Winchester Holiday Rentals

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Holiday Rentals in Winchester

"The Big Cozy"- WiFi, Hot tub, Grill, Sleeps 8
9.4 out of 10, Exceptional, (12)
"We wish we could give 10 stars! A wonderful place to relax with your family. We cooked a big meal and gathered to eat as a family. Comfy bed. Lots of space. Looks better in person than in the pictures. Has everything you need. "
The price is AU$316
includes taxes & fees
30 Nov - 1 Dec
"The Big Cozy"- WiFi, Hot tub, Grill, Sleeps 8
This house is a 4 bedroom(s), 2 bathrooms, located in Tulsa, OK.
9.2 out of 10, Wonderful, (27)
"Nice, quiet location, everything was clean, and the beds were excellent."
This house is a 4 bedroom(s), 2 bathrooms, located in Tulsa, OK.
Cozy house in Tulsa - 10 min to major HWY& Malls. 7- 9 miles to major hospitals
9.6 out of 10, Exceptional, (41)
"Really nice property. Owner was very communicative. Would stay there again when staying in Tulsa."
Cozy house in Tulsa - 10 min to major HWY& Malls. 7- 9 miles to major hospitals
Casa Joya - A Jenks Gem Professionally designed three-bedroom luxury home!
10.0 out of 10, Exceptional, (38)
"This property was perfect for us. We had plenty of room - 2 adults, teen and tween. Each bedroom has a TV which the kids liked but the living room was nice & cozy for our movie night on Saturday. The master bedroom is quite large and the bed was comfortable. Bonus the master bath has a tub/shower combo AND separate shower. We didn’t need to cook but I noticed the kitchen had everything we’d need to make meals. Appliances look new and in good condition. This is definitely a property...
Casa Joya - A Jenks Gem Professionally designed three-bedroom luxury home!
Beautifully Remodeled 3-Bedroom Cozy Home!!
9.8 out of 10, Exceptional, (20)
"Absolutely loved it, we had everytbing we needed and it felt so clean and safe , it was an amazing experience will definitely have to book again "
Beautifully Remodeled 3-Bedroom Cozy Home!!
10,000 sq ft Luxury Venetian Mansion with a Slice of Italy in Tulsa
9.6 out of 10, Exceptional, (25)
"Beautiful property; perfect for hosting an out of town wedding party, and having a "after rehersal" reception. There were a few issues. There are 2 very nice, high-end refridgerators; Icemaker on neither of the worked. Owner brought over a portable, counter-top ice maker. Major issue was lack of hot water. After complaining to the owner, he turned up the thermostat for downstairs bath. I later learned that the upstairs tenants also have virtually no hot (barely warm) water, and it seem to shut...
10,000 sq ft Luxury Venetian Mansion with a Slice of Italy in Tulsa
4 Bedroom spacious and peaceful house!
9.2 out of 10, Wonderful, (5)
"House was in great location and very accommodating. Good set up"
The price is AU$437
includes taxes & fees
3 Dec - 4 Dec
4 Bedroom spacious and peaceful house!
Family-Friendly Broken Arrow Retreat w/ Yard!
9.8 out of 10, Exceptional, (30)
"The home was in a great location and had many amenities for the whole family! "
Family-Friendly Broken Arrow Retreat w/ Yard!
Stay in a classically designed apt near ORU, exercise trails, and restaurants!
9.4 out of 10, Exceptional, (44)
"The apartment was super clean and well furnished. The master bed was comfortable. The apartment complex didn’t do the apartment itself justice. Reserved parking was a nice perk. Communication with the hostess was great."
The price is AU$317
includes taxes & fees
24 Nov - 25 Nov
Stay in a classically designed apt near ORU, exercise trails, and restaurants!
Family Size Home, 5 Mins from Rose District, King Bed & Fire Pit, 2,100 sq ft!
10.0 out of 10, Exceptional, (3)
"Had a family reunion and the house was perfect!! Clean, all the essentials you need plus felt very safe. The long dining room table was the best part because it’s the ultimate place to visit. We were close to stores, restaurants and entertainment. Our host is amazing. Great communication!!"
The price is AU$644
includes taxes & fees
24 Nov - 25 Nov
Family Size Home, 5 Mins from Rose District, King Bed & Fire Pit, 2,100 sq ft!
Urban Wilderness Home on Full Acre close to shopping and Hwy
9.8 out of 10, Exceptional, (22)
