Winchester Vacations from $339

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The Latest Winchester vacation packages

Price found within the past 48 hours. Click for updated prices.
Magnuson Hotel Sand Springs - Tulsa West

Magnuson Hotel Sand Springs - Tulsa West

2.5 out of 5
Price was $381, price is now $339 per person
$339
per person
Mar 25 - Mar 29
found 13 hours ago
Roundtrip flight included
Phoenix (PHX) to Tulsa (TUL)
7.8/10 Good! (679 reviews)
Nice spacious room and great water pressure in the shower. Good value.

Reviewed on Jan 19, 2026

DoubleTree by Hilton Tulsa Downtown

DoubleTree by Hilton Tulsa Downtown

4 out of 5
Downtown Tulsa
Price was $507, price is now $407 per person
$407
per person
Mar 19 - Mar 22
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Tulsa (TUL)
8/10 Very Good! (534 reviews)
Our suite was huge which was very nice!! The food was great from the restaurant , and the hotel staff was very accommodating. Only reason didn’t give 5 stars, is because the bathroom was slightly dirty and the shower was the worst shower I’ve ever had at a hotel. The shower head didn’t work at all completely, there was no exhaust for the steam, and the water was extremely inconsistent, it kept going from warm to very hot along with inconsistent pressure. If you pay for a suite you expect better from the shower. Aside from that, we would stay here again, but will check out the shower before settling.

Reviewed on Feb 8, 2026

Tulsa Club Hotel, Curio Collection by Hilton

Tulsa Club Hotel, Curio Collection by Hilton

4 out of 5
Downtown Tulsa
Price was $637, price is now $518 per person
$518
per person
Mar 19 - Mar 22
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Tulsa (TUL)
9/10 Wonderful! (514 reviews)
Beautiful and clean

Reviewed on Feb 1, 2026

BarDew Valley Inn

BarDew Valley Inn

4 out of 5
Price was $598, price is now $518 per person
$518
per person
May 1 - May 4
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tulsa (TUL)
9.8/10 Exceptional! (119 reviews)
The BarDew Valley Inn was amazing, from the history of the building to the home cooked breakfast with the host! Great stay...too bad we could only stay one night. We'll be back, however...

Reviewed on Dec 2, 2025

Hyatt Regency Tulsa Downtown

Hyatt Regency Tulsa Downtown

4 out of 5
Downtown Tulsa
Price was $821, price is now $719 per person
$719
per person
Mar 19 - Mar 22
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Tulsa (TUL)
9/10 Wonderful! (1,904 reviews)
The room was so clean and this was one of the quietest hotels I’ve ever stayed in! We had a corner room, overlooking the main road and didn’t hear any road noise. In addition, usually you expect to hear some noise from people walking around above you etc….i heard nothing! The beds were so comfy! I enjoyed the nightly happy hour right downstairs and coffee at the coffee shop was excellent! I loved to accessibility to the BOK center. It was great that we were able to walk to our event and not have to worry with traffic. I highly recommend staying here!

Reviewed on Feb 9, 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
$159 nightly
The price is $185 total per night from Feb 11 to Feb 12
$185 total
Feb 11 - Feb 12
Total with taxes and fees
9.4/10 Exceptional! (2,633 reviews)
I've stayed at this resort several times, the customer service is always excellent, the rooms are impeccably clean and spacious. I also enjoy the concert venue, the Cove, a great deal. That said, if you're coming to gamble, you may find that the slots favor the house more than other casinos in the ...

Reviewed on Feb 9, 2026

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
$101 nightly
The price is $118 total per night from Feb 22 to Feb 23
$118 total
Feb 22 - Feb 23
Total with taxes and fees
8.6/10 Excellent! (1,004 reviews)
Very clean, staff suoer professional. Amazing security in parking lot. Friendly and helpful staff. Definitely will be numbrr one choice.

Reviewed on Feb 8, 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
$111 nightly
The price is $129 total per night from Feb 22 to Feb 23
$129 total
Feb 22 - Feb 23
Total with taxes and fees
8.2/10 Very Good! (674 reviews)
G

Reviewed on Jan 22, 2026

DoubleTree by Hilton Tulsa - Warren Place
See all 267 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 $339 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.