Oswego Vacations from $491
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Your Oswego Vacation
With a vacation package to Oswego, say goodbye to endless planning and hello to stress-free adventure. Every detail of your escape has been taken care of before you depart, so you can get on with discovering this interesting city. A trip to Oswego is a superb opportunity to go sightseeing. Be sure to look around well-known attractions like Chapman Lakes, Wagon Wheel Theatre and Hidden Lake. Whoever you're taking a break with and whatever you plan to spend, your dream Oswego vacation is just a few clicks away with Expedia.
The Latest Oswego vacation packages
Price found within the past 48 hours. Click for updated prices.
Blisspoint Inn Columbia City
$491
per person
Nov 24 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Washington (WAS) to Fort Wayne (FWA)
6.8/10 (331 reviews)
There were some spots on the bedding. The mattresses were very hard. The bathroom was clean-ish. There was a lot on the floors up next to the walls. The pool was closed for remodel, over 2 years now. Breakfast was minimal but decent. Parking is good. We stayed 1 out of 3 nights we had booked.
Reviewed on Oct 20, 2026
Holiday Inn Express & Suites Columbia City by IHG
$575
per person
Nov 24 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Washington (WAS) to Fort Wayne (FWA)
7.6/10 Good! (234 reviews)
Hotel has ring door bell cameras all over the lobby. No one was at front desk for 5 minutes when we arrived. Once someone came out she barely spoke loud enough to hear her. The blinds in the room needed replaced. There was white bodily fluid on the lounge chair in the room. Stains all over sheets and comforter. Comforter had no duvet.
Reviewed on Oct 18, 2026
Holiday Inn Express New Haven by IHG
$700
per person
Nov 24 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Washington (WAS) to Fort Wayne (FWA)
8.4/10 Very Good! (749 reviews)
No coffee makers in the room anymore. You can get a coffee maker at the front desk but inconvenient. They do have good coffee in the lobby 24/7 but would be nice if the staff asked you if you wanted a coffee maker in your room and gave it to you when checking in. Also, toilets do not flush properly! I have stayed here many times and always have to call maintenance to plunge the toilet. Never have problems at any other hotels and I travel frequently. They admit they know about the issue.
Reviewed on Oct 19, 2026
Oswego Hotel Deals
Amish Inn
1234 W Market St Nappanee IN
Fully refundableReserve now, pay when you stay
$87 nightly
$98 total
Oct 29 - Oct 30
Total with taxes and fees
8.6/10 Excellent! (487 reviews)
"Very reasonably priced and very clean hotel./inn. The staff was friendly and accommodating."
Reviewed on Oct 18, 2026
Wyndham Garden Warsaw
2519 E Center St Warsaw IN
Fully refundableReserve now, pay when you stay
$77 nightly
$86 total
Nov 1 - Nov 2
Total with taxes and fees
7.4/10 Good! (1,003 reviews)
"The hotel was under renovation. No restaurant no bar elevator didnt work. Pool area and game room was nice."
Reviewed on Oct 19, 2026
Blisspoint Inn Columbia City
701 W Connexion Way Columbia City IN
Fully refundableReserve now, pay when you stay
$63 nightly
$67 total
Oct 28 - Oct 29
Total with taxes and fees
6.8/10 (337 reviews)
"There were some spots on the bedding. The mattresses were very hard. The bathroom was clean-ish. There was a lot on the floors up next to the walls. The pool was closed for remodel, over 2 years now. Breakfast was minimal but decent. Parking is good. We stayed 1 out of 3 nights we had booked."
Reviewed on Oct 20, 2026
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.
Find the Best Oswego Vacation Packages
Oswego Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Top Sights | Wagon Wheel Theatre, Chapman Lakes and City-County Athletic Complex |
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Frequently asked questions
How much does an Oswego vacation package cost?
You'll find cheap prices from $491 on Expedia for your Oswego escape. However, a range of factors like your choice of hotel, the season and length of stay will determine how much your vacation to Oswego costs.
What are the cheapest months to go to Oswego?
If you're hoping to snag a cheap Oswego vacation package, consider traveling in November, December and January. You'll typically find lower prices on accommodations and flights during these months — ideal for budget-conscious travelers.
How many days is enough for Oswego?
With a well-planned itinerary, you can easily tick off the most popular Oswego sights in a handful of days. But if you'd like to discover lesser-known spots or go on day trips, think about booking your Oswego vacation for longer.
How to find the best Oswego package deals?
Use Expedia's filters to help you find some tempting Oswego package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or browse for Oswego package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book an Oswego vacation as a package?
You can enjoy significant savings on your next Oswego retreat by booking a customized vacation package. Click on the "Package" heading, then select your travel dates and destination to see some great hotel prices and airfares. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Oswego?
If you're considering a spontaneous Oswego vacation, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can find terrific deals on your flights and hotels by booking well in advance.
Does Expedia offer Book Now, Pay Later Oswego vacation packages?
Secure your perfect trip to Oswego with Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or hold off until payday — we've teamed up with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans allow you to split the cost across 3, 6 or 12 months. With no late payment fees or extra charges, you can easily stick to your budget and snag great deals before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.