Winchester Vacations from $505

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The Latest Winchester vacation packages

Price found within the past 48 hours. Click for updated prices.
WorldMark Grand Lake

WorldMark Grand Lake

3 out of 5
Price was $663, price is now $505 per person
$505
per person
Jul 10 - Jul 14
found 4 hours ago
Roundtrip flight included
Dallas (DFW) to Tulsa (TUL)
9.6/10 Exceptional! (127 reviews)
This place was excellent! A little dated but so clean! Beds are very comfortable! Staff was so kind at check in. Will be back!!

Reviewed on May 12, 2026

Harwelden Mansion

Harwelden Mansion

3.5 out of 5
Maple Ridge
Save 100% on your flight
Price was $1,076, price is now $741 per person
$741
per person
Aug 7 - Aug 9
found 1 day ago
Roundtrip flight included
Denver (DEN) to Tulsa (TUL)
9.8/10 Exceptional! (35 reviews)
Staff was great, rooms were very clean.

Reviewed on Mar 26, 2026

Duets Bed & Breakfast

Duets Bed & Breakfast

3.5 out of 5
Pearl District
Price was $730, price is now $565 per person
$565
per person
Aug 7 - Aug 9
found 1 day ago
Roundtrip flight included
Denver (DEN) to Tulsa (TUL)
10/10 Exceptional! (11 reviews)
Duets was the PERFECT stay for my wife and I on our wedding night. The location is perfect and the room was AMAZING. Even if you’re from Tulsa, consider this a little staycation due to the Leon Russell memorabilia and location. 10/10 we will be back!!

Reviewed on Oct 26, 2025

Shangri-La Resort

Shangri-La Resort

4 out of 5
Price was $986, price is now $776 per person
$776
per person
Jul 10 - Jul 14
found 4 hours ago
Roundtrip flight included
Dallas (DFW) to Tulsa (TUL)
9/10 Wonderful! (341 reviews)
Heated Pool wasn't functioning well

Reviewed on May 17, 2026

Hampton Inn & Suites Tulsa Downtown

Hampton Inn & Suites Tulsa Downtown

2.5 out of 5
Downtown Tulsa
Price was $666, price is now $538 per person
$538
per person
Aug 6 - Aug 9
found 24 hours ago
Roundtrip flight included
Houston (HOU) to Tulsa (TUL)
8.6/10 Excellent! (1,009 reviews)
Clean room and staff were great and helpful.

Reviewed on May 13, 2026

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Winchester Hotel Deals

River Spirit Casino Resort

River Spirit Casino Resort

4 out of 5
8330 Riverside Parkway Tulsa OK
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $152 total per night from Jun 14 to Jun 15
$152 total
Jun 14 - Jun 15
Total with taxes and fees
River Spirit Casino Resort
Marriott Tulsa Hotel Southern Hills

Marriott Tulsa Hotel Southern Hills

3.5 out of 5
1902 E 71st St Tulsa OK
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $128 total per night from Jun 7 to Jun 8
$128 total
Jun 7 - Jun 8
Total with taxes and fees
8.8/10 Excellent! (1,006 reviews)
"Was all good.!"

Reviewed on May 20, 2026

Marriott Tulsa Hotel Southern Hills
DoubleTree by Hilton Tulsa - Warren Place

DoubleTree by Hilton Tulsa - Warren Place

4 out of 5
6110 S Yale Ave Tulsa OK
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $125 total per night from May 31 to Jun 1
$125 total
May 31 - Jun 1
Total with taxes and fees
8.2/10 Very Good! (759 reviews)
"Front desk people were very nice and great and their jobs. Shout out to Jayda, she was fantastic! Good location for a group outing. Great breakfast."

Reviewed on May 18, 2026

DoubleTree by Hilton Tulsa - Warren Place
See all 287 properties in Winchester
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 Winchester Vacation Packages

Winchester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Tulsa Intl. Airport (TUL)
Population
510
Top Sights
Creek Council House Museum, Hawthorn Park and Oklahoma State University Institute of Technology

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Frequently asked questions

How much does a Winchester vacation package cost?
You'll find cheap prices from $505 on Expedia for your Winchester break. However, factors like the season, length of stay and your choice of hotel will influence how much your vacation to Winchester costs.
What are the cheapest months to go to Winchester?
You can usually find reduced prices and better availability in July, August and December. Take a look at our cheap Winchester vacation packages and you could get some great off-season deals.
How many days is enough for Winchester?
Usually, a handful of days is enough to go to the top attractions during your Winchester vacation. But if you prefer to have more time to relax or go on day trips, consider extending your trip.
How to find the best Winchester package deals?
Landing a cheap Winchester package deal is easy with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, apply a few filters and see what's available. You can customize your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most economical Winchester package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are usually lower.
Is it cheaper to book a Winchester vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging accommodations and flights separately. Better still, you can personalize your Winchester getaway to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Winchester?
If you have your Winchester travel dates locked in, book as soon as you can to snap up some fantastic deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are ideal for setting off on a whim.
Does Expedia offer Book Now, Pay Later Winchester vacation packages?
Your Winchester break is meant to be an escape from your daily routine, not a reason for money worries. So to give you a bit more flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.