Winchester Vacations from $534

Book a Hotel + Flight or Car together to unlock savings

The Latest Winchester vacation packages

Price found within the past 48 hours. Click for updated prices.
Arts District Apartments By Landing

Arts District Apartments By Landing

3.5 out of 5
Downtown Tulsa
Price was $655, price is now $534 per person
$534
per person
Nov 13 - Nov 17
found 3 hours ago
Roundtrip non-stop flight included
Portland (PDX) to Tulsa (TUL)
No reviews
Harwelden Mansion

Harwelden Mansion

3.5 out of 5
Maple Ridge
Save 100% on your flight
Price was $1,703, price is now $1,127 per person
$1,127
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) to Tulsa (TUL)
10/10 Exceptional! (27 reviews)
The Sycamore Suite was very comfortable and inviting. Lots of room. The patio was nice as well. Beautiful grounds.

Reviewed on Jul 7, 2025

Duets Bed & Breakfast

Duets Bed & Breakfast

3.5 out of 5
Pearl District
Price was $1,190, price is now $923 per person
$923
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) to Tulsa (TUL)
10/10 Exceptional! (8 reviews)
I love this place. This was my first time there and the staff could not have been more accommodating. Very cool property. Secluded as well. The singing from the restaurant downstairs was a little annoying but they stopped right when they closed.

Reviewed on Oct 3, 2025

River Spirit Casino Resort

River Spirit Casino Resort

4 out of 5
South Tulsa
Price was $679, price is now $543 per person
$543
per person
Nov 21 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Tulsa (TUL)
9.4/10 Exceptional! (2,501 reviews)
Stayed there to see a Ziggy Marley concert that was held there, awesome venue. Nice clean place.Would stay here again.

Reviewed on Oct 3, 2025

Landing Tulsa Southbrook

Landing Tulsa Southbrook

4 out of 5
South Tulsa
Price was $679, price is now $550 per person
$550
per person
Nov 13 - Nov 17
found 3 hours ago
Roundtrip non-stop flight included
Portland (PDX) to Tulsa (TUL)
No reviews
Don't see what you're looking for?
See all available trips from Columbus to Winchester
View all trips

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 Oct 5 to Oct 6
$185 total
Oct 5 - Oct 6
Total with taxes and fees
9.4/10 Exceptional! (2,492 reviews)
"Hotel staff very friendly. Attentive to needs. Rooms were clean. Restaurants are clean and well staffed."

Reviewed on Oct 1, 2025

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 Oct 12 to Oct 13
$118 total
Oct 12 - Oct 13
Total with taxes and fees
8.6/10 Excellent! (1,009 reviews)
"Nice place"

Reviewed on Sep 25, 2025

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
$100 nightly
The price is $116 total per night from Oct 12 to Oct 13
$116 total
Oct 12 - Oct 13
Total with taxes and fees
8.2/10 Very Good! (592 reviews)
"Clean, convenient, great staff."

Reviewed on Sep 29, 2025

DoubleTree by Hilton Tulsa - Warren Place
See all 255 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.

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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Winchester vacation package cost?
You'll find cheap prices from $534 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.