Oswego Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Oswego

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

Syracuse
9.8 out of 10, Exceptional, (6)
The price is AU$516
includes taxes & fees
16 Nov - 17 Nov
Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm

Cozy lakefront home on Big Barbee Lake

Pierceton
10.0 out of 10, Exceptional, (11)
"The cottage was perfect for my husband and I to get away for a few days. We completed the NE region of the All Indiana Shop Hop (quilt stores) and went fishing several days. Looking forward to our next stay hopefully over Labor Day."
United States
Candy S.
The price is AU$411
includes taxes & fees
10 Nov - 11 Nov
Cozy lakefront home on Big Barbee Lake

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

Warsaw
10.0 out of 10, Exceptional, (15)
"We had a wonderful stay! The house was beautiful and accommodating! We ate our meals on the beautiful deck every day and enjoyed the beautiful view! The fire pit was wonderful to have fires at every night! We loved Kim the property manager very nice and easy to get ahold of! Tom the owner was very gracious and a great communicator as well! We definitely recommend 10/10"
United States
Kelsey B.
The price is AU$484
includes taxes & fees
10 Nov - 11 Nov
Memorable Vacation Awaits on Big Chapman Lake! Sleeps 8! Optional Pontoon!

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

Goshen
10.0 out of 10, Exceptional, (119)
"A cozy, beautiful cabin in the countryside was perfect for our family time over Thanksgiving! Staying here was a treat"
United States
Rod and Barb S.
The price is AU$536
includes taxes & fees
10 Nov - 11 Nov
Beautiful and Historic Log Cabin: cozy, quiet, huge hot tub! Quiet getaway!

Trail Side in the Heart of Winona Lake

Winona Lake
9.8 out of 10, Exceptional, (36)
"House very comfortable, we enjoyed being close to the trails"
United States
Dennis A.
The price is AU$392
includes taxes & fees
10 Nov - 11 Nov
Trail Side in the Heart of Winona Lake

Woodside Retreat in the Heart of Amish Country

Nappanee
10.0 out of 10, Exceptional, (10)
"We had a wonderful time here. We stayed here to "unplug" and refresh and it was the perfect place to do so! Comfortable, very clean, with personal touches down to the snacks provided- all made for a stay we will be back for!"
United States
Caleb
The price is AU$315
includes taxes & fees
10 Nov - 11 Nov
Woodside Retreat in the Heart of Amish Country

Waters Edge Cottage on Big Barbee Lake!

Pierceton
9.8 out of 10, Exceptional, (30)
"This cottage was super nice, very clean and a perfect little place to get away. It is right on the lake and has a great back patio to just sit and relax while watching the boats. Host was quick and responsive with communication and this place is definitely somewhere to come back to for another visit. "
United States
Corey W.
Waters Edge Cottage on Big Barbee Lake!

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

2.0 star property
Leesburg
10.0 out of 10, Exceptional, (6)
"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!!"
United States
Tami S.
Irish Lakefront, Hot Tub! Pets, dock, fishing, kayaks, ice fishing, hunting!

Lakefront Home on Lake Webster

North Webster
9.4 out of 10, Exceptional, (34)
"Very comfortable, had everything we needed."
United States
Sheila S.
Lakefront Home on Lake Webster

Swim, fish, have fun at the sandbar & cruise the lake! Sleeps 8!

Warsaw
10.0 out of 10, Exceptional, (49)
"We had a wonderful time at the lake. Emerson was fantastic at communicating and he was available anytime we needed him. We were out on the lake before a storm, so with the waves and the wind, the boat kept moving away from the dock as we tried to bring it in. Emerson and his wife were johnny on the spot with a rope to help pull us toward the dock. The neighbors around us were kind and friendly. We enjoyed our time with our family and would recommend this place to anyone."
United States
Donna K.
Swim, fish, have fun at the sandbar & cruise the lake! Sleeps 8!

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

Syracuse
9.6 out of 10, Exceptional, (30)
"Anjum was so accommodating. The tiki bar and pontoon were lots of fun."
United States
Heather E.
Lake Wawasee 2 Bedroom Premier Condo on Channel with 1 Boat Slip, Sleeps 6,

Water front cottage on beautiful Upper Long Lake

Albion
9.4 out of 10, Exceptional, (83)
"All was great at the property"
United States
David C.
Water front cottage on beautiful Upper Long Lake

NEW Spacious Lakehouse Retreat +private pier

Mentone
9.6 out of 10, Exceptional, (30)
"Comfortable and spacious and exactly as advertised "
United States
Becky V.
NEW Spacious Lakehouse Retreat +private pier

⚓️Direct lake view with available Tritoon boat rental

Syracuse
9.8 out of 10, Exceptional, (13)
"Ideal lakefront property, wonderful location. Great for any age group. Offered all we were looking for. Would recommend to anyone!! Thanks"
United States
Daniel R.
⚓️Direct lake view with available Tritoon boat rental

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

Leesburg
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 "
United States
Lenora F.
The price is AU$797
includes taxes & fees
26 Nov - 27 Nov
Beautiful Lakefront home, pets welcome, fully fenced, dock, kayaks, fishing!!

Inviting Lakefront Home with Patio and Dock

Syracuse
10.0 out of 10, Exceptional, (13)
"Enjoyed our stay. It was close to friends in the area Hope to be back sometime!"
United States
John
Inviting Lakefront Home with Patio and Dock

Indoor pool with 4-bedrooms in charming Goshen with WiFi and so many extras

Goshen
10.0 out of 10, Exceptional, (5)
"This residence was exceptionally clean and featured a very well-equipped kitchen with top-of-the-line cooking equipment. It was the perfect place to entertain teenagers, offering plenty of activities such as a pool, basketball hoops, an infinity game table, ping pong and more. There was lots of space for everyone to spread out, making it easy to enjoy different activities simultaneously without feeling crowded. A fantastic setup for a fun and relaxing stay!"
United States
Sandra J.
The price is AU$1,617
includes taxes & fees
10 Nov - 11 Nov
Indoor pool with 4-bedrooms in charming Goshen with WiFi and so many extras

Little Barbee Lakefront Bungalow

Warsaw
10.0 out of 10, Exceptional, (5)
"Beautiful setting. Has all the amenities needed. The owner/manager was very responsive to all communications. A bonus was that the neighbors across the street that own the dock to the right, when looking out to the lake, were very friendly. We used Aloha boat rental. That was also a very positive experience. "
United States
Miles F.
Little Barbee Lakefront Bungalow

Country View Retreat - 3 bedroom, Private family-friendly home

North Manchester
9.8 out of 10, Exceptional, (13)
"It has everything we needed. Great property "
United States
Charles W.
Country View Retreat - 3 bedroom, Private family-friendly home

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

Milford
10.0 out of 10, Exceptional, (29)
"The stay was just arpund the corber from our home but felt like a getaway!"
United States
Mary G.
The price is AU$569
includes taxes & fees
10 Nov - 11 Nov
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!
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.
Save an average of 15% on thousands of hotels when you're signed in

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 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$315 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?

Cozy lakefront home on Big Barbee Lake: This holiday home rental outside of Oswego is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop and a microwave.

What can I see and do in Oswego?

While you're exploring the area, Tippecanoe Lake and Big Chapman Lake 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.