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Oswego Holiday Rentals

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Holiday Rentals in Oswego

Clarendon Hills Top Floor

Clarendon Hills
7.4 out of 10, Good, (19)
"This property is a great choice for the price and location, however both bathrooms are in need of cleaning. "
United States
Reginald S.
Clarendon Hills Top Floor

3-bedroom hillside property in woods with fireplace and lake view

Lemont
6.8 out of 10, (5)
"Was nice and secluded. Driveway is very steep. Not all windows had curtains. Kitchen is pretty tiny. "
United States
kim h.
The price is NZ$445
includes taxes & fees
1 Dec - 2 Dec
3-bedroom hillside property in woods with fireplace and lake view

Pet Friendly-Cozy 1-bedroom apartment just 6 minutes drive to Morton Arboretum

Downers Grove
9.6 out of 10, Exceptional, (30)
"We loved the location! It was perfect for us. Denise was very pleasant. We will definitely stay there again."
United States
Rene M.
The price is NZ$187
includes taxes & fees
14 Nov - 15 Nov
Pet Friendly-Cozy 1-bedroom apartment just 6 minutes drive to Morton Arboretum

Spacious open concept home w/ game room + firepit

Winfield
9.8 out of 10, Exceptional, (74)
"Very spacious home, bedrooms good sized, really liked the game room to keep the kids occupied."
United States
Patricia
Spacious open concept home w/ game room + firepit

- Beautiful Condo - King Bed - Free Waffle Breakfast -

Geneva
10.0 out of 10, Exceptional, (19)
"Beautiful place! Every detail was thought of for their guest!"
United States
Libby M.
The price is NZ$641
includes taxes & fees
24 Nov - 25 Nov
- Beautiful Condo - King Bed - Free Waffle Breakfast -

Lovely 2-Bdrm unit with pool. Home away from home.

Naperville
8.6 out of 10, Excellent, (26)
"We had a great stay at Tristan’s condo. It was in a great location. We took several trips into Chicago and it was easy to get to the train station. Condo was very clean and had everything we needed for our stay. "
United States
Hallie H.
Lovely 2-Bdrm unit with pool. Home away from home.

Modern 4 Bedroom Private Vacation Home

2.5 star property
Shorewood
The price is NZ$1,110
includes taxes & fees
11 Nov - 12 Nov
Modern 4 Bedroom Private Vacation Home

✽ Charming Cottage ✽ close to College/Town/Station

Wheaton
10.0 out of 10, Exceptional, (53)
"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!"
United States
Mary
The price is NZ$549
includes taxes & fees
11 Nov - 12 Nov
✽ Charming Cottage ✽ close to College/Town/Station

Warrenville Rep 2

4.0 star property
Warrenville
Warrenville Rep 2

Cozy 5-bedroom with lake views and spacious deck

Westmont
10.0 out of 10, Exceptional, (14)
"We had a great time, and there was plenty of room for 5+ very large men."
United States
Micah M.
Cozy 5-bedroom with lake views and spacious deck

Modern Home in Trendy Neighborhood 40 from Downtown Chicago

Plainfield
9.8 out of 10, Exceptional, (16)
"Property owner was very helpful when we had to change dates after reserving. House was very nice and perfect for our family. House is in a great location, perfect for anyone traveling to Joliet!"
United States
Anna L.
Modern Home in Trendy Neighborhood 40 from Downtown Chicago

Fox Valley Farmhouse Overlooking The Fox River!

St. Charles
10.0 out of 10, Exceptional, (41)
"We were able to walk to the fireworks and loved our proximity to our family events in Geneva, st Charles and Batavia. We will likely return for the next family reunion."
United States
ben a.
Fox Valley Farmhouse Overlooking The Fox River!

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

Aurora
9.2 out of 10, Wonderful, (30)
"Nice space size, clean, enough rooms, internet works greats, quiet neighborhood"
United States
Christopher R.
Spread out - Renovated 5BR+Loft, Sleeps 12+

Mokena Manor: Luxury Living - Your Elite Escape!

2.0 star property
Mokena
8.0 out of 10, Very good, (5)
"Lovely suburb outside Chicago, with all the amenities you'd need for a relaxing getaway. The area was peaceful with plenty of local restaurants and shops. I’d definitely recommend it for a cozy and convenient stay near Chicago. I had a great time!"
United States
Sean M.
Mokena Manor: Luxury Living - Your Elite Escape!

Spacious 4BR Home - Perfect for Groups!

Warrenville
10.0 out of 10, Exceptional, (3)
"The property was great and worked very well for our family on a trip that was Chicago-centric. It was effectively 35-55 min from downtown based on traffic and was easy to to as well as easy to park more than one car. The bathrooms were well appointed and had everything we needed. It wasn't mentioned in the description, but there is a public bike/walking trail right across the street. We had a couple of great strolls right along a scenic river, really really pleasant."
United States
John O.
Spacious 4BR Home - Perfect for Groups!

Fully-Equipped Suite | Gym Access

York Center
The price is NZ$324
includes taxes & fees
16 Nov - 17 Nov
Fully-Equipped Suite | Gym Access

Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry

Geneva
9.4 out of 10, Exceptional, (23)
"I can’t say enough about Cita our host. I was very ill and we were able to check in early and also stay an extra day. Accommodating in every way any."
United States
Dawn B.
The price is NZ$496
includes taxes & fees
3 Dec - 4 Dec
Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry

Furnished Private home in Aurora sleeps 9 guests

Aurora
9.2 out of 10, Wonderful, (96)
"Great location and stay. Lots of family rooms for sitting and even a few toys and videos games for the kids."
United States
Aaron S.
Furnished Private home in Aurora sleeps 9 guests

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

2.0 star property
St. Charles
10.0 out of 10, Exceptional, (11)
"Charming amenities in a great location!"
United States
David M.
Walk to Downtown Restaurants, Cozy Stay, Grand Porch, Bike on the river trails!

Modern 4BR Townhouse w/ Parking & Lake Views

2.0 star property
Warrenville
Modern 4BR Townhouse w/ Parking & Lake Views
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

Find out more about Oswego

Everything you need to know about Oswego holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oswego holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oswego holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Oswego holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oswego. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oswego holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oswego holiday rentals we have selected for you start as low as NZ$187 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Oswego rentals

At Expedia, we put the best Oswego holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Oswego rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oswego holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oswego. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Oswego?

Yes, there are holiday rentals in Oswego close to Keller's Farmstand, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Oswego has a good selection of restaurants. Make sure you have time to check out the art and museums during your trip.

What are some of the best holiday rentals that Oswego has to offer?

Modern 4 Bedroom Private Vacation Home : This holiday home rental outside Oswego offers a BBQ and free WiFi to help you feel comfortable in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals are there in Oswego?

With 5 Expedia holiday rentals, you're guaranteed to find just the right place for your Oswego stay.

What can I see and do in Oswego?

Family-friendly attractions include Keller's Farmstand, whereas Hudson Crossing Park is a spot to enjoy the outdoors. Fox Valley Winery and Aurora University are a couple of places you'll find in the wider area.

What are holiday rentals like in Oswego?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Oswego. Holiday rentals offer extras like laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for families.