Holiday Rentals in Winchester

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Our top choices for Winchester holiday rentals

10.0 out of 10, Exceptional, (2 reviews)
"Great place great ppl will book again the following year."
United States
Flav
The price is €134
includes taxes & fees
3 Feb - 4 Feb
Super cute studio apartment south of Tulsa! Newly renovated and ready to go!
10.0 out of 10, Exceptional, (31 reviews)
"This is the perfect couples retreat in a beautiful location in south Tulsa. It is so cute and has everything you need plus a tennis/pickleball court which we really enjoyed. The hosts are amazing. "
United States
Melinda P.
The price is €141
includes taxes & fees
21 Jan - 22 Jan
Secluded Studio-Style 1-Bed/1-Bath Poolhouse in Southern Hills/Tulsa
2.0 star property
Cozy RV with AC and WiFi in serene Haskell
10.0 out of 10, Exceptional, (1 review)
"Everything was great, clean, Susan responded promptly."
United States
Nathan M.
Beautiful 4-bedroom house with 4 beds in a pleasant South Tulsa neighborhood.
9.4 out of 10, Exceptional, (35 reviews)
"Perfect place with great location for my job and recreation. "
United States
Randy M.
The price is €190
includes taxes & fees
21 Jan - 22 Jan
"The Big Cozy"- WiFi, Hot tub, Grill, Sleeps 8
9.6 out of 10, Exceptional, (44 reviews)
"Cute cozy place! Comfy beds!"
United States
Katelyn M.
The price is €208
includes taxes & fees
21 Jan - 22 Jan
Beautifully Remodeled 3-Bedroom Cozy Home!!

Holiday Home in South Tulsa

A Harmonious Escape in Tulsa
9.0 out of 10, Wonderful, (7 reviews)
"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 €251
includes taxes & fees
21 Jan - 22 Jan
A Harmonious Escape in Tulsa
9.6 out of 10, Exceptional, (5 reviews)
"The property is decorated Alice and Wonderland, and they nailed it! There was clearly lots of attention to detail in the design. We loved the numerous coffee options. Lily was great host. Friendly and prompt. Would recommend!"
United States
Jeffrey S.
We're All Mad Here! - A Wonderland Escape in Tulsa

Holiday Home in South Tulsa

Enjoy Comfort On 66th
7.8 out of 10, Good, (7 reviews)
"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 €229
includes taxes & fees
25 Jan - 26 Jan
Enjoy Comfort On 66th
2.0 star property
The price is €233
includes taxes & fees
31 Jan - 1 Feb
Downtown Okmulgee Aviator Apartment
9.0 out of 10, Wonderful, (2 reviews)
"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 €199
includes taxes & fees
18 Feb - 19 Feb
Brand New Modern Getaway on Private Land!
10.0 out of 10, Exceptional, (5 reviews)
"Great place! Would definitely come back to this location!"
United States
Roger H.
The price is €249
includes taxes & fees
21 Jan - 22 Jan
Newly Built Modern Getaway on Private Acreage!
Groovy Getaway - Retro Vibes and Modern Comfort
10.0 out of 10, Exceptional, (1 review)
"Our stay was awesome. We were in town for a funeral which was a sad reason but family was able to come and visit. The kitchen was so well stocked with necessities there was no need to purchase paper plates, silverware or glassware. We gathered as a family, ate great meals and remembered great times with our grandmother. THANK YOU!"
United States
Lisa W.
Heart of Tulsa, game room, fireplace, Sleeps 8, grill, pool.

Holiday Home in Broken Arrow

4 Bedroom Family-Friendly Retreat w/ Yard
10.0 out of 10, Exceptional, (1 review)
"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.
4 Bedroom Family-Friendly Retreat w/ Yard

Holiday Home in South Tulsa

King Suite-4 Bedroom-Brookside-Riverside
9.4 out of 10, Exceptional, (11 reviews)
"Nice place. "
United States
Roger B.
The price is €293
includes taxes & fees
21 Jan - 22 Jan
King Suite-4 Bedroom-Brookside-Riverside

Holiday Home in South Tulsa

Breezy Two Bedroom in South Tulsa
9.0 out of 10, Wonderful, (12 reviews)
"The house was in a great location for us. Quiet neighborhood. Had all the kitchen equipment we needed to make our own meals. "
United States
Amey P.
Breezy Two Bedroom in South Tulsa
10.0 out of 10, Exceptional, (1 review)
"Good location"
United States
Gavin H.
The price is €126
includes taxes & fees
22 Jan - 23 Jan
Comfortable Suite in Tulsa | FREE Breakfast + Fitness Center + Seasonal Outdoor Pool
The price is €263
includes taxes & fees
3 Feb - 4 Feb
Charming and unique upscale 1-bedroom apartment in downtown Okmulgee
10.0 out of 10, Exceptional, (12 reviews)
"My family had a relaxing and comfortable stay. Great property, great location, we would stay here again when we're in the area!"
United States
Cerenity C.
New! 5/3 with Hot tub, Arcade, Playground, Coffee bar, large TV and dining table
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, apart-hotels, 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 favorite 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 depends 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 €141 per night. Entering your travel dates in the search wizard you might find 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?

Beautifully Remodeled 3-Bedroom Cozy Home!!: This holiday home rental outside of Winchester is equipped with a selection of games, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 3 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 Haikey Creek Park. In the wider area, you’ll find Okmulgee State Park and Tulsa Premium Outlets.

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.