A stone bridge over a calm river, surrounded by lush greenery and buildings.

Oswego Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Oswego vacation rentals

A modern kitchen with white cabinetry, a dining area with a wooden table and chairs, and a large island with a stove.

1. River Access•Game room•Backyard•King•W/D•Parking

River Access•Game room•Backyard•King•W/D•Parking
Yorkville
10.0 out of 10, Exceptional, (4 reviews)
"Absolutely loved this place. The backyard was amazing and the house was clean and had everything we needed."
United States
Daniela M.
$348 nightly
The price is $369
Oct 26 - Oct 27
Total with taxes and fees
River Access•Game room•Backyard•King•W/D•Parking
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a stove.

2. Family-Friendly 3BR Home • Sleeps 6 • 2.5 Bath

Family-Friendly 3BR Home • Sleeps 6 • 2.5 Bath
Aurora
7.4 out of 10, Good, (3 reviews)
"Overall good I would stay there again if I was to travel to Chicago again"
United States
Avo H.
$343 nightly
The price is $364
Nov 2 - Nov 3
Total with taxes and fees
Family-Friendly 3BR Home • Sleeps 6 • 2.5 Bath
A patio area with outdoor furniture, a gazebo, and a barbecue grill.

3. Spacious and family friendly getaway. 8 mins from Chicago Premium Outlet Mall.

Spacious and family friendly getaway. 8 mins from Chicago Premium Outlet Mall.
Aurora
10.0 out of 10, Exceptional, (35 reviews)
"The property was perfect for our family! There was plenty of room, indoors and out, for us, our kids, and our grandkids. The house was spotless and the kitchen was extensively stocked with dishes, cookware, etc. We also appreciated the numerous comfy places to gather."
United States
Mila M.
$1,083 nightly
The price is $1,148
Oct 26 - Oct 27
Total with taxes and fees
Spacious and family friendly getaway. 8 mins from Chicago Premium Outlet Mall.
Immediately feel at home when you step into the grand entryway.

4. 2-Acre Retreat on the Fox River with Spectacular Views & Hot Tub!

2-Acre Retreat on the Fox River with Spectacular Views & Hot Tub!
Plano
9.8 out of 10, Exceptional, (16 reviews)
"This is our second year in a row for our annual Friendsgiving. We love the place and plan to make it our annual house for our group! "
United States
Aaron P.
$1,071 nightly
The price is $1,135
Oct 26 - Oct 27
Total with taxes and fees
2-Acre Retreat on the Fox River with Spectacular Views & Hot Tub!
A modern kitchen with a central island, bar stools, and pendant lighting.

5. Spacious 7-bedroom house with AC in wonderful Naperville

Spacious 7-bedroom house with AC in wonderful Naperville
Naperville
8.0 out of 10, Very good, (1 review)
"Very smooth booking, checking in, and checking out process. The house was older, and it showed, but was big enough to hold my group. There were problems with the fire detectors randomly beeping, and some mold in the basement, but everything else was fine."
United States
Brett H.
$1,051 nightly
The price is $1,114
Oct 26 - Oct 27
Total with taxes and fees
Spacious 7-bedroom house with AC in wonderful Naperville
A wooden deck with wicker furniture and a view of a green landscape.

6. Spacious 5-bedroom house in perfect Plano with AC for relaxing stays

Spacious 5-bedroom house in perfect Plano with AC for relaxing stays
Plano
$590 nightly
The price is $625
Oct 26 - Oct 27
Total with taxes and fees
Spacious 5-bedroom house in perfect Plano with AC for relaxing stays
(OUTDOOR SPACE) Where comfort and charm come together. Unwind in the outdoor lounge set under an inviting gazebo with twinkling lights. Stay fresh with a gentle breeze from the fan as you relax.

7. 30 mins to CHI, 3 Kings, BBQ Grill, TV, Spacious

30 mins to CHI, 3 Kings, BBQ Grill, TV, Spacious
Plainfield
9.4 out of 10, Exceptional, (18 reviews)
"Great place to stay."
United States
Taylor E.
$607 nightly
The price is $643
Oct 26 - Oct 27
Total with taxes and fees
30 mins to CHI, 3 Kings, BBQ Grill, TV, Spacious
A modern living room with a sofa set, a coffee table, and a rug.

