Winchester Holiday Rentals

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Our top choices for Winchester holiday rentals

10.0 out of 10, Exceptional, (1)
1800s Farmhouse—King Bed~Big Kitchen~Games & DVDs
10.0 out of 10, Exceptional, (2)
"Great place great ppl will book again the following year."
United States
Flav
The price is AU$213
includes taxes & fees
1 Jan - 2 Jan 2026
Super cute studio apartment south of Tulsa! Newly renovated and ready to go!
9.0 out of 10, Wonderful, (2)
"I really enjoyed my stay. This property is located on a lovely piece of land in a peaceful and quiet neighborhood. My side of the duplex was super clean and decorated very nicely. The host was responsive and super helpful (there was a glitch with the VRBO system, not the property). I would 100% book this property again. "
United States
David J.
The price is AU$341
includes taxes & fees
3 Jan - 4 Jan 2026
Brand New Modern Getaway on Private Land!
9.4 out of 10, Exceptional, (31)
"Great experience. Will stay again!"
United States
Stephen C.
The price is AU$327
includes taxes & fees
1 Jan - 2 Jan 2026
"The Big Cozy"- WiFi, Hot tub, Grill, Sleeps 8
9.6 out of 10, Exceptional, (4)
"THE ALICE AND WONDERLAND THEME WAS CUTE AND A EXPERIENCE. COMFY BED. QUITE NEIGHBORHOOD, CLOSE TO EVERYTHING"
United States
Phyllis E.
The price is AU$444
includes taxes & fees
12 Jan - 13 Jan 2026
We're All Mad Here! - A Wonderland Escape in Tulsa
2.0 star property
9.4 out of 10, Exceptional, (9)
"Nice property, great location."
United States
Crystal S.
The price is AU$521
includes taxes & fees
5 Jan - 6 Jan 2026
Charming 3-bedroom house with fitness room in peaceful Broken Arrow
9.6 out of 10, Exceptional, (40)
"This is the second year in a row that we have stayed here and just like last year it was perfect. The house was clean and just what we needed while we visited family in the area. We will stay here again."
United States
Michael D.
The price is AU$369
includes taxes & fees
4 Jan - 5 Jan 2026
Beautifully Remodeled 3-Bedroom Cozy Home!!
10.0 out of 10, Exceptional, (30)
"The property was cozy and it's very clean"
United States
Jennifer L.
The price is AU$251
includes taxes & fees
4 Jan - 5 Jan 2026
Secluded Studio-Style 1-Bed/1-Bath Poolhouse in Southern Hills/Tulsa

Holiday Home in South Tulsa

4 bedrooms+Outdoor gazebo+Garage+office
8.2 out of 10, Very good, (27)
"Location was fantastic for our trip. The house is very spacious and no one felt like they were on top of each other. "
United States
christa a.
The price is AU$290
includes taxes & fees
4 Jan - 5 Jan 2026
4 bedrooms+Outdoor gazebo+Garage+office

Holiday Home in Broken Arrow

4 Bedroom Family-Friendly Retreat w/ Yard
10.0 out of 10, Exceptional, (1)
"Wonderful home and host. Very clean and comfortable. Quiet neighborhood that was less than 5 miles to everywhere we needed to go. Great for families with little ones. Although it's pet friendly, it did not smell like it or have fur anywhere. Great find!"
United States
Richard & Marjorie M.
The price is AU$543
includes taxes & fees
29 Jan - 30 Jan 2026
4 Bedroom Family-Friendly Retreat w/ Yard
10.0 out of 10, Exceptional, (5)
"Great place! Would definitely come back to this location!"
United States
Roger H.
The price is AU$429
includes taxes & fees
4 Jan - 5 Jan 2026
Newly Built Modern Getaway on Private Acreage!
10.0 out of 10, Exceptional, (1)
"Good location"
United States
Gavin H.
The price is AU$241
includes taxes & fees
4 Jan - 5 Jan 2026
Comfortable Suite in Tulsa | FREE Breakfast + Fitness Center + Seasonal Outdoor Pool
10.0 out of 10, Exceptional, (8)
"Great Stay"
United States
Jennifer T.
The price is AU$408
includes taxes & fees
31 Dec - 1 Jan 2026
Charming 2-Bedroom Bungalow: Historic Route 66 & Crossroads of America!

Holiday Home in South Tulsa

Tulsa Twilight Terrace@StFrancis
2.0 star property
10.0 out of 10, Exceptional, (2)
"We had a very comfortable stay. The managers were very prompt and pleasant with our questions and requests. Important to us are comfortable beds and bedding. They were outstanding. In the kitchen we had everything we needed. My husband couldn’t stop finding a reason to grill on the the Blackstone grill. Thank you for a wonderful stay."
United States
Elicia H.
The price is AU$609
includes taxes & fees
19 Jan - 20 Jan 2026
Tulsa Twilight Terrace@StFrancis
9.6 out of 10, Exceptional, (8)
"Great"
United States
Josh B.
The price is AU$367
includes taxes & fees
3 Jan - 4 Jan 2026
Charming 3-bedroom house in Jenks with AC, WiFi. Enjoy your stay

Holiday Home in South Tulsa

Enjoy Comfort On 66th
7.8 out of 10, Good, (7)
"I loved it. My host was accommodating and made it easy for me to contact them. The neighborhood was quiet and decent. The decoration in the home was nice and the beds were very comfortable to sleep in. My favorite area was the dining area with the most comfortable sitting chairs I’ve ever sat in at a table to eat. The home was roomy with the three bedrooms far apart from each so that was a plus as well. It was great!"
United States
Crystal T.
The price is AU$388
includes taxes & fees
19 Jan - 20 Jan 2026
Enjoy Comfort On 66th
9.0 out of 10, Wonderful, (12)
"It was great for all of the family to be together "
United States
Kelli J.
The price is AU$511
includes taxes & fees
3 Jan - 4 Jan 2026
“Big Cozy Cottage” -WiFi, Hot Tub, Grill

Holiday Home in South Tulsa

A Harmonious Escape in Tulsa
9.0 out of 10, Wonderful, (7)
"Great place to stay with plenty of room. It's well cared for and comfortable. It also has a wonderful coffee bar. Also the people at Victory are amazing to work with/really good customerservice. We are loving our stay here."
United States
Becky J.
The price is AU$426
includes taxes & fees
20 Jan - 21 Jan 2026
A Harmonious Escape in Tulsa
2.0 star property
The price is AU$406
includes taxes & fees
31 Dec - 1 Jan 2026
Downtown Okmulgee Aviator Apartment
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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Top Winchester Hotel Reviews

Find out more about Winchester

Everything you need to know about Winchester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winchester holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester holiday rentals we have selected for you start as low as AU$251 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Winchester?

Yes, there are holiday rentals close to the most popular sights in Winchester, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Winchester has to offer?

Spacious 5-bedroom house, 2 living areas, in Tulsa, centralized location!: This holiday home rental outside of Winchester offers a fireplace, a selection of games and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What’s there to see and do in Winchester?

Explore the area and family-friendly sights such as Oklahoma Aquarium, or get out into nature at a spot like Hawthorn Park. In the wider area, you’ll find Creek Council House Museum and Okmulgee State Park.

What’s a holiday rental in Winchester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchester. Holiday rentals feature extras such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from shared hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for a family trip or a small group gathering.