Oswego Holiday Rentals

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Holiday Rentals in Oswego

Memorable Vacation Awaits on Big Chapman Lake! Sleeps 8! Optional Pontoon!

9.8 out of 10, Exceptional, (10)
The price is AU$476
includes taxes & fees
28 Sept - 29 Sept
Memorable Vacation Awaits on Big Chapman Lake! Sleeps 8! Optional Pontoon!

Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm

10.0 out of 10, Exceptional, (2)
"The cottage fits the description perfectly! It was probably the cleanest place I've ever stayed, which meant so much. It is as nice outside as in. Will definitely book again for a quiet weekend away."
The price is AU$508
includes taxes & fees
24 Sept - 25 Sept
Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm

Charming farmhouse in peaceful countryside

10.0 out of 10, Exceptional, (157)
"It was a nice spot, near to the events we took in, over the weekend."
Charming farmhouse in peaceful countryside

Woodside Retreat in the Heart of Amish Country

10.0 out of 10, Exceptional, (8)
"It was a very unique place to stay for a few days. Very clean and thoughtful in items provided"
The price is AU$307
includes taxes & fees
28 Sept - 29 Sept
Woodside Retreat in the Heart of Amish Country

Spacious 4-bedroom 3-bathroom lake house on Shriner Lake in Columbia City.

10.0 out of 10, Exceptional, (1)
"Great place, easy check-in, very quiet location. "
Spacious 4-bedroom 3-bathroom lake house on Shriner Lake in Columbia City.

Irish Lakefront, Hot Tub! Pets, dock, fishing, kayaks, ice fishing, hunting!

2.0 star property
10.0 out of 10, Exceptional, (5)
"Our family group of 14 really enjoyed this lake house. It had everything we needed. The outside areas were really nice & the game room was a real hit with kids & adults. Communication with host Joe was great. We hope to stay there again!!"
Irish Lakefront, Hot Tub! Pets, dock, fishing, kayaks, ice fishing, hunting!

Lakefront Home on Lake Webster

9.6 out of 10, Exceptional, (32)
"Great little get away. Nice view and amenities. Plan to do again soon "
Lakefront Home on Lake Webster

Year Round Lake Front Cottage on Quiet Cove on Webster Lake

9.0 out of 10, Wonderful, (38)
"Everything was pretty good! We enjoyed some much needed family time! The house fit 3 adults and 2 kids perfectly. The only few things that may need to be taken care of was the smell of dog in the rental, and the boat dock really didnt have tall poles to dock the boat on. And there was one frying pan and one boiling pot to cook with. And parking was a little rough but ok.Overall was a nice stay! The owner was quick with a return phone call! And was very nice! "
Year Round Lake Front Cottage on Quiet Cove on Webster Lake

Beautiful and Historic Log Cabin: cozy, quiet, huge hot tub! Quiet getaway!

10.0 out of 10, Exceptional, (118)
"Well appointed cottage, clean and quiet. We enjoyed our stay."
The price is AU$535
includes taxes & fees
25 Sept - 26 Sept
Beautiful and Historic Log Cabin: cozy, quiet, huge hot tub! Quiet getaway!

“Stay Anchored” Lake Tippecanoe channel front with pier and great lake views

10.0 out of 10, Exceptional, (22)
"House had the perfect set up for our family and needs for our stay. We loved the view. We will be back!"
“Stay Anchored” Lake Tippecanoe channel front with pier and great lake views

⚓️Direct lake view with available Tritoon boat rental

9.8 out of 10, Exceptional, (12)
"The house and location are phenomenal. The pictures on the website don’t do it justice. You are on the lake and the view is amazing! The owners are super nice and very accommodating. Book now! You won’t be disappointed. "
⚓️Direct lake view with available Tritoon boat rental

Inviting Lakefront Home with Patio and Dock

10.0 out of 10, Exceptional, (13)
"The vacation house was nice and to dock your boat was easy. We rented a boat from the marina."
Inviting Lakefront Home with Patio and Dock

NEW Spacious Lakehouse Retreat +private pier

9.8 out of 10, Exceptional, (28)
"The property is very clean, most things are provided by the host. The views are spectacular. Very nice plce for vacation or weekend stay. We were very stisfied during our stay. "
NEW Spacious Lakehouse Retreat +private pier

3 bedrooms sleeps up to 10 people

9.8 out of 10, Exceptional, (47)
"Excellent accommodations and location. Had a great time, absolutely no issues."
3 bedrooms sleeps up to 10 people

Beautiful cozy cottage 1 block from the lake and Oakwood hotel.

9.4 out of 10, Exceptional, (33)
"We loved this cozy cottage! We were in town for a wedding and it was perfect! "
Beautiful cozy cottage 1 block from the lake and Oakwood hotel.

Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!

10.0 out of 10, Exceptional, (27)
"We love this place we were hear last October for sweetest day and came back on memorial day wknd we love the pool ,hot tub and the river in the back it's beautiful and also the game room with the massage chair ."
The price is AU$735
includes taxes & fees
24 Sept - 25 Sept
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!

Lake Wawasee/HOT TUB/GAME ROOM/PONTOON RENTAL

10.0 out of 10, Exceptional, (24)
"House and property had more than enough activities to keep up completely entertained for our entire stay. Loved the game room, pickleball court, hot tub and kayaks!!"
Lake Wawasee/HOT TUB/GAME ROOM/PONTOON RENTAL

Lakefront Cottage on Webster Lake with Beautiful Sunsets, 2 bed, 1 bath

10.0 out of 10, Exceptional, (51)
"Love Indiana lake country. This property let's you experience all that nature has to offer."
Lakefront Cottage on Webster Lake with Beautiful Sunsets, 2 bed, 1 bath

Beautiful Lakefront home, pets welcome, fully fenced, dock, kayaks, fishing!!

10.0 out of 10, Exceptional, (1)
"Fantastic place to get away right on the water. Enjoyed our 3 day stay with my husband and our puppy. There is a fenced in yard and a dock. Wonderful place to relax. Our host was very helpful and easy to get in touch with.Recommend highly "
The price is AU$837
includes taxes & fees
24 Sept - 25 Sept
Beautiful Lakefront home, pets welcome, fully fenced, dock, kayaks, fishing!!

Lake Wawasee 2 Bedroom Premier Condo on Channel with 1 Boat Slip, Sleeps 6,

9.6 out of 10, Exceptional, (30)
"Easy to access, great owner and an amazing location!"
Lake Wawasee 2 Bedroom Premier Condo on Channel with 1 Boat Slip, Sleeps 6,
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

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 favourite 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 depend 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 AU$307 per night. Entering your travel dates in the search wizard might find you 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

Can I find a holiday rental in Oswego?

Yes, there are holiday rentals close to the most popular sights in Oswego, or you can select a more secluded option if you're looking for a relaxing stay.

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

Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!: This holiday home rental outside of Oswego offers an outdoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

What can I see and do in Oswego?

While you're exploring the area, Tippecanoe Lake and Chapman Lakes are a couple of picturesque spots to get outside and enjoy nature. Dewart Lake and Big Barbee Lake 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 have everything you need. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for small groups.