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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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A serene riverside scene is captured, featuring calm waters that reflect the colors of a sunset. Lush greenery frames the image, with a large tree on the right and a grassy area leading to the riverbank. Clouds scatter softly across the sky.

Guest suite in Saint Charles

4.85 out of 5 average rating, 136 reviews

Cozy, Comfy, Close to Downtown

AlexisRating, 5 stars1 month ago

Absolutely loved staying here! I had to be nearby to help my best friend prepare for her wedding. Brooke was a great host and was very responsive. The space is so nice and I would absolutely stay here again. Thank you for the accommodations Brooke!

A path of stone steps leads through a garden adorned with greenery and colorful flowers towards the side of a two-story house. Large windows allow natural light to fill the interior. Mature trees provide a serene backdrop.

Villa in Ottawa

4.92 out of 5 average rating, 13 reviews

22min to Starved Rock: Ultimate Vacay Villa - 3891

TerumiRating, 5 stars3 weeks ago

Beautiful, spacious home. Had the amenities that were listed. Will need to bring shampoo, conditioner, shower gel, and extra rolls of toilet paper, and this is listed in the details. The home was spotless and welcoming for our executive team retreat. How to instructions were provided and worked perfectly. Grateful for this opportunity to share dedicated time with my team in a space that allowed everyone to have personal space even when sharing a room. The bedrooms are enormous and lovely.

A relaxing outdoor space is depicted at night, featuring a small artisan tiny house and a fire pit surrounded by several chairs. Warm light glows from within the tiny house, and smoke gently rises into the night sky, set against a backdrop of trees.

Guesthouse in Oswego

4.9 out of 5 average rating, 105 reviews

The Loft-Rustic Retreat and Sauna

TaraRating, 5 stars1 month ago

Sara’s place was exactly as described! It was clean and comfortable- very private. The sauna was such a nice luxury! We appreciated all of the little niceties - like coffee , candles, and beach towels for the sauna. It was near everything, but still on a quiet street. Sara was very responsive and friendly. She had great suggestions for breakfast and really made us feel at home. We’d definitely go back!

A welcoming living space is bathed in natural light, featuring large windows adorned with elegant curtains. A plush, tufted sofa with decorative pillows invites relaxation. Neutral walls complement the modern décor, which includes a sleek table and artwork, creating a harmonious atmosphere.

Home in Homewood

4.91 out of 5 average rating, 123 reviews

Peaceful & Private Hot Tub Vacation Home Getaway

YoshiRating, 5 stars1 month ago

This small quaint home packs a HUGE punch when it comes to amenities and that home away from home feel. We couldn't have asked for more in an airbnb during our stay in the Chicago area. From the kuerig, to the decor, to the hot tub to the amazing bathroom and shower, this Airbnb had everything we needed and everything we didn't even know we wanted. I would HIGHLY recommend this airbnb along with the amazing and attentive hosts to anyone traveling through the area.

Top guest favorite

A modern kitchen featuring a large island with seating for six, complemented by sleek cabinetry and stainless steel appliances. Natural light fills the space through a nearby window, and an adjacent dining area is visible, offering a blend of functionality and style.

Home in Avondale

5 out of 5 average rating, 11 reviews

Alluring Avondale Abode

MichaelRating, 5 stars1 week ago

Beth’s home was perfect for our group trip, which centered around cooking together for a Passover Seder! The kitchen had great appliances and equipment, with the space for many of us to cook at once. The house had everything we needed and we were all comfortable.

Vacation rentals for every style

Get the amount of space that is right for you

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Hotels

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Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Oswego vacation rentals

Free parking on premises

Air conditioning

Stay near Oswego's top sights

Meijer5 locals recommend

Fox Valley Winery Inc5 locals recommend

GQT Kendall 11 GDX4 locals recommend

Fox Bend Golf Course3 locals recommend

Village Grind Coffee & Tea Co3 locals recommend

Saw Wee Kee Park3 locals recommend

Other great vacation rentals in Oswego

Top guest favorite

A spacious living area features comfortable seating arranged around a central coffee table. A wall-mounted TV is visible above a white fireplace. Soft lighting is provided by a contemporary chandelier, and large windows are dressed with light curtains, enhancing the room's bright ambiance.

