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Oswego Vacation Rentals

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Our top choices for Oswego vacation rentals

1. Heart Jacuzzi · Kayaks · Firepit · Pier

Heart Jacuzzi · Kayaks · Firepit · Pier
Warsaw
10.0 out of 10, Exceptional, (18 reviews)
"This cottage was very cute and cozy, a true lovers retreat. Host was very accommodating and check in and out was easy."
United States
Lisa S.
The price is CA $170
CA $405 total
includes taxes & fees
Oct 20 - Oct 21
Heart Jacuzzi · Kayaks · Firepit · Pier

2. Indigo Hideaway | Romantic + Fire pit

Indigo Hideaway | Romantic + Fire pit
Nappanee
The price is CA $180
CA $407 total
includes taxes & fees
Oct 20 - Oct 21
Indigo Hideaway | Romantic + Fire pit

3. Cozy lakefront home on Big Barbee Lake

Cozy lakefront home on Big Barbee Lake
Pierceton
9.8 out of 10, Exceptional, (29 reviews)
"Very enjoyable place to rest and relax after tournament musky fishing."
United States
Michael A.
The price is CA $205
CA $405 total
includes taxes & fees
Oct 26 - Oct 27
Cozy lakefront home on Big Barbee Lake

4. Fishing · Kayaks · Firepit · Paddleboat

Fishing · Kayaks · Firepit · Paddleboat
Pierceton
10.0 out of 10, Exceptional, (34 reviews)
"We had a wondeful week at the cottage. One of the cleanest that we have been to which I really appreciate. Communication was great."
United States
Amy G.
The price is CA $165
CA $399 total
includes taxes & fees
Oct 20 - Oct 21
Fishing · Kayaks · Firepit · Paddleboat

5. Charming 3 bedroom 2 bath A frame home on channel to Kuhn Lake & Barbee Chain

Charming 3 bedroom 2 bath A frame home on channel to Kuhn Lake & Barbee Chain
Pierceton
9.8 out of 10, Exceptional, (24 reviews)
"Love this space! Clean and welcoming! Super host, great to work with! Looking forward to our next stay! "
United States
John K.
The price is CA $255
CA $507 total
includes taxes & fees
Oct 24 - Oct 25
Charming 3 bedroom 2 bath A frame home on channel to Kuhn Lake & Barbee Chain

6. Trail Side in the Heart of Winona Lake

Trail Side in the Heart of Winona Lake
Winona Lake
9.8 out of 10, Exceptional, (69 reviews)
"Fabulous place to stay! Great location, easily accessible to anything you need or want to see in Winona Lake and surrounding areas. The house very clean and comfortable and safe. Thank you, had a wonderful time."
United States
Shea
The price is CA $191
CA $380 total
includes taxes & fees
Oct 20 - Oct 21
Trail Side in the Heart of Winona Lake

7. Cozy lake Cottage on Dewart Lake , 1 mile from Blue Barn Berry Farm, Hottub!

Cozy lake Cottage on Dewart Lake , 1 mile from Blue Barn Berry Farm, Hottub!
Syracuse
9.4 out of 10, Exceptional, (18 reviews)
"Lovely little place to stay"
United States
Panacea G.
The price is CA $260
CA $496 total
includes taxes & fees
Oct 20 - Oct 21
Cozy lake Cottage on Dewart Lake , 1 mile from Blue Barn Berry Farm, Hottub!

8. Lakefront Fun on Papakeechie - Kayaks & More!

Lakefront Fun on Papakeechie - Kayaks & More!
Syracuse
10.0 out of 10, Exceptional, (2 reviews)
"This location has a very beautiful view"
United States
Jennie S.
The price is CA $225
CA $602 total
includes taxes & fees
Nov 3 - Nov 4
Lakefront Fun on Papakeechie - Kayaks & More!

