Oswego Vacation Rentals

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Check prices for these dates

In two weeks
Dec 5 - Dec 7
In two months
Jan 16 - Jan 18
In three months
Feb 13 - Feb 15
In four months
Mar 13 - Mar 15

Vacation Rentals in Oswego

Interior
Welcome to our Home in Ligonier

Welcome to our Home in Ligonier

2.0 star property
Ligonier
10.0 out of 10, Exceptional, (2)
"This is our third time renting this property. The hosts are awesome and pay attention to detail. Couldn't be happier with our stay!"
United States
Jeremiah A.
The price is ￥18,102
￥38,257 total
includes taxes & fees
Nov 23 - Nov 24
Welcome to our Home in Ligonier
Property grounds
Fishing · Kayaks · Firepit · Paddleboat

Fishing · Kayaks · Firepit · Paddleboat

Pierceton
10.0 out of 10, Exceptional, (22)
"Clean property, gewat location, loved the lake and the stars."
United States
joseph b.
The price is ￥17,807
￥38,944 total
includes taxes & fees
Nov 23 - Nov 24
Fishing · Kayaks · Firepit · Paddleboat
Exterior
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)
"This isn't our first time staying here and we love it. It's easy to find, simple living and quiet. Also, there is food delivery available so we don't have to cook after a long hunt."
United States
Michael G.
The price is ￥21,115
￥47,123 total
includes taxes & fees
Nov 25 - Nov 26
3 bedroom 2 bath renovated A frame on channel to Kuhn lake and the Barbee Chain
Microwave, oven, stovetop
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, (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 ￥28,779
￥51,677 total
includes taxes & fees
Nov 23 - Nov 24
Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm
Interior
Heart Jacuzzi · Kayaks · Firepit · Pier

Heart Jacuzzi · Kayaks · Firepit · Pier

Warsaw
10.0 out of 10, Exceptional, (11)
"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 ￥21,585
￥43,877 total
includes taxes & fees
Nov 23 - Nov 24
Heart Jacuzzi · Kayaks · Firepit · Pier
Exterior
Trail Side in the Heart of Winona Lake

Trail Side in the Heart of Winona Lake

Winona Lake
9.8 out of 10, Exceptional, (38)
"This is a fantastic property. Very clean and comfortable! Great neighborhood for walking and close to shops and restaurants. Will definitely stay here again."
United States
Eric B.
The price is ￥20,412
￥41,257 total
includes taxes & fees
Nov 29 - Nov 30
Trail Side in the Heart of Winona Lake
Dining
Woodside Retreat in the Heart of Amish Country

Woodside Retreat in the Heart of Amish Country

Nappanee
10.0 out of 10, Exceptional, (10)
"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 ￥16,292
￥29,223 total
includes taxes & fees
Nov 23 - Nov 24
Woodside Retreat in the Heart of Amish Country
Outdoor pool
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, (29)
"We had a really great time and the host was very very responsive to all our questions. "
United States
Mary B.
The price is ￥21,115
￥57,108 total
includes taxes & fees
Nov 24 - Nov 25
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!
Exterior
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, (17)
"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 ￥27,372
￥52,028 total
includes taxes & fees
Dec 21 - Dec 22
Memorable Vacation Awaits on Big Chapman Lake! Sleeps 8! Optional Pontoon!
Exterior
Gram's Cottage on Lake Webster in North Webster, Indiana is the perfect getaway.

Gram's Cottage on Lake Webster in North Webster, Indiana is the perfect getaway.

North Webster
The price is ￥18,183
￥53,299 total
includes taxes & fees
Nov 23 - Nov 24
Gram's Cottage on Lake Webster in North Webster, Indiana is the perfect getaway.
Property grounds
3-BR + Firepit, Coffee Bar & Grill

3-BR + Firepit, Coffee Bar & Grill

Bourbon
10.0 out of 10, Exceptional, (1)
"Our stay was perfect, starting with communication, spotless, decorated for FALL and it felt like we were at home! Our son’s college was 24 minutes from the house and it worked out perfect for him to come visit and us enjoy Family Weekend at the school to watch him play baseball! Our next visit will be this exact place! We hope to get to come at Christmas because we want to see how beautiful it’s decorated in Christmas! 10/10 stay! Sweetest Host! The basket of smores and apples was the best! "
United States
Brandy T.
The price is ￥15,034
￥44,342 total
includes taxes & fees
Dec 2 - Dec 3
3-BR + Firepit, Coffee Bar & Grill
Fridge, microwave, oven, stovetop
Cozy lakefront home on Big Barbee Lake

Cozy lakefront home on Big Barbee Lake

Pierceton
10.0 out of 10, Exceptional, (11)
"Great location with everything you need for a weekend on the lake. We will definitely be back! "
United States
dunchbox 1.
The price is ￥20,412
￥41,257 total
includes taxes & fees
Nov 23 - Nov 24
Cozy lakefront home on Big Barbee Lake
Smart TV, fireplace
Lake access directly in front of Cottage on high speed watercraft Big Barbee

Lake access directly in front of Cottage on high speed watercraft Big Barbee

Pierceton
10.0 out of 10, Exceptional, (2)
The price is ￥39,103
￥74,101 total
includes taxes & fees
Dec 23 - Dec 24
Lake access directly in front of Cottage on high speed watercraft Big Barbee
Dining
Private Lake Front Home on Wawasee - Exclusive and Quiet Ogden Island Retreat

Private Lake Front Home on Wawasee - Exclusive and Quiet Ogden Island Retreat

Syracuse
10.0 out of 10, Exceptional, (2)
"Great views, spacious, clean home, responsive owner. "
United States
Bob T.
The price is ￥47,392
￥85,662 total
includes taxes & fees
Dec 4 - Dec 5
Private Lake Front Home on Wawasee - Exclusive and Quiet Ogden Island Retreat
Property grounds
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)
"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 ￥39,103
￥80,057 total
includes taxes & fees
Nov 26 - Nov 27
Beautiful Lakefront home, pets welcome, fully fenced, dock, kayaks, fishing!!
Outdoor dining
4BR Lakefront · Pier · Game Room · Sleeps 16+

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

North Webster
10.0 out of 10, Exceptional, (16)
"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 ￥47,306
￥105,924 total
includes taxes & fees
Nov 24 - Nov 25
4BR Lakefront · Pier · Game Room · Sleeps 16+
Dining
Rock Run Creek House

Rock Run Creek House

Goshen
10.0 out of 10, Exceptional, (3)
"was a fantastic rental. Thank you so much!"
United States
Lavern Y.
The price is ￥71,858
￥106,044 total
includes taxes & fees
Nov 23 - Nov 24
Rock Run Creek House
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

Oakwood Resort

Oakwood Resort

10/10 Excellent
"Everything was great. Lovely hotel and beautiful area. Will book directly with the hotel next time instead of using Expedia. Paid almost $100 more. "
Crystal Dawn 3-night trip
Posted 3 days ago
Oakwood Resort

Find out more about Oswego

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Frequently asked questions

Can I find a vacation rental in Oswego?

Yes, we have vacation rentals close to well known attractions in Oswego, or you can choose a more secluded option if you're looking for a relaxing stay.

What are some of the best vacation rentals in Oswego?

Cozy lakefront home on Big Barbee Lake: This vacation home rental near Oswego is equipped with a barbecue grill, 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 larger area.

What are vacation rentals like in Oswego?

Vacation rentals are private properties you can stay in for a couple days or more in Oswego. Vacation rentals offer amenities like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a clean environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for a family trip or a small group gathering.