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Oswego Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Oswego vacation rentals

Terrace/patio

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
9.6 out of 10, Exceptional, (17 reviews)
"Lovely little place to stay"
United States
Panacea G.
$312 nightly
The price is $349
Aug 25 - Aug 26
Total with taxes and fees
Cozy lake Cottage on Dewart Lake , 1 mile from Blue Barn Berry Farm, Hottub!
Exterior

2. 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, (37 reviews)
"Very Good place to stay"
United States
Alex K.
$363 nightly
The price is $406
Sep 22 - Sep 23
Total with taxes and fees
Memorable Vacation Awaits on Big Chapman Lake! Sleeps 8! Optional Pontoon!
Property grounds

3. 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.
$488 nightly
The price is $547
Aug 25 - Aug 26
Total with taxes and fees
Beautiful Lakefront home, pets welcome, fully fenced, dock, kayaks, fishing!!
Exterior

4. 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.
$236 nightly
The price is $264
Aug 28 - Aug 29
Total with taxes and fees
Cozy lakefront home on Big Barbee Lake
Exterior

5. 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.
$320 nightly
The price is $358
Aug 28 - Aug 29
Total with taxes and fees
3 bedroom 2 bath renovated A frame on channel to Kuhn lake and the Barbee Chain
Exterior

6. Biscayne Ln Retreat/Pool, Game Room & Wawasee Fun

Biscayne Ln Retreat/Pool, Game Room & Wawasee Fun
Cromwell
$635 nightly
The price is $711
Sep 1 - Sep 2
Total with taxes and fees
Biscayne Ln Retreat/Pool, Game Room & Wawasee Fun
Terrace/patio

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

Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!
Milford
10.0 out of 10, Exceptional, (36 reviews)
"Everything was very clean and we loved the layout of the house and the game room!"
United States
Rachel A.
$447 nightly
The price is $501
Aug 25 - Aug 26
Total with taxes and fees
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!
Terrace/patio

8. 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.
$296 nightly
The price is $318
Aug 30 - Aug 31
Total with taxes and fees
Heart Jacuzzi · Kayaks · Firepit · Pier
Terrace/patio

9. 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.
$944 nightly
The price is $1,057
Aug 25 - Aug 26
Total with taxes and fees
Best Views of Webster Lake! Paddleboards + Swimming
Interior

10. 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.
$768 nightly
The price is $830
Aug 25 - Aug 26
Total with taxes and fees
4BR Lakefront · Pier · Game Room · Sleeps 16+
Living area

11. Charlee's Cabin - Family Escape on Webster Lake | Pier & Swimming!

Charlee's Cabin - Family Escape on Webster Lake | Pier & Swimming!
North Webster
$602 nightly
The price is $675
Aug 31 - Sep 1
Total with taxes and fees
Charlee's Cabin - Family Escape on Webster Lake | Pier & Swimming!
Outdoor dining

12. Backwater Lake Cottage | Tiki Bar & Paddleboat

Backwater Lake Cottage | Tiki Bar & Paddleboat
North Webster
$377 nightly
The price is $422
Aug 25 - Aug 26
Total with taxes and fees
Backwater Lake Cottage | Tiki Bar & Paddleboat
Property grounds

13. 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.
$271 nightly
The price is $290
Sep 13 - Sep 14
Total with taxes and fees
Fishing · Kayaks · Firepit · Paddleboat
Living area

14. Dog-Friendly 2BR | Private Fenced Yard & Fire Pit | Walk to Village & Grace

Dog-Friendly 2BR | Private Fenced Yard & Fire Pit | Walk to Village & Grace
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.
$350 nightly
The price is $392
Aug 31 - Sep 1
Total with taxes and fees
Dog-Friendly 2BR | Private Fenced Yard & Fire Pit | Walk to Village & Grace
Outdoor dining

15. 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.
$367 nightly
The price is $411
Sep 7 - Sep 8
Total with taxes and fees
Lakefront Fun on Papakeechie - Kayaks & More!
Property grounds

16. Trail Side in the Heart of Winona Lake

Trail Side in the Heart of Winona Lake
Winona Lake
9.8 out of 10, Exceptional, (56 reviews)
"Excellent experience we will definitely stay there again "
United States
Nick H.
$225 nightly
The price is $251
Sep 3 - Sep 4
Total with taxes and fees
Trail Side in the Heart of Winona Lake
Property grounds

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

Wawasee - Minutes from Sandbar! Swim, Fish, Relax!
Syracuse
$552 nightly
The price is $618
Aug 30 - Aug 31
Total with taxes and fees
Wawasee - Minutes from Sandbar! Swim, Fish, Relax!
Dining

18. Lake Wawasee/HOT TUB/GAME ROOM/PONTOON/PICKLEBALL

Lake Wawasee/HOT TUB/GAME ROOM/PONTOON/PICKLEBALL
Cromwell
9.8 out of 10, Exceptional, (29 reviews)
"Went for a guys grouping outing and had a great time! Great location with lots of outdoor space for yard games etc!"
United States
Zakk R.
$1,048 nightly
The price is $1,174
Sep 18 - Sep 19
Total with taxes and fees
Lake Wawasee/HOT TUB/GAME ROOM/PONTOON/PICKLEBALL
Interior

19. 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.
$583 nightly
The price is $653
Sep 21 - Sep 22
Total with taxes and fees
Premier Lake Wawasee Lakefront Home - Private Dock & Sandy Bottom
Room

20. Quiet cul-de-sac home near Syracuse

Quiet cul-de-sac home near Syracuse
Syracuse
$192 nightly
The price is $215
Sep 21 - Sep 22
Total with taxes and fees
Quiet cul-de-sac home near 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

Holiday Inn Express Hotel & Suites Goshen by IHG

Holiday Inn Express Hotel & Suites Goshen by IHG

10/10 Excellent
"We were in town for a funeral. We asked for a late checkout and there was no problem with that. We left in a hurry when we checked out and left three items in the room. While we were down the road we realized it, called the hotel, and the front desk clerk said they had the bag in lost and found. We returned and picked it up. Thank you!"
Glenda 1-night trip
Posted less than an hour ago
Holiday Inn Express Hotel & Suites Goshen by IHG

Find out more about Oswego

Everything you need to know about Oswego vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Oswego vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oswego vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Oswego vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oswego. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Oswego in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $251 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Oswego rentals

At Expedia, we put the best Oswego vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Oswego rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oswego vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oswego. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Oswego?

Yes, we have vacation rentals close to well known attractions in Oswego, or you can choose a more secluded option if you're looking for a relaxing stay.

What are some of the best vacation rentals in Oswego?

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

What are vacation rentals like in Oswego?

Vacation rentals are private properties you can stay in for a couple days or more in Oswego. Vacation rentals offer amenities like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a clean environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for a family trip or a small group gathering.