Winchester Vacation Packages

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Top Winchester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Tulsa Downtown

DoubleTree by Hilton Tulsa Downtown

4 out of 5
Downtown Tulsa
per person
Oct 7 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Tulsa (TUL)
8/10 Very Good! (336 reviews)
Very friendly check in and lovely view from my room.

Reviewed on Jul. 20, 2025

Harwelden Mansion

Harwelden Mansion

3.5 out of 5
Maple Ridge
per person
Oct 7 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Tulsa (TUL)
10/10 Exceptional! (26 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
per person
Oct 7 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Tulsa (TUL)
10/10 Exceptional! (7 reviews)
They were so friendly, place was spotless! loved the décor and hospitality. will definitely come back and refer others

Reviewed on Apr. 3, 2023

River Spirit Casino Resort

River Spirit Casino Resort

4 out of 5
South Tulsa
per person
Oct 7 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Tulsa (TUL)
9.4/10 Exceptional! (2,447 reviews)
The lights in my room was flicking on and off

Reviewed on Jul. 25, 2025

Tulsa Club Hotel, Curio Collection by Hilton

Tulsa Club Hotel, Curio Collection by Hilton

4 out of 5
Downtown Tulsa
per person
Oct 7 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Tulsa (TUL)
9/10 Wonderful! (473 reviews)
Nice people at front desk

Reviewed on Jul. 15, 2025

Ready to book your vacation to Winchester?

 

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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
The price is CA $196 per night from Jul 30 to Jul 31
CA $196
CA $228 total
Jul 30 - Jul 31
includes taxes & fees
9.4/10 Exceptional! (2,467 reviews)
Dr visits
"Had an early Dr appointment. It was perfect"

Reviewed on Jul. 24, 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
The price is CA $126 per night from Aug 17 to Aug 18
CA $126
CA $147 total
Aug 17 - Aug 18
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
"Check in was simple and easy. Even though we stayed on a busy weekend and the hotel had many guest, we had pleasant restful nights. There is plenty of parking spaces."

Reviewed on Jul. 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
The price is CA $137 per night from Aug 10 to Aug 11
CA $137
CA $160 total
Aug 10 - Aug 11
includes taxes & fees
8.2/10 Very Good! (534 reviews)
"Great all around"

Reviewed on Jul. 24, 2025

DoubleTree by Hilton Tulsa - Warren Place
See all 244 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.
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Frequently asked questions

How much does a Winchester vacation package cost?
Offering great value package deals from CA $1,963 on Expedia, you'll be thrilled with how little a vacation to Winchester costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Winchester?
You're likely to find reduced prices and better availability in January, February and November. 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?
With a well-planned itinerary, you can easily visit the most popular Winchester attractions in a few days. But if you want to discover hidden spots or take day trips, think about booking your Winchester vacation for longer.
How to find the best Winchester package deals?
Use Expedia's filters to find some unbeatable Winchester package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for Winchester package deals in the low season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as early as possible.
Is it cheaper to book a Winchester vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking flights and stays separately. Better still, you can personalize your Winchester escape to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Winchester?
If you have your Winchester travel dates confirmed, book as early as you can to grab some incredible deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are great for quick escapes.
How to plan a trip to Winchester?

  1. Choose your dates: What you plan to do in Winchester and your preferred season will help you decide when to travel.
  2. Calculate your budget: Ensure you have enough money to pay for everything from transportation and dining out to flights and experiences. Your accommodations will likely be the largest expense during your trip to Winchester.
  3. Decide your trip length: Consider how long you'd like to spend exploring Winchester. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a comfortable pace.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to pick a Winchester vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.