Oswego Holiday Rentals

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Holiday Rentals in Oswego

Charming farmhouse in peaceful countryside

10.0 out of 10, Exceptional, (132)
"We just got back from a really great weekend! The rental house was the cutest farmhouse and was decorated so so nicely. It’s so warm and inviting! Dixie, the dog that lives on the property was our absolute favorite. The house is located on a farm and it was fun to watch the farm animals and it was such a beautiful setting. All of the beds were super comfortable and the house was nicely stocked with the necessities. The owners were super responsive and helpful and made sure that our stay was top...
Charming farmhouse in peaceful countryside

Lakefront Cottage on Webster Lake with Beautiful Sunsets, 2 bed, 1 bath

10.0 out of 10, Exceptional, (38)
"The cottage was perfect for us. It was very clean, fully equipped and the views were amazing. A big thank you to Lois and Todd for their kindness."
Lakefront Cottage on Webster Lake with Beautiful Sunsets, 2 bed, 1 bath

Beautiful and Historic Log Cabin: cozy, quiet, huge hot tub! Quiet getaway!

10.0 out of 10, Exceptional, (107)
"Our stay was very relaxing! The cabin was cozy for the two of us. We loved the jacuzzi! "
Beautiful and Historic Log Cabin: cozy, quiet, huge hot tub! Quiet getaway!

Lakefront Syracuse Home w/ Deck & Private Dock!

9.8 out of 10, Exceptional, (8)
"In town for a wedding and it was the perfect location. "
Lakefront Syracuse Home w/ Deck & Private Dock!

Barbee Lake Big House! Sleeps 14+ Game Garage! Pier and Dock to Barbee!

9.6 out of 10, Exceptional, (5)
"Worked for the ten of us comfortably. Would absolutely book again"
Barbee Lake Big House! Sleeps 14+ Game Garage! Pier and Dock to Barbee!

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

10.0 out of 10, Exceptional, (14)
"Awesome recharge for my husband and I!"
Eagle's View Indiana waterfront home on a premier fishing lake pontoon included!

Waters Edge Cottage on Big Barbee Lake!

10.0 out of 10, Exceptional, (16)
"Overall our stay was great! The VRBO and property are both really small, but we knew that from the listing. The kitchen is stocked with basic necessities and a few extras, but it is difficult to find what you’re looking for. I did not find the washer and dryer right away so we ended up not using it but it does tell you where it’s located if you read more carefully the check in info."
Waters Edge Cottage on Big Barbee Lake!

Spacious FiveStar Lakefront Retreat-4BR/4BA w/HotTub,GameRoom, FirePit, SUP

8.8 out of 10, Excellent, (19)
"Very clean spacious Great Lake house. Would stay here again. "
The price is AU$995
includes taxes & fees
1 Dec - 2 Dec
Spacious FiveStar Lakefront Retreat-4BR/4BA w/HotTub,GameRoom, FirePit, SUP

Lakefront|Kayaks|Paddleboat|Fishing

10.0 out of 10, Exceptional, (11)
"I’d give 6 stars if I could. I have stayed many places in my 77 years but never have I seen a place where so much thought has been given to their guests’ comfort. The kitchen was better equipped than my own. The bed was quite comfortable. The view of the lake beautiful. What wonderful memories we made!"
The price is AU$356
includes taxes & fees
1 Dec - 2 Dec
Lakefront|Kayaks|Paddleboat|Fishing

Cozy Goshen Farmhouse ~ 9 Mi to Amish Acres

9.4 out of 10, Exceptional, (23)
"Great cottage, outside of city life. Absolutely adorable dog on property to greet you coming and going. Nice set-up, everything we needed. GPS takes you past the cottage to another farm nearby; be careful if traveling in the dark. "
Cozy Goshen Farmhouse ~ 9 Mi to Amish Acres

Silver Lake IN cottage sleeps 9. Two full baths. Water sports, games, and movies

9.8 out of 10, Exceptional, (32)
"Host very easy to work with. "
Silver Lake IN cottage sleeps 9. Two full baths. Water sports, games, and movies