8. Spacious 4BR Home Family & Pet-Friendly 2 Living Rooms + Game Fun in Plainfield

Spacious 4BR Home Family & Pet-Friendly 2 Living Rooms + Game Fun in Plainfield
Plainfield
10.0 out of 10, Exceptional, (3 reviews)
"Great host and the home location is awesome for hosting family. "
United States
Yolanda P.
$475 nightly
The price is $504
Nov 3 - Nov 4
Total with taxes and fees
Spacious 4BR Home Family & Pet-Friendly 2 Living Rooms + Game Fun in Plainfield
A spacious living room with a fireplace, a large sofa, a coffee table, and a TV.

9. 4BR Tudor • Wooded Lot • 10 Min to Downtown

4BR Tudor • Wooded Lot • 10 Min to Downtown
Naperville
9.6 out of 10, Exceptional, (5 reviews)
"This is a spacious house in a very nice, quiet neighborhood. The backyard is a perfect spot to relax and soak in the sun/play games. This is a great house for families. We had a nearby wedding and this was a wonderful house to get ready at. The hosts are extremely welcoming and communicate wonderfully. "
United States
Alicia F.
$596 nightly
The price is $632
Oct 27 - Oct 28
Total with taxes and fees
4BR Tudor • Wooded Lot • 10 Min to Downtown
A wooden interior hallway with a staircase, a wooden wardrobe, and a cabinet with glass doors.

10. River Park Paradise w/ Fire Pit & Chef's Kitchen

River Park Paradise w/ Fire Pit & Chef's Kitchen
Bolingbrook
10.0 out of 10, Exceptional, (16 reviews)
"Excellent just what we were looking for"
United States
Sue B.
$825 nightly
The price is $874
Oct 26 - Oct 27
Total with taxes and fees
River Park Paradise w/ Fire Pit & Chef's Kitchen
A kitchen with white cabinets, a stainless steel sink, and a light-colored countertop.

11. Cozy condo

Cozy condo
Aurora
6.0 out of 10, (2 reviews)
"Good for short term stays."
United States
Lindsey H.
$164 nightly
The price is $193
Nov 7 - Nov 8
Total with taxes and fees
Cozy condo
A covered outdoor seating area with wicker furniture, a sign reading 'Our Happy Place,' and a view of trees through large windows.

12. Naperville Oasis: 3 Kings, Yard, Patio, Ping-Pong

Naperville Oasis: 3 Kings, Yard, Patio, Ping-Pong
Naperville
$519 nightly
The price is $550
Oct 26 - Oct 27
Total with taxes and fees
Naperville Oasis: 3 Kings, Yard, Patio, Ping-Pong
A modern kitchen with white cabinets, stainless steel appliances, a wooden island, and a view of the outside through the windows.

13. 2CHICAGO Train 1MI/WIFI/KING/Free parking/Fox River Bike Trail

2CHICAGO Train 1MI/WIFI/KING/Free parking/Fox River Bike Trail
Geneva
9.8 out of 10, Exceptional, (40 reviews)
"Property was very clean and well-kept. The neighborhood was quiet and felt safe. In a great location too, about a mile from the Metra/downtown Geneva"
United States
Ethan D.
$286 nightly
The price is $316
Oct 26 - Oct 27
Total with taxes and fees
2CHICAGO Train 1MI/WIFI/KING/Free parking/Fox River Bike Trail
Two twin beds in a hotel room with a green accent wall, a framed picture, and a nightstand with a lamp.

14. 2 Full Beds | Non-Smoking, Kitchen

2 Full Beds | Non-Smoking, Kitchen
Chicago
9.2 out of 10, Wonderful, (30 reviews)
"Nice people,nice rooms!"
United States
Anonymous traveler
$84 nightly
The price is $93
Nov 15 - Nov 16
Total with taxes and fees
2 Full Beds | Non-Smoking, Kitchen
A modern living room with a sofa, coffee table, and bar stools. There is a kitchen area with cabinets and a countertop.

