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Oswego Holiday Rentals

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Our top choices for Oswego holiday rentals

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 NZ$577
includes taxes & fees
20 Aug - 21 Aug
Cozy lake Cottage on Dewart Lake , 1 mile from Blue Barn Berry Farm, Hottub!

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 NZ$522
includes taxes & fees
23 Aug - 24 Aug
Heart Jacuzzi · Kayaks · Firepit · Pier

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 NZ$465
includes taxes & fees
28 Aug - 29 Aug
Cozy lakefront home on Big Barbee Lake

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 NZ$708
includes taxes & fees
16 Sept - 17 Sept
Memorable Vacation Awaits on Big Chapman Lake! Sleeps 8! Optional Pontoon!

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 NZ$488
includes taxes & fees
20 Aug - 21 Aug
Fishing · Kayaks · Firepit · Paddleboat

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 NZ$588
includes taxes & fees
23 Aug - 24 Aug
3 bedroom 2 bath renovated A frame on channel to Kuhn lake and the Barbee Chain

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 NZ$420
includes taxes & fees
20 Aug - 21 Aug
Trail Side in the Heart of Winona Lake

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 NZ$917
includes taxes & fees
23 Aug - 24 Aug
Beautiful Lakefront home, pets welcome, fully fenced, dock, kayaks, fishing!!

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.
Lake Wawasee, Outdoor TV, Surround Sound & Bikes

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 NZ$658
includes taxes & fees
31 Aug - 1 Sept
Dog-friendly, Short Walk to Grace, Village, Trails | Fast Wi-Fi & Workspace

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 NZ$620
includes taxes & fees
9 Sept - 10 Sept
Lakefront Fun on Papakeechie - Kayaks & More!

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 NZ$335
includes taxes & fees
17 Sept - 18 Sept
Woodside Retreat in the Heart of Amish Country

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 NZ$1,395
includes taxes & fees
23 Aug - 24 Aug
4BR Lakefront · Pier · Game Room · Sleeps 16+

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 NZ$1,610
includes taxes & fees
30 Aug - 31 Aug
Best Views of Webster Lake! Paddleboards + Swimming

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

Wawasee - Minutes from Sandbar! Swim, Fish, Relax!
Syracuse
The price is NZ$908
includes taxes & fees
30 Aug - 31 Aug
Wawasee - Minutes from Sandbar! Swim, Fish, Relax!

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 NZ$1,082
includes taxes & fees
14 Sept - 15 Sept
Premier Lake Wawasee Lakefront Home - Private Dock & Sandy Bottom

17. Backwater Lake Cottage | Tiki Bar & Paddleboat

Backwater Lake Cottage | Tiki Bar & Paddleboat
North Webster
The price is NZ$641
includes taxes & fees
20 Aug - 21 Aug
Backwater Lake Cottage | Tiki Bar & Paddleboat

18. Quiet cul-de-sac home near Syracuse

Quiet cul-de-sac home near Syracuse
Syracuse
The price is NZ$385
includes taxes & fees
24 Aug - 25 Aug
Quiet cul-de-sac home near Syracuse

19. Waterfront Family Gem w/ Private Dock in Syracuse

Waterfront Family Gem w/ Private Dock in Syracuse
Syracuse
The price is NZ$970
includes taxes & fees
24 Aug - 25 Aug
Waterfront Family Gem w/ Private Dock in Syracuse

20. Waterfront Family Gem w/ Private Dock in Syracuse

Waterfront Family Gem w/ Private Dock in Syracuse
3.0 star property
Syracuse
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

Find out more about Oswego

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Oswego holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Oswego. 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 Oswego. 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 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 holiday 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 Oswego short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Oswego?

Yes, there are holiday rentals close to the most popular sights in Oswego, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Oswego has to offer?

Lakefront Cottage on Webster Lake with Beautiful Sunsets, 2 bed, 1 bath: This holiday home rental outside of Oswego is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most 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 wider area.

What are holiday rentals like in Oswego?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Oswego. Holiday rentals offer extras like laundry facilities and kitchens so you'll have everything you need. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for small groups.