"Everything was perfect except for the bed pillows. They were horrible, my daughter even went and bought her some after the first night. It would be nice to have a lamp in the living room ceiling fan lights are really bright"
Urban Wilderness Home on Full Acre close to shopping and Hwy
Private Home w/ Hot Tub & Patio Near Dtwn Tulsa
8.8 out of 10, Excellent, (30)
"The house is a gem, all the amenities you need in a super quiet and safe Cul De Sac. The owner is extremely responsive and has a beautiful house. Thank you Mrs Teresa we will see you again soon. "
Private Home w/ Hot Tub & Patio Near Dtwn Tulsa
Mid Century home in the heart of Sapulpa
10.0 out of 10, Exceptional, (4)
"The home was clean, lovely, and very comfortable for the 5 of us. The owner stocked the kitchen better than any home I have stayed in. I took my dogs walking in the morning to a nice little park just a few blocks away. The neighborhood was clean and quiet. We had family over for my mother-in-law's 95th birthday party. Everyone was impressed with the place. I would definitely stay there again."
The price is AU$415
includes taxes & fees
24 Nov - 25 Nov
Mid Century home in the heart of Sapulpa
3 BR by Mabee Center ORU, Casino, Jenks, Victory Church
9.4 out of 10, Exceptional, (27)
"Home was very clean, spacious, and has everything one would need. Perfect for families. Great communication from host. "
3 BR by Mabee Center ORU, Casino, Jenks, Victory Church
Charming 3bed/2 bath near Gathering Place, Riverparks and Downtown
10.0 out of 10, Exceptional, (12)
"We enjoyed our time in Tulsa. This was the perfect location to get anywhere. The beds were comfortable and plenty of space."
Charming 3bed/2 bath near Gathering Place, Riverparks and Downtown
Comfy Hangout House - Sleeps 16 - Pool & Hot Tub!
10.0 out of 10, Exceptional, (2)
"Kids loved the pool and hot tub. Plenty of beds. "
Comfy Hangout House - Sleeps 16 - Pool & Hot Tub!
Cozy Cabin, firepit, with 10 acres to roam, private pond and Dock, s’more’s
10.0 out of 10, Exceptional, (17)
"My son graduated from college and relocated with his 1st job offer to Tulsa. We met away from the city to enjoy a fantastic father-son weekend hiking, fishing and enjoying a quiet country weekend. We are planning another visit in the future."
Cozy Cabin, firepit, with 10 acres to roam, private pond and Dock, s’more’s
Midtown pool house
9.8 out of 10, Exceptional, (16)
"Great"
Midtown pool house
Modern yet Cozy Beauty in Jenks with Hot Tub!
10.0 out of 10, Exceptional, (1)
Modern yet Cozy Beauty in Jenks with Hot Tub!
Comfortable 4 bedroom home in South Tulsa
10.0 out of 10, Exceptional, (24)
"Perfect location. Nice quiet neighborhood. House was roomy yet cozy!"
Comfortable 4 bedroom home in South Tulsa
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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Other types of properties in Winchester you may be interested in

River Spirit Casino Resort
4.0 star property
9.4 out of 10, Exceptional, (2723)
"We had a great time. Love the pool area. We love going there for a short getaway."
The price is AU$284
includes taxes & fees
24 Nov - 25 Nov
River Spirit Casino Resort
DoubleTree by Hilton Tulsa - Warren Place
4.0 star property
8.2 out of 10, Very good, (290)
"Staff very nice and very friendly! Had trouble with room key getting into the parking garage. "
The price is AU$177
includes taxes & fees
23 Dec - 24 Dec
DoubleTree by Hilton Tulsa - Warren Place
Marriott Tulsa Hotel Southern Hills
3.5 star property
8.6 out of 10, Excellent, (973)
"I’ve stayed at this Marriott on annual trips I make for business. I typically don’t sleep well while away from Home but not here. Excellent stay including breakfast buffet. Could not be more pleased. Will definitely stay again. "
The price is AU$204
includes taxes & fees
23 Dec - 24 Dec
Marriott Tulsa Hotel Southern Hills
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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?

"The Big Cozy"- WiFi, Hot tub, Grill, Sleeps 8: 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 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

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 Okmulgee State Park. In the wider area, you’ll find RiverWalk and SpiritBank Event Center.

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.