Beautiful lakefront property

9.8 out of 10, Exceptional, (26)
"Everything was perfect! There were no details left out in this home. It had everything you could imagine in a home and then some. Warm and cozy feel and nicely decorated! Would definitely stay here again😊"
Beautiful lakefront property

Lakefront Home on Lake Webster

9.6 out of 10, Exceptional, (26)
"It was great "
Lakefront Home on Lake Webster

Big Barbee Lake House

10.0 out of 10, Exceptional, (3)
"My friends (6 adults males) stayed at the location and enjoyed it very much. The host provided pretty much everything we needed. Good AC. Fair amount of cooking supplies. We enjoy the location as there are two bar/restaurants in walking distance and there are multiple lakes connected here and a bigger one if you feel like going 7 miles. The only pause is that for adults the location really sleeps 5 unless you can get two adults/kids on a double bed."
Big Barbee Lake House

Adorable Wawasee Cottage in Oakwood Park

10.0 out of 10, Exceptional, (8)
"Enjoyed our stay/would stay again."
The price is AU$562
includes taxes & fees
2 Dec - 3 Dec
Adorable Wawasee Cottage in Oakwood Park

Beautiful Lake Home in a quiet relaxing setting. Access to paddle boats.

9.8 out of 10, Exceptional, (61)
"We rented this beautiful, spacious home for the weekend to celebrate my sister’s birthday. There were twelve adults and we had plenty of room. We were pleasantly surprised to see that everything was supplied including paper towels, dish washing detergent, and showers essentials. "
Beautiful Lake Home in a quiet relaxing setting. Access to paddle boats.

Idyllic Lake Cottage on Papakeechie Lake

10.0 out of 10, Exceptional, (32)
"Just what we needed for a peaceful and relaxing long weekend. Can’t wait to come back!"
Idyllic Lake Cottage on Papakeechie Lake

Lake Wawasee waterfront home overlooking Johnson's Bay. New Renovations for 2024

9.2 out of 10, Wonderful, (40)
"The house was perfect for our group. Nice kitchen and living space to gather in the evening to visit. Loved sitting on the patio by the water to play games and socialize, boats going back-and-forth to the lake very nice. Maybe a 15 minute drive to restaurants and shopping. The manager, Brian was always quick to answer any questions or resolve any issues. We all enjoyed our stay."
Lake Wawasee waterfront home overlooking Johnson's Bay. New Renovations for 2024

FAMILY HOME ON WEBSTER LAKE!

9.6 out of 10, Exceptional, (7)
"Beautiful home and great location. Plenty of room inside and out."
FAMILY HOME ON WEBSTER LAKE!

Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!

10.0 out of 10, Exceptional, (21)
"I loved this vrbo stay! So clean and nice. "
The price is AU$600
includes taxes & fees
2 Dec - 3 Dec
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!
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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Other types of properties in Oswego you may be interested in

Best Western Plus Warsaw

2.5 star property
7.8 out of 10, Good, (712)
"Nice hotel, staff friendly. The only down side is the elevator has been out of order for approx 3 weeks"
The price is AU$116
includes taxes & fees
8 Dec - 9 Dec
Best Western Plus Warsaw

Wyndham Garden Warsaw

3.0 star property
7.8 out of 10, Good, (913)
"No ice machines working was a bummer. It is an older building and it was kept pretty clean. Restaurant attached is very good. "
The price is AU$115
includes taxes & fees
19 Dec - 20 Dec
Wyndham Garden Warsaw

Quality Inn & Suites

2.5 star property
7.8 out of 10, Good, (780)
"The breakfast was very good! The hot tub was wonderful! The staff is so very nice! We will stay here again!"
The price is AU$87
includes taxes & fees
21 Dec - 22 Dec
Quality Inn & Suites
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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 Big Barbee Lake are a couple of picturesque spots to get outside and enjoy nature. Webster Lake and Grace College 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.