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Oswego Vacation Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Oswego vacation rentals

A black house with a patio area featuring outdoor furniture and a grill.

1. 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
9.6 out of 10, Exceptional, (17 reviews)
"Lovely little place to stay"
United States
Panacea G.
The price is AED 676
AED 1,209 total
includes taxes & fees
30 Sep - 1 Oct
Cozy lake Cottage on Dewart Lake , 1 mile from Blue Barn Berry Farm, Hottub!
A lakeside property with a dock, boats, and a grassy area with outdoor seating.

2. 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 AED 441
AED 976 total
includes taxes & fees
30 Sep - 1 Oct
Heart Jacuzzi · Kayaks · Firepit · Pier
A wooden deck with picnic tables and a view of a lake.

3. Fishing · Kayaks · Firepit · Paddleboat

Fishing · Kayaks · Firepit · Paddleboat
Pierceton
10.0 out of 10, Exceptional, (31 reviews)
"Clean property, gewat location, loved the lake and the stars."
United States
joseph b.
The price is AED 415
AED 947 total
includes taxes & fees
30 Sep - 1 Oct
Fishing · Kayaks · Firepit · Paddleboat
A lakeside patio with outdoor seating and a fire pit.

4. 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 AED 1,017
AED 1,876 total
includes taxes & fees
30 Sep - 1 Oct
Beautiful Lakefront home, pets welcome, fully fenced, dock, kayaks, fishing!!
A cabin with a wooden deck, a front door, and a garage.

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 AED 661
AED 1,312 total
includes taxes & fees
2 Oct - 3 Oct
Charming 3 bedroom 2 bath A frame home on channel to Kuhn Lake & Barbee Chain
A house with a dock extending into a pond, surrounded by trees and other houses.

6. Cozy lakefront home on Big Barbee Lake

Cozy lakefront home on Big Barbee Lake
Pierceton
9.8 out of 10, Exceptional, (26 reviews)
"Very enjoyable place to rest and relax after tournament musky fishing."
United States
Michael A.
The price is AED 533
AED 1,020 total
includes taxes & fees
5 Oct - 6 Oct
Cozy lakefront home on Big Barbee Lake
A room with a large window, two bean bags, a small round table, and two stools.

7. 4BR Lakefront · Pier · Game Room · Sleeps 16+

4BR Lakefront · Pier · Game Room · Sleeps 16+
North Webster
10.0 out of 10, Exceptional, (25 reviews)
"The property is fantastic and perfect for large families. We easily slept 14. Lots of extras like a paddle boat, kayaks, life jackets, games. We had a great time during our 5 night stay! Pontoon was rented from Aloha and they were great, too."
United States
Tiha K.
The price is AED 1,047
AED 2,263 total
includes taxes & fees
30 Sep - 1 Oct
4BR Lakefront · Pier · Game Room · Sleeps 16+
A small, single-story building with a porch, outdoor seating, and a view of the surrounding trees.

8. Barbee Lake Lodge/kayaks

Barbee Lake Lodge/kayaks
Warsaw
The price is AED 643
AED 1,008 total
includes taxes & fees
30 Sep - 1 Oct
Barbee Lake Lodge/kayaks
A covered porch with wooden flooring, two chairs, a table, and a window with blinds.

9. Trail Side in the Heart of Winona Lake

Trail Side in the Heart of Winona Lake
Winona Lake
9.8 out of 10, Exceptional, (65 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 AED 496
AED 946 total
includes taxes & fees
30 Sep - 1 Oct
Trail Side in the Heart of Winona Lake
A wooden deck with a table and chairs, overlooking a lake, surrounded by trees.

10. 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 AED 511
AED 1,386 total
includes taxes & fees
30 Sep - 1 Oct
Lakefront Fun on Papakeechie - Kayaks & More!
A living room with a ceiling fan, a black sofa, a black cabinet, and a sign that says 'LIVE LAUGH LOVE'.

11. Backwater Lake Cottage | Tiki Bar & Paddleboat

Backwater Lake Cottage | Tiki Bar & Paddleboat
North Webster
The price is AED 511
AED 1,406 total
includes taxes & fees
30 Sep - 1 Oct
Backwater Lake Cottage | Tiki Bar & Paddleboat
A dining area with a wooden table and black chairs, a fireplace with a decorative tile surround, and a large mirror on the wall.

12. Sawmill Lakefront - Dock + Kayaks + Firepit

Sawmill Lakefront - Dock + Kayaks + Firepit
Warsaw
Sawmill Lakefront - Dock + Kayaks + Firepit
Living area

13. Quiet cul-de-sac home near Syracuse

Quiet cul-de-sac home near Syracuse
Syracuse
The price is AED 588
AED 740 total
includes taxes & fees
30 Sep - 1 Oct
Quiet cul-de-sac home near Syracuse
Terrace/patio

14. 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 AED 1,686
AED 3,883 total
includes taxes & fees
30 Sep - 1 Oct
Best Views of Webster Lake! Paddleboards + Swimming
A modern living room with a flat-screen TV, a sofa, a coffee table, and a blue patterned rug.

15. 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 AED 595
AED 1,242 total
includes taxes & fees
5 Oct - 6 Oct
Dog-Friendly 2BR | Private Fenced Yard & Fire Pit | Walk to Village & Grace
A compact kitchen with white cabinets, a black stove, and a microwave.

16. Cozy cottage cabin with fire pit ,lake and beach access Indiana

Cozy cottage cabin with fire pit ,lake and beach access Indiana
Albion
The price is AED 381
AED 571 total
includes taxes & fees
30 Sep - 1 Oct
Cozy cottage cabin with fire pit ,lake and beach access Indiana
A modern living room with a dining area, large windows, and a surfboard mounted on the wall.

17. 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 AED 1,451
AED 2,308 total
includes taxes & fees
20 Oct - 21 Oct
Premier Lake Wawasee Lakefront Home - Private Dock & Sandy Bottom
A modern kitchen with white cabinets and a wooden dining table.

18. Lake Wawasee/HOT TUB/GAME ROOM/PONTOON/PICKLEBALL

Lake Wawasee/HOT TUB/GAME ROOM/PONTOON/PICKLEBALL
Cromwell
9.8 out of 10, Exceptional, (29 reviews)
"Went for a guys grouping outing and had a great time! Great location with lots of outdoor space for yard games etc!"
United States
Zakk R.
Lake Wawasee/HOT TUB/GAME ROOM/PONTOON/PICKLEBALL
A covered swimming pool with a slide, surrounded by glass walls and a patio area.

19. 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
10.0 out of 10, Exceptional, (15 reviews)
"The host was so wonderful, accommodating and helpful during the entire process. The home was beautiful and fit our group well. The pool was nice and warm in the middle of winter! "
United States
Kala Y.
Indoor pool with 4-bedrooms in charming Goshen with WiFi and so many extras
A long table with candles and greenery, set against a wooden backdrop with vertical strings of lights.

20. Rock Run Creek House

Rock Run Creek House
Goshen
9.6 out of 10, Exceptional, (5 reviews)
"was a fantastic rental. Thank you so much!"
United States
Lavern Y.
The price is AED 1,690
AED 2,489 total
includes taxes & fees
30 Sep - 1 Oct
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

Super 8 by Wyndham Columbia City

Super 8 by Wyndham Columbia City

10/10 Excellent
"A very, very helpful and friendly staff who were always available, if you needed extra towels, etc. It is an older hotel but they are doing vast remodeling. I would definitely stay there again."
Tamara 2-night trip
Posted 3 hours ago
Super 8 by Wyndham Columbia City

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.