Holiday rentals in Oswego

Guest suite in Saint Charles

4.85 out of 5 average rating, 137 reviews

Cozy, Comfy, Close to Downtown

CarolRating, 5 stars4 days ago

I needed a place to recuperate from sinus surgery, peaceful, comfortable and pet friendly. My husband and I could prepare meals, go for walks or bike along the River. There are ducks in the back yard that are cute and like veggies. Our hosts made us feel very welcome. I would go back again without a second thought. The area is safe and friendly with lovely old homes. Downtown is easy to get to and Geneva is nearby with many enchanting shops and restaurants. Many located in old homes. They is also laundry access in the apartment which is very handy since we were there about a week and a half.

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!

5 out of 5 average rating, 11 reviews

Home in Avondale

Alluring Avondale Abode

MichaelRating, 5 stars2 weeks 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.

4.85 out of 5 average rating, 68 reviews

Home in Austin

A Comfortable Stay While You are Away in Oak Park

KarenRating, 5 stars2 weeks ago

The house looked just like the beautiful photos & Jay was incredibly responsive throughout the visit. This home is located close to 290 to go downtown or further out to the 'burbs quickly. We needed a home to stay last minute, and Jay was accommodating to that as well - we were happy to find this spot with all the space we needed inside and out. As a bonus, we met neighbors who were very friendly.

4.85 out of 5 average rating, 34 reviews

Guest house in Evanston

Tiny house in West Village Arts District

JoelRating, 5 stars3 months ago

Lisa was a great host and this is a great place. It's a small house, but worked great for what we needed it for and was close to our family that live in Evanston. It was also a great price. Additionally, there were games which was nice because we had our child with us. I would definitely recommend this place and I will be staying here again when we're in Evanston, hopefully Lisa's schedule will be open!

Guest suite in Naperville

4.95 out of 5 average rating, 414 reviews

Cozy Lakeview Studio with Private Access

YuRating, 5 stars5 days ago

Thank you so much for the wonderful stay! I was so glad to have chosen your place! Also, it was wonderful meeting you all! I had a nice time chatting with you! I hope to be back with my husband next! Happy Spring! Thanks, again!

4.95 out of 5 average rating, 104 reviews

Guest house in Oak Park

O'Malley Oasis!

AndreaRating, 5 stars3 months ago

Clean, beautiful space. Has everything needed and the most comfortable seating space to relax. Clear instructions, easy parking. Be aware that there are several stairs to enter as seen in the pictures. They are well maintained with a handrail. This was not an issue at all for us but could be for someone with mobility limitations. Otherwise one of the best places I have stayed in Oak Park. Hope it is available when I come back.

4.96 out of 5 average rating, 280 reviews

Flat in Irving Park

Spacious 1BR apartment in a central location

GilRating, 5 stars1 month ago

I have stayed in a number of AirBnB‘s throughout the years, this may have been my favorite stay. There is absolutely everything you would need for a comfortable stay. Everything is clean. Alex is a five-star communicator. It is a busy little neighborhood, but the bedroom is toward the back of the apartment. I heard nothing but dead silence at night.

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

4.92 out of 5 average rating, 39 reviews

Home in West Lawn

Family Friendly Duplex/9 min from MDW/Free Parking

JoannaRating, 5 stars2 weeks ago

Came for c2e2 with my friends and it was perfect for all of us! Would recommend 💗💗

Guest suite in Plainfield

4.86 out of 5 average rating, 78 reviews

Relaxing Suite with Independent Entrance

CindyRating, 5 stars1 week 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.

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 stars1 month 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 stars4 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, 22 reviews

Home in Aurora

Evergreen Retreat

LoreineRating, 5 stars1 week ago

This is a very beautiful house with TONS of space, big and perfect for my healing retreat, I hosted 9 ladies, the backyard is huge plus there was an outdoor event area. The place looked exactly like pictures, clean, host was responsive and polite. The house is very relaxing and peaceful. I would definitely recommend!