Oswego Vacation Rentals

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Check prices for these dates

Tonight
Jan 11 - Jan 12
Tomorrow
Jan 12 - Jan 13
Next weekend
Jan 16 - Jan 18
In two weeks
Jan 23 - Jan 25

Our top choices for Oswego vacation rentals

Property grounds
Fishing · Kayaks · Firepit · Paddleboat

Cabin in Pierceton

Fishing · Kayaks · Firepit · Paddleboat
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 ￥16,886
￥37,917 total
includes taxes & fees
Jan 13 - Jan 14
Fishing · Kayaks · Firepit · Paddleboat
Exterior
Memorable Vacation Awaits on Big Chapman Lake! Sleeps 8! Optional Pontoon!

Cottage in Warsaw

Memorable Vacation Awaits on Big Chapman Lake! Sleeps 8! Optional Pontoon!
10.0 out of 10, Exceptional, (17 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 ￥24,868
￥51,019 total
includes taxes & fees
Jan 19 - Jan 20
Memorable Vacation Awaits on Big Chapman Lake! Sleeps 8! Optional Pontoon!
Terrace/patio
Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm

Cottage in Syracuse

Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm
9.8 out of 10, Exceptional, (7 reviews)
"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. "
United States
Ty M.
The price is ￥20,368
￥40,319 total
includes taxes & fees
Jan 13 - Jan 14
Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm
Property grounds
Trail Side in the Heart of Winona Lake

Vacation Home in Winona Lake

Trail Side in the Heart of Winona Lake
9.8 out of 10, Exceptional, (38 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 ￥20,605
￥41,470 total
includes taxes & fees
Jan 13 - Jan 14
Trail Side in the Heart of Winona Lake
Interior
Woodside Retreat in the Heart of Amish Country

Vacation Home in Nappanee

Woodside Retreat in the Heart of Amish Country
10.0 out of 10, Exceptional, (11 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 ￥18,157
￥31,930 total
includes taxes & fees
Jan 13 - Jan 14
Woodside Retreat in the Heart of Amish Country
Interior
Lake Wawasee FROG House, Surround Sound & Bikes

Vacation Home in Syracuse

Lake Wawasee FROG House, Surround Sound & Bikes
2.0 star property
10.0 out of 10, Exceptional, (7 reviews)
"It was a fantastic comfortable house to continue a long standing tradition if visitong Lake Wawasee. Nice being so close to the Frog Tavern."
United States
Mike H.
The price is ￥22,736
￥39,258 total
includes taxes & fees
Jan 13 - Jan 14
Lake Wawasee FROG House, Surround Sound & Bikes
Fridge, microwave, oven, stovetop
Charming farmhouse in peaceful countryside

Vacation Home in Nappanee

Charming farmhouse in peaceful countryside
10.0 out of 10, Exceptional, (166 reviews)
"It was a clean nice place to stay. We loved the ping pong table. "
United States
Tracy M.
The price is ￥14,068
￥23,500 total
includes taxes & fees
Jan 15 - Jan 16
Charming farmhouse in peaceful countryside
Terrace/patio
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!

Vacation Home in Milford

Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!
10.0 out of 10, Exceptional, (29 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 ￥19,752
￥55,015 total
includes taxes & fees
Jan 13 - Jan 14
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!
Interior
CozyHome-HotTub-Pool-WI-FI-KingBed-ArcadeGames-PoolTable

Vacation Home in Goshen

CozyHome-HotTub-Pool-WI-FI-KingBed-ArcadeGames-PoolTable
10.0 out of 10, Exceptional, (10 reviews)
"Great place to relax, children loved the pool!"
United States
Delmer Y.
The price is ￥19,736
￥52,372 total
includes taxes & fees
Jan 13 - Jan 14
CozyHome-HotTub-Pool-WI-FI-KingBed-ArcadeGames-PoolTable
Terrace/patio
Heart Jacuzzi · Kayaks · Firepit · Pier

Cabin in Warsaw

Heart Jacuzzi · Kayaks · Firepit · Pier
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 ￥25,965
￥49,499 total
includes taxes & fees
Jan 13 - Jan 14
Heart Jacuzzi · Kayaks · Firepit · Pier
Property grounds
3-BR + Firepit, Coffee Bar & Grill

Vacation Home in Bourbon

3-BR + Firepit, Coffee Bar & Grill
10.0 out of 10, Exceptional, (1 review)
"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 ￥16,200
￥46,084 total
includes taxes & fees
Jan 20 - Jan 21
3-BR + Firepit, Coffee Bar & Grill
Interior
Tippecanoe Lakefront Classic Cottage

Cottage in Leesburg

Tippecanoe Lakefront Classic Cottage
The price is ￥35,814
￥82,477 total
includes taxes & fees
Jan 13 - Jan 14
Tippecanoe Lakefront Classic Cottage
Interior
4BR Lakefront · Pier · Game Room · Sleeps 16+

Vacation Home in North Webster

4BR Lakefront · Pier · Game Room · Sleeps 16+
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 ￥47,754
￥106,042 total
includes taxes & fees
Jan 13 - Jan 14
4BR Lakefront · Pier · Game Room · Sleeps 16+
Property grounds
Beautiful Lakefront home, pets welcome, fully fenced, dock, kayaks, fishing!!

Vacation Home in Leesburg

Beautiful Lakefront home, pets welcome, fully fenced, dock, kayaks, fishing!!
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 ￥43,736
￥86,297 total
includes taxes & fees
Jan 13 - Jan 14
Beautiful Lakefront home, pets welcome, fully fenced, dock, kayaks, fishing!!
Interior
Private Lake Front Home on Wawasee - Exclusive and Quiet Ogden Island Retreat

Vacation Home in Syracuse

Private Lake Front Home on Wawasee - Exclusive and Quiet Ogden Island Retreat
10.0 out of 10, Exceptional, (2 reviews)
"Great views, spacious, clean home, responsive owner. "
United States
Bob T.
The price is ￥47,841
￥86,474 total
includes taxes & fees
Jan 14 - Jan 15
Private Lake Front Home on Wawasee - Exclusive and Quiet Ogden Island Retreat
Dining
Rock Run Creek House

Vacation Home in Goshen

Rock Run Creek House
10.0 out of 10, Exceptional, (3 reviews)
"was a fantastic rental. Thank you so much!"
United States
Lavern Y.
The price is ￥72,629
￥106,984 total
includes taxes & fees
Jan 18 - Jan 19
Rock Run Creek House
Indoor pool, a heated pool
Indoor pool with 4-bedrooms in charming Goshen with WiFi and so many extras

Vacation Home in Goshen

Indoor pool with 4-bedrooms in charming Goshen with WiFi and so many extras
9.8 out of 10, Exceptional, (7 reviews)
"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! "
United States
Jill S.
The price is ￥118,260
￥218,781 total
includes taxes & fees
Jan 13 - Jan 14
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

Wyndham Garden Warsaw

Wyndham Garden Warsaw

10/10 Excellent
"Clean rooms hotel was remodel ing but very accommodating "
James 2-night trip
Posted 7 days ago
Wyndham Garden Warsaw

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?

Charming farmhouse in peaceful countryside: This vacation home rental near 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 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 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.