9. Quiet cul-de-sac home near Syracuse

Quiet cul-de-sac home near Syracuse
Syracuse
The price is CA $226
CA $285 total
includes taxes & fees
Nov 2 - Nov 3
Quiet cul-de-sac home near Syracuse

10. Backwater Lake Cottage | Tiki Bar & Paddleboat

Backwater Lake Cottage | Tiki Bar & Paddleboat
North Webster
The price is CA $212
CA $569 total
includes taxes & fees
Oct 20 - Oct 21
Backwater Lake Cottage | Tiki Bar & Paddleboat

11. Barbee Lake Lodge/kayaks

Barbee Lake Lodge/kayaks
Warsaw
10.0 out of 10, Exceptional, (1 review)
"Beautiful place, right on the canal. Clean and well equipped with everything we needed. Really enjoyed our stay."
United States
Kim W.
The price is CA $247
CA $401 total
includes taxes & fees
Oct 20 - Oct 21
Barbee Lake Lodge/kayaks

12. Dog-Friendly 2BR | Private Fenced Yard & Fire Pit | Walk to Village & Grace

Dog-Friendly 2BR | Private Fenced Yard & Fire Pit | Walk to Village & Grace
Winona Lake
10.0 out of 10, Exceptional, (2 reviews)
"Place is amazing. We will be back!"
United States
Patrick L.
The price is CA $229
CA $511 total
includes taxes & fees
Oct 27 - Oct 28
Dog-Friendly 2BR | Private Fenced Yard & Fire Pit | Walk to Village & Grace

13. 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, (5 reviews)
"This guest house was perfect for two people, though it could sleep six. It was clean and had all the amenities we needed. We had a very comfortable and relaxing stay there."
United States
Gretchen E.
The price is CA $392
CA $773 total
includes taxes & fees
Oct 25 - Oct 26
Beautiful Lakefront home, pets welcome, fully fenced, dock, kayaks, fishing!!

14. Autumn getaway cozy cottage cabin with fire pit ,lake and beach access Indiana

Autumn getaway cozy cottage cabin with fire pit ,lake and beach access Indiana
Albion
8.0 out of 10, Very good, (1 review)
"Very quiet location. Relaxing deck to sit on. Fire pit and grill were stocked with charcoal and firewood which was appreciated. Pet friendly. Close to a lot of lakes and recreation areas. Communication was great with the host."
United States
Joan P.
The price is CA $147
CA $220 total
includes taxes & fees
Oct 31 - Nov 1
Autumn getaway cozy cottage cabin with fire pit ,lake and beach access Indiana

15. Charlee's Cabin - Family Escape on Webster Lake | Pier & Swimming!

Charlee's Cabin - Family Escape on Webster Lake | Pier & Swimming!
North Webster
The price is CA $280
CA $791 total
includes taxes & fees
Nov 16 - Nov 17
Charlee's Cabin - Family Escape on Webster Lake | Pier & Swimming!

16. Sunrise on Sawmill - Kayaks, Paddleboat, Firepit, Arcade!

Sunrise on Sawmill - Kayaks, Paddleboat, Firepit, Arcade!
Leesburg
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful views and full of amenities. Absolutely perfect for our group. Great communication from the host."
United States
Wendy S.
The price is CA $369
CA $1,065 total
includes taxes & fees
Oct 20 - Oct 21
Sunrise on Sawmill - Kayaks, Paddleboat, Firepit, Arcade!

17. Best Views of Webster Lake! Paddleboards + Swimming

Best Views of Webster Lake! Paddleboards + Swimming
North Webster
10.0 out of 10, Exceptional, (2 reviews)
"Absolutely beautiful rental. We had such a wonderful time my son wants to come back again. Friendly people all around and beautiful sunrise we saw."
United States
John D.
The price is CA $366
CA $1,061 total
includes taxes & fees
Oct 20 - Oct 21
Best Views of Webster Lake! Paddleboards + Swimming

18. Turtle Alley on Wawasee

Turtle Alley on Wawasee
Syracuse
The price is CA $294
CA $731 total
includes taxes & fees
Oct 20 - Oct 21
Turtle Alley on Wawasee

19. Your home @ Jellystone Pierceton, lot 525.

Your home @ Jellystone Pierceton, lot 525.
Pierceton
The price is CA $283
CA $363 total
includes taxes & fees
Oct 20 - Oct 21
Your home @ Jellystone Pierceton, lot 525.

20. Lovely 3 bedroom waterfront home on Irish lake part of the Barbee Chain of Lakes

Lovely 3 bedroom waterfront home on Irish lake part of the Barbee Chain of Lakes
Leesburg
The price is CA $382
CA $941 total
includes taxes & fees
Oct 20 - Oct 21
Lovely 3 bedroom waterfront home on Irish lake part of the Barbee Chain of Lakes
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Oswego. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

The Boat House w/ Dock: Enjoy Lake Life!: This vacation home rental near Oswego is located on the waterfront and has a patio, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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.