Holiday Rentals in Oswego

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Holiday Rentals in Oswego

Our top choices for Oswego holiday rentals

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

10.0 out of 10, Exceptional, (5)
The price is €316
includes taxes & fees
2 Sept - 3 Sept
Memorable Vacation Awaits on Big Chapman Lake! Sleeps 8! Optional Pontoon!

Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm

The price is €292
includes taxes & fees
26 Aug - 27 Aug
Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm

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

10.0 out of 10, Exceptional, (48)
"We loved our weekend getaway. It was charming and relaxing and everything we were looking for. "
Lakefront Cottage on Webster Lake with Beautiful Sunsets, 2 bed, 1 bath

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

9.4 out of 10, Exceptional, (28)
"The place was very nice and the manager helped me enjoy my stay every day."
The price is €396
includes taxes & fees
23 Aug - 24 Aug
New Kid in Town, Lake Wawasee , 2 Bedroom Condo Channel Front with Boat Pier

Charming farmhouse in peaceful countryside

10.0 out of 10, Exceptional, (155)
"It was a nice spot, near to the events we took in, over the weekend."
Charming farmhouse in peaceful countryside

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

9.4 out of 10, Exceptional, (30)
"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.

Lakefront Home on Lake Webster

9.6 out of 10, Exceptional, (31)
"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

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

9.8 out of 10, Exceptional, (22)
"Very nice, wish there was bars or restaurants on the lake"
beautiful cottage by the lake. Relax and enjoy your stay.

Lake Wawasee 2 Bedroom Condo on Channel . NO SHOES, NO SHIRT, NO PROBLEMS !!!

8.8 out of 10, Excellent, (33)
"Great rentals...easy to get to. Property owner was amazing to work with. We can't wait to book again next year!!!!"
The price is €368
includes taxes & fees
23 Aug - 24 Aug
Lake Wawasee 2 Bedroom Condo on Channel . NO SHOES, NO SHIRT, NO PROBLEMS !!!

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

10.0 out of 10, Exceptional, (26)
"The stay was just arpund the corber from our home but felt like a getaway!"
The price is €419
includes taxes & fees
4 Sept - 5 Sept
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!

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

9.6 out of 10, Exceptional, (29)
"Easy to access, great owner and an amazing location!"
Lake Wawasee 2 Bedroom Premier Condo on Channel with 1 Boat Slip, Sleeps 6,

Indoor pool with 4-bedrooms in charming Goshen with WiFi and so many extras

10.0 out of 10, Exceptional, (2)
"This residence was exceptionally clean and featured a very well-equipped kitchen with top-of-the-line cooking equipment. It was the perfect place to entertain teenagers, offering plenty of activities such as a pool, basketball hoops, an infinity game table, ping pong and more. There was lots of space for everyone to spread out, making it easy to enjoy different activities simultaneously without feeling crowded. A fantastic setup for a fun and relaxing stay!"
Indoor pool with 4-bedrooms in charming Goshen with WiFi and so many extras

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

8.6 out of 10, Excellent, (20)
"Very clean spacious Great Lake house. Would stay here again. "
Spacious FiveStar Lakefront Retreat-4BR/4BA w/HotTub,GameRoom, FirePit, SUP

Irish Lakefront home. Hot Tub! 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. Hot Tub! Pets, dock, fishing, kayaks.

Lake Wawasee/HOT TUB/GAME ROOM/PONTOON RENTAL

10.0 out of 10, Exceptional, (24)
"House and property had more than enough activities to keep up completely entertained for our entire stay. Loved the game room, pickleball court, hot tub and kayaks!!"
Lake Wawasee/HOT TUB/GAME ROOM/PONTOON RENTAL

⚓️Direct lake view with available Tritoon boat rental

9.8 out of 10, Exceptional, (11)
"The house and location are phenomenal. The pictures on the website don’t do it justice. You are on the lake and the view is amazing! The owners are super nice and very accommodating. Book now! You won’t be disappointed. "
⚓️Direct lake view with available Tritoon boat rental

Year Round Lake Front Cottage on Quiet Cove on Webster Lake

9.0 out of 10, Wonderful, (36)
"We had a great time getting away from Fort Wayne for the weekend."
Year Round Lake Front Cottage on Quiet Cove on Webster Lake

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

10.0 out of 10, Exceptional, (117)
"Wonderful place to stay for my wife and I while visiting the area! Melody was great to work with. The accommodations worked very well for us and we greatly enjoyed our stay!"
Beautiful and Historic Log Cabin: cozy, quiet, huge hot tub! Quiet getaway!

“Stay Anchored” Lake Tippecanoe channel front with pier and great lake views

10.0 out of 10, Exceptional, (21)
"House had the perfect set up for our family and needs for our stay. We loved the view. We will be back!"
“Stay Anchored” Lake Tippecanoe channel front with pier and great lake views

Inviting Lakefront Home with Patio and Dock

10.0 out of 10, Exceptional, (12)
"The vacation house was nice and to dock your boat was easy. We rented a boat from the marina."
Inviting Lakefront Home with Patio and Dock
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?

Beautiful cozy cottage 1 block from the lake and Oakwood hotel. : This holiday home rental outside of Oswego is on a lake, and equipped with air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and kitchenware.

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.