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Oswego Vacation Rentals

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Oswego vacation rentals

Terrace/patio

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
9.4 out of 10, Exceptional, (16 reviews)
"Lovely little place to stay"
United States
Panacea G.
The price is ￥29,333
￥55,886 total
includes taxes & fees
Aug 20 - Aug 21
Cozy lake Cottage on Dewart Lake , 1 mile from Blue Barn Berry Farm, Hottub!
Terrace/patio

2. Heart Jacuzzi · Kayaks · Firepit · Pier

Heart Jacuzzi · Kayaks · Firepit · Pier
Warsaw
10.0 out of 10, Exceptional, (14 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 ￥23,937
￥50,817 total
includes taxes & fees
Aug 23 - Aug 24
Heart Jacuzzi · Kayaks · Firepit · Pier
Exterior

3. Cozy lakefront home on Big Barbee Lake

Cozy lakefront home on Big Barbee Lake
Pierceton
9.6 out of 10, Exceptional, (24 reviews)
"Very enjoyable place to rest and relax after tournament musky fishing."
United States
Michael A.
The price is ￥23,116
￥44,995 total
includes taxes & fees
Sep 1 - Sep 2
Cozy lakefront home on Big Barbee Lake
Exterior

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

Memorable Vacation Awaits on Big Chapman Lake! Sleeps 8! Optional Pontoon!
Warsaw
9.8 out of 10, Exceptional, (36 reviews)
"Very Good place to stay"
United States
Alex K.
The price is ￥32,594
￥66,353 total
includes taxes & fees
Sep 15 - Sep 16
Memorable Vacation Awaits on Big Chapman Lake! Sleeps 8! Optional Pontoon!
Property grounds

5. Fishing · Kayaks · Firepit · Paddleboat

Fishing · Kayaks · Firepit · Paddleboat
Pierceton
10.0 out of 10, Exceptional, (27 reviews)
"Clean property, gewat location, loved the lake and the stars."
United States
joseph b.
The price is ￥20,586
￥46,527 total
includes taxes & fees
Aug 20 - Aug 21
Fishing · Kayaks · Firepit · Paddleboat
Exterior

6. 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
9.8 out of 10, Exceptional, (21 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 ￥28,696
￥57,137 total
includes taxes & fees
Sep 1 - Sep 2
3 bedroom 2 bath renovated A frame on channel to Kuhn lake and the Barbee Chain
Property grounds

7. Trail Side in the Heart of Winona Lake

Trail Side in the Heart of Winona Lake
Winona Lake
9.8 out of 10, Exceptional, (55 reviews)
"Excellent experience we will definitely stay there again "
United States
Nick H.
The price is ￥19,370
￥40,087 total
includes taxes & fees
Aug 31 - Sep 1
Trail Side in the Heart of Winona Lake
Property grounds

8. 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)
"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 ￥44,159
￥87,132 total
includes taxes & fees
Aug 31 - Sep 1
Beautiful Lakefront home, pets welcome, fully fenced, dock, kayaks, fishing!!
Interior

9. Lake Wawasee, Outdoor TV, Surround Sound & Bikes

Lake Wawasee, Outdoor TV, Surround Sound & Bikes
Syracuse
10.0 out of 10, Exceptional, (9 reviews)
"Very nice and clean. Enjoyed our stay! Great location! "
United States
Becky J.
The price is ￥28,006
￥56,390 total
includes taxes & fees
Aug 20 - Aug 21
Lake Wawasee, Outdoor TV, Surround Sound & Bikes
Smart TV, books, offices

10. Dog-friendly, Short Walk to Grace, Village, Trails | Fast Wi-Fi & Workspace

Dog-friendly, Short Walk to Grace, Village, Trails | Fast Wi-Fi & Workspace
Winona Lake
10.0 out of 10, Exceptional, (1 review)
"Nice five minute walk to beach and restaurants. So excellent location. The added amenities were great as we used the provided pickel ball paddles and inflatable watercraft."
United States
Jonathan J.
The price is ￥29,843
￥62,736 total
includes taxes & fees
Aug 31 - Sep 1
Dog-friendly, Short Walk to Grace, Village, Trails | Fast Wi-Fi & Workspace
Outdoor dining