Home in Schaumburg

5 out of 5 average rating, 51 reviews

Great location-King beds-Kids playroom

AdamRating, 5 stars2 weeks ago

Ninna's place was fantastic! It was exactly as described, and the process was proactive. Ninna communicated very well and anticipated questions we may have. We had friends from the area join us for dinner, and Ninna was accommodating of that request. Her place was perfect, with everything we may need during our stay. The kitchen was stocked with all the things we needed, and the coffee nook was a nice touch! The kids enjoyed the little playroom upstairs, and the mattresses were very comfortable.

A concrete pathway leads to a grassy area, bordered by a white fence, with several planters on both sides. The planters include a tall, woven design and a smaller, elegant style, featuring greenery that adds a touch of nature to the outdoor space.

Guest suite in Plainfield

4.86 out of 5 average rating, 78 reviews

Relaxing Suite with Independent Entrance

CindyRating, 5 stars4 days ago

Maria’s place was great! Easy access to the Airbnb & the yard was a bonus for our two dogs. Lots of little touches that made the stay pleasant; coffee, water, snacks were all appreciated. The bed was very comfortable too! I would definitely stay again when in the area.

A modern living space is presented with a white sofa and two accent chairs, arranged around a minimalist coffee table. A dining area is visible in the background, featuring a gold and glass table set with decorative items. Natural light filters in through large windows.

Home in Chicago

5 out of 5 average rating, 5 reviews

Birthday?Anniversary?Showers?3500 sq ft, sleeps 16

ArissRating, 5 stars1 week ago

Vince’s place was amazing, it was such a good location, easy to drive to anywhere in Chicago. Vince was very easy to contact and was responsive within minutes. He made our stay very comfortable. The house was amazing and there was a lot of space, and there was a lot of amenities available for use, for example kitchen utensils and shower amenities. Overall this stay was amazing and I would book this again if I came back in the future

A cozy living area is presented, featuring a stone fireplace as a focal point. Two armchairs are positioned around a coffee table, with decor additions providing a touch of greenery. Natural light enters through nearby windows, illuminating the light-colored walls and hardwood floors.

Apartment in Albany Park

4.86 out of 5 average rating, 42 reviews

Elegant 4Bedroom with Free Parking in Albany Park

MatthewRating, 5 stars2 months ago

Wonderful stay as always, thank you so much!

A modern kitchen is equipped with sleek stainless steel appliances, including a microwave and dishwasher. Light countertops complement dark cabinetry, while a small countertop with two barstools provides a casual dining option. Natural light filters in through a window near the door.

Apartment in Jefferson Park

4.63 out of 5 average rating, 24 reviews

City Gem: Stylish 3BR for Urban Explorers

AnnikaRating, 5 stars3 weeks ago

Peaceful, felt like home, very spacious and comfortable

Top guest favorite

A modern kitchen features sleek gray cabinetry and a white countertop. Stainless steel appliances are prominent along the back wall, and a window provides natural light over a farmhouse sink. Decorative tile backsplash adds texture, complemented by ample space for meal preparation.

5 out of 5 average rating, 22 reviews

Little Blue House

BriannaRating, 5 stars3 months ago

Alex is a great host! Dog friendly places are hard to find and his place made my dog feel super comfortable. Love this place and definitely will be back.

Top guest favorite

A modern kitchen area features a white bar counter with four dark wooden stools. Minimalistic tableware is arranged on woven placemats. Large windows allow natural light to fill the space, showcasing a glimpse of the outdoors through the decorative glass door.

Home in Lombard

5 out of 5 average rating, 25 reviews

Spacious Home in Chicago Suburbs

JenniferRating, 5 stars1 week ago

It was great! The house was lovely and looked newly renovated. It was much roomier than I expected. The beds were very comfortable.

The entrance features a wooden front deck with a single teal chair near lush greenery, creating a serene outdoor space. A concrete pathway leads to the deck, surrounded by vibrant shrubs and small flowering plants.

Home in Marseilles

5 out of 5 average rating, 3 reviews

Country Living At Granny’s Place

CullieRating, 5 stars30 months ago

I could not have asked for a better person to rent from Got a great personality very helpful And a very beautiful and quiet property If I’m in the area and it’s available I will definitely book it Thanks lisa

Quick stats about vacation rentals in Oswego

Total rentals
30 properties
Nightly prices starting at
ﺩ.ﺇ147 before taxes and fees
Total number of reviews
1.4K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace

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.
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.
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.

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