out of 5 average rating, 298 reviews

A charming porch is seen, adorned with lush green vines and vibrant purple flowers climbing along the white railing. The surrounding greenery adds a natural touch, creating an inviting entryway to the house.

Guesthouse in Batavia

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.

Guest suite in Naperville

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.

4.95 out of 5 average rating, 431 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.

4.88 out of 5 average rating, 173 reviews

A clean, simple bathroom is presented with a white vanity and a light-colored countertop. A mirror above the sink reflects the room, and a white towel hangs conveniently on the nearby rack. A neutral color palette enhances the calming environment.

Apartment in Naperville

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.

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Popular amenities for Oswego vacation rentals

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Other great vacation rentals in Oswego

4.71 out of 5 average rating, 7 reviews

A modern kitchen setup features white cabinets with glass fronts and a hexagonal tile backsplash. A gas stove, microwave, and various utensils are visible. A round wooden table adorned with a decorative vase and a stack of magazines adds a touch of warmth to the space.

Home in Oswego

Your Unique Stay by the Tracks | LCP Collection

4.96 out of 5 average rating, 24 reviews

Guest suite in Joliet

Home Sweet Home

4.93 out of 5 average rating, 42 reviews

A neatly maintained bathroom corner features a white toilet beside a roll of toilet paper. A small, vibrant floral artwork adorns the wall, while a bright blue mat lies on the floor, adding a splash of color to the space.

Home in Aurora

Spacious family friendly home away from home

Guest suite in Plainfield

A functional kitchenette area is visible, featuring a countertop with a coffee maker and a selection of complimentary beverages. A large sofa is positioned in the background, providing a comfortable seating option. The area is complemented by decorative wall art and a waste bin.

4.87 out of 5 average rating, 82 reviews

Relaxing Suite with Independent Entrance

4.81 out of 5 average rating, 79 reviews

A spacious game room features a ping pong table, with paddles placed on the surface. Soft lighting illuminates the area, while seating is visible in the background. The walls have a plain finish, contributing to a modern and functional entertainment space.

Home in Oswego

Moxie - w/ Game Room- 4 Kings, Sleeps 15

5 out of 5 average rating, 34 reviews

The wooden ranch house features a welcoming facade with large windows and a stone fireplace. Surrounded by lush greenery, a stone pathway leads to the entryway, framed by wooden railings. The structure is nestled under the shade of mature oak trees, highlighting its serene setting.

Cabin in Sugar Grove

The Ranch

4.91 out of 5 average rating, 47 reviews

The kitchen area showcases modern cabinetry and sleek countertops, with a dining table set for four. Appliances include a stainless steel refrigerator and an oven, while natural light streams through the adjacent entry door, highlighting the inviting open layout.

Apartment in Warrenville

“The remote retreat”