Oswego Holiday Rentals

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Holiday Rentals in Oswego

Charming farmhouse in peaceful countryside
10.0 out of 10, Exceptional, (112)
"Absolutely amazing place, very clean and quiet. Very well furnished especially in the kitchen. Everything you need to cook!"
The price is AU$278
per night
17 June - 18 June
Charming farmhouse in peaceful countryside
Recently renovated, cozy lake home on relaxing Big Barbee Lake Channel!
10.0 out of 10, Exceptional, (16)
"We stayed here because mother inlaw lives right around the corner and she had a zoo full. Was nice when the rain hit we were close enough to come back to our place and get peace from everybody else. Slept in the front room and felt like I was being peeped on all weekends with no curtains."
The price is AU$473
per night
17 June - 18 June
Recently renovated, cozy lake home on relaxing Big Barbee Lake Channel!
Adorable Wawasee Cottage in Oakwood Park
10.0 out of 10, Exceptional, (6)
"Great communication, personal touch with welcoming card and fresh baked cookies! Exceeded expectations. Will stay again. Thank you C&R!"
The price is AU$794
per night
10 June - 11 June
Adorable Wawasee Cottage in Oakwood Park
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Lake Wawasee waterfront home overlooking Johnson's Bay. New Renovations for 2024
9.2 out of 10, Wonderful, (37)
"Desperately needs updating Carpet needs removed Good location Great bed layout for us it was swimmable but not as good a it could be. Ample dock for our boat Good fishing for the little ones Need to reorganize the kitchen and have more serving bowls and less bad pans"
Lake Wawasee waterfront home overlooking Johnson's Bay. New Renovations for 2024
Silver Lake IN cottage sleeps 9. Two full baths. Water sports, games, and movies
9.6 out of 10, Exceptional, (24)
"The property is beautiful and very well managed. Property has a lot of water equipment for all guest to enjoy. Owner was very nice and communicated well. This is a great place to take your friends and family to escape reality for a bit!"
Silver Lake IN cottage sleeps 9. Two full baths. Water sports, games, and movies
Barbee Lake Big House! Sleeps 14+ Game Garage! Pier and Dock to Barbee!
Barbee Lake Big House! Sleeps 14+ Game Garage! Pier and Dock to Barbee!
FAMILY HOME ON WEBSTER LAKE!
8.8 out of 10, Excellent, (3)
"Has plenty of room. Great for large gatherings. Well appointed necessities. Nice view of water."
FAMILY HOME ON WEBSTER LAKE!
Water front cottage on beautiful Upper Long Lake
9.4 out of 10, Exceptional, (66)
"Nice little cottage and very quiet setting."
Water front cottage on beautiful Upper Long Lake
Spacious FiveStar Lakefront Retreat-4BR/4BA w/HotTub,GameRoom, FirePit, SUP
9.8 out of 10, Exceptional, (12)
"The house was in good shape and well suited for a large group. We had 10 that slept comfortably. Property manager responded promptly. Some minor misinformation on the VBRO site (likely just out of date) such as an incorrect WiFi password and sending the door code the day prior to arrival, but these were minor things that were resolved promptly with no issue. Overall an enjoyable experience and a nice setting on the lake. Some nearby gunshots in the early morning hours both days could be heard......
Spacious FiveStar Lakefront Retreat-4BR/4BA w/HotTub,GameRoom, FirePit, SUP
Cozy Cottage on Cedar Lake with Children's Club House. Perfect For Families
10.0 out of 10, Exceptional, (13)
"We were in the area for a hockey weekend in Fort Wayne but we would 100% return for a longer stay when it gets warm. The house was very clean and described perfectly. My husband loved the little town and was able to get in a very scenic 15 mile run. Marion is an amazing host and extremely communicative. 12/10! Would stay again!"
Cozy Cottage on Cedar Lake with Children's Club House. Perfect For Families
Beautiful cozy cottage 1 block from the lake and Oakwood hotel.
9.4 out of 10, Exceptional, (19)
"We were looking for a small place near the lake for our small family (myself, wife and daughter). Clean, simple and on point with the description in the listing. Nice touches and some upgrades for an older cottage. It’s all we needed and very convenient to Oakwood Resort and the water. Would book again. Thanks!"
Beautiful cozy cottage 1 block from the lake and Oakwood hotel.
