Oswego Holiday Rentals

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Holiday Rentals in Oswego

Charming farmhouse in peaceful countryside

10.0 out of 10, Exceptional, (150)
"it was a nice place to stay "
Charming farmhouse in peaceful countryside

Webster Lake Home w/ Patio ~ 3 Mi to Town!

6.0 out of 10, (1)
"We enjoyed being so close to the water. There was a great view of the lake and sunsets. The kitchen and living room were updated and pleasant to be in. There were new TVs in the rooms with good viewing selections. The air conditioners in each room were newer worked well. But the kitchen sink was dirty and stained and there was no dish soap. Cookware was provided but the skillets were olds and nonstick services were scratched up and the plates and utensils were like the cheapest ones from the...
Webster Lake Home w/ Patio ~ 3 Mi to Town!

Lake Wawasee 2 Bedroom Premier Condo on Channel with 1 Boat Slip, Sleeps 6,

9.6 out of 10, Exceptional, (26)
"Easy to access, great owner and an amazing location!"
Lake Wawasee 2 Bedroom Premier Condo on Channel with 1 Boat Slip, Sleeps 6,

Lakefront Home on Lake Webster

9.6 out of 10, Exceptional, (29)
"It was amazing spot! Very cozy and peaceful the view of the water was amazing will be recommend others to this location! "
Lakefront Home on Lake Webster

New Kid in Town, Lake Wawasee , 2 Bedroom Condo Channel Front with Boat Pier

9.6 out of 10, Exceptional, (23)
"The place was very nice and the manager helped me enjoy my stay every day."
New Kid in Town, Lake Wawasee , 2 Bedroom Condo Channel Front with Boat Pier

Cozy lakefront home on Big Barbee Lake

10.0 out of 10, Exceptional, (5)
The price is NZ$509
includes taxes & fees
28 July - 29 July
Cozy lakefront home on Big Barbee Lake

Woodside Retreat in the Heart of Amish Country

10.0 out of 10, Exceptional, (5)
"We had a wonderful time here. We stayed here to "unplug" and refresh and it was the perfect place to do so! Comfortable, very clean, with personal touches down to the snacks provided- all made for a stay we will be back for!"
The price is NZ$339
includes taxes & fees
21 July - 22 July
Woodside Retreat in the Heart of Amish Country

Eagle's View Indiana waterfront home on a premier fishing lake pontoon included!

10.0 out of 10, Exceptional, (20)
"Very clean and lots of updates here. Having the pontoon included was great even if we did some paddling. The fishing was pretty good and we all enjoyed swimming and floating in the lake. Would stay here again for sure. "
Eagle's View Indiana waterfront home on a premier fishing lake pontoon included!

Lake access directly in front of Cottage on high speed watercraft Big Barbee

The price is NZ$579
includes taxes & fees
3 Aug - 4 Aug
Lake access directly in front of Cottage on high speed watercraft Big Barbee

Views, Swimming & Family Fun: Chapman Lake Retreat

10.0 out of 10, Exceptional, (5)
"We came this gorgeous massive house with our kids and in laws. Everything was absolutely amazing! Not only is this house spacious and beautiful, but it has everything you need to keep kids entertained: pool table, ping pong, darts, golden 2025 live big buck hunger games! We enjoyed family dinners and moving nights with large screen and huge comfy couch. The best part was watching the kids catch fish off the pier. Can't wait to come back this summer and swim! The hosts were very kind and...
Views, Swimming & Family Fun: Chapman Lake Retreat

Spacious & Newly Renovated 3-bedroom house in Warsaw/Winona Lake

9.6 out of 10, Exceptional, (7)
"The house was comfortable. We came to town for a wedding and had little time for more. The home served our needs and we felt safe and comfortable "
The price is NZ$387
includes taxes & fees
22 July - 23 July
Spacious & Newly Renovated 3-bedroom house in Warsaw/Winona Lake

Irish Lakefront home. Pets, dock, fishing, kayaks.

2.0 star property
10.0 out of 10, Exceptional, (4)
"Our family group of 14 really enjoyed this lake house. It had everything we needed. The outside areas were really nice & the game room was a real hit with kids & adults. Communication with host Joe was great. We hope to stay there again!!"
Irish Lakefront home. Pets, dock, fishing, kayaks.

NEW Spacious Lakehouse Retreat +private pier

9.8 out of 10, Exceptional, (27)
"Rented ourselves a pontoon and had a great weekend with the family! Would love to do it again sometime!"
NEW Spacious Lakehouse Retreat +private pier

Water front cottage on beautiful Upper Long Lake

9.4 out of 10, Exceptional, (80)
"The cottage was quaint. We enjoyed the pontoon and lake. I would highly recommend this property."
Water front cottage on beautiful Upper Long Lake

Beautiful cozy cottage 1 block from the lake and Oakwood hotel.

9.6 out of 10, Exceptional, (26)
"We loved this cozy cottage! We were in town for a wedding and it was perfect! "
Beautiful cozy cottage 1 block from the lake and Oakwood hotel.

Spacious Syracuse Getaway w/ Waterfront Deck!

9.8 out of 10, Exceptional, (22)
"Our family had a great stay. The home was in a great location for easy access to the sandbar. We enjoyed the large yard and deck. The long boat dock was great to accommodate our boats."
Spacious Syracuse Getaway w/ Waterfront Deck!

3 bedrooms sleeps up to 10 people

9.8 out of 10, Exceptional, (45)
"The place is cute and has a lot of room for a large family. Kathy is very nice and very accommodating."
3 bedrooms sleeps up to 10 people

Park model located at Yogi Jellystone Park. Not far from the beach.

10.0 out of 10, Exceptional, (5)
"The camper was very nice and spacious. My family loved staying here. Definitely recommend to anyone who would want to stay here . "
Park model located at Yogi Jellystone Park. Not far from the beach.

beautiful cottage by the lake. Relax and enjoy your stay.

9.8 out of 10, Exceptional, (19)
"Very nice, wish there was bars or restaurants on the lake"
beautiful cottage by the lake. Relax and enjoy your stay.

Cozy 2-bedroom campground in peaceful Claypool with AC, WiFi. Overlooking lake

1.0 star property
7.4 out of 10, Good, (3)
"Clean and well maintained "
Cozy 2-bedroom campground in peaceful Claypool with AC, WiFi. Overlooking lake
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

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?

Charming farmhouse in peaceful countryside: This holiday home rental outside of 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 that 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 Chapman Lakes 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.