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Oswego Vacation Rentals

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Browse Select Oswego Vacation Homes

Our top choices for Oswego vacation homes

Minutes to Downtown Saint Charles, Cozy/Chic Home

9.8 out of 10, Exceptional, (10)
"Perfect location Very clean house and lots of rooms"
Minutes to Downtown Saint Charles, Cozy/Chic Home

Clarendon Hills Top Floor

6.8 out of 10, (10)
"The house was nice, in a quiet area. The bedrooms were great. It was a little nerve wracking when the lower unit was rented, as we didn't want to disturb them. "
Clarendon Hills Top Floor

✽ Charming Cottage ✽ close to College/Town/Station

10.0 out of 10, Exceptional, (47)
"We loved how cute this house was! It was very convenient for visiting our daughter and nice to have plenty of space and amenities. Our host was very prompt communication. Would definitely stay here again!"
The price is CA $236
CA $433 total
includes taxes & fees
Aug 25 - Aug 26
✽ Charming Cottage ✽ close to College/Town/Station

Furnished Private home in Aurora sleeps 9 guests

9.2 out of 10, Wonderful, (89)
"Great yard to grill in the evening. Front room and family room both have TVs so kids can watch different things than the adults, if that's what you need or want. The couch in the family room is really comfortable to unwind on. Bedrooms all have their own TVs as well. The communication was amazing with the owner. They were incredibly responsive! I would definitely rent from them again if the option arises. "
Furnished Private home in Aurora sleeps 9 guests

Feel good, live well in this cozy Wheaton 3 bedroom!

10.0 out of 10, Exceptional, (1)
"Very clean. Spacious, open living area, lots of storage and comfortable beds. "
Feel good, live well in this cozy Wheaton 3 bedroom!

Spread out - Renovated 5BR+Loft, Sleeps 12+

9.2 out of 10, Wonderful, (27)
"We had a large group (11) the property had plenty of room for everyone to be comfortable. The host was very helpful and quickly responded to any inquiries we had."
Spread out - Renovated 5BR+Loft, Sleeps 12+

Great place to stay in Warrenville

10.0 out of 10, Exceptional, (65)
"Property is a wonderful and beautiful place to enjoy time as a family. "
Great place to stay in Warrenville

4bd house, Hot-tub, full-basement, pool table & big yard,3 full bathroom.

10.0 out of 10, Exceptional, (23)
"Great house, great neighborhood, host was amazing!"
4bd house, Hot-tub, full-basement, pool table & big yard,3 full bathroom.

Spacious Unit w/ Free Parking and Breakfast Near I-88 Corridor - Pets Allowed

9.0 out of 10, Wonderful, (2)
"It was nice and everyone was very friendly!!"
The price is CA $152
CA $199 total
includes taxes & fees
Aug 31 - Sep 1
Spacious Unit w/ Free Parking and Breakfast Near I-88 Corridor - Pets Allowed

Historic home with easy access to Chicago

9.8 out of 10, Exceptional, (169)
"The Davis House is wonderful—large, spacious—and just as described in the listing. It really is fully equipped with just about anything one would need. Beds are comfortable, water pressure is great and the laundry room on the second floor is terrific. William is a gracious owner and answered all our questions promptly. He was a pleasure to work with and it was a pleasure to stay here. We will definitely be back."
Historic home with easy access to Chicago

4BR Family Home w/ Great Light | LCP Collection

9.2 out of 10, Wonderful, (7)
"As advertised. Comfortable. Plenty of space for a family. We enjoyed walking past the pond and geese - convenient to oak brook area and Graue mill natural areas. "
The price is CA $503
CA $976 total
includes taxes & fees
Sep 16 - Sep 17
4BR Family Home w/ Great Light | LCP Collection

Family Escape w/ Large Yard + Near Oakbrook Mall | LCP Collection

4.0 out of 10, (2)
"Big things: - THIS IS NOT A TWO BATH HOUSE. There is one full bathroom and a powder room. The listing is wrong, there is no second shower and we would never have booked for our party of 6 knowing this, so now you know too. - The cleaning standards are subpar, DO NOT STAY WITH YOUNG CHILDREN. So many examples I could list but, sticking with big things, the worst was the floors were so dirty everyone's feet/socks turned black and we found a plate of moldy hamburgers in the microwave. When we...
The price is CA $229
CA $658 total
includes taxes & fees
Aug 25 - Aug 26
Family Escape w/ Large Yard + Near Oakbrook Mall | LCP Collection

WATER FRONT LUXURY HOME WILL FEEL LIKE A RESORT FOR 10

10.0 out of 10, Exceptional, (29)
"This property was perfect for our visit. Lots of space and had everything we needed for a comfortable and fun stay."
WATER FRONT LUXURY HOME WILL FEEL LIKE A RESORT FOR 10

Walk to Downtown Restaurants, Cozy Stay, Grand Porch, Bike on the river trails!

2.0 star property
10.0 out of 10, Exceptional, (9)
"We enjoyed our time at The Fox Den. Great location and cleanliness of the house. Definitely recommend and would stay again!"
Walk to Downtown Restaurants, Cozy Stay, Grand Porch, Bike on the river trails!

Modern Tranquil Boho Getaway in Glen Ellyn

Modern Tranquil Boho Getaway in Glen Ellyn

Comfortable Naperville Escape – Close to Downtown & Train!

10.0 out of 10, Exceptional, (2)
"Lovely house, fenced in yard, raised deck neighborhood; great location… a perfect haven for a busy time we had there helping with a friend’s outdoor wedding at a local venue."
Comfortable Naperville Escape – Close to Downtown & Train!

Desirable chic home in a Prime Location!

8.8 out of 10, Excellent, (6)
"This home was clean and comfortable and located in an excellent and safe area - easy access to main roads and downtown Chicago travel. We were glad for this “find.”"
Desirable chic home in a Prime Location!

Riverfront rental

9.8 out of 10, Exceptional, (32)
"It is a small house but it has everything you need to be comfortable and the host is very friendly."
The price is CA $229
CA $349 total
includes taxes & fees
Aug 24 - Aug 25
Riverfront rental

The Plainfield Inn - Plainfields first historic boutique hotel

The price is CA $1,106
CA $1,590 total
includes taxes & fees
Aug 27 - Aug 28
The Plainfield Inn - Plainfields first historic boutique hotel

Downtown St. Charles: Walk to Bars & Restaurants

10.0 out of 10, Exceptional, (1)
The price is CA $496
CA $1,009 total
includes taxes & fees
Aug 27 - Aug 28
Downtown St. Charles: Walk to Bars & Restaurants
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Oswego Hotel Reviews