Cozy Goshen Farmhouse ~ 9 Mi to Amish Acres
9.8 out of 10, Exceptional, (16)
"Loved our stay at this cozy farmhouse. It was perfect for our family and our dog. Huge, fully stocked kitchen, washer and dryer and three full bedrooms. All in the scenic country of Indiana,"
Cozy Goshen Farmhouse ~ 9 Mi to Amish Acres
Waterfront Syracuse Home w/Deck, Fire Pit & Kayaks
9.6 out of 10, Exceptional, (20)
"Upon arrival the house was smaller than expected but after we checked in it was perfect . Everything worked as it should and there were no issues the whole time we were there . The owner supplied free firewood for the late nights outside while the deck at the waterfront and large docking area for the boats was appreciated much as well . Property manager was so easy and nice to work with and was very useful when getting area information . Thank you much for a great family made memory , we will be...
Waterfront Syracuse Home w/Deck, Fire Pit & Kayaks
Beautiful lakefront property
10.0 out of 10, Exceptional, (22)
"top rate"
Beautiful lakefront property
Lakefront Home on Lake Webster
9.8 out of 10, Exceptional, (14)
"Beautiful view. Quiet. Lovely little cottage."
Lakefront Home on Lake Webster
Lakefront Cottage on Webster Lake with Beautiful Sunsets, 2 bed, 1 bath
10.0 out of 10, Exceptional, (25)
"Amazing location!! We rented a boat at the nearby marina and enjoyed the lake to the fullest!! Definitely recommend!!"
Lakefront Cottage on Webster Lake with Beautiful Sunsets, 2 bed, 1 bath
Beautiful and Historic Log Cabin: cozy, quiet, huge hot tub! Quiet getaway!
10.0 out of 10, Exceptional, (97)
"We loved the hot tub, the porch and the cabin. We loved venturing to Goshen and Elkhart and visiting the towns. There was a coffee table with lighting above that was perfect for our puzzle! We were looking for an isolated cabin, and this is not that, but it was very nice and the beds were super comfy."
Beautiful and Historic Log Cabin: cozy, quiet, huge hot tub! Quiet getaway!
Welcoming Grace College parents, fall weddings, traveling for work, or anything
9.8 out of 10, Exceptional, (9)
"Fantastic hosts! The home was super clean and had all the amenities we needed. It was a perfect location our events in Warsaw. We hope to be back next year!"
Welcoming Grace College parents, fall weddings, traveling for work, or anything
Lake Cottage with amazing sunset view on Lake Tippecanoe
10.0 out of 10, Exceptional, (41)
"Perfect house for a long weekend. The owner was very responsive throughout our stay and went above and beyond. Highly recommend."
Lake Cottage with amazing sunset view on Lake Tippecanoe
Lakefront Syracuse Home w/ Deck & Private Dock!
10.0 out of 10, Exceptional, (3)
"3 adults, 4 teens and 2 under 12. House was as described with plenty of sleeping options for our 2 families. Location right on the main body of Syracuse was great and we docked both fishing boats right at the house. Will stay again!"
Lakefront Syracuse Home w/ Deck & Private Dock!
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See all available properties in Oswego
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.

Oswego Holiday Home Travel Info

Number of holiday homes
3
Known landmarks
Wagon Wheel Theatre, Hidden Lake and Chapman Lakes
International airport
South Bend, IN (SBN-South Bend Intl.)

Other types of properties in Oswego you may be interested in

Wyndham Garden Warsaw
3.0 star property
7.8 out of 10, Good, (831)
"It was close to the lake and college"
The price is AU$135
per night
6 July - 7 July
Wyndham Garden Warsaw
Best Western Plus Warsaw
2.5 star property
7.6 out of 10, Good, (579)
"Great "
The price is AU$137
per night
10 June - 11 June
Best Western Plus Warsaw
Quality Inn & Suites
2.5 star property
7.8 out of 10, Good, (726)
"Great service friendly staff, quietly area"
The price is AU$123
per night
17 June - 18 June
Quality Inn & Suites
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.

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$278 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 can I see and do in Oswego?

While you're exploring the area, Tippecanoe Lake and Big Barbee Lake are a couple of picturesque spots to get outside and enjoy nature. Webster Lake and Grace College 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.

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