Holiday Rentals in Oswego

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Holiday Rentals in Oswego

Memorable Vacation Awaits on Big Chapman Lake! Sleeps 8! Optional Pontoon!
10.0 out of 10, Exceptional, (11)
The price is €276
includes taxes & fees
15 Oct - 16 Oct
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, (3)
"Great clean little cabin by the lake. Hot tub and outdoor area is nice! Very private with a view of the water on the porch. "
The price is €293
includes taxes & fees
20 Oct - 21 Oct
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, (161)
"Family stay."
The price is €158
includes taxes & fees
26 Oct - 27 Oct
Charming farmhouse in peaceful countryside
Irish Lakefront, Hot Tub! Pets, dock, fishing, kayaks, ice fishing, hunting!
2.0 star property
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!!"
Irish Lakefront, Hot Tub! Pets, dock, fishing, kayaks, ice fishing, hunting!
Lakefront Home on Lake Webster
9.4 out of 10, Exceptional, (33)
"Very comfortable lakeside cottage with a beautiful view."
Lakefront Home on Lake Webster
Trail Side in the Heart of Winona Lake
10.0 out of 10, Exceptional, (33)
"House very comfortable, we enjoyed being close to the trails"
The price is €221
includes taxes & fees
19 Oct - 20 Oct
Trail Side in the Heart of Winona Lake
Beautiful and Historic Log Cabin: cozy, quiet, huge hot tub! Quiet getaway!
10.0 out of 10, Exceptional, (119)
"Well appointed cottage, clean and quiet. We enjoyed our stay."
Beautiful and Historic Log Cabin: cozy, quiet, huge hot tub! Quiet getaway!
NEW Spacious Lakehouse Retreat +private pier
9.6 out of 10, Exceptional, (30)
"Host was very accommodating and helpful with extra information during the holiday! (fourth of July) Took advantage of all the great amenities!"
NEW Spacious Lakehouse Retreat +private pier
Cozy lakefront home on Big Barbee Lake
10.0 out of 10, Exceptional, (10)
"Great location with everything you need for a weekend on the lake. We will definitely be back! "
The price is €234
includes taxes & fees
15 Oct - 16 Oct
Cozy lakefront home on Big Barbee Lake
Woodside Retreat in the Heart of Amish Country
10.0 out of 10, Exceptional, (9)
"It was a very unique place to stay for a few days. Very clean and thoughtful in items provided"
The price is €167
includes taxes & fees
28 Oct - 29 Oct
Woodside Retreat in the Heart of Amish Country
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
Lakefront Cottage on Webster Lake with Beautiful Sunsets, 2 bed, 1 bath
10.0 out of 10, Exceptional, (54)
"Great cottage and view, definitely recommend."
Lakefront Cottage on Webster Lake with Beautiful Sunsets, 2 bed, 1 bath
Waters Edge Cottage on Big Barbee Lake!
9.8 out of 10, Exceptional, (29)
"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. "
Waters Edge Cottage on Big Barbee Lake!
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,
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 €485
includes taxes & fees
15 Oct - 16 Oct
Beautiful Lakefront home, pets welcome, fully fenced, dock, kayaks, fishing!!
Lakefront|Kayaks|Paddleboat|Fishing
10.0 out of 10, Exceptional, (20)
"Great location with lake access! Lots of games to keep the little ones entertained! "
The price is €233
includes taxes & fees
22 Oct - 23 Oct
Lakefront|Kayaks|Paddleboat|Fishing
Inviting Lakefront Home with Patio and Dock
10.0 out of 10, Exceptional, (13)
"This house was perfect for our family of four. It was quiet, extremely clean, and well stocked with everything we needed. The owner was communicative and everything was easy. You can see the lake from the front windows and the channel in back is also very nice. Would stay here again!"
Inviting Lakefront Home with Patio and Dock
Water front cottage on beautiful Upper Long Lake
9.4 out of 10, Exceptional, (83)
"All was great at the property"
Water front cottage on beautiful Upper Long Lake
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.
Indoor pool with 4-bedrooms in charming Goshen with WiFi and so many extras
10.0 out of 10, Exceptional, (3)
"Amazing place with plenty of room for the entire family! Our hosts were wonderful and answered all the questions and concerns we had! The host made sure we had all the amenities and more, had a wonderful pool, game room, fire pit, plenty of space for everyone! We will be back! "
The price is €921
includes taxes & fees
16 Oct - 17 Oct
Indoor pool with 4-bedrooms in charming Goshen with WiFi and so many extras
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, apart-hotels, 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 €158 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?

Charming farmhouse in peaceful countryside: This holiday home rental outside of Oswego is located in a rural location, and has a fireplace, a patio and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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.