Holiday rentals in Oswego

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!

4.96 out of 5 average rating, 338 reviews

Guest suite in West Town

Secret Garden @ The Noble Farmhouse | Wicker Park

EliRating, 5 stars2 weeks ago

Great cozy spot near Wicker Park, Chicago. Easy check in and heather held our bags after check out before our flight. Be aware that this unit does not have a stove. Microwave and toaster oven were useful, though!

4.92 out of 5 average rating, 13 reviews

Villa in Ottawa

22min to Starved Rock: Ultimate Vacay Villa - 3891

TerumiRating, 5 stars4 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.

4.9 out of 5 average rating, 105 reviews

Guest house in Oswego

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!

4.91 out of 5 average rating, 123 reviews

Home in Homewood

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.

5 out of 5 average rating, 11 reviews

Home in Avondale

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.

Holiday rentals for every style

Get the amount of space that is right for you

Houses

A space that's all yours, with room for everyone

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Oswego holiday rentals

Kitchen

Wifi

Pool

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 holiday rentals in Oswego

5 out of 5 average rating, 51 reviews

Home in Schaumburg

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.

Guest suite in Plainfield

4.86 out of 5 average rating, 78 reviews

Relaxing Suite with Independent Entrance

CindyRating, 5 stars5 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.

5 out of 5 average rating, 5 reviews

Home in Chicago

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

4.86 out of 5 average rating, 42 reviews

Flat in Albany Park

Elegant 4Bedroom with Free Parking in Albany Park

MatthewRating, 5 stars2 months ago

Wonderful stay as always, thank you so much!

4.63 out of 5 average rating, 24 reviews

Flat in Jefferson Park

City Gem: Stylish 3BR for Urban Explorers

AnnikaRating, 5 stars4 weeks ago

Peaceful, felt like home, very spacious and comfortable

5 out of 5 average rating, 22 reviews

Home in Elgin

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.

5 out of 5 average rating, 25 reviews

Home in Lombard

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.