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

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Oswego holiday homes

A two-story house with a garage, surrounded by snow-covered ground and trees.

1. PROMO 10% WEEKLY AND 15% MONTHLY OFF Naperville/Aurora, King Bed, Fenced Yard!

PROMO 10% WEEKLY AND 15% MONTHLY OFF Naperville/Aurora, King Bed, Fenced Yard!
Aurora
9.2 out of 10, Wonderful, (15 reviews)
"The beds were super comfortable and the location for Naperville/Aurora/Wheaton activities was ideal--about 10 minutes or so for everything."
United States
Scott D.
The price is £230
includes taxes & fees
4 Nov - 5 Nov
PROMO 10% WEEKLY AND 15% MONTHLY OFF Naperville/Aurora, King Bed, Fenced Yard!
A modern living room with a grey sofa, a coffee table, a TV stand, and a window with blinds.

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.
The price is £298
includes taxes & fees
2 Nov - 3 Nov
Family-Friendly 3BR Home • Sleeps 6 • 2.5 Bath
A deck with outdoor furniture overlooking a lake, surrounded by trees.

3. 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)
"Great location, great place...perfect!"
United States
David Z.
The price is £925
includes taxes & fees
2 Nov - 3 Nov
2-Acre Retreat on the Fox River with Spectacular Views & Hot Tub!
A modern living room with a sofa, coffee table, and TV. There is a dining area with a table and chairs. The room has hardwood floors and a large window with blinds.

4. 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.
The price is £380
includes taxes & fees
1 Nov - 2 Nov
Spacious 4BR Home Family & Pet-Friendly 2 Living Rooms + Game Fun in Plainfield
A modern living room with a grey sofa, a wooden coffee table, and a ceiling fan.

5. 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, (36 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.
The price is £861
includes taxes & fees
5 Nov - 6 Nov
Spacious and family friendly getaway. 8 mins from Chicago Premium Outlet Mall.
(GUEST BEDROOM) Relax in our deluxe guest bedrooms, featuring king-sized beds, enough closet space, and natural light. These calm retreats are your perfect oasis for restful nights.

6. 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.
The price is £529
includes taxes & fees
2 Nov - 3 Nov
30 mins to CHI, 3 Kings, BBQ Grill, TV, Spacious
A gravel pathway flanked by grass and trees, leading to an arched stone structure with lights.

7. 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
The price is £481
includes taxes & fees
1 Nov - 2 Nov
Spacious 5-bedroom house in perfect Plano with AC for relaxing stays
A modern kitchen with a white marble countertop, built-in appliances, and pendant lighting.

8. 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.
The price is £849
includes taxes & fees
12 Nov - 13 Nov
Spacious 7-bedroom house with AC in wonderful Naperville
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.
The price is £489
includes taxes & fees
29 Nov - 30 Nov
4BR Tudor • Wooded Lot • 10 Min to Downtown
A backyard with a fire pit, four Adirondack chairs, and a house in the background.

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.
The price is £694
includes taxes & fees
1 Nov - 2 Nov
River Park Paradise w/ Fire Pit & Chef's Kitchen
An outdoor patio with a ceiling fan, a glass door leading to a covered area, and a seating arrangement with a table and chairs.

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

Naperville Oasis: 3 Kings, Yard, Patio, Ping-Pong
Naperville
The price is £358
includes taxes & fees
1 Nov - 2 Nov
Naperville Oasis: 3 Kings, Yard, Patio, Ping-Pong
A spacious living room with a fireplace, leather sofas, a coffee table, and a large TV.

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

- Fully-Equipped Condo - King Bed - Massive yard -
Geneva
10.0 out of 10, Exceptional, (49 reviews)
"We had everything we needed, the host was very responsive and we would stay there again."
United States
Mike A.
The price is £218
includes taxes & fees
2 Nov - 3 Nov
- Fully-Equipped Condo - King Bed - Massive yard -
A living room with a red accent wall, a ceiling fan, a glass coffee table, a brown sofa, and a beige armchair.

13. PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central

PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Lisle
9.4 out of 10, Exceptional, (36 reviews)
"This property was perfect for our weekend stay in the Chicagoland area. It was conveniently located to activities, shops and restaurants. Vic is a wonderfully attentive host who responds quickly and is happy to answer any questions or concerns."
United States
Christine M.
The price is £204
includes taxes & fees
1 Nov - 2 Nov
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
A dining room with a wooden table set for six, flanked by bookshelves, and a view into another room through a glass door.

14. Travelers Retreat/King Beds/Game Room/Play House

Travelers Retreat/King Beds/Game Room/Play House
Joliet
10.0 out of 10, Exceptional, (2 reviews)
"Great place to stay"
United States
Ken B.
The price is £351
includes taxes & fees
4 Nov - 5 Nov
Travelers Retreat/King Beds/Game Room/Play House
A dining area with a wooden table set for six, surrounded by black chairs. There are two paintings on the wall, a chandelier above the table, and a kitchen area to the right.

15. 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.
The price is £361
includes taxes & fees
23 Nov - 24 Nov
Lockport Haven/3 King Beds/Wi-fi/Near Downtown!
A compact kitchen with a dining table and chairs, a stove, and wooden cabinets.

16. Back Unit Patio, Balcony, Yard, Smart TVs, W/D

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
The price is £202
includes taxes & fees
2 Nov - 3 Nov
Back Unit Patio, Balcony, Yard, Smart TVs, W/D
A living room with two grey sofas, a wooden coffee table, and a staircase leading to an upper floor.

17. The Heron House, King Bed Suite, *Spacious Remodeled House*

The Heron House, King Bed Suite, *Spacious Remodeled House*
Joliet
10.0 out of 10, Exceptional, (55 reviews)
"Great house that worked out perfectly for our group."
United States
Rich D.
The price is £277
includes taxes & fees
22 Nov - 23 Nov
The Heron House, King Bed Suite, *Spacious Remodeled House*
A kitchen with a stainless steel refrigerator, gray cabinets, a white door, and a black stove.

18. Verbena Executive Cottage

Verbena Executive Cottage
Morris
10.0 out of 10, Exceptional, (5 reviews)
"Great host...very clean house."
United States
Kim A.
The price is £207
includes taxes & fees
29 Nov - 30 Nov
Verbena Executive Cottage
A grassy area with a body of water, two stone structures, and several birds.

19. Riverfront rental

Riverfront rental
South Elgin
10.0 out of 10, Exceptional, (51 reviews)
"Incredible host and property."
United States
John V.
The price is £186
includes taxes & fees
1 Nov - 2 Nov
Riverfront rental
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

Hotel Arista

Hotel Arista

10/10 Excellent
"Lovely staff, beautiful facility. Room was great, best bed we’ve slept in for a long time. Wish we could have stayed longer."
Hans 1-night trip
Posted 1 day ago
Hotel Arista

Find out more about Oswego

Oswego Holiday Homes information

Number of reviews
306
Accommodation
159 Holiday Homes
Lowest Price
£186
Highest Price
£925