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

Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry
Geneva
9.6 out of 10, Exceptional, (29 reviews)
"The location is amazing! What a cute place. Just right for two people."
United States
Shara B.
$286 nightly
The price is $316
Nov 9 - Nov 10
Total with taxes and fees
Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry
A covered porch with wicker furniture, a coffee table, and a potted plant.

16. - Fully-Equipped Condo - King Bed - Massive yard -

- Fully-Equipped Condo - King Bed - Massive yard -
Geneva
10.0 out of 10, Exceptional, (48 reviews)
"We had everything we needed, the host was very responsive and we would stay there again."
United States
Mike A.
$283 nightly
The price is $300
Oct 27 - Oct 28
Total with taxes and fees
- Fully-Equipped Condo - King Bed - Massive yard -
Dining

17. 4 BR 3 BATH Naperville Downtown with Wi-fi Desk, Near HighwayTrainStation

4 BR 3 BATH Naperville Downtown with Wi-fi Desk, Near HighwayTrainStation
Naperville
6.8 out of 10, (3 reviews)
"My God the host was extremely helpful and responsive when reaching out, place was super clean, place and area was super peaceful and quiet. She over delivered guys"
United States
Marquis M.
$760 nightly
The price is $805
Oct 26 - Oct 27
Total with taxes and fees
4 BR 3 BATH Naperville Downtown with Wi-fi Desk, Near HighwayTrainStation
A room with a sofa, armchair, and ottoman, a lamp, and large windows with a view of a garden.

18. Tranquil 3-bedroom house with AC in charming Wheaton, Illinois

Tranquil 3-bedroom house with AC in charming Wheaton, Illinois
Wheaton
$500 nightly
The price is $530
Oct 26 - Oct 27
Total with taxes and fees
Tranquil 3-bedroom house with AC in charming Wheaton, Illinois
A modern kitchen with dark wood cabinets, stainless steel appliances, a granite countertop, and a small island with stools.

19. Lockport Haven/3 King Beds/Wi-fi/Near Downtown!

Lockport Haven/3 King Beds/Wi-fi/Near Downtown!
Lockport
10.0 out of 10, Exceptional, (16 reviews)
"Perfect spot for our group of 6! More than enough dishes/silverware etc. the house was clean and comfortable. Would definitely stay again if in the area."
United States
Kathy L.
$461 nightly
The price is $475
Oct 26 - Oct 27
Total with taxes and fees
Lockport Haven/3 King Beds/Wi-fi/Near Downtown!
A modern kitchen with stainless steel appliances, white cabinetry, a gas stove, and a window with plants.

20. Historic Hideaway*King Bed*Remodeled* fast Wi-Fi

Historic Hideaway*King Bed*Remodeled* fast Wi-Fi
Joliet
9.8 out of 10, Exceptional, (37 reviews)
"Was a great stay, easy to get in and out off"
United States
Unspecified U.
$340 nightly
The price is $362
Oct 26 - Oct 27
Total with taxes and fees
Historic Hideaway*King Bed*Remodeled* fast Wi-Fi
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

Chicago Club Inn & Suites

Chicago Club Inn & Suites

8/10 Good
"Currently still doing renovations but overall stay was good."
Emanuel 1-night trip
Posted less than an hour ago
Chicago Club Inn & Suites

Find out more about Oswego

Everything you need to know about Oswego vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Oswego vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Oswego vacation 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 low season months. For more hustle and bustle, you may prefer to visit Oswego in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $88 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Oswego rentals

At Expedia, we put the best Oswego vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Oswego?

Yes, we give you a choice of vacation rentals in Oswego close to Keller's Farmstand, or you can select a more remote option if you're looking for extra privacy while you relax. Our travelers 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 vacation home rentals that Oswego has to offer?

Cozy Mother-in-Law Suite w/Laundry, Kitchenette, Walk-In Closet, and Rain Shower: This vacation home rental outside of Oswego offers a garden, a hot tub, and air-conditioning to help you feel perfectly comfortable in your new surroundings.

How many vacation rentals are there in Oswego?

With 5 Expedia vacation rentals, you're sure 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 larger area.

What are vacation rentals like in Oswego?

Vacation rentals are privately owned properties you can stay in for a few days or a quick weekend in Oswego. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from public hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for a small group gathering.