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

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

Cottage in 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!
Microwave, oven, stovetop
Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm

Cottage in 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
View from property
Irish Lakefront, Hot Tub! Pets, dock, fishing, kayaks, ice fishing, hunting!

Vacation Home in Leesburg

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!!"
United States
Tami S.
Irish Lakefront, Hot Tub! Pets, dock, fishing, kayaks, ice fishing, hunting!
Exterior
Trail Side in the Heart of Winona Lake

Vacation Home in 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
Living area
Lakefront Home on Lake Webster

Cottage in North Webster

9.4 out of 10, Exceptional, (34)
"Very cute place. Great views, everything you need for a stay. Parking is the only downfall but not enough for us to return. "
United States
Lisette M.
Lakefront Home on Lake Webster
Outdoor spa tub
Beautiful and Historic Log Cabin: cozy, quiet, huge hot tub! Quiet getaway!

Cabin in Goshen

10.0 out of 10, Exceptional, (120)
"Well appointed cottage, clean and quiet. We enjoyed our stay."
United States
EV O.
Beautiful and Historic Log Cabin: cozy, quiet, huge hot tub! Quiet getaway!
Fridge, microwave, oven, stovetop
Cozy lakefront home on Big Barbee Lake

Vacation Home in 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
Fridge, microwave, stovetop, dishwasher
Lake Wawasee Retreat: private pool, hot tub & pier

Vacation Home in Syracuse

2.0 star property
Lake Wawasee Retreat: private pool, hot tub & pier
Outdoor pool
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!

Vacation Home in 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
Lake Wawasee 2 Bedroom Premier Condo on Channel with 1 Boat Slip, Sleeps 6,

Condo in Syracuse

9.6 out of 10, Exceptional, (30)
"This was a good spot for our family lake getaway. We were able to put the boat at the dock for easy lake access. The host was very accommodating and friendly. "
United States
Lindsay K.
Lake Wawasee 2 Bedroom Premier Condo on Channel with 1 Boat Slip, Sleeps 6,
Property grounds
Water front cottage on beautiful Upper Long Lake

Cottage in Albion

9.4 out of 10, Exceptional, (83)
"All was great at the property"
United States
David C.
Water front cottage on beautiful Upper Long Lake
Dining
Woodside Retreat in the Heart of Amish Country

Vacation Home in 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
Property grounds
Beautiful Lakefront home, pets welcome, fully fenced, dock, kayaks, fishing!!

Vacation Home in 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!!
Dining
NEW Spacious Lakehouse Retreat +private pier

Vacation Home in Mentone

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!"
United States
Karla R.
NEW Spacious Lakehouse Retreat +private pier
Exterior
Charming 3-bedroom lake house on Tri lakes 6 miles north of Columbia City.

Vacation Home in Columbia City

9.8 out of 10, Exceptional, (17)
"The host had great communication. The house was very clean and had a great view. We enjoyed our stay."
United States
Deborah H.
Charming 3-bedroom lake house on Tri lakes 6 miles north of Columbia City.
Interior
Indoor pool with 4-bedrooms in charming Goshen with WiFi and so many extras

Vacation Home in 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.
Indoor pool with 4-bedrooms in charming Goshen with WiFi and so many extras
Fridge, microwave, oven, stovetop
Country View Retreat - 3 bedroom, Private family-friendly home

Vacation Home in North Manchester

9.8 out of 10, Exceptional, (13)
"Beautiful, clean, we loved it!"
United States
Gloria A.
Country View Retreat - 3 bedroom, Private family-friendly home
Property grounds
Lake Tippecanoe, Little Tippy retreat—sleeps 12, dog friendly, private lakefront

Cabin in Leesburg

10.0 out of 10, Exceptional, (3)
"We had a wonderful time. The views from the deck and three upper bedrooms are beautiful. 10/10"
United States
Michelle F.
Lake Tippecanoe, Little Tippy retreat—sleeps 12, dog friendly, private lakefront
Exterior
Stunning lakefront log cabin on a private acre

Vacation Home in Syracuse

9.6 out of 10, Exceptional, (43)
"2nd year staying at this property and we will definitely be returning for more years. Amazing rustic cabin; this home is full of character that takes you back in time and makes you slow down and relax. The 1 acre property is the best Lake Wawasee has to over. Once again, we made some wonderful family memories!"
United States
Kim B.
Stunning lakefront log cabin on a private acre
Property grounds
Fishing · Kayaks · Firepit · Paddleboat

Cabin in 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
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

Search for holiday rentals in Oswego on Expedia! You can easily find your home rentals, villas, holiday apartments in Oswego using one of the methods below:

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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.