Oswego Holiday Rentals

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Holiday Rentals in Oswego

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

Spacious Syracuse Getaway w/ Waterfront Deck!

9.8 out of 10, Exceptional, (20)
"Really beautiful lake property with easy-access dock. We brought our own boat since the pontoon season was over, but the canals to the house were easy to navigate and really a lot of fun to use. Firepit was great, and the outdoor spaces (deck, grill, etc.) were really enjoyable. The house does have a few "rustic" touches, but we were extremely comfortable, and it was the first time staying in an A-frame house. We recommend the experience!"
Spacious Syracuse Getaway w/ Waterfront Deck!

Charming farmhouse in peaceful countryside

10.0 out of 10, Exceptional, (140)
"We enjoyed our stay here! It was clean and fire made it cozy. Would recommend this place if you need somewhere to stay in Nappanee. "
Charming farmhouse in peaceful countryside

Country Cottage

10.0 out of 10, Exceptional, (20)
"Amazing property with plenty of blankets, pillows, and towels. Coffee and snacks were great additions. It was probably the cleanest Vrbo we have ever stayed in."
Country Cottage

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

10.0 out of 10, Exceptional, (24)
"This house had everything my family and I needed to ring in the new year. We loved the clean, cozy feel of the house. Between the hot tub with outside TV and the game room, we had everything we needed to relax and enjoy the best family time without leaving the house. everything we needed, reason for us to "
The price is AU$590
includes taxes & fees
24 Feb - 25 Feb
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!

Lake Wawasee Escape: private pool, hot tub, pier, kayaks & paddleboat!!!

10.0 out of 10, Exceptional, (15)
"A great place for six old guys to gather. Clean, spacious, great location. Absolutely perfect for us."
Lake Wawasee Escape: private pool, hot tub, pier, kayaks & paddleboat!!!

Channel Front Lake Wawasee

9.6 out of 10, Exceptional, (21)
"Loved the location and dock. Fun Lake with easy access from the rental."
Channel Front Lake Wawasee

Lakeside A-frame|Heart tub|Kayaks|Firepit

10.0 out of 10, Exceptional, (3)
"We came for a couple of days from Tennessee to visit family and stayed here. Very clean, host quickly responded to my questions, everything you need is provided. "
The price is AU$355
includes taxes & fees
23 Feb - 24 Feb
Lakeside A-frame|Heart tub|Kayaks|Firepit

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

Webster Lakefront Luxury! Fishing! Boating!

10.0 out of 10, Exceptional, (12)
"Loved the house and location. Unusual not to have a tv. We shouldn’t have to bring a tv. West bedroom is hot in the evenings. Loved all the amenities kayaks, paddle boat, floating toys. House great for large families."
The price is AU$895
includes taxes & fees
24 Feb - 25 Feb
Webster Lakefront Luxury! Fishing! Boating!

Waterfront Syracuse Home w/ Patio & Fire Pit!

10.0 out of 10, Exceptional, (17)
"Great job of space utilization! Kitchen cabinets well organized… easy to access utensils. Everything looked brand new…. Were we the first guests?!? Enjoyed the stay immensely. 🤔Pillows were way too hard!! Sorry. Jay"
Waterfront Syracuse Home w/ Patio & Fire Pit!

Lake Wawasee Pet-Friendly Cottage with Pontoon, Firepit, 3 decks, large lot

9.6 out of 10, Exceptional, (24)
"We really enjoyed this property and our stay. Easy access to lake and sandbar. The property is so well provisioned, it made the stay even better than we expected! Would totally stay again!"
Lake Wawasee Pet-Friendly Cottage with Pontoon, Firepit, 3 decks, large lot

⚓️Direct lake view with available Tritoon boat rental

9.8 out of 10, Exceptional, (7)
"The house was better than we expected. It had everything we needed. Communication with owner was good! Neighbors were lovely. Would stay again. "
⚓️Direct lake view with available Tritoon boat rental

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.

Lakefront Home on Lake Webster

9.6 out of 10, Exceptional, (27)
"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

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!

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

2.0 star property
"We met a group of 4 other friends/couples including 7 kids/teens for a February long weekend. The house was easy to find and there was plenty of parking in the driveway. It snowed 2 nights we were there, and by 10am the sidewalk & driveway had been shoveled both mornings! There was plenty of space for kids to spread out, play games and be loud without affecting the adults (& vice versa). The lake was frozen over during our visit but the view is beautiful & I imagine even more so during warm...
Irish Lakefront home. Pets, dock, fishing, kayaks.

Lake Wawasee/HOT TUB/GAME ROOM/PONTOON RENTAL

10.0 out of 10, Exceptional, (21)
"Wonderful Host! "
Lake Wawasee/HOT TUB/GAME ROOM/PONTOON RENTAL

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!

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

10.0 out of 10, Exceptional, (110)
"We enjoyed a weekend of quiet away from the normal busyness of life! This was perfect in every way!"
Beautiful and Historic Log Cabin: cozy, quiet, huge hot tub! Quiet getaway!
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

Wyndham Garden Warsaw

3.0 star property
7.8 out of 10, Good, (935)
"We wished the hot tub worked "
The price is AU$124
includes taxes & fees
23 Feb - 24 Feb
Wyndham Garden Warsaw

Best Western Plus Warsaw

2.5 star property
7.8 out of 10, Good, (766)
"It was a nice stay for my family "
The price is AU$123
includes taxes & fees
27 Feb - 28 Feb
Best Western Plus Warsaw

Quality Inn & Suites

2.5 star property
7.8 out of 10, Good, (798)
"We stay there often. Great place great people"
The price is AU$108
includes taxes & fees
26 Feb - 27 Feb
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.

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.