Holiday Rentals in Oswego

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Our top choices for Oswego holiday rentals

Woodside Retreat in the Heart of Amish Country

Woodside Retreat in the Heart of Amish Country
Nappanee
10.0 out of 10, Exceptional, (12 reviews)
"It was a very unique place to stay for a few days. Very clean and thoughtful in items provided"
United States
VICKI
The price is €174
includes taxes & fees
8 Mar - 9 Mar
Woodside Retreat in the Heart of Amish Country

Fishing · Kayaks · Firepit · Paddleboat

Fishing · Kayaks · Firepit · Paddleboat
Pierceton
10.0 out of 10, Exceptional, (22 reviews)
"Clean property, gewat location, loved the lake and the stars."
United States
joseph b.
The price is €190
includes taxes & fees
9 Mar - 10 Mar
Fishing · Kayaks · Firepit · Paddleboat

4BR Lakefront · Pier · Game Room · Sleeps 16+

4BR Lakefront · Pier · Game Room · Sleeps 16+
North Webster
10.0 out of 10, Exceptional, (16 reviews)
"Excellent lakehouse on lake Webster! Our family loved staying at this property and the owners take care of all the details. From water rafts, kayaks, air hockey, and Foosball, this is the house to choose for a large family stay, and I highly recommend it!"
United States
dpersky1
The price is €510
includes taxes & fees
8 Mar - 9 Mar
4BR Lakefront · Pier · Game Room · Sleeps 16+

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

Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!
Milford
10.0 out of 10, Exceptional, (32 reviews)
"We very much enjoyed our stay. The pool and hot tub were amazing and the home was thoughtfully prepared. We would definitely love to stay here again. "
United States
Mariah C.
The price is €296
includes taxes & fees
9 Mar - 10 Mar
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!

Trail Side in the Heart of Winona Lake

Trail Side in the Heart of Winona Lake
Winona Lake
9.8 out of 10, Exceptional, (39 reviews)
"The house was perfect for our weekend stay. It was very clean and the check in & check out process were super easy!"
United States
Melissa S.
The price is €225
includes taxes & fees
13 Mar - 14 Mar
Trail Side in the Heart of Winona Lake

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

Memorable Vacation Awaits on Big Chapman Lake! Sleeps 8! Optional Pontoon!
Warsaw
10.0 out of 10, Exceptional, (18 reviews)
"Wonderful home, lovely views on the lake, great communication with owner and host. We very much enjoyed our stay!"
United States
Carol B.
The price is €285
includes taxes & fees
9 Mar - 10 Mar
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

Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm
Syracuse
9.8 out of 10, Exceptional, (8 reviews)
"The hot tub was clean and ready to go as soon as we got there.. very relaxing stay… we loved it"
United States
Samantha T.
The price is €221
includes taxes & fees
8 Mar - 9 Mar
Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm

Heart Jacuzzi · Kayaks · Firepit · Pier

Heart Jacuzzi · Kayaks · Firepit · Pier
Warsaw
10.0 out of 10, Exceptional, (11 reviews)
"Was a wonderful weekend get-away for the wife and I. Quiet, relaxing, and stress free but with everything we needed. "
United States
Ed R.
The price is €220
includes taxes & fees
15 Mar - 16 Mar
Heart Jacuzzi · Kayaks · Firepit · Pier

3 bedroom 2 bath renovated A frame on channel to Kuhn lake and the Barbee Chain

3 bedroom 2 bath renovated A frame on channel to Kuhn lake and the Barbee Chain
Pierceton
9.6 out of 10, Exceptional, (14 reviews)
"Everything was wonderful "
United States
William R.
The price is €271
includes taxes & fees
6 Apr - 7 Apr
3 bedroom 2 bath renovated A frame on channel to Kuhn lake and the Barbee Chain

Lake View Lodge

Lake View Lodge
Syracuse
The price is €343
includes taxes & fees
8 Mar - 9 Mar
Lake View Lodge

Rock Run Creek House

Rock Run Creek House
Goshen
10.0 out of 10, Exceptional, (3 reviews)
"was a fantastic rental. Thank you so much!"
United States
Lavern Y.
Rock Run Creek House

Premier Lake Wawasee Lakefront Home - Private Dock & Sandy Bottom

Premier Lake Wawasee Lakefront Home - Private Dock & Sandy Bottom
Syracuse
10.0 out of 10, Exceptional, (2 reviews)
"Great views, spacious, clean home, responsive owner. "
United States
Bob T.
The price is €472
includes taxes & fees
10 Mar - 11 Mar
Premier Lake Wawasee Lakefront Home - Private Dock & Sandy Bottom

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

Beautiful Lakefront home, pets welcome, fully fenced, dock, kayaks, fishing!!
Leesburg
10.0 out of 10, Exceptional, (1 review)
"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 €458
includes taxes & fees
8 Mar - 9 Mar
Beautiful Lakefront home, pets welcome, fully fenced, dock, kayaks, fishing!!

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

Indoor pool with 4-bedrooms in charming Goshen with WiFi and so many extras
Goshen
9.8 out of 10, Exceptional, (8 reviews)
"We decided to get away for a special occasion, and it didn’t disappoint! Thank you"
United States
Anna G.
The price is €1,253
includes taxes & fees
1 Apr - 2 Apr
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 €221 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 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.