Winchester Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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Top hotels in Winchester

River Spirit Casino Resort

River Spirit Casino Resort

4 out of 5
8330 Riverside Parkway, Tulsa, OK
Fully refundableReserve now, pay when you stay
The price is S$214 per night from 25 Aug to 26 Aug
S$214
25 Aug - 26 Aug
includes taxes & fees
9.4/10 Exceptional! (2,467 reviews)
"Great service"

Reviewed on 19 Aug, 2025

River Spirit Casino Resort
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
The price is S$146 per night from 31 Aug to 1 Sept
S$146
31 Aug - 1 Sept
includes taxes & fees
8.2/10 Very Good! (557 reviews)
"Property and staff were nice."

Reviewed on 19 Aug, 2025

DoubleTree by Hilton Tulsa - Warren Place
Affordable Suites of America Tulsa

Affordable Suites of America Tulsa

2 out of 5
10008 E 73rd St, Tulsa, OK
Fully refundableReserve now, pay when you stay
The price is S$125 per night from 23 Aug to 24 Aug
S$125
23 Aug - 24 Aug
includes taxes & fees
8.6/10 Excellent! (103 reviews)
"It was further than I thought from expo square but the room was great, clean with basic kitchen amenities and a full fridge"

Reviewed on 18 Aug, 2025

Affordable Suites of America Tulsa
See all 249 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.

Frequently asked questions

How much does a Winchester holiday package cost?
You'll find cheap prices on Expedia for your Winchester break. However, factors like the season, length of stay and your choice of hotel will influence how much your holiday to Winchester costs.
What are the cheapest months to go to Winchester?
If you'd like to snag a cheap Winchester holiday package, consider planning a trip in January, February and November. You'll usually find better rates on flights and accommodation during these months — ideal for a budget-friendly break.
How many days is enough for Winchester?
The ideal length for your Winchester holiday depends on what you'd like to see and do. Typically, a few days to a week will give you enough time to tick off all the main attractions and discover some hidden spots along the way.
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 customise 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 travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Winchester holiday as a package?
An Expedia holiday package could land you considerable savings when compared to arranging accommodation and flights separately. Better still, you can personalise 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 holiday 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.
How to plan a trip to Winchester?

  1. Choose when to get away: Check your calendar and pack your bags. Your preferred season and the activities available will also help you decide when to holiday in Winchester.
  2. Plan your budget wisely: On top of the cost of your stay, you should consider other expenses. These include transportation, food and flights. Also, set aside a little extra for unexpected expenses that may come up during your trip to Winchester.
  3. Decide how long to go for: Now that you're up to speed on Winchester, you can work out the ideal length of your holiday. Create a rough plan and allocate enough time to get through everything on your must-do list.
  4. Bundle your accommodation and airfare: After you've settled on your travel dates and duration, lock in the right Winchester holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.