Oswego Holiday Rentals

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Holiday Rentals in Oswego

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

Warsaw
10.0 out of 10, Exceptional, (16)
"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 NZ$545
includes taxes & fees
18 Nov - 19 Nov
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

Syracuse
9.8 out of 10, Exceptional, (6)
"Very nice property clean nicely decorated very nice for the couple nights that we stayed there. I would recommend it highly"
United States
patricia c.
The price is NZ$583
includes taxes & fees
17 Nov - 18 Nov
Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm

Trail Side in the Heart of Winona Lake

Winona Lake
9.8 out of 10, Exceptional, (37)
"House very comfortable, we enjoyed being close to the trails"
United States
Dennis A.
The price is NZ$464
includes taxes & fees
17 Nov - 18 Nov
Trail Side in the Heart of Winona 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

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

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 NZ$464
includes taxes & fees
17 Nov - 18 Nov
Cozy lakefront home on Big Barbee Lake

Lake Wawasee Retreat: private pool, hot tub & pier

2.0 star property
Syracuse
Lake Wawasee Retreat: private pool, hot tub & pier

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 NZ$643
includes taxes & fees
17 Nov - 18 Nov
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!

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)
"We really loved the setting and the cottage was adorable. The "
United States
Julie D.
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

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 NZ$354
includes taxes & fees
17 Nov - 18 Nov
Woodside Retreat in the Heart of Amish Country

⚓️Direct lake view with available Tritoon boat rental

Syracuse
9.8 out of 10, Exceptional, (14)
"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 NZ$901
includes taxes & fees
26 Nov - 27 Nov
Beautiful Lakefront home, pets welcome, fully fenced, dock, kayaks, fishing!!

Charming 3-bedroom lake house on Tri lakes 6 miles north of Columbia City.

Columbia City
9.8 out of 10, Exceptional, (16)
"Great little cottage right on the lake! Has everything you need to enjoy the Tri Lakes area. Only feedback is the listing mentions having 2 bathrooms and it despite my best effort to find a second, there's for sure only 1 here. Great, affordable option otherwise, would recommend. "
United States
Tim W.
Charming 3-bedroom lake house on Tri lakes 6 miles north of Columbia City.

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 NZ$1,827
includes taxes & fees
17 Nov - 18 Nov
Indoor pool with 4-bedrooms in charming Goshen with WiFi and so many extras

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

Lake Tippecanoe, Little Tippy retreat—sleeps 12, dog friendly, private lakefront

Leesburg
10.0 out of 10, Exceptional, (3)
"The Twisted Pine was a very unique and fun place to stay! We liked how the house and property were laid out, which encouraged us to explore, and every room essentially gets its own bathroom which was an added bonus. It also felt very private being tucked away against the lake and the woods. We spent our days paddle boarding and swimming in the lake and our nights playing games and hanging out on the spacious terrace. Our hostess, Katie, was very pleasant to work with and accommodating and...
United States
Nicolas H.
Lake Tippecanoe, Little Tippy retreat—sleeps 12, dog friendly, private lakefront

Stunning lakefront log cabin on a private acre

Syracuse
9.6 out of 10, Exceptional, (43)
"This was our second year renting this property for our family reunion. It is the place where we have made so many happy memories."
United States
Deborah M.
Stunning lakefront log cabin on a private acre
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$354 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

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.