11. Lakefront Fun on Papakeechie - Kayaks & More!

Lakefront Fun on Papakeechie - Kayaks & More!
Syracuse
10.0 out of 10, Exceptional, (1 review)
"Beautiful location and views! The hosts have thought of everything a visitor might need. Only caveat, not for those with mobility issues due to steep walkway and interior stairs. Exceeded my expectations. Would absolutely stay there again."
United States
Karen E.
The price is ￥23,754
￥59,203 total
includes taxes & fees
Sep 8 - Sep 9
Lakefront Fun on Papakeechie - Kayaks & More!
Interior

12. Woodside Retreat in the Heart of Amish Country

Woodside Retreat in the Heart of Amish Country
Nappanee
10.0 out of 10, Exceptional, (12 reviews)
"Clean, courteous and a great place to get away from distractions and burdens and relax!!! Wife and I are really looking forward to visiting soon."
United States
Go N.
The price is ￥16,500
￥29,938 total
includes taxes & fees
Sep 17 - Sep 18
Woodside Retreat in the Heart of Amish Country
Interior

13. 4BR Lakefront · Pier · Game Room · Sleeps 16+

4BR Lakefront · Pier · Game Room · Sleeps 16+
North Webster
10.0 out of 10, Exceptional, (23 reviews)
"The rental was everything one could ask for. Family from Wisconsin and Indiana met for the weekend. We had a great weekend making memories. We enjoyed the fire pit and playing corn hole. We also enjoyed cooking meals together. The view of the lake was beautiful and very relaxing. I would love to come back and enjoy the lake during warmer weather."
United States
Katherine B.
The price is ￥69,667
￥132,345 total
includes taxes & fees
Aug 23 - Aug 24
4BR Lakefront · Pier · Game Room · Sleeps 16+
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 ￥73,174
￥152,361 total
includes taxes & fees
Sep 1 - Sep 2
Best Views of Webster Lake! Paddleboards + Swimming
Property grounds

15. Wawasee - Minutes from Sandbar! Swim, Fish, Relax!

Wawasee - Minutes from Sandbar! Swim, Fish, Relax!
Syracuse
The price is ￥41,290
￥89,766 total
includes taxes & fees
Aug 31 - Sep 1
Wawasee - Minutes from Sandbar! Swim, Fish, Relax!
Interior

16. 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 ￥63,034
￥106,165 total
includes taxes & fees
Sep 14 - Sep 15
Premier Lake Wawasee Lakefront Home - Private Dock & Sandy Bottom
Outdoor dining

17. Backwater Lake Cottage | Tiki Bar & Paddleboat

Backwater Lake Cottage | Tiki Bar & Paddleboat
North Webster
The price is ￥23,913
￥61,000 total
includes taxes & fees
Sep 1 - Sep 2
Backwater Lake Cottage | Tiki Bar & Paddleboat
3 bedrooms, WiFi (free), bed sheets

18. Quiet cul-de-sac home near Syracuse

Quiet cul-de-sac home near Syracuse
Syracuse
The price is ￥28,696
￥36,782 total
includes taxes & fees
Aug 31 - Sep 1
Quiet cul-de-sac home near Syracuse
Terrace/patio

19. Waterfront Family Gem w/ Private Dock in Syracuse

Waterfront Family Gem w/ Private Dock in Syracuse
Syracuse
The price is ￥34,948
￥92,224 total
includes taxes & fees
Aug 24 - Aug 25
Waterfront Family Gem w/ Private Dock in Syracuse
House (4 Bedrooms) | Interior

20. Waterfront Family Gem w/ Private Dock in Syracuse

Waterfront Family Gem w/ Private Dock in Syracuse
3.0 star property
Syracuse
The price is ￥43,522
￥92,429 total
includes taxes & fees
Aug 27 - Aug 28
Waterfront Family Gem w/ Private Dock in Syracuse
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

Tru by Hilton Warsaw

Tru by Hilton Warsaw

10/10 Excellent
"My daughters and I had an amazing stay here ! Everything was clean, everyone was pleasant, beds were comfy, shower was fantastic, breakfast was good … we all said we would definitely stay here again and again !"
Kristi 1-night trip
Posted 14 hours ago
Tru by Hilton 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?

Lakefront Cottage on Webster Lake with Beautiful Sunsets, 2 bed, 1 bath: This vacation home rental near Oswego is